Category: Le Podcast

Le Podcast equips you to make a positive change in your organization. Each episode turns insight into actions that you can use straight away to build momentum and create lasting change from yourself to your team, from your team to other teams, and from other teams to the entire organization.

  • Cloud Infrastructure Leadership: What Changes When You Lead the Platform

    Cloud Infrastructure Leadership: What Changes When You Lead the Platform

    Cloud infrastructure has changed radically in 20 years. We moved from standing in line to request hardware to provisioning global resources in minutes. Yet the leadership challenges didn’t disappear. They evolved.

    In this episode of Le Podcast on Emerging Leadership, I’m joined by Michael Galloway, a platform and infrastructure leader with experience at Yahoo, Netflix, and HashiCorp. We explore the evolution of infrastructure, but also the human side of platform engineering: trust, ownership, change, and the realities of operating systems at scale.

    From “tin” to cloud: speed increased, responsibility didn’t vanish

    Michael shares an early Yahoo story that captures the shift: the era of physical requests, committees, and scarce resources. Virtualization and cloud unlocked a new world, but they didn’t erase complexity. They moved it.

    The question is no longer “How do we get machines?”
    It becomes: “How do we design defaults, behaviors, and systems that make operations reliable?”

    “Don’t just use the interface”

    A key theme in our conversation is what happens when abstraction goes too far.

    Michael learned early in his career that using an interface without understanding what sits underneath limits your ability to solve real problems. The same applies to internal platforms and infrastructure products: if teams can’t see what’s under the hood, they can’t operate their services confidently in production.

    This matters for DevOps and full-cycle ownership. If the platform hides everything, it also centralizes responsibility again. And that’s exactly the anti-pattern many organizations are trying to escape.

    Setting the right defaults (instead of hiding complexity)

    Michael makes a distinction I find extremely useful:

    • Abstractions can help with the zero-to-one problem (get a service running fast).
    • But sustainable systems require teams to drill down, understand decisions, and troubleshoot effectively.

    His closing line on this topic is simple and sharp:
    Predictability is more valuable than velocity.

    A crisis story: ownership, outcomes, and early wins

    Shortly after joining HashiCorp, Michael faced a real incident: a workflow engine falling behind at scale, with work piling up and trust already eroded. The technical work mattered, but what stood out was the leadership sequence:

    1. Take ownership publicly
      People need to hear: “We own this, and we will fix it.”
    2. Form a durable team around the problem
      Not a temporary war room. A team with a mandate.
    3. Define outcomes that matter
      Not “deliver X,” but “stability,” “scalability,” and “confidence.”
    4. Deliver early wins
      Not a 24-month plan. Evidence now, then progress each week.

    That combination rebuilt credibility and made it possible to redesign the system properly.

    Change at scale: the lesson of urgency

    We also discuss a platform adoption challenge from Michael’s Netflix experience, and what he learned about change management: good ideas don’t spread by themselves.

    Two levers made a huge difference in later roles:

    • A real deadline (a cliff, not a wish)
    • Executive alignment to keep that deadline real

    Michael’s practical insight:
    A target like nine months is close enough to feel real, far enough that teams don’t immediately say no.

    Advice for emerging leaders

    Michael closes with three themes that translate well beyond infrastructure:

    • Understand your stakeholders deeply (including what isn’t said)
    • Deliver a meaningful win in the first 90 days to earn credibility
    • Define the purpose of your team so priorities become easier and autonomy grows

    Here are a few links:

    Here is the transcript:

    Alexis: [00:00:00] Welcome to Le Podcast on Emerging Leadership. I’m your host, Alexis Monville. In this episode, we are excited to welcome Michael Galloway, a visionary leader in the tech industry with over two decades of experience. Currently shaping the future of cloud infrastructure at HashiCorp, Michael brings a wealth of knowledge from his dynamic roles at companies like Yahoo and Netflix.

    Today, he shares his journey, insights on platform engineering and the evolving landscape of technology leadership.

    Welcome to the podcast on Emerging Leadership. Michael, how do you typically introduce yourself to someone you just met?

    Michael: Yes. Thank you for inviting me. Alexis. The way I think I typically introduce myself is I live in California. I’ve been working in the tech industry for about 20 years. Father of two rambunctious girls and husband to a wife of [00:01:00] almost 20 years now.

    Alexis: Wow. Wow, wow. I would love to unpack all those things, but maybe we’ll time for, for some of it. Let’s look at your, your journey in the tech industry. A fascinating journey. I’ve heard about your experiences both at Netflix and now at Hashicorp. Could you give us a, a snapshot of your trajectory and what drew you to that field of cloud infrastructure?

    Michael: Sure. Well, like I mentioned, I’ve been in the industry for more than 20 years. I was actually part of the early two thousands crew at Yahoo. Just before the Google IPO. So that was an interesting experience to start off my career. yeah, that was you know, everything, everything was possible.

    And some of the most brilliant minds that I have the opportunity to work with many years later in my career started there. In fact, my current boss at HashiCorp was also part of that crew back at Yahoo and And and, you know, it’s, [00:02:00] it’s, the Valley is ultimately very small from Yahoo. I went through a number of different ranges of companies.

    So I actually did a startup in the enterprise software space, which I was fortunate to sell. I would say it’s more of an Acqui-hire but it was a great experience to go through what is a startup life like in Silicon Valley. Eventually, I landed in Netflix around 2016. And moved into the platform engineering organization. From there I led a bunch of teams in Delivery Engineering. I think the most famous part of Netflix that people may know of is the Spinnaker product that was developed for the most part between Netflix and Google. And that’s what we evolved and, and worked on. After that, that was really where I fell in love with platform engineering as, as a concept.

    The whole concept of full cycle development and DevOps as we were pioneering it at Netflix was just fascinating and working with some of the greatest minds I I’ve had the opportunity to work in that space. I eventually moved to leading platform organizations [00:03:00] at mid-tier companies, and now I’m over at HashiCorp. Running the infrastructure part of the organization personally. you asked about infrastructure. Infrastructure specifically is a fascinating and evolving space. You know, I actually have experience going in front of David Filo, one of the founders of Yahoo, and making physical hardware requests.

    I remember standing in line a little anecdote there as I I was we all queued up at, at, at, at these hardware request committee meetings. And David Filo is one of several members. And I was right behind this gentleman. I had just started my job. Maybe I was a month, two months in. And the, the person in front of me was from Yahoo Photos, and he goes up to David Filo and he’s making requests for several multimillion dollar filer machines that we needed for the Yahoo Photos footprint. And they discussed and, and, you know, okay, we will ultimately approve. And then my number’s called, and I, I get up and. I said, I’m, I’m looking for $300 to buy a hard drive for one of our [00:04:00] machines. And Yeah. Philo had this look on his face of like, yeah, maybe this, maybe we can do, do some efficiency improvements for this meeting.

    Might not be the best use of everybody’s time. And I say, I, I really appreciated that he saw it that way. But you know, the, so I was, you know, I think a lot of us have experience with the actual tin, but now, but with the introduction of virtualization that really came out many years later, unlocked, you know, all kinds of, of capabilities like you know, immutable deployment patterns and, and real ephemeral infrastructure started to become a thing. And, and finally I think. So, so what we’re seeing is, is the outcome of those innovations and the, and the, this idea that you can allocate virtual global infrastructure in minutes. But I truly think that that’s actually just the beginning of where, where we’re headed as an industry. So it’s an exciting space to be.

    Alexis: Oh, whoa, whoa. Wait, that’s, that’s very [00:05:00] interesting because yeah, with, the introduction of virtualization, basically a lot of people thought, oh yeah, that you, you don’t need to care really about cloud infrastructure anymore, and.

    Michael: Right,

    Alexis: Anyway, everything will be fine with, that’s just infrastructure as code and, and let’s, let’s do everything.

    But that’s not really what happened. Even if we I don’t remember DevOps. It’s what, 2009? Something like that. We are still not there yet. Completely. In your, in your, during your talk at Plato Elevate you mentioned that. Cloud Infra was not about hiding complexities, but setting the right defaults.

    I would like to you to discuss that a little bit more, because that will maybe tell us what, what is coming, what, what the future looks like.

    Michael: Yeah. This is a very fascinating conversation. It’s, it’s something that we can quickly get into Modern applications and lose a sense of principles. So I [00:06:00] like to come at this more from a principles first approach than, than just you know, the common conversation that I hear in many platform organizations or many companies is, how do we become, should we present a Heroku environment? And I think that that’s missing some grounding. you’re talking about how to use it. As opposed to the philosophies of behavior that you want to encourage or support in an organization. So like everything else in software development, the answer is maybe The answer is nuanced, right? But let’s start with the an early, I’ll give you an early story that, that really grounded my thinking on this. It goes back to my Yahoo days actually. So I was a software engineer there and I worked on the Confabulator product. It was a Desktop Widgets product that worked on both Mac and Windows. Actually, the modern Apple widgets experience on the iPhones, as well as Netflix’s tv or Netflix’s video capabilities on tv. And, and all the modern TV [00:07:00] widgets all are actually born from some of the actual same humans that worked on Confabulator. I, I actually worked with some of those guys.

    One of ’em I actually hired into to Yahoo. So just a little short history there. So all things are connected, but I was working on this and I was around much smarter minds than mine. And one of the lead engineers in the group emphasized to me, he said, don’t just use the interfaces to these libraries that, that are, you know, available to us from the, the, the TVs or from the, the OSS systems that we’re trying to operate on.

    Don’t just use the interfaces. You said you need to understand What they do underneath, you need to understand those in order for you to be able to solve the real problems, the hard problems. And he was right. How often we end up grabbing a library and just using it without thought of how is it actually performing these actions.

    And when you do that, and we’ve seen this in software development all the time, where you have higher and higher level frameworks, and [00:08:00] the understanding of the magic underneath is ultimately .Limited to the few that actually care to try to introspect, and some of those frameworks actually actively try to encapsulate and block the ability for you to really understand what’s under the covers. Why does that matter? Is because if it fails to do the thing I need it to do, if my application calls into an interface and for whatever reason that interface has an unexpected side effect, I now have no ability other than to just abandon that interface. To solve that problem. And that becomes really a, a limiting factor. So if you take it from that perspective and you, you, you view software platforms and you view infrastructure platforms or platform engineering platforms, they’re all the same concept, right? They’re encapsulation their abstraction. There’s the same software principles. You start to get to the point where you realize, where do you want to put The responsibility for resolving and solving problems. In a true [00:09:00] DevOps world, you ideally want to enable application teams to ultimately have the ability to understand and operate their products in production. And if you don’t, don’t enable them to be able to see below the details for how something is being done. They have no ability to perform that task. They have to rely on a central team to do it. just like if I am, if I am the provider of a framework, but they can never see into the code of that framework. If that framework fails to do the thing they need to do, they’re going to abandon it or do something different, which will create heterogeneity in the environment and more complexity. So when I think about the right experience, what I look at is Not about hiding the complexity per se. I think you can follow abstraction or present a an interface facade if you want to simplify the zero to one problem that most of the time, this is what they’re talking about. I just wanna get my application out.

    I just wanna get a database. I that’s a zero [00:10:00] to one problem. Provide a simple facade. That’s where the abstraction actually can have value, but. It should be an abstraction that you can drill further down if you want to. You can go further and you can see what actually was done. How did how does this machine perform the actual instantiation of that database? What is the instance size? If it was, say, Amazon, of that database that was set up, I should be able to introspect these things because those can lead to me understanding why a failure occurred. In my production system or how better to architect. A good example of this is a situation that we just recently encountered you know in, in my current universe at HashiCorp, where one of our products has a stateful, it wants to perform in a very stateful way. Well, it is a stateful application. And stateful is a particularly tricky monster to, to from an infrastructure standpoint, right? We really, [00:11:00] very much on the infrastructure side, wanna see the world as I. As, as cattle they say not pets, right? That’s a common euphemism. And and so the idea that I can truly lose or blow away my infrastructure if I needed to and that the resiliency is actually supported both at the application tier as well as other parts of the infrastructure to support the idea that any virtual thing can fail. And the truth is, is that whether anybody likes to think of it or not, I have a lot of experience with yeah. Virtual things fail because physical things fail. So you very much need to have that. If you a stateful application doesn’t like to operate that way. It likes to believe that, that there is a permanence with the thing that it’s in. This is a really tricky problem with infrastructure systems to date. If we have a full abstraction of what is actually happening on the infrastructure tier, especially when we need to version the infrastructure underneath the covers, it can, [00:12:00] it can be a real problem for that, that application team, because they don’t understand why systems are periodically being disconnected or broken or having any predictability around it. So as a result of that, they have to offload all of the operation problems and all of the ops that are specific to their application universe, to the central and infrastructure, the central infrastructure team. And that is the anti-pattern that we all wanna avoid, that the whole point of DevOps was to move out of a central team operating applications in production as much as possible. So that was a long-winded answer. The short nugget here I would say is predictability is more valuable than velocity.

    Alexis: Mm. Yeah. , I guess that that summary helps really to to understand the, the whole thing. Could you tell us about a particular challenge you, you facedworking on that realm of cloud of platform at Corp and how you approached it.[00:13:00] 

    Michael: Yeah I’ll give you a different challenge ’cause life’s full of those. When I joined Hashi Corp let’s see, I joined December of 2022, so December last year. So I’m almost at my one year anniversary actually. About a month and a half in, I would say, so sometime in January all these alarms started going off. It was not my fault. I had just started. That’s okay. I don’t mind if it is. But it was not alarms are going off all these, you know, 3:00 AM things blown up. And so the issue was a big portion of our System relies on a workflow. It, it’s basically, it’s a workflow engine that, that a lot of our use cases require to be operating effectively.

    It’s a, it’s a, the engine’s cadence, it’s used, it’s pioneered by Uber. And temporal is, is maybe a more well known modern name is a, is a Next iteration of that workflow engine. Anyway, [00:14:00] so this thing started to blow up, and the reason it started to blow up was that it was backed by a, a single, very hard, a large database instance. And that database instance was struggling to, to keep up with. An unanticipated load. And this was not necessarily a new issue. In fact, cadence had rather this, this, nothing to say about the cadence Service is perfectly fine workflow engine, but the design was just not well des it was not well designed to be very scalable. And so as a result over the last several years, people had kind of wanted to avoid This system ’cause it was known to be problematic and it had burned people out trying to support it. So, but it had finally tipped over and, and by tipped over, I meant it actually stopped keeping up with the abil, all of the workflows coming in.

    So it started building a history list. I think something on the order of maybe a million. Runs behind and it was continuing to fall behind. Yeah. So, you know, when you see that it’s, [00:15:00] it’s a downward spiral, right? It’s, it, it, and so we brought in AWS people and we performed a quick crew. I. To, to set up basically like a war room situation, to try to triage and stop the internal bleeding.

    And so what’s the first thing you do? You say, okay, well let’s, let’s, if we can’t horizontally scale because we hadn’t sharded this system, let’s scale up. Right? And whenever I hear scale up, I think all of us, and especially in the infrastructure space, kind of cringe ’cause you know, there is a finite limit to scaling up and scaling up. Doesn’t actually solve the underlying problem. Ultimately it just delays the problem. yoU know so we did, there’s, again, our first focus was stop the bleeding. We scale up. It, it helped. Still some things were, were not quite as stable as we wanted. anD this is where I think the more interesting part of the story it comes in because all these kinds of technical problems in my whole 20 year experience. I’ve very rarely been [00:16:00] on what I would consider you know, a Mars landing kind of problem where you’re maybe doing something fairly novel and even that maybe isn’t as novel anymore because we’ve done it before. Uh, most problems are not, in other words, insurmountable technical problems, where there just is no answer. generally, I’ve found that 99% of problems that I’ve had to deal with are more about organizational problems. And, you know, you might even go to say leadership problems in the sense of how do you, how do you think about approaching this kind of crisis? What are the right things to do when a crisis like this happens? And so the steps we took first, the very first thing is recognize that. Upper leadership partners, customers who are relying on this thing all want somebody to say, I’m gonna raise my hand and say, I’ll take ownership of this problem. That’s the very first thing everybody needs. They need to hear you

    Alexis: Mm-Hmm.

    Michael: And so [00:17:00] we did. I I basically said, okay, we recognize this as a problem. I’m not gonna make up stories about this. It’s a problem and it needs to be resolved, so we’re gonna take ownership of it. And what we did was formed a permanent team around this. And that sent a very clear signal, we’re gonna own this problem.

    We’re going to move it to a, a place where you can trust it. anD that was actually a really important thing, not just for the ownership aspect, but there was real lack of trust in building these, these workflows by teams because of the instability history. And so, as a result, teams started to look for alternative approaches, and that would’ve led to a much more complicated universe to manage. So it was very important that they, they knew somebody was going to own solving it. Once we did that we defined some specific outcomes towards stability and scalability that we needed to be able to achieve. It needs to be horizontally scalable, not vertically. I think that was one of the most important things that we emphasized, that the thing we did today [00:18:00] to bandaid, this is not a solution. It’s, it’s a bandaid. What we need is not to try to put all our cargo on one ship. We need multiple ships. And, and so once some of the fundamental, and these are not complicated concepts, but they are complicated to execute on because having multiple ships means a whole lot of additional complexity and logistics up front for figuring out what goes on those ships and so on.

    I don’t know, I just suddenly jumped into a nautical analogy. But these, this is You know, establishing this is what we are, are, this is our success criteria, this is our strategy was critical to get out early. What are the outcomes, not the physical deliverables. The next thing we had to do deliver short-term wins. And by that I mean short term, what anybody ever cared about was stability in, in the short term, as well as enabling products to launch. So the products that we’re afraid to Right on this. We [00:19:00] immediately engaged them, prioritize, making sure that they were stable. They had the resources within the system to be reliable.

    And so we enabled those product launches. And then we pumped out every week what the reliability status was, what were there any issues and any updates or communication on progress towards those outcomes that we had. This was critical. Those two things were vital for us to establish credibility and for people to actually feel like the wind had changed and that this ship was actually going to turn that built.

    Confidence and trust gave us momentum. And, and as we continued to execute, this team has completely revamped the architecture, the system. They’ve migrated a bunch of the critical systems to starting to be able to Have better resource isolation, which are fundamental things in an infrastructure universe to be able to isolate workloads and manage resource consumption by each of those workloads. We didn’t have some of these fundamental abilities before. Now we’re in a state where we’re executing on the we’ve moved away from RDS and we’re bringing in. A scalable [00:20:00] backend, which is, you know, a, a Cassandra backend, which will allow us to horizontally scale. So we’re in a much different space, to the point where a leader about a week ago said to me ” not only do I no longer worry about cadence, I, I’ve basically entirely forgotten that it was ever a problem”. wHich is great except that I said just make sure that we don’t think we can remove people from this team right now. I’m glad you are confident.

    Alexis: Yeah, exactly. But yeah, I, I believe that’s, that’s very interesting. The what, what you offer as a solution. If I put aside the technical solution I, we could apply that to basically a lot of different problems that we have. Having a team that is able to say, okay, we are owners of that thing. And now we own that problem and we will solve it.

    Being really clear about what are the outcomes, where we are today, how we measure those ourselves compared to those outcomes. That’s very, very critical. And and [00:21:00] knowing that you will not win the trust of people by announcing 24 months plan. You will win the trust of people because you are delivering something now.

    yes.

    Michael: yes. 

    Alexis: Getting into that mindset is critical also. So I, I love what you’re saying about all that. Have I missed anything in what you, what you propose?

    Michael: No, I think you sum some, summarized it exceptionally well. I will say generally this you are, I fully agree with you. This is not a unique situation. This is a pattern and a strategy for approaching a, what is, what comes up fairly often in every job I’ve taken, there is always a crisis and I’m going to misquote the person.

    But it’s what I think the famous saying is, never let a good crisis go to waste.

    Alexis: Yeah.

    Michael: these are hugely valuable opportunities to actually have a tangible impact on the business.[00:22:00] anD you know where others may be afraid to tread. These are the opportunities that really enable you to shine as a leader.

    Alexis: I, I really like that. Are there other pivotal moments in your career when, when you, you really learn something significant about change and leadershIp? 

    Michael: Oh my gosh, yes. Well first, if anything I’m saying here sounds at all polish, please understand it comes from the many battle scars that I have over my history of, of making mistakes and reading and learning from, from the wisdom of others, and then having the opportunity again to apply them. But yes, let me answer your question more directly.

    So at Netflix .We and delivery engineering embarked on this initiative called Managed Delivery. It was a very ambitious project that is still very near and dear to my heart. It’s it’s, it’s fundamentally what it is, is delivery in [00:23:00] Spinnaker is done using pipeline, basically articulating pipelines. And what we found from From the way that we were operating where every team was defining their own pipelines. In Spinaker, I think we had about 16,000 pipelines at that time. We across about 4,000 applications, about 400 teams was about the size we were at. Platform Engineering has some challenges. One of the specific challenges was as we, we were still very VM based as we would release new base OS AMI s. That might include security improvements, patches, other things that needed to be there. We had an adoption rate of it took on the order of months to years for certain patches or updates to be rolled out. That was really problematic for us because you can imagine that there is, sure. I mean, if you did a security sev one incident, they could broadcast across the company and people might take action, but that’s a pretty disruptive thing to do. [00:24:00] What you want is, is a design that helps enable the, the bottom tier to be as evergreen as possible.

    Right. But we had a, we had a problem. All the teams owning their own pipelines Spinnaker had no intelligence about those pipelines. It, it just knew, run this, it, it was a workflow engine in many ways. Right. Run this step if that step Gives me a green light. Go to this next step, go to this next step, and, and maybe some conditional logic, but what do those steps represent? And, and what is the confidence after you know, step two as to whether this, this new update is safe to roll out? All of that was opaque to the engineering system. So what we needed was a way that we could evolve our infrastructure and we could evolve our amis, we could evolve our strategies under the covers. anD do so without having to get all the teams involved. So that was one of the motivations. Another motivation was we thought it would make it easier for [00:25:00] teams to also not need to articulate or come up with strategies in their pipelines for safe delivery, right? We teams would deliver applications to multiple regions. What’s the right sequence of steps that would enable you to catch a problem and roll back the change? If, if a failure happened in, say, the second region you rolled out to, which is a very complicated problem, right? First region successful, second region fails, most of the time pipelines would just die. And now you have this very confusing universe where you have different versions of your shafter running and, and problems

    can surface. So we thought, Hey, let’s take that problem away from teams two. Let’s create a declarative form of delivery that basically enables people to define the Criteria for success that would enable promotion from one lower environment to higher environments.

    That was essentially the goal of managed delivery, was move them towards the description of what needed to happen as opposed to defining how it should happen. [00:26:00] Very ambitious on the size that I was mentioning, especially because Netflix culture very much operated with a freedom and responsibility concept, and so that meant that teams were never Really obligated to use a service or a new system. So imagine operating in an environment where you have lots of very smart and talented people from all around the world that are working on their problems, their projects, and you ask them, you, you need to engage them on something that they honestly would prefer to not really have to think about.

    Right? I don’t con like, it, it, the water company doesn’t reach out to me to talk about Repiping .You know, pipes to my house. Like I have no interest in that conversation. If you need to do it, sure.

    Go ahead. Right. It, it’s the same way in delivery, engineering and reaching out to these teams. I don’t know it, my software always continues to deliver.

    It’s fine. Why do I need to care about this? thIs is a very common problem in [00:27:00] platform engineering, but also come from for library producers, API producers, anybody that’s producing something that others are consuming

     you almost always have more interest in in making that happen. Than they do especially when you, the value proposition may be more on one side and the other.

    And that was the key mistake I made. At that time you know, we very much wanted to take the approach of, if we built something really valuable and very interesting for folks they would adopt it. And I think there was merit to that. And so we spent a lot of time thinking about, you know, the early adopters.

    We got some early successes. We got some people to enjoy it. But then we hit that classic crossing the chasm problem where we couldn’t get past the early innovators to the early adopters. And we struggled on that. What was it, was it some combination of features? Was it some combination of capabilities, something that this could do that other things couldn’t? What, what I miscalculated personally was the actual value to the business was the platform engineering side of the, the, the [00:28:00] equation platform engineering needed to see this adopted. Across the fleet for there to be real value. And so given that the strategy may not necessarily be one of slow adoption, but rather it may be more important to take a little bit stronger of, of a, of a, of an approach. And John Kotter talks about this in, in leading he has an article in HBR called Leading Change, but he has a book called, why Transformations Fail. And I will say I read that book during that time and I failed in probably at least the top three even after I read it. So it’s, I will tell you, there is a very, I, I learned how big the gap is between knowledge and wisdom. And, and, and that that gap being how wide experience needs that gap, that that which is experience is that gap, right? And how much of that you actually need. Long story short [00:29:00] you know, managed deliveries, value proposition. Very much is alive, it is moving forward. But that was an experience where I realized because our adoption was very slow, you could imagine that we did not take as an aggressive of an approach, specifically by aggressive, I mean, we didn’t establish a sense of urgency. So teams were necessarily complacent in the adoption. And it’s not no fault to them, that’s the way the culture was designed to operate. But as a result it’s getting adoption, getting that change to actually happen. It was much harder. Now I know that they are doing amazing stuff now over there in terms of, of growing it.

    They, we’ve learned a lot of those lessons and the impact of that approach is really being felt. In fact, years later, I landed at HashiCorp. My peer came from Samsung. Smart Things. He recognized me and said, oh you know, managed delivery. And they apparently larger footprint than Netflix much higher traffic than Netflix.

    All the iot devices right, call into their[00:30:00] and they. Overnight, basically. Maybe it’s not quite overnight, but they, they they fully adopted it and saw some of the benefits of that adoption as a result. And, and and so it was, it was a cathartic to hear or comforting rather to hear. But yes, it was a, it was a good experience in the challenges of change.

    Alexis: Yeah, it’s, it’s very interesting that we are coming, going, going back to that idea of a team owns a problem and now tries to solve it. Unfortunately it’s really a problem for the business, but it’s not necessarily a problem for the other teams. thAt are consuming something from that team. And now how do you create a sense of urgency for the other team when they are not even aware that it’s really a problem for the business and you cannot count on that for them to investigate that part.

    So maybe that it’s other nudge.

    Michael: Well, and I have a, a story about creating the urgency because I, [00:31:00] that’s what one of the things I learned, there’s actually two pieces to that that I learned. And I applied at the next job, actually after I left Hashi after, sorry, after I left Netflix. It was a mid-tier company. We were on a, a, all the entire fleet was on a, a Heroku actually.

    We were hitting problems with that platform. Going back to the ability to introspect and understand how things work, Heroku was too abstract, too high level for us to be able to operate it effectively for the things that we wanted to be able to do. You know, it got us the zero to one, but that, that hard abstraction. mAde a a, it made it impossible for us to get past that one. loNg story short, though, we needed to migrate, we decided the business decided we needed to migrate off. But even with that, we wanna migrate off like all things that happen in a business, they are good goals. They’re, they’re set, like you said, the 24 month goal.

    Oh yes, we should be But how important is that? How urgent is that? I. [00:32:00] This is from my experience with managed delivery, this is what I, I learned. Okay, so two things. One you need a sense of urgency. So how do we create that urgency? You need to get a date set and that date needs to have consequences. So we talked specifically about setting a nine month target from the point that I had started that job and, and the reason for nine months is nine months. Feels close enough that it will happen, but far enough away that virtually no engineering team says no. Right? And, and and I mean this very much affectionately, we all believe that the world is possible in nine months, not three months, but nine months.

    Yes. Nine months. I for sure we’ll have time. So we we got alignment that in nine months we would, we would hit this target. We made sure that the other aspect of this was we were going to shut off Heroku. We were going to actually disable and tear up the contract. And so that was the, the cliff date. [00:33:00] That’s great to have that date. And there’s a lot to unpack on the importance of setting dates, but the other bit that was vital was we needed to get executive, Alignment with that, that needed to be something that the executives would back. And by that I mean you know, the term leadership or executives is, is nebulous just someone in a position of authority at, at the right level that can basically say once you get to that three months away from landing this. That this is a date that will not move. And we, we were able to get that. And those two things ensured that this, that project very ambitious. We moved the entire fleet out and over to Azure, and we had zero service disruption. It was a, it was a remarkable feat. The, the team did an amazing job, but I truly believe having both of those factors Enabled us to do that Herculean task because the last three, three months you can imagine were brutal, stressful[00:34:00] you know we we bought lots of DoorDash for people to, to and, and, you know, and supported them as they were executing on all of this stuff. But once we landed that the entire crew, Could look back and they did and said this was an amazing thing we were able to accomplish, and there was real pride with being able to do it. So very good lessons learned.

    Alexis: I love it. I love it. And once again, that’s, that’s really interesting to, to unpack the learnings about that. Yeah. You need a date and when, when people hear that. They can hear that, yeah, that’s a date, but maybe we can be late and no, that’s really a cliff that’s, there’s nothing behind. And and you need that support, that alignment.

    So nobody will dare to change the date. There’s no option around that. And that’s absolutely clear for everybody. So now they can make plans. They have the time. Nine months is, is is a good one. We were thinking, yeah, it’s feasible. And, and, and I, and then, you know, thing about it, I, I realized that when you [00:35:00] were saying it, that if you would’ve said three months, I would’ve say, oh, no.

    That I would’ve started to think why it was not possible. But nine months I was comfortable to say, yeah, okay. And I know nothing about the challenge, the reality of the challenge. funny. So yeah, you can start making plans. That’s a, that’s a, that’s a.

    Michael: That’s right.

    Alexis: What, what would be your advice to emerging leaders or who want to make a meaningful impact?

    Michael: The first thing I would say is you need to understand your stakeholders. I have learned the enormous value in getting, developing those relationships and deeply understanding who your customers are who your peers are. Who and what leadership is expecting of your organization? A lot of people, I think, focus, especially emerging leaders, they focus on their team and down. I have a lot of experience in [00:36:00] doing that and failing beautifully because I misunderstood what was expected, what was not spoken, but expected by my peers and by upper leadership. And so you really need to understand not just the the surface statements of here’s our goals, here’s our outcomes. What you want to ask is what keeps you up at night You want to ask where things have failed in the past. You want to hear the, the, the reactions. More than you want to hear the thoughtful process of, of desires, right? It’s those emotional reactions, those small perceptions of your team and of what is expected of, of your organization that actually will influence whether or will, will influence whether or not you are. Well, it’ll affect whether or not you are successful because those are the micro perceptions that actually determine whether they are are, they’re going to think of your team as a team to rely upon for those next strategic steps that they want [00:37:00] to take. Right. So understand them very well, and that takes a lot of time, and there’s great books on this. But this is where it truly is around a psych the, the psychological approach far more than it is that technical execution or delivery. The next one is you need to deliver wins within the first 90 days of starting a new job. And there is a great book, first 90 Days. I think it’s a fantastic book on this topic. I Have, I’ve applied it and successfully a few times now. It very much is correct. Get that, get that win. You have to have credibility when you go into a room. You have to be able to be believed when you say we should do X or Y. Otherwise, you’re gonna stay in the tactical level always because you haven’t established that you can actually solve bigger problems. The key thing with getting that credibility in the first 90 days is you don’t need a big win. You just need something meaningful, something that addresses a concern. Peers of mine had actually mentioned this to me years before too. Don’t [00:38:00] try to run after. The biggest thing you can run after, especially when you first start, start with something. yoU, you, you can own and influence, so it’s something within your control. Don’t do something that’s gonna require a bunch of other folks to be aligned, especially when you first start. It’s challenging to do that, so it should be something for the most part, you can control. I. Second part, it’s gotta be something that matters to other people.

    It doesn’t really matter what it is. It doesn’t have to be a technical solution. It could be an organizational solution. It could be an information solution. It could be a communication solution. It could be any of these things, but it needs to be something that actually addresses a, a, a fear or concern. A great example of this is just starting a monthly newsletter for your organization and ensuring the rest of the business understands even what your team does or your group does. That’s surprisingly a big problem in many places is just the awareness factor, and doing that suddenly puts you on the radar of a lot of people, and it can really, it can really move things forward.

    That’s not a technical problem at all,

    Alexis: Yeah.

    Michael: but it is a problem and it can establish you. [00:39:00] The third thing that emerging leaders need to be taking a look at to have real meaningful impact, define The purpose for your team. And by that I mean you need to bring your team into that. But defining a purpose is one of the most fundamentally powerful actions that I have ever learned to take with my team.

    And purpose is different from mission and vision. a Purpose is. It is the, it lives the lifetime of that team or that group that you are managing. And a purpose is not it, it sometimes it’s referred to as a North star. I don’t think it’s quite that. It’s not quite that right way of seeing it. A purpose.

    This establishes a philosophy that everything stems from. So one of my favorite examples of this was I think he was a, gosh, and the name is gonna slip outta my mind, but he was a, a French designer actually, I think that helped establish the purpose for Disneyland and that purpose was to create happiness in the visitors. Now, if you think about that, that sounds very simple, [00:40:00] but it’s a very powerful fulcrum. Because at that point, when you have that, everything from how you name the parking lots, you name them after Mickey and Goofy, not A and B and C, the design of the trash cans, the uniforms, the decision to have very pleasing flower beds that are millions and millions of dollars of investment for each of these things. Why do you do that? Because each of these pieces maybe make somebody smile a little bit more. Establishing a purpose for your organization enables you to prioritize. It gives your teams freedom to execute and to think more broadly and it enables you to align with what your next strategic steps need to be. It it really is the guiding, you can think of it as a guiding principle. So there’s, I, I’ve written articles on this and, but there’s much better, smarter minds than mine that have, have spoken on this

    Alexis: Ah, I will link to that and we will let people [00:41:00] people decide. About that . So what, what’s next for you? Any exciting projects or initiatives you, you, you want to share?

    Michael: Yeah, so well with Hashi Corp I think one of the exciting things that we have coming up next from the platform engineering organization is really trying to crack this self-service nut. You know, Hashi Corp is an organization that has, we we build tools for infrastructure management, right?

    I mean, we build tools for platform engineering. How do we, how do we leverage all of the, the tools that we have and the patterns and behaviors that we wanna encourage to enable self-service within our organization? So a team being able to go from zero to one. I know this is a nut that a lot of people have cracked in the sense of they’ve created, you know, IDPs, right?

    In, in internal developer platforms. But I think that that’s more of a, a, a how, and I think I wanna get back to again, the principles. What should that, what, what are we caring about enabling the actual day One [00:42:00] problem of give me a service is not a hard problem to solve. It’s been solved a lot. The day two problem of now I wanna add a database to my service. That’s a harder problem. And that’s one of the ones I’m excited to see get moved forward. Yeah, so that’s, that’s, I’m looking forward to that next

    Alexis: That’s very cool. So let’s talk again. Thank you very much Michael for joining. have fun solving that.

    Michael: Thank you, Alexis. 

  • The Conductor’s Magic Wand: Transforming Leadership

    The Conductor’s Magic Wand: Transforming Leadership

    In the latest episode of Le Podcast on Emerging Leadership, I had the pleasure of hosting Noah Max, a visionary in the realm of classical music. Noah, a composer and conductor, shares his profound insights on leadership within the creative arts.

    🔹 Creative Leadership: Noah describes his role as a composer akin to being a thought leader, constantly striving to innovate and push the boundaries of classical music.

    🔹 Challenges in Classical Music: He highlights the difficulties in bridging the gap between classical music and wider audiences, emphasizing the need to communicate its relevance and vitality in people’s lives.

    🔹 The Power of Art: Noah passionately speaks about the personal and almost therapeutic impact of engaging with the arts, beyond intellectual understanding.

    🔹 Leadership in Practice: Sharing his experience with the opera “The Child in the Striped Pyjamas,” Noah reflects on the importance of team synergy and the challenges of leading a creative project.

    🔹 The Conductor’s Role: He delves into the unique dynamics of conducting, where a blend of vision, listening, and collaboration is key to creating a harmonious performance.

    🔹 Immersive Leadership Workshops: Noah discusses his innovative workshops that allow individuals to experience the role of a conductor, emphasizing self-discovery and personal growth.

    🔹 Personal Development: He stresses the importance of continually challenging oneself to grow as a leader, drawing parallels to physical training.

    🔹 Mentorship and Inspiration: Noah shares his experiences with mentorship, both as a mentee and a mentor, highlighting the reciprocal nature of these relationships.

    🔹 Future Projects: Looking ahead, Noah is excited about his upcoming compositions, including his first symphony.

    🔹 Advice for Leaders: He advises emerging leaders to tune out the noise and listen to themselves, making decisions based on what truly matters to them.

    Tune in this enlightening conversation with Noah Max, where music and leadership intertwine to create a symphony of insights. Tune in to this episode to be inspired, regardless of your field!

    Listen now and let the music of leadership elevate your day! 🎧

    References:

    Transcript:

    Alexis: Today, we have a truly enchanting episode lined up for you. Noah Max masterfully blends the art of music with the essence of leadership. He’s a creative artist, not only a composer and a conductor he’s an innovator in the world of classical music.

    Alexis: Welcome to Le Podcast on Emerging Leadership, Noah. How do you typically introduce yourself to someone you just met? 

    Noah: Well, it’s lovely to see you, Alexis. Thanks for having me on the podcast. I suppose I would go in with creative artist. Because that’s something everyone can relate to immediately and understand. I work specifically in the field of music. I do a number of different things within the field of music, including conducting, which I know we’re going to speak about later on.

    But primarily, at heart, I’m a composer, which means I write music. And that sometimes leaves people a little bit nonplussed, because they’re not quite sure what [00:01:00] it means to create music from scratch, or You know for what context are you creating music? What does your life look like if you’re getting out of bed every morning and what writing music?

    I mean, how does it work? So the way I would describe it is that I’m attempting to imagine sounds that nobody’s heard before and then notate those sounds either for existing instruments, combinations of instruments, or perhaps even inventing an instrument physically or electronically which doesn’t yet exist, in such a way, so notating it in such a way that Performers could then realize that vision for an audience.

    And often for me, that’s within the context of classical music in the concert hall. Sometimes it will be for television, film, something of that description.

    Alexis: Okay, that’s fantastic. So now I guess people are wondering, are, are we on a [00:02:00] podcast about leadership? And I’d say, yes, we are. And I will ask a question about how do you define leadership in that context of composing and conducting? And what are some of those unique challenges you face as a leader?

    in the musical world. 

    Noah: I suppose there’s two ways that you can look at a question like that. And one of them is intensely creative and one of them is intensely practical. So from the perspective of composing, I suppose it’s sort of like being a thought leader or a philosopher in that you’re trying to move things forward.

    You don’t simply want to repeat things that have already been done although there’s nothing inherently wrong with that but you want to bring something original and valuable to the table, which is going to in some way move the dialogue forward during the course of your creative lifetime. And then there’s the more practical side, which I suppose Through my composing [00:03:00] through my conducting, excuse me, and my other activities one gets a little bit closer to this, which is the fact that there’s a lot of worry in the classical music world that we are in a sort of declining landscape.

    It’s certainly a very confusing landscape at the moment. I think there has been a great failure in the world of classical music to communicate itself to the wider world and to build bridges with the wider world. To show people who may feel no great connection in their life with classical music, contemporary classical music, romantic classical music, baroque or renaissance music it’s felt to communicate the ways in which that can be an important, an incredibly vital and, and life giving and sustaining force in, in people’s lives. 

    And so, you know, having failed to communicate that, no wonder people don’t necessarily feel as connected to it as maybe they could or should. And so, part of my mission in all the different things that I do is to connect people [00:04:00] with the arts in any which way, no matter what they spend their life.

    doing. I would like them to have an inroad so that they can, you know, feel the beauty and the sometimes overwhelming power of these mediums in their own life.

    Alexis: Wow, that’s beautiful. Ah, that’s beautiful. And I hope that will trigger the interest of people to have a taste at it without the intellectual knowledge that is coming to that. I’ve, I’ve observed times and times that people don’t Listen, or don’t watch paintings or look at it because they don’t have the knowledge that is going with it.

    And I’m saying that’s, that’s like tasting food. You, you don’t necessarily have all the knowledge behind it, but you can taste it and maybe you like it. Maybe you don’t, or that could be a drink, that could be food, and that could be music, or that could be painting. Maybe just have a look at it and listen to what is happening inside [00:05:00] yourself.

    That would be. Maybe your first time, don’t you think? 

    Noah: Oh, absolutely. And the wonderful thing with these things is that there’s no incorrect response. Including, you know, perhaps a work of art which everyone says is a great piece of genius leaves you feeling cold. And, you know, that’s fine. It’s an intensely personal thing. I think to just sit and observe a work of art or to sit in a concert hall, which feels incredibly formal and sometimes quite rigid.

    And to experience a work of music over a period of time. It’s an incredibly intense experience and it’s a beautiful experience, but beauty can be terrifying. particularly if you’re not used to it, if you’re not accustomed to it immersing yourself in that beauty can be a terrifying experience, and that’s one of the reasons I’d encourage everyone to do it.

    I think that’s part of the vital nature of it. But you also mentioned the intellect there, Alexis, so just to pick up on that for a minute. Often I [00:06:00] find we over intellectualize, actually, the problems in our lives, whereas accessing the creative arts is to do with intuition and the realm which is beyond the intellectual and beyond the statistical and the scientific and the measurable, although all those do come to play in their own.

    special, interesting ways. But so much of what’s important is not that. And actually, I think this is the sense in which this is a life giving force. So you compared the analogy with food and in some sense that’s correct, except that we all have to eat three times a day or thereabouts in order to sustain ourselves.

    So food is a life giving force in a physical sense. We need the calories in order to sustain our lives. Just like we need a roof over our heads. Et cetera, et cetera. But You might say, well, why do I need painting in my life? Why do I need theatre in my life? Why do I need cinema, for that matter, in my life?

    it gives you something which is completely personal to you and which is [00:07:00] not quantifiable, no matter whether you think you’re a creative person or not. And I used to be incredibly naive and evangelical about this. I felt that everybody was creative. And I no longer think that’s True.

    And I think a lot of people actually feel tremendous pressure that maybe they should be creative and actually it’s not part of their nature to produce things from scratch. And that’s completely fine. a work of art can feel as though it’s judging you, but there should be nothing judgmental about the process of appreciating art.

    And I would like everybody to have their own way in, perhaps to step out of the intellect. And this is something I continually remind myself that I need to do. as well, because it’s not always the best way to solve a problem.

    Alexis: I love it! Thank you for sharing that. Can you share an experience where your leadership skills were put to the test. 

    Noah: Well, the obvious one which comes to mind, and there might be some listeners who are aware of this, as I know you are I’ve spent the last five [00:08:00] years bringing an operatic adaptation of John Boyne’s novel, The Boy in the Striped Pyjamas. And you know this because you were at one of the instrumental rehearsals actually in London back in early January.

    Can’t believe it’s so long ago already. But every single part of that process was a struggle. Writing the music was a struggle. Doing the research in order to take the entire project with the requisite seriousness was a struggle. Digging into my own family history and my connection with the topic matter was an immense.

    Uphill climb spiritually and the logistics of putting on the performance, which we did pretty much single handedly myself and the Echo Ensemble, which is my orchestra, which sort of morphed into an opera production company for that project. And everything went wrong, which could possibly have gone wrong on ways to, I mean, I would.

    We could just [00:09:00] sit here for an hour talking about the litany of things which went wrong and I was working all hours in a very unhealthy way. So it’s not something I would hold up as a model of good practice per se. And it’s certainly not an experience I would like to repeat. But it was in its own way, the best of times.

    And the reason for that was because of the wonderful synergy in the team. And the only thing which functioned properly on that whole project. Was my team and I told them that and I even with all the other things vying for my attention. I made my priority to Nurture the synergy of that team and fortunately that turned out to be a good investment of resources.

    Alexis: Yeah, it’s, it’s, it’s very interesting what you’re saying about the unhealthy way and all the things going wrong. I was, I was listening to the serial entrepreneur, who created several companies not all of them were [00:10:00] successful. In reality a few of them were successful and a lot were small disaster and bigger disasters.

     and he was reflecting on that and he was saying, oh, you, read on LinkedIn and you believe all those people are very highly successful and highly driven and they are really good at all what they are doing and, and everything is going well for them. in reality everything is going wrong every day. And you just need to handle it. And sometimes you do it well, and sometimes you learn something in the process of, in your experience, and sometimes you don’t. And it’s even getting worse. So, there’s just a few things that matter, and that That’s how you are doing that, not all by yourself, but building a support team, you just mentored on that.

    That was your team. So what happened with that team? What, what is that team and how it works [00:11:00] for you to work with the team? 

    Noah: Well, there are certain differences, I suppose in that making music is a process which is incredibly emotionally vulnerable. and very intimate and you have to be sharing of yourself whenever you’re doing it. I was conducting this project as well. So it was my own music that I was conducting with a team that I had hand picked.

    So these were all musicians I deeply admired and. respected and enjoyed working with, but when you’re working on topic matter, that’s as dark as that for a sustained period of time, it’s just a great challenge. And the endurance is a challenge. I mean, on a personal level, what I kept reminding myself whenever I was fatiguing, which was often was It’s never going to get better than this.

    So just enjoy every minute, which seems counterintuitive again, given the topic matter, but, [00:12:00] but it was necessary to get through it. And actually on the team level, I think that was reflected too, because I wanted to make sure that there was enough room for. levity and a bit of risque gallows humor, you know, because you can’t just be heavy and serious all the time.

    And opera making is fun. It should be fun. It’s very interesting to me what you’re saying about the, you know, the, the, the front facing is, is always incredibly. Successful. And then, you know, generally the failures are kept private. I mean, there was just such a huge litany of failures and false starts on the road to this project.

    And without the support of, I mean, the whole team, but particularly certain individuals who were attached to it for, you know, right from the start years earlier. I don’t know whether I would have pushed through all of those, but it’s just interesting as well, when you zoom out. You know, if you read the daily news feed, it’s always bad news because bad news happens in the short term.

    I do, I don’t do any social media. I deleted all my social media. I do a newsletter once a month and when you zoom out And you only [00:13:00] do your news once a month, generally the news is more positive over the mid and the long term. Just an interesting thing to, keep in mind. I mean, it’s wonderful that with pyjamas, I think, you know, given that I’d never put so much energy and effort into anything in my life.

    And to see it rewarded and to see my team rewarded through the reviews that we got and the recognition that the project got was, was absolutely wonderful. But that’s not an accurate reflection of what was going on under the surface. You know, the duck’s legs were, were very much tangled in the weeds there.

    Alexis: you mentioned the rehearsal I was amazed of a lot of different things, but things that I still have in mind, there were the composer and the conductor. And so that was your own music. But you were already comfortable with the musician to challenge a little bit the composer or to to make fun of the composer [00:14:00] in some ways about the music itself.

    And I thought it was really funny to say they are, and you are making fun of yourself or Separating yourself from the composer, from the music, because now we are trying to to play the music. it’s two different times. And I was looking at that, it was really interesting.

    And there was sometimes the, the explanation of the music also. What is happening? That to give the context of, okay, we are, we are starting at that particular measure and you give the context about what is going on and you you explain what is going on what you would like to hear and and there’s a dialogue with the the musician and i i saw them taking notes on the on the score about what was going on and and you give them feedback And they ask something and I was that dialogue was fantastic in a way in my mind the music is on the score.

    You just play [00:15:00] it and you’re done and that’s absolutely not what is happening Which was amazing to me Do you have some some reflection about what is going on when you are doing the rehearsal with the team? 

    Noah: Well, that situation was very specific. And I think being a composer who conducts creates a very specific. Scenario whereby you can offer certain insights. into the process of how something’s been created and what the thought process was behind it. Whereas if it’s somebody else’s music, you’re not necessarily in a position to do that.

    Although even that only goes so far, interestingly. I often feel as British composer William Walton must have felt, there’s a possibly apocryphal story of a occasion when he was conducting his own great oratorio, huge orchestra and choir called Belshazzar’s Feast. Tremendous piece. I recommend everybody who is listening to this should go and find it on YouTube, but he was conducting a performance of it and somebody asked him a very [00:16:00] specific question of, oh, you know, you wrote this marking in this bar.

    What did you mean? And he said, well, I’ve got no idea. I wrote it 20 years ago.

    Not the response you’d expect or maybe hope for, but by the time we were performing that I had written the piece a year and a half ago in a frenzy of creative activity. And so much of the creative process is a mystery, even to the creator. So there were situations where people were saying, you know, what did you mean by this?

    It’s like, well, you know, what did I mean then? What do I? think I might want now, and you know, are they the same thing? Possibly not, and neither of them might be right. So it’s tricky, but you know, under more normal circumstances, I, I mean, see with conducting, there are no normal circumstances. It’s an extraordinarily strange situation you find yourself in.

    [00:17:00] Just to give people an idea, just the slightest idea if you’re an international conductor, say, and you are guest conducting with a series of symphony orchestras around the world, you’ll be traveling one week, one place, one week, another place, one week, another place, maybe you’ve never gone to these places before, maybe you don’t speak.

    the languages in any of them, and you’re confronted with 80 people who you’ve never met before, and you’re all performing music in three days time that none of you have ever performed before, and somehow you’ve got to create a performance that is going to be spiritually valuable to the 5, 000 people who are paying to see it.

    Or however many people it is. So it comes with extraordinary pressure, and it’s an extraordinarily aspirational job. There’s so much of it which is mysterious. It’s actually the mysterious elements of it which I really love. And when I’m introducing people who have no idea about conducting to it, as you know, I know you want to talk about these workshops a little bit [00:18:00] later on I think those mysterious and magical elements are the ones which are worth paying the greatest attention to, in a way.

    But there is that magical synergy between the group, almost like a murmuration of birds. You know, how they know when the next one’s going to turn in that direction. It’s, it’s all just, you know, it shouldn’t be possible. It really shouldn’t be possible. According to science, it shouldn’t be possible for a string player to play their instrument in tune.

    And yet everyone does. I mean, to get your finger within a nanomillimeter of whatever it is, it shouldn’t be physically possible. So, you know, what we’re doing here is the impossible. That’s what we’re talking about. And I mean that literally, not figuratively.

    Alexis: and that and that’s a that’s a very interesting thing and I would like to go back to What is the level of freedom for the musicians to express themselves, express themselves when they are playing that music? [00:19:00] I thought there was a dialogue between the conductor and the musician. And so that means they have a degree of freedom in that process, individually and together.

    So there’s something going on there, I believe. 

    Noah: Yes, I think It’s very interesting because I think a group is looking to, the leader for the vision of the whole because everybody has their part to play in the whole. So you need to present a vision of the whole but not in a way that feels dictatorial. It’s got to start with listening and assessing what’s the player’s needs are as specialists.

    You are essentially a generalist as a conductor and you are there to help a group of specialists achieve something together, which perhaps they hadn’t even dreamed of possible was possible when they were just individuals in their practice room or, or, you know, whatever it was [00:20:00] sometimes an individual will have an idea which is incredibly valuable.

    Sometimes the hive mind will just come out with something which, you know, you never would have thought of. Much better than anything you could have thought of. And so rather than feeling as though you’ve got to impose your vision, I think there’s always got to be a dialogue between the two. And if you are trying to convince people to do something your way then first of all, you really need to be sure about it.

    But also, you know, just telling people to do it isn’t enough. You sort of need to coax them to, to sort of, to try it and explore it and, and to maybe feel as though they thought of it themselves. And there’s a little bit of You know, magic about that as well. Maybe misdirection, but

    Alexis: I love that because now I can see the parallel with the world of business and all the teams that needs or so the to assemble the creativity of specialists to accomplish something bigger. [00:21:00] and speaking of that, you offer. Immersive sessions with musicians for people to understand what happens behind the scenes.

    And so what inspired you to start those sessions? 

    Noah: that’s right. It’s an incredibly exciting journey, sort of honing these sessions into what they are now. I think I was inspired by the figure of the conductor itself, which looms large over the popular culture in a very strange way, because nobody really knows how it works. Conducting. Sort of this person who stands up on a podium and waves a magic wand, and there is that image there, that archetype of the magician, the wise old sage, and you’re sort of harnessing that power.

    And that’s been an incredibly powerful icon, I mean all these films coming out now, there’s a film just coming out very soon about Leonard Bernstein who was a big force in the culture. There was a film with Cate Blanchett, the name of which I forget. [00:22:00] And you know, there was a film about 10 years ago now called Whiplash, which is an extraordinary movie with a great performance from J.

    K. Simmons in that. So people sort of have these preformed ideas of what a conductor might be. What I’m very interested in is the fact that when one steps onto the conducting podium, your personality transforms. this is as true of me as it is of anyone else, and it’s as true of as it is of non musicians.

    that self transformation can be, I mean, it’s incredibly volatile. But I think it can be a great vehicle for self discovery and for self actualization. And in that space where you can no longer verbalize, going back to this thing of intellectualizing, you know, when you’re confronted with a bunch of specialists who do something that you know, nothing about.

    And all you can do is wave your arms at them and communicate yourself physically. Suddenly you strip away all the nonsense and you’ve got a space in which there’s this [00:23:00] embodied learning experience. And you can, oh, you can discover things through this, which I promise you, you could not discover any other way, given years and endless streams of cash.

    It’s a unique experience and I recommend it to everyone. So this is part of my mission to sort of coax everyone into trying it, I suppose, and to see what it can offer them.

    Alexis: you describe a little bit how it works? 

    What people are supposed to be doing? 

    Noah: So we have an ensemble and we have some music and the participants and I will do a little crash course on how you hold the stick, what the basic moves are, just get a little bit comfortable with that. And then we throw people in the deep end and we invite you up to stand in front of the group and We see what happens and whatever your starting point is, we work from there and it’s quite extraordinary because I’ve never [00:24:00] had a situation where we’re unable to make progress.

    I mean, even somebody who’s never listened to a piece of classical music in their life. Sometimes people who have that actually have no foreknowledge. Often end up being the best at it, strangely. But you can make a lot of progress. And once you sort of got used to the very strange sensory overload, all these different things coming at you at once things start happening.

    It’s very hard to verbalize. You know, I struggle to verbalize it. All I do in my situation as sort of mentor is I just try and again, just sort of lead people along and see if I can get them to notice the sensations within themselves and how they can modify what they’re doing to get a better more vibrant response from the musicians.

    And we get the musicians feedback as well, which is It’s incredibly exciting because obviously they’ve played for many, many conductors. And I’ve heard behind closed doors from some of my players that actually some of the conducting they witness in these sessions is better than [00:25:00] some of the conducting they witness in their professional lives as performers.

    So you’d be surprised at what you’re capable of, man. I mean, I don’t know. You should.

    Alexis: really love that idea that people who know nothing about it able to feel it in a way. So, basically Listen to what is going on in themselves. Listen to what is the feedback they have from the team and adjust their behavior so that the result will be different. And basically that’s what we are trying to tell leaders in other fields to really understand.

    How they should.

    adjust what they are doing to have a different response. And that’s not, that’s not changing the others, that’s changing yourself. and look at what is going on, what is really going on. And it’s it’s very interesting that the parallel is so obvious. I am, and I’m now really excited and I would like to try that. 

    Noah: [00:26:00] You should.

    Alexis: When the people are going through that immersive experience what do you believe they take away from that? 

    Noah: they won’t necessarily take away What they want, but I believe they will take away what they need. And it may not be something that they’re capable of verbalizing at the time. It will start off as a felt difference in the way they operate. And then maybe when you step away from that slightly remarkable experience and go back to your life, which is also remarkable.

    I mean, everyone’s life is remarkable in its own way, but you know, it’s, it’s also repetitive and it’s the world that you know. You take the treasure back from the cave into the world that you know, and you see if there’s things you can do, optimize, streamline in order that you can find that sensation again you find out what [00:27:00] that embodied knowledge means to you.

    I’m hesitant to say too much because. I don’t want people to come along thinking that they should. I mean, you might come to the session thing. Oh, I really just want to increase my confidence in front of a crowd. And, and, you know, my, my presentation skills, it could be something as simple as that, but that’s not, I mean, you’ll get that.

    Don’t get me wrong. You will get that. And then some, but. it goes much deeper. There’s almost something therapeutic about it. And I’m very interested in the depth psychologists and their writings. And I’ve also, because of my, my Viennese heritage, my ancestors escaped from Vienna at the same time as the Freuds. 

    And they were very much in that scene, which was filled with you know, these great thinkers and artists and stuff. So I, I’m very interested in all that literature and all that thought. You know, I’m hesitant to say too much because I think it’s something deep I don’t want people to have too many preconceptions.

    Alexis: But I love it. I believe that we discussed [00:28:00] enough so that people can understand that that’s an experience that you need to live and something will happen. And I, I love what you are saying about, that’s not necessarily what you want, but that’s what you need. And that’s a kind of Nanny McPhee experience.

    So, sorry, 

    Noah: it’s funny you say that, because I, I often think of the Nanny McPhee thing, that when you, you want me, but you, sorry, you need me, but you don’t want me, I have to stay. Is this right? And when you want me, but you no longer need me, I have to go. It’s one of the tragic truths of, of life, I think.

    Alexis: that’s, that’s a, that’s a very interesting, interesting one. So, how do you continue to, to grow and develop yourself as a leader? 

    Noah: Well, you have to do things which are going to stress you and stretch you regularly. Anybody who goes to the gym knows this. It’s, you know, relaxation is no good, and pure tension is no good. It’s a [00:29:00] cycle of tension and relaxation which creates hypertrophy. And I think the same is true in terms of the challenges one needs to take on.

    So I’ve recently completed this huge challenge and I spent some time after that feeling slightly listless with a big striped pajamas shaped hole in my life. But now I’ve got myriad new challenges which are really stretching me in completely unexpected and completely different directions. So I’m flexing muscles that I hadn’t used before and I hadn’t maybe even known were there.

    And I think that’s, that’s crucial. 

    Alexis: Excellent. I, I, I love the stress and stretch and the part with the, the gym that will really help to, to understand that. Do you have any mentors or role models who have influenced you? 

    Noah: Well, I, I did. In some sense I still do. But I had a mentor called [00:30:00] John Whitfield, who was a bassoonist and a conductor. He founded his own ensemble, just as I have my echo ensemble. He founded Endymion Ensemble, which was a jewel in the crown of British chamber music making in the 80s if anyone’s interested in Endymion, again, you can find their recordings on Spotify, YouTube tremendous stuff to be found there.

    I met John in the last years of his life. He was very unwell. He died quite young. He was in his mid sixties when he died. He’d had health problems throughout his life, but he was a tremendous mentor and support to me. We met completely by chance at a concert. So, go to concerts, you never know who you’ll meet. it’s strange to me now, because it’s been several years since he passed away. And Stripe Pyjamas originally was his idea, actually, we, we, it came up in a conversation that we had. he would have loved to have seen it realised. And, and that made [00:31:00] me think, you know, that he was investing all this time and energy in me, knowing that he wouldn’t live to see me fulfil my potential.

    But it was what he wanted to do, and actually I’m convinced that, I mean, I, I supported him with his endeavours as well, and those were life giving for him in his state. But the ability to engage with. musicians and players to arrange and orchestrate music, which he’d always loved doing. And he did some of his best work in those last few years of his life.

    So he was an incredibly inspiring man, a difficult man as well. And I think he wanted me to avoid some of the pitfalls that he felt he’d fallen into. when he was my age, particularly regarding the vicissitudes of a creative lifestyle, which maybe are more volatile than if one were working in a different, slightly more stable field.

    Alexis: Do you have other people now? that are that are inspiring [00:32:00] you? And the second question that is coming just after is are you are you mentoring other people yourself? 

    Noah: Hmm. Well, there are plenty of people I find inspiring. I find you inspiring, Alexis. But in terms of mentorship, you know, John was my mentor and I was very, very fortunate. Nowadays, I keep my own counsel and I do my own thing. So life has changed in that regard over the last few years. And yes, I do try my best to be a support to my own colleagues and to my students of whom I have a few and they’re tremendously bright and, you know, many of them conductors, some of them composers.

    And so I try to just nudge them in the direction of interesting things. in order that they might shape themselves, which I think is what John did for me. And I mean, also [00:33:00] in funny sort of ways, I was a mentor to John as well, in that I encouraged him to remain musically active despite his ill health. I have a lot of friends of mine who are of older generations as well, and I occasionally try to provoke them and poke them into some kind of creative activity, which I think might be good for them and usually I’m right, so.

    Alexis: Yeah, I love it. I love it. So, What are some upcoming projects you’re excited about? 

    Noah: Oh, well, it’s mostly writing at the moment. I’m very deeply involved in writing projects. I’m currently writing my first symphony, which is a huge undertaking, very, very different from the first opera. And that is a commission for the London Mozart players, which is a chamber orchestra here in London, tremendous group, really lovely, lovely people as well, which is a wonderful thing.

    I feel very fortunate to be doing that. And that will be premiered [00:34:00] in the summer as the opening concert of the Thaxted Festival, which was the birthplace of a composer called Gustav Holst. So if you’re new to classical music, you’re getting loads of names here today. Gustav Holst is one to stick into your browser, particularly because next year will be 150 years since he was born.

    So it’s sort of commemorating that happy occasion, that milestone. So, so it’s all, it’s a great honor to be doing that. And I’ve got a number of Very exciting composing projects, which are lined up for the new year as well. So it’s going to be busy for the next bit. But at some stage, I look forward to getting back to some, some carving, some conducting as well.

    Alexis: Love it! there will be a lot of references to add to the companion blog post And, and finally do you have any advice for emerging leaders, regardless of their 

    Noah: See, I’m always just hyper aware of how specific my field is and in giving general advice. I never want to, you know, I’m just so [00:35:00] conscious of the fact that. Music can feel like an alien world, so could I really give advice more, more generally? Well, you know, maybe, maybe I can. At the risk of sounding blithe and clichéd, I think you’ve really got to learn to tune out the noise and listen to yourself. It’s very easy to expend a lot of energy on stuff that you do not care about and which you’re not really interested in pursuing for whatever reason. And there is so much static and noise out there now.

    So learning how to tune your radio set so that you can figure out a good principle on which to make decisions so that you know what it is you want to do and where it is you want to go. I think, you know, whatever kind of entrepreneur you might be. That’s useful because you could [00:36:00] invest a huge amount of your time, energy, money, other people’s money into creating something that you don’t really believe in.

    And I know people who’ve done that and, you know, they always learn from it, but never ends well. if you can avoid it, then perhaps that’s a good thing too.

    Alexis: that’s beautiful. love it. I will add a few links about where the people can find your work, follow your work and get in touch with you. And I’m very thankful for having you join the podcast today. So thank you very much, Noah. 

    Noah: Oh, well, Alexis, it’s been a pleasure. Thank you for having me, and if anybody wants to know more about what I do, they can go to www. noahmax. net. That’s n o a h m a x dot net. That has my music, my paintings as well and various other things. It has a place where you can get in touch. You can also find my music on YouTube, on Vimeo, on [00:37:00] SoundCloud, and you can also, through the website, you can sign up to my monthly newsletter that I mentioned earlier.

    And that’s just a monthly burst of creative energy from my part of the world. And you can find out what I’m doing. And if you want to come be a groupie then you can find out where I’m performing, what’s going on. And nine times out of 10, I will be there. So if you want to say hello, that is also really the best way to do it.

    Alexis: Thank you very much, Noah. 

    Noah: Thanks. Bye.

  • Ioanna Mantzouridou on Revolutionizing Leadership with AI

    Ioanna Mantzouridou on Revolutionizing Leadership with AI

    In our latest episode of Le Podcast on Emerging Leadership, I am honored to feature Ioanna Mantzouridou, Co-founder & CEO of Dextego. Join us as we delve into Ioanna’s inspiring journey from her roots in HR to leading an innovative AI coaching platform.

    Key Highlights of the Episode:

    1. Journey to Dextego: Ioanna shares her transition from considering a PhD in organizational psychology to spearheading an AI-driven talent development platform.
    2. Dextego’s Mission: Learn about her vision for reducing talent attrition through personalized soft skills training and the role of AI in democratizing leadership development.
    3. Overcoming Remote Work Challenges: Insights into the challenges of developing talent in remote settings, especially during the COVID era.
    4. Empathy in Leadership: Discover Ioanna’s emphasis on empathy, discipline, and a continuous learning mindset when building her team.
    5. Addressing CEO Challenges: Ioanna discusses balancing fundraising, sales, and maintaining vision in the early stages of a startup.
    6. Innovation Culture: How employee-driven innovation and aligning with company strategy can revolutionize workplaces.
    7. Success Metrics at Dextego: The focus on top talent retention and the transformative impact of personalized development tools.
    8. AI Tailoring for Career Stages: Exploring how Dextego’s AI coach adapts to individual skill levels and career phases.
    9. Ioanna’s Leadership Evolution: Her personal growth since starting Dextego and embracing ambiguity and vulnerability.
    10. Advice to Her Younger Self: Ioanna reflects on the virtues of patience and enjoying the journey.
    11. Upcoming Events: Get a sneak peek into Dextego’s future events, including LinkedIn Audio and LinkedIn Live sessions, and the exclusive ‘Dextagon’ event for HR leaders.

    Don’t miss this episode if you’re interested in how AI is transforming leadership and talent development. Tune in to gain invaluable insights from a visionary leader in the tech world.

    References

    Transcript

    Alexis: [00:00:00] Welcome to Le Podcast on Emerging Leadership. I’m your host, Alexis Monville. Today, we are thrilled to bring you insights from a distinguished guest whose dedication to enhancing leadership through technology sets her apart. Ioana Mantzouridou, a community builder, talent development strategist, and fervent advocate for applied AI, join us to share her groundbreaking journey. As the co-founder and CEO of Dextego Ioana is pioneering and AI coaching platform dedicated to revolutionizing talent development. Johanna, how do you introduce yourself to someone you just met?

    Ioanna: Awesome. That’s a great question. So I would say that my name is Ioana, I’m the co founder and CEO of Dextego, an AI coaching platform for reducing top talent attrition by half. I’m from Greece, so I’ve been living in the U. S. for seven years now, [00:01:00] and really focused on leveraging technology to push human capital further.

    That’s my quick intro.

    Alexis: Excellent, I love it. What inspired you to start Dextego?

    Ioanna: So, my background is in HR I actually thought I was going to pursue my PhD for a second on organizational psychology, but then I ended up working in startups. I was the VP of people and chief of staff at the, at the end of another B2B SaaS startup here in New York. And I quickly realized, you know, the importance of developing talent and also the challenges.

    that come with this development when it is in a remote setting, because especially during COVID, you know, everyone started working from home and I saw how hard it was for us to develop entry and mid level managers. And that’s primarily because [00:02:00] soft skills like communication, collaboration and leadership take time to be developed, right?

    You need life experience. You need to go through situations where you talk to multiple people, you negotiate, you handle conflict between colleagues. And so it was very hard for us to do this and talking to other, you know, HR leaders and learning and development experts. I quickly realized it was not just a struggle we faced, but the whole industry, and that the current organizational tools we had, e learning tools, learning management tools, were not sufficient enough, because they lacked the personalization needed to develop such skills and also the interaction with the learner and the experiential learning, if you wish.

    Alexis: hmm,

    Ioanna: That is the moment when I realized that I had to do something and I created the team around [00:03:00] Dextego to develop an AI coach that can democratize access to such skills across the organization, especially for anyone outside of the C suite that couldn’t afford an executive coach or didn’t have access to an executive coach.

    And make it in a way that it can leverage also the company’s internal know how. So we can integrate with the existing systems that a company has again, whether this is a learning management system or PDFs or, you know, information they have, we can fine tune our model to that so that it can speak their language and really maximize, the value it can give to its employee to support them during their day.

    So high level, that is, you know everything behind the reasoning. And for me personally, there’s another layer of equity, which [00:04:00] in my opinion, you know, people with soft skills sometimes tend to have. Access to more opportunities, whether we like it or not. Because they’re not afraid of asking for help.

    They’re not afraid of meeting people. And on the contrary, you have some people, like introverts, that without the perfect pitch, they won’t go out of their way to, like, go to conferences or meet mentors. And as a result they might stay behind. And I think this is very unfair. And it shouldn’t be the case.

    But the right training can equalize, you know, the playing field for, for everyone.

    Alexis: Very, very, very interesting. So I love, the mission of Dextego and how it, it aligns with , your leadership philosophy. you spoke about hiring new people and growing talents. So tell me what, what qualities do you look for in team members?

    Especially in those [00:05:00] early stage of of a startup.

    Ioanna: Yeah, I love this question because I was just talking to a friend of mine who were talking about the fact that outside of the U. S. recruiters tend to see employee, both as a person and as a professional. But in the U S we tend to have this distinction between okay, professional versus personal, like the same thing for coaching.

    Sometimes you go to a corporate coach and they just talk about how to boost your revenue. And then you go to someone that has more of the personal life coach approach and you see that the way they coach people is different. And to me, Also coming from Greece, I think the lines get blurry a little bit.

    And I like to work with people, but also hire people that I can see myself spending time with outside of work. So to find this like culture [00:06:00] personal fit I think it’s very hard, but it’s the number one thing I look for. I look for people that have empathy, because when times get rough this empathy will allow us to work well together and overcome any difficulties.

    I like people who are very hardworking and disciplined. So that I can count on them and I know that if they say, you know, they will be on a task, they will actually do it successfully and on time. That doesn’t mean perfectly, that just means that, you know, they, they do what they say. And I think that is something I really value, trustworthiness. 

    And lastly I love to work and hire people that are always eager to learn, like they want to be developed, because if you don’t have that willingness, no matter, you know, what your employer throws at you, it won’t [00:07:00] land, right? So this, I would say, is the most important part. 

    Alexis: So let’s let’s speak about a specific challenge that you faced as a CEO and how you managed it.

    Ioanna: Very interesting. There is a lot I can think right now, but if I was to pick one, as a CEO, you know, for an early stage company, there are two main things you should focus on, and this is fundraising, if you are not bootstrapped, and getting sales in. I don’t think that what I’ll say is just specific to me, honestly, it’s probably something other founders of our states face, but I think there is always a difference between where you’re in now and where you want to get as a startup, right?

    Like you have limited resources, so you do what you can today, but you have this grand vision. And so [00:08:00] that gap is sometimes. It’s very difficult to put in words and to be explained to someone that just is getting introduced, for instance, to your venture. So when I’m talking to investors or I’m talking to potential partners and companies that are super established and it’s, it could obviously be a risk of association for them to work with a company that’s new, that doesn’t have the brand awareness and recognition in the field.

    I found myself many times, you know. Struggling to find the confidence. To persuade them that they should work with us now, because I know how far we can get, and that this might take some time, but if I, as the CEO, don’t speak into existence this vision today, right, to get to that level, then what am I doing?

    So, it’s Someone gave me very good advice. [00:09:00] It’s the fear, you know, of overselling and under delivering sometimes that holds us back. Or, you know, imposter syndrome, all these things, different terminologies, but I cannot wear all the hats at the same time because I won’t move the company further.

    Like I have to think, okay, right now, I’m selling, then I’m doing customer success. Then I’m doing investor relations. So I think the biggest thing I’ve learned. This last month since starting Dextego is how to split these roles. So don’t get overwhelmed and don’t act for the best, you know, of the company.

    Alexis: that’s in a way balancing the, the needs of different stakeholders. By playing different personas and you know, yeah, that’s, that’s really hard when you need to do a lot of different things by yourself. Yeah.

    Ioanna: You know, as a chief of staff, it’s the same thing, but now it’s, I would say, with more responsibility.

    Alexis: Yeah, that’s absolutely true. Yeah.[00:10:00] how do you feel, how do you believe we can really foster an innovative mindset?

    Ioanna: Even a time where Suddenly, the innovation doesn’t come from the top. It comes from the bottom. I think employees have so much power today to drive innovation and to speak up about what they want to see in a company. So I think, you know, the responsibility is. Spread across organization like anyone today can bring innovation, I think, to a company because we see, and I’ll speak on the L& D side, like 70 percent of employees today say that they’re willing to leave. 

    To go to a company that develops them. So, similarly, I feel like there is a lot of fear from leadership to not satisfy employees when it comes to [00:11:00] innovation, to leveraging AI in particular because the employees could easily go somewhere else. So to me, to drive innovation successfully, you just have, if I speak to an employee now, right, you have to understand how the outcome, the ROI of whatever solution you’re bringing in will help leadership achieve their goals.

    So if you speak their language. They will say yes. I think most of the times employees find such cool tools they want to use, but they can’t make a case to actually implement them because they’re missing that piece of, okay, but how will it really help us achieve our, like, five year plan or, you know, our quarterly goals.

    And at the end of the day, whether we like it or not, the leadership cares about these things because they have to report to someone else. So I would say. It’s more [00:12:00] about understanding the strategy of the company and identifying the right type of innovation rather than a question of is the company open to innovation, yes or no?

    Alexis: it’s very interesting because you are looking at some success metrics that, that could be met using something. for your company, what, what success metrics do you focus on and why?

    Ioanna: Yes. So we focus on top talent retention. Because no matter who, what CEO you take from what field today they really care about their top talent, right? They care about the people that can call and they know they will get it done. these are people that they’ll do anything to keep in their company.

    And so when you’re able to bring them a tool that is very personalized, that it matches their needs where they are today and you help them develop for the next day. You’re able to retain [00:13:00] them, but the other part and I made a post about this is totally on the company is how the company does the right change management to explain to the company that implementing a tool like Dextego is for them.

    It’s not just the checkbox. It’s something that they understand they need for their personal and professional growth, whether they’re. Working at this company or not, but as a result, the employees will become loyal because they will. be part of this company where the culture is always about personal development and moving forward and improving each other. 

    But today, unfortunately for, you know, the lack of technology, technological advancements in L and D for the last years, HR leaders have had the misconception that they have no power because they can’t drive revenue. They can’t drive a significant[00:14:00] you know, metric in the company. So for us being able to deliver reduction of top talent attrition by half in just a quarter makes them the heroes they wish they were all these years. 

    And now we can have a seat at the table and really have others understand that they can make or break a company. At the end of the day, we know without talent. You got nothing. No matter what strategy you have on paper, you have no one to execute. So, to me, it’s a very important metric, and we see it across industries from, like, consulting firms that are really suffering from attrition, to startups, to big enterprises, and it’s a way to impact, you know the workforce overall, and knowing that, It’s for their own development.

    It’s, it’s a, to me, it’s a just cause.

    Alexis: So you, you mentioned that the tool is [00:15:00] adjusted to the needs of the people. 

    Ioanna: Yes.

    Alexis: what kind of adjustment are, I mean If I, if I’m early in my career or if I am a little bit later in my career, like me, for example, with over 50, how does the tool with, will adjust to our needs?

    Ioanna: Excellent question. So, let’s take an example of something that will not adjust first. Like you go to a learning management system and you take the same course. On leadership that everyone else in your organization takes, for instance, right? What we do with DexEgo is the AI coach is able to understand through your answers, the way you answer to scenario based challenges, your level of skills, and adjust the level of Difficulty or the types of questions it asks you, and I’ll give you an example, to really make sure you develop the right skills.

    So, [00:16:00] for instance, let’s take an example of a salesperson, and the scenario could be, hey, you have this client, that they’re throwing you this objection. How would you handle it? So you record yourself through video. The coach is your facial expressions, your tone, your pits and content of what you’re saying.

    And it gives you personalized feedback back on what you did great, what you can improve. And over time, by you completing some more challenges, it understands. For instance, you might lack negotiation skills so you can close the deal. So we’ll give you more feedback and more related challenges to these till it sees that you improve.

    And what we have behind the scenes to track that is our proprietary coachability index framework, which shows you. Basically, how coachable you are, how fast you’re implementing that feedback and how you’re improving your [00:17:00] skills over time. Because at the end of the day, it doesn’t matter if you start at, let’s say, 4 out of 10 in negotiation.

    What matters is that you’re able to improve to 8 to 9 over time. And that’s, I think, what any employer cares about today because we’re moving into this skills culture. It’s not just what you have on paper. Can you actually learn on the spot and develop? And can we see you becoming an important part of Our company, you know, in years to come, I

    Alexis: Excellent. So now I turn back the questions to you, to you. Have you evolved as a leader since starting Dextego?

    Ioanna: think so. No, for sure. I think you know, in startups, we have talked about this before one year equals 10. If you will, you learn so much, you see so much, you meet so many people like every day [00:18:00] putting myself out of my comfort zone being in like a situation for the first time. I love it.

    It’s super, Intriguing and challenging, but it allows for a lot of self reflection. I think the people that are following my journey can see that, you know, since the last time we meet, for instance, a lot has happened, or I’m improving, or the way I handle things is developing. So, I, I feel like I get feedback from others, and also from my self reflection, I can definitely see that growth.

    I think the most challenging thing is to be okay with ambiguity, right? And vulnerability as a leader, whether you’re like a leader for the first time or the 10th time in your career, there will always be some ambiguity. And I’m definitely learning to, to handle that better than I did some months ago.

    Alexis: [00:19:00] So if you, if you could give an advice to your younger self. Before starting Dextego what would it be?

    Ioanna: that’s a great one. You know, my number one weakness, I’ve always said, is my patience. I’ve always said that. Since I was young, I feel like I’m very impatient. So, life has a way to Teach you to become patient or else, you know I wouldn’t be able to do what I’m doing now, but I would tell myself that it’s okay when, when things take time, there’s actually a beauty in it.

    Cause you can. Be more excited when you get to the end result, and you can Develop more as a result as well. So I would tell myself to, to be patient and to Enjoy each moment, whether it’s tough or not. I think looking back, obviously every difficult moment in your life has made you right for who you are [00:20:00] today.

    And if you took that away, you wouldn’t be who you are. Thanks. My little speech to my younger self.

    Alexis: I love it. Thank you for that. Oh, can you tell us about an upcoming event? You’re particularly excited about?

    Ioanna: Yes, a lot. We have three events in November on LinkedIn Audio and LinkedIn Live. We’re talking about leadership. We’re talking about why mentorship programs fail and how to overcome that. About flexibility. And then in 2024, I can say we’re preparing what’s called Dextagon. It’s basically an invite only event for HR leaders and C suite here in New York. But yeah, I, I won’t say much more. It will be very exciting and we’ll talk about human potential and how to drive us further as a human race.[00:21:00] 

    Alexis: Excellent. I love it. So where can people learn more about Dextego and get in touch with you?

    Ioanna: They can go to our website at dextego. com. That’s D E X T and ego, dextego. com as well as our LinkedIn. And mine as well, you know, Ioana Mantzouridou and check out all our events and upcoming shows.

    Alexis: Excellent. Thank you very much Ioana for joining the podcast today.

    Ioanna: Thank you, Alex. Thank you very much for your time.

  • Better Humans, Better Leaders: A Conversation with Ali Schultz (Reboot.io)

    Better Humans, Better Leaders: A Conversation with Ali Schultz (Reboot.io)

    Some leadership conversations stay with you because they don’t add more techniques. They change your attention.

    That’s what happened for me with Ali Schultz, co-founder of Reboot.io. Reboot has been around for ten years now, and their work has influenced an entire generation of founders and leadership teams. But what struck me most is not a new framework. It’s a stance.

    Better humans make better leaders. Better leaders create more humane organizations.

    It sounds simple. It is not simplistic.

    Reboot’s bet: leadership is personal work

    Ali described Reboot as a platform for leadership coaching and organizational development that goes beyond skill-building. Not because skills don’t matter, but because skills are not the full story.

    When someone steps into leadership, something predictable happens. Responsibilities increase. Visibility increases. Pressure increases. And we meet ourselves, fast.

    Self-doubt. Imposter syndrome. Old patterns. Defensive reactions. The need to control. The need to please. The reflex to perform instead of relate.

    Emerging leadership is not only about learning what to do. It’s about learning who you are while doing it.

    Ali offered a simple equation that captures Reboot’s philosophy:

    Practical skills + radical self-inquiry + shared experiences = greater resilience and stronger leadership.

    I like this because it holds the tension. Not one or the other. Both.

    A company built on diversity, not a single method

    One of the early challenges Reboot faced was building a brand bigger than its founders. Ali shared how intentional they were about not building a company around one personality, one coach, or one method.

    Instead, they built what Jerry Colonna calls a “wildflowers” approach. Biodiversity in coaching. Different styles. Different life experiences. Different ways of being with people.

    It matters because coaching is not about fitting humans into a method. It’s about meeting humans where they are.

    This also resonates with how organizations grow. Diversity is not just a value statement. It’s a design choice.

    A small shift that changes everything: make space for the humans in the room

    Ali shared something that I’ve experienced myself.

    When you’re action-oriented, when you want to “not waste anyone’s time,” you can rush into agenda and execution. It feels efficient. It often isn’t.

    Sometimes, the fastest way to move is to slow down enough to see what’s actually present.

    A few minutes of human check-in changes the quality of the entire meeting. It reduces hidden friction. It surfaces what needs to be named. It creates conditions for real alignment.

    This is not soft. It’s operationally sound.

    Hiring in startups: the Sunday test, and the reality of stages

    We also talked about what Ali looks for when building teams, especially in startups.

    People who can create something from nothing. People who can execute and keep the bigger picture in mind. People whose heart is in it.

    And one heuristic I’ll remember: the Sunday test.

    Would you choose to spend time with this person on a non-work day?

    It’s not a perfect filter. But it points to something important. Work is a human place. Toxicity does not scale. Neither does charm without integrity.

    Ali also named something that more founders should normalize: not everyone scales with the organization, and that’s okay.

    Some people thrive in the earliest stages. Some people want clarity and structure. Some people love the chaos. Some people don’t. The healthiest organizations design for transitions, rather than treating them as failures.

    What horses, art, and ecology have to do with leadership

    Ali’s personal influences were not what you’d expect from a standard leadership conversation: deep ecology, art, and horses.

    Yet it makes perfect sense.

    Leadership is a relationship practice. Presence matters. Authenticity matters. Power-with matters.

    Horses, Ali said, don’t accept anything except the most grounded, most honest version of you. They offer immediate feedback. If you’re off, they know. If you’re performing, they feel it.

    That’s leadership training, in a very direct form.

    The next five to ten years: more human, not less

    We ended with a question that’s hard to avoid right now: how will leadership coaching evolve with AI?

    Ali’s answer was clear: work will remain human. Leadership will remain relational. If anything, the need for leadership development will become more important, not less.

    AI may change tasks. It won’t remove the human complexity of trust, conflict, fear, meaning, belonging, and responsibility.

    If we gain time, the question becomes what we do with it.

    My hope is the same as Ali’s: that leadership and organizational development become even more human.

    References

    • Reboot.io, where you can find the resources and the newsletter
    • Reboot by Jerry Colonna
    • Reunion by Jerry Colonna (the book mentioned by Ali that was launching the day after we recorded)

    Here is the transcript of the episode

    Alexis: [00:00:00] Welcome to Le Podcast on Emerging Leadership. I’m Alexis Monville. And today, I’m honored to have Alison Schultz with us, the co founder of Reboot. io, an organization that’s been in reshaping the landscape of leadership coaching and organizational development. This year marks a significant milestone for Reboot. io as they celebrate their 10th anniversary. A decade of empowering leaders and team across various industries. So, without further ado, let’s welcome Alison Shultz to the podcast on emerging leadership. 

    Hey Ali. How do you introduce yourself to someone you just met?

    Ali: Well, I guess I would say, 

    Hi, I’m Ali. I’m one of the co-founders of Reboot. How are you?

    Alexis: That’s nice, that’s direct. 

    Ali: Yeah, 

    Alexis: could you walk us through the inception of reboot.

    Ali: Yeah, so Jerry and I met in 2013[00:01:00] and we began doing the CEO bootcamps together. we did three bootcamps, including one in Italy, which is not too far from you. Before we formed Reboot with our partner Dan Putt the bootcamps proved that our instincts were right and that we were onto something. And so Reboot really came out of a vision to create a coaching and leadership development platform that would support people not only in better leadership, but also the work in the work that it takes to become a better human.

    Alexis: I think that’s the part I’m very impressed with in all your communications with Reboot. there’s sometimes when you look at leadership or leadership development, there’s that kind of thing that are really technical. I. that seems to forget that behind all those skills, all those things that we learned to do there’s a human being and that’s probably something really important.

    And I feel 

    that you are really touching regularly very well. So that, [00:02:00] that’s something I really appreciate. 

    Ali: Hmm. Thank you.

    Alexis: what, what were some of the initial challenges you faced and how did you overcome them?

    Ali: Yeah, so this is a great question. We had to build a brand for the company that was bigger than Jerry. So we had to build something that went beyond just Jerry Colonna. And by the end of our first year we had that, which was pretty cool to see. People were searching for reboot, they weren’t just searching for Jerry Colonna. And, you know, in the process of building that brand, we, we took advantage of Jerry’s notoriety and his reach and the work that he had been doing in the space for over a decade at that point. And we carefully crafted a brand and a voice that could stand on its own. I would say another thing that. We wanted to do, which kind of relates to that, is we wanted to build a company that was built, that wasn’t built around just one coach, one personality, or one method. We [00:03:00] wanted to bring together a team of coaches that were distinct and unique in their experiences and in their styles to better serve our clients. And internally, Jerry kind of refers to this as like wild flowers and, as a, I don’t know. I have a biology minor going decades back when I was in college. But if you know anything about biodiversity, there’s a strength, there’s an inherent strength in that. And so it, it serves our clients better when our coaches are unique so people can come to reboot and really get fit with a coach Just within our, our herd of coaches, I say lovingly

     it’s kind of cool because you have a variety of, of humans that can meet the variety of humans that come to us for, for help and support. But it’s also like, I mean, can you imagine going to a therapist or a coach or, that just tries to fit you into their style or their method without really meeting you where you are as a human.

    It just [00:04:00] like, it doesn’t match. So we wanted to create something that was really I don’t know, just a unique coaching experience that was in service to, you know, anyone that would come to us for, for help.

    Alexis: This is, this is very, very interesting. And a quick question about the, the brand. Does Jerry’s book reboot was already out when you, when you created the brand?

    Ali: No no. We started in 2014, so we started reboot in 2014. So we were doing this before Jerry’s first book came out. And his book came out in 20 17, 16 or 17, I believe. Maybe it was 2017. Maybe it was 2018. but it was much, you know, it was further down the line. So we had already had a brand and a larger platform established. the book came out and it had a place to be. It was kind of cool.

    Alexis: Yeah, it’s very[00:05:00] very tempting to use , Jerry’s notoriaty and the work he did in the past and say, okay, that’s the one method we will propose. And I really like what you’re saying now. No, that’s not what we are doing. We are not like this. We are uniquely different and Yeah. 

    you, you can find a good match for you at the right time for you.

    I really like that that approach.

    you will celebrate the 10 years anniversary of of reboot io. what are the significant milestone that stand out for you?

    Ali: Yeah. Man, I’ve got a, I’ve got a couple handfuls I, I jotted down so. Things. I think pulling off our first bootcamp was a big deal. And then I lost count after 25 bootcamps. So that. I mean, that, that’s a significant thing to successfully produce that many events, you know year after year. [00:06:00] And I would say another really big memorable event was getting the reboot podcast out and shipped. And that happened, that, that happened pretty quick. I remember it was probably September and three months of, of 2014, so it was three months since we had started. And, and we had the podcast out. it was really cool to, like Dan and I had been working on it, and Dan probably more so at that point. but it was cool to have Jerry listen to it for the first time and you know, to see his reaction. So that was really special. And then after that we just kept together products and services that were really , on our roadmap and that we had wanted to kind of put out in the world, including our, our peer groups, our circles we had put together a 360, review process for clients. So a lot of services that were really in support [00:07:00] of, one-on-one coaching, but it expanded and complimented just the one-on-one coaching work. Internally we had produced some really fun things too for our clients, mainly ’cause they were like educational, but we had a, a chatbook of poetry that we would use at events. we had made a branded journal. So it was cool to have kind of some tangible takeaways that we could, would give, you know, reboot clients in our work with them. And then of course, like Jerry’s first book Jerry’s second book, which is coming out soon. Tomorrow actually it launches it’s, I don’t know, in 10 years. That feels like a lot. I mean, on top of what, what I think is also kind of celebratory for us, and maybe for me, ’cause I hold this seat a little bit more than some of my colleagues ’cause I’m, I’ve just been the one kind of defaulted to being the brand voice.

     You know, the [00:08:00] amount of content that we consistently put out into the world for free, because we know that, you know, not everybody can afford our coaching rates, but everyone should have access to frameworks or ways of thinking or questions for reflection that can help them become a better leader if they’re interested in this work. it’s nice to be able to provide such a rich At this point, library of resources for folks to kind of come to our site and mainline our content and kind of get a taste for what we’re about. and then, you know, maybe at some point know, if their comfort company sponsors them or budgets are such that it allows for it, they, they end up working for us.

    But none of that’s like a requirement. we really put, a lot of good content out in the world as a Service to the entrepreneurial community and, and the emergent leaders, you know, to use your language, the emergent leaders that are there because they need support. You know, they need to recognize, you know, what are the practical skills that I need [00:09:00] and what’s the radical self-inquiry piece that I need?

    Like, what are, what’s the inner reflection piece that I need to, to bring into this leadership space? And then what are the shared experiences, right? And so how can they then Find their people or their communities or their support or places for support, you know, in order to give them greater resiliency and enhance their leadership.

    Alexis: Yeah, that’s beautiful. and among all the resources you are exposing to the world. I, I really like the, the journaling prompt.,

    Ali: yes. 

    Alexis: so, that’s so simple and that’s so helpful to help people start with journaling , and usually there’s the, some people tell, told me, but I don’t know what to write.

    I’ve said, all write what? What’s on your mind? And so I said, no, I’m, I’m stuck. I am, I cannot write anything I said. Okay. That’s a, that’s a good one. Let’s start with some prompts. And when I discovered your journaling prompt, I say, oh yeah, that’s, that’s really cool.

    Ali: I’m glad [00:10:00] you think so. I think so as well. It’s it’s a, a, a really beautiful practice to, I mean, journaling takes work, you know, and it’s personal for everybody. There’s no right way or wrong way to do it. It just has to support you, you know? That’s why people do it. And so, Margaret and I, Margaret, who’s my, like partner in content creation and she’s the brilliant editor to our, our podcast we sat down and I was like, we have enough journaling prompts from all the content we’ve put out in the world and from all the events that we have done where we could just do an email Course, even though it’s zero cost, but like, sign up, get a daily email in your inbox. you know, the questions that we pulled together are very rebooting. And they’re very applicable to anyone in leadership, like anyone in leadership or management, or even people who don’t think of themselves as CEOs or founders or anything. They can be really handy. Just in terms of helping someone to establish a journal practice or, [00:11:00] giving them like that external prompt so that they can sit down and, and do some self-reflection.

    So it’s such an important piece, I think, of being an, being a leader. I’m really delighted that, that we re release that this year.

    Alexis: Over those, 10 years, how has your role evolved within the company?

    Ali: Oh yeah. yeah. It’s, I feel like I’ve, I’ve, I’ve, been around done a lot I started in ops primarily, so I was like, you know, making sure that the trains ran on time and taking care of a lot of the internal structure, really the business structure of, of what are we doing and really leading the, the marketing and content efforts.

    And I mean, we’ve been very lucky as a company that because of kind of like Jerry’s notoriety and whatnot. The, the PR efforts and the traditional marketing efforts, we really didn’t need so much of, but, you know, we could be really creative I don’t know, kind of like specific [00:12:00] with the content we put out.

    And so I I really leaned in there and after five years, we came to a, a moment in the company where we were no longer a loose consultancy of, of coaches which is kind of what we began as, as we, we, as we tried the experiment of, you know, what is, what is this company and what does it need to be? we, we began employing our coaches. And so that was a, just a slight shift in the business model. Not too bad, but it was at that point that I handed over the operational reigns to just a, a small ops team within the org and I just stepped into coaching full-time. So it was a, it was a big shift, but it was also welcomed, so.

    Alexis: Yeah, that’s a, that’s a big one. But yeah, that’s probably very satisfying to have built something, build a team that can run on, on its own and enables you to, to do something that has a different kind of impact. That’s a, that’s [00:13:00] interesting.

    Ali: Yeah. Yeah.

    Alexis: So. Emerging leadership mean to you, and how does it align with the mission of reboot?

    Ali: Yeah, this was another really great question. I mean, we believe that better humans make better leaders and better leaders create more humane organizations. And we love working with the, with emerging leaders because we can instill in them during those emergent years, like the, the soft skills that are so important.

    And we can also stress the importance of doing the radical self-inquiry work alongside the practical skills, right? But it’s a way to really support what’s emerging in each individual as they’re stepping into their leadership. you know, anyone who takes a leadership role that has not done that before is gonna run up into a ho, run up against a host of, of issues including [00:14:00] self-doubt, imposter syndrome all these things that really stem from who am I and what am I bringing into this role. But it also kind of stems from, I’ve never done this before, and what do I need to know to do the job? I kind of feel like, I mean, I kind of hinted or spoke to our formula before, but kind of the formula or the bet that we, that we take at reboot is that practical skills plus radical self-inquiry plus shared experiences equal greater resiliency and enhanced leadership.

    Or it might be enhanced resiliency and greater leadership, whatever, but but it really fits that emerging leadership sensibility where You know, I don’t know. When I think about emerging leaders, there’s something emerging. It’s emerging in you. It’s emerging from a need in the world. It’s emerging from a need in the organization.

    And how are you gonna meet that? How are you gonna a, listen to what’s showing up? Listen for what’s showing up. How can you be attuned to that? And how can you meet that need [00:15:00] or meet what’s emerging and be agile about it.

    Alexis: I love it. So thanks for, for sharing. Can you share with us an example of a time when your leadership skills were put to.

    Ali: Yeah. When I, when I operate, I’m really, I don’t know that tactical is the word, but transactional. Like when I go into, Get shit done. I go in to just get shit done. Like that’s, I assume, like that’s why we’re here. So I think it took a while for me to really, pause or trust that holding space for everything else that’s in the room is actually gonna get things done more smoothly and potentially more quickly.

    Right, because you’re not just meeting with people who are always ready to go tracking the same agenda items that [00:16:00] you are seeing everything the way that you wanna see them. and so, yeah, I would say learning the, to just kinda sit back Not drive so much with the get shit done mentality but to really create enough space for the humans in the room and kind of meet and be able to meet that humanity, right?

    Like personal check-ins how are we doing, how are we feeling about these things? And then go moving into what may be the agenda items, but it’s, it’s, it’s more like realizing. What are the other issues that aren’t maybe so tactical or get shit done oriented that are also in the room that need to be unpacked and talked about? And I think for early leaders, and I don’t know a lot of clients that I work with too, it’s like learning that, shift can be really impactful. And it’s hard I think during early startup days when everybody’s kind of doing everything and there’s an [00:17:00] urgency to just like Get everything done as fast as possible. Cause it feels like there is no time to pause or to take, take things slow or to, to ask big questions. I guess my invitation is, and my learning was, you to create the space for, for that way of being, with the to-do list. It, it’s, it’s more powerful in the long run.

    Alexis: Hmm. Yeah, it’s a thank you for sharing that because I, I believe it’ll help a lot of people to, to think and reflect about it. I have the, the, the tendency also to, to look at the time we have, we have allocated to do something and to say, okay, I don’t want to waste the time of anybody, so let’s, let’s get to it immediately.

    that’s, that’s kind of that urge that is there. And it’s hard to pause, so it’s a, it’s very, very helpful to say Yeah. But, Make enough space for the human being in the role. [00:18:00] And that’s, yeah, very powerful. I love it. If we look at the startup environment, what are, what are some key qualities you look for when you, when you are building a team?

    Ali: Yeah. Key qualities I think, I think there’s. There’s a lot of power in finding people that are good people. Like you just really want good people. But I mean, as far as qualities a willingness to dive in and face problems, that’s key. And I think a willingness to be a little bit obsessed and dedicated also goes a long way at first, especially when teams are small and new and there’s a lot of exciting stuff happening. I mean, I say that in the sense that. The obsession or the dedication can help people, can really help the focus [00:19:00] and the, the small team cohesion a little bit. Yet that certainly doesn’t scale. mean it can, but it needs to be named, it needs to be checked in on and it needs to be maintained in a healthy way. you want people that are engaged in the work like they wanna be there. They’re eager to solve these problems. They’re eager to show up every day and solve these problems, and they get a little bit of aliveness out of it. I mean, you want people that really wanna be there. Cause you’re gonna get so much more out of not just the team. there’s no sense. I mean, it’s just hard to work with people who their heart isn’t in it. I don’t know. I think Someone who’s willing to kind of put their heart into it a little bit is, makes things kind of fun at the beginning. You also need a balance of like contextual thinking and execution, especially at first, because at first you have, I mean, I’m thinking of like startup teams of like maybe five to 10 people or five to 15 people, but. At that stage, [00:20:00] everybody’s kind of doing everything and it’s, it’s a little bit like, you know, a kindergarten soccer team where everybody’s on the field and not everybody has a defined role, but you know, you’re on the same team and you’re kind of playing certain parts of the, of the field, but but you’re also getting coffee and taking up the trash and doing all those other things.

    So it’s such a mixed bag of an experience early on. And then of course, as at, at as things grow and roles scale and the company scales and roles get defined, then there’s more clear parameters and more clarity and more expectation around what your key role on the team or on the field is.

    You know? I think you need people who are able to, kind of going along the execution line. It’s really great to have people that can execute, but you also need people who can create something from nothing, you know, because in a lot of startup spaces, there’s, I mean, that’s art really is to be, to create something from nothing, right? [00:21:00] But so many of the problems that get funded and companies are built around, like they didn’t exist. You know, before funding it was like, I have this idea, let’s do this. And so you need someone who can really see the whole picture of where this is going. And also also be able to know, okay, this is my role execution wise in the org and this is how I can contribute to this. And a lot of this is kind of set too, I think with leadership parameters, you know, like your leader’s gonna, a good leader will help you know, the team see these things. But honestly, I’d say when it comes to hiring people there is no sociopath filter. However, I know after working with a lot of clients that sociopaths exist. you have to trust your gut when hiring. And you have to be quick to really Get toxic people, I think, off the team. But one of the [00:22:00] ways to really test for this, it’s not foolproof because there are some really charming and toxic people that can just be in the world and then wreak havoc in your organization. But we always say, you know, the Sunday test. Here at Reboot, and that is, would you want to hang out with this person by choice on a Sunday? Like it’s a non-work day? You don’t have to be in their presence and yet you would, you would choose to hang out with them on some relaxing non-work activity. someone passes the Sunday test, that’s a pretty substantial thing. And you can tell a lot too about people And how they make you feel meeting in person, you know? So like when you’re hiring, really pay attention. How does this person make me feel? Are there any red flags? Are there any like suspicions or feelings that come up? I’m with this person that I either wanna get clarity around and lean in and [00:23:00] ask them about and or does it remind me of anything else in my life that with a red flag for another relationship that may have headed south. Those are just, they’re signals to pay attention to, I would say. it’s, there’s a lot of magic at the start of startup And then, you know, as teams scale, I think it’s key to also know that, not everybody scales with the organization and so, so turnover is like, natural turnover in many ways can be celebrated. Like, oh, we have reached this point in our organization where we need to bring in like a CFO, not just a director of finance or we need to bring in, A really like a main leader, not just someone who’s grown up and kind of fulfilled some, territory in the organization, like with marketing or, or some part of the org. And so, I mean, that can be really hard, you know, especially as teams grow because you get attached to people. But there’s ways to also build it into culture [00:24:00] and say, you know, we’re bringing you in. We know this might be. A short term thing, but we want this to be the best place that you’ve worked and you know, we’re gonna celebrate what’s here. And, you know, whatever tenure anyone does have, So I guess a lot of this is like, there are qualities that you want in your team, right? But not all those qualities, not all the people will necessarily scale with your org.

    Alexis: Yeah.

    Ali: And what are the qualities too, I guess as part of what I’m responding to here, as what are the qualities you can bring to like your hiring process and your culture and tending to those, those, those parts which are equally as important.

    Alexis: I really like your, your, your answer and setting the right expectations also for people. And I like what you say. That’s, that’s a good balance between that for people who can grow with the, the team or with, with the company. That’s celebrate what they brought to the [00:25:00] team.

     And there, there’s, there’s people who don’t want to go in the, in the next stage. They, prefer really the, the infancy in the incubation mode, and they don’t want to go to the next stage. That’s not, that’s not. Maybe they could , but they don’t want,

    so,

    Ali: Yeah.

    Alexis: so that’s okay. And and, and that’s great to, to affirm those people for that period of time.

    What, whatever along there that was. how, how do you approach your own personal and professional development?

    Ali: Yeah, so my, yeah, this is a great question. an ongoing process really of. Kind of discovery from, you know, within me, but also a commitment to being curious about what’s showing up for me and my work. I believe we need guides in this life. We can’t do this alone. got a great body worker. I’ve got a great therapist. I have a small herd of beautiful horses[00:26:00] where I get to go and decompress. I have great colleagues that I get to share my work with and They share their work with me. So there’s like this cross pollination that happens. And I have a very loving and wonderful partner with whom I’m lucky to share both life and work.

    So that’s a’s a big part of, I think what supports me in, in my work. I live a pretty cloistered life on purpose. So that I can kind of hear my own voice clearly stay attuned to what’s emerging within me and within the world And, you know, that quiet life really ensures that I have the resources that I need to do the work that I do with my clients. So, yeah.

    Alexis: Okay. Excellent. Are there any books, mentors, [00:27:00] experiences that have profoundly impacted your, your style, your leadership style, or your way of doing your work?

    Ali: Yeah, there’s probably too many books to mention. But I’ll say that it’s probably been informed by three things that are really important to me, and that is deep ecology, you know, this belief that the world in order to really amend the climate crisis or the ecological disaster that is kind of impending in the world we really need to tune into a shift in consciousness, which, helps people like awaken into self-actualization versus less woke, less aware way of being in the world. Right? So I’m a deep ecologist at heart it’s kind of cloaked, I would say, in, in all of my work at Reboot. It’s, I don’t speak about it that directly most of the time, but [00:28:00] I mean, for me it’s, it’s right there every day. say another practice that’s really informed, the work that I do is art. I’ve been an artist for my whole life. I’m not formally trained, nor do I think you need formal training to really be an artist. Same with leadership in many respects. but there’s something about, for me, the the practice of art where you are alone with your, with yourself and this idea or you in a blank page or a blank canvas, and it’s like, what am I gonna.

    Bring to this. And it’s much less about what am I going to be creating? And it’s more about how am I with that creative force, that’s arising in me and how do I trust my, in my intuition and my instincts? And what then comes out of that? And how do I work with, you know, what’s in front of me? I think there’s, I don’t know, something about beauty and truth in that whole process. And it’s really personal and it’s really [00:29:00] intimate, but I think it’s, I think it’s key to leadership. And then hands down I would say horses are, have definitely impacted, my beliefs about leadership and probably my leadership style and. It’s a, it’s, there’s so much there for me in the, in the horse aspect, like I can’t even talk about it.

    I just start crying. but there’s something about learning to be in relationship with another being that is not a power over relationship really. It’s power with, that’s, I mean, that goes a long way into anybody’s, you know, leadership or management roles. But for me, in my small herd of beautiful horses, it’s, you know, they, they don’t put up with anything really other than the best me, the most authentic. Me that I bring forward. And so for me, every, every moment spent in the barn is I’m not gonna knock my therapist ’cause I love [00:30:00] her. She’s fantastic But it’s there, it’s, it’s it’s immediate feedback in the sense that if I am off base or if I am not owning some state of mind, or I’m bringing some really grumpy state of mind into the interaction with them, like they know it and they’re like, You don’t feel great about yourself right now. Why should I feel really great about you? Or know, it’s, you know, they demand really the best of us in order to really have a good relationship with them, you know, harmonious. And it’s a, it’s a really wonderful, Attunement practice. probably three totally like outta left field answers, but they are, they’re, they’re the three cornerstones for me.

    Alexis: That’s, that’s absolutely perfect. You, you brought me back many years. when we, we had horses at, at home and when you, when you spoke about that, that brought me with the, I was a small kid, so I, I was [00:31:00] small. When I was approaching the horses, they were always, trying to, to, to smell and and so through the nose and you, you approach your head close to their nose and they don’t move and they, they they smell slowly and it’s, and it’s warm and it’s, and it’s and you feel something is happening. And that’s, that brought that memory to my mind.

    Ali: Yeah. Well, it’s such a, well, I’m really glad you brought up that, that memory, because I mean, I think if the horse industry really needed, to convert people into the horse industry, all you need is to just have a horse blowing on your face or your hand or something, and it, there’s something, there’s something really potent about that you’re hooked at me.

    Anyway. Totally hooked. Yeah.

    Alexis: Yeah. Oh yes. Oh yes. That’s.[00:32:00] 

    Let’s take a, a look at what will happen in the future. Let’s take our crystal ball . How do you see the landscape of leadership coaching and organizational development all those things changing during the next five to 10 years?

    Ali: Yeah. I think the trajectory of the last five years has been important just to look back a little bit cause it put the emphasis. On the importance of leadership development within any startup or any organization. I sense that’s gonna continue. You know, there was a time when it was a hard sell to get an executive coach or bring in. L and d work, and now it’s just the norm. It’s kind of a norm, especially kind of in companies like startup companies that have been funded and other organizations too, and in other, [00:33:00] other verticals and other industries, not just tech. Which is really great to see because, you know, now that these like coaching and l and d are, are part of, you know, budgets and budgeting, they’re seeing the impact as well. I think because the payoff of those line items are so great for the individuals and the teams and then the organization and business as a whole. You know, I suspect that we’ll continue. I, the thing is like, we’re. Work is a very peopley place. Work is a very human place. Right. I really don’t think AI is gonna shift that too much. I mean, there are still gonna be humans doing human work and, humans need tending to, and those humans that are working in relational spaces need tending to, whether it’s their teammates or their customers or the service that they’re providing. So, I mean, I would, I would hope, I guess If I look into that crystal ball, it’s that the, the landscape of [00:34:00] l and d or the landscape of leadership coaching will just become more human, more and more human.

    Alexis: I love it. And you guessed that my question was also connected with AI because it seems everything is related to AI nowadays.

    Ali: I know. Yeah.

    Yeah.

    Alexis: I love your answer. That’s that’s reassuring . Mm-Hmm.

    I’ve heard a lot of people thinking they will solve everything with a little bit of ai.

     Interesting problem can, can be solved that yeah, I would love us to use the time that we gain to engage in more meaningful relationship Yeah, well said. 

    hope for that. 

    Ali: said. 

    Alexis: So what, what’s next for, for reboot? Any, any exciting projects or initiative you, you can share with us?

    Ali: We’ve kind of got a lot of ideas in the hopper but I think [00:35:00] the big, the big and Easily ready to share. Tidbit is Jerry’s second book launches tomorrow. So you can find it on bookshelves everywhere for real, not just in pre-order. So we’re excited, we’re excited to see how, how that emerges. Tomorrow we were kind of aiming for some bestseller lists with a lot of presale efforts. But you know, the book industry is a really crazy space. So we’ll see what happens,

    Alexis: Yeah.

    Ali: other than that, you know I’d just say watch this space carefully for any projects and expansions. But you can count on us to continue to provide. Meaningful and helpful content as a corollary to the services we provide. And the newsletter, our new newsletter is always a great place to dive into what we’re currently doing and kind of what’s coming up in the next like months, in what might be emerging. I [00:36:00] don’t know, in the next year or so.

    Alexis: I definitely will put links in in the companion blog post to make sure that people can find those resources in the, the newsletter and so on. And and the book, of that’s that’s cool. That reminds me that I did not prior order. I will. So that’s good. I will order now. So thank you very much for, for joining Ali.

     That was really fantastic.

    Ali: Oh yeah. Thank you for having me. Thank you for having me.

    The horse picture is from Missi Köpf (on Pexel)

  • Remote Collaboration: Team Agreements, Conflict, and Connection with Lisette Sutherland

    Remote Collaboration: Team Agreements, Conflict, and Connection with Lisette Sutherland

    Remote work is often treated as a question of tools: video calls, chat, shared documents, and the right stack.

    Lisette Sutherland disagrees.

    For her, the real topic is remote collaboration, and the hard part is not technology. It’s the human side: how we handle conflict, how we build trust, how we manage overload, and how we stay connected without relying on proximity.

    Lisette is the founder of Collaboration Superpowers, host of the Collaboration Superpowers podcast, and author of Work Together Anywhere (now available in French). Her work draws on an international life across Germany, the United States, and the Netherlands, and on years helping teams learn to work together from anywhere.

    Remote collaboration changes what becomes visible

    Lisette started with remote work almost 20 years ago, back when tools were primitive and connectivity was painful. Today, the tech has mostly improved. What remains challenging is what was always there: personalities and relationships.

    She names it clearly. The biggest struggle is navigating people without slipping into judgment or defensiveness, and intentionally choosing curiosity instead.

    Remote doesn’t create these dynamics. It reveals them.

    Two classic failure modes: rhythm and conflict

    Lisette shared two examples from her experience on a distributed team:

    • One person worked at a very different rhythm, moving faster than everyone else, taking over tasks unintentionally, and leaving others feeling stepped on. The team wanted to applaud the energy, but also needed to name the disruption.
    • In another situation, personalities didn’t gel. Conflict escalated into back-channel conversations and private chats. The team eventually added a conflict handling section to their team agreement and brought in an external facilitator.

    A key detail matters here: the team had a flat structure. No manager meant no clear decision owner, which made conflict harder to resolve. When nobody holds the responsibility to decide, teams need explicit protocols and skilled facilitation even more.

    And an important reminder: you don’t have to be friends to work well together. Professional trust is enough, and sometimes that’s the realistic goal.

    Start with yourself, then build the agreement

    Lisette’s sequence is practical:

    1. Create a personal user manual. Get clear on what you need to be productive, connected, and healthy.
    2. Create a team agreement. Most teams still don’t have one, even when they know they should.
    3. Address communication overload. Meetings multiply, channels multiply, messages never stop. Proximity used to hide this. Hybrid and remote make it unavoidable.

    This overload is not only tiring. It also makes teams reactive. And reactivity kills good collaboration.

    Innovative models: fewer messages, more clarity

    Lisette points to WordPress as a gold standard. They largely eliminated email years ago by documenting decisions in a structured way: a trail where context, input, and outcomes are recorded so teams don’t have to reinvent the same discussions repeatedly. Over time, it becomes an organizational memory.

    She also shared a strong example from a large German company running hybrid PI planning sessions for around 100 people across Malaysia, Canada, and Europe. What made it work was not a magic tool. It was rehearsal. They ran practice sessions before the real event, so teams learned how to use the whiteboard, how to communicate during planning, and how to avoid wasting the first hour on tool confusion.

    That investment creates a capability the company can reuse.

    Face-to-face is a powerful accelerator

    Lisette doesn’t treat in-person time as mandatory, but she does treat it as a catalyst. It speeds up bonding and trust.

    You can build real relationships remotely, even deep friendships, but it can take longer. In-person moments compress time.

    Remote is failing on a mass scale, but not for the reason people think

    Lisette observes the current backlash: return-to-office mandates, leaders claiming productivity is down, culture is suffering, people are less connected.

    She doesn’t deny the symptoms. But she challenges the diagnosis.

    Remote work is often being used as a scapegoat for poor management. Many companies had weak engagement and weak culture long before remote. Remote simply makes it harder to hide.

    Two experiments she’s excited about

    Lisette is currently exploring two formats:

    • An Icebreakers Playground: experimenting with icebreakers and tools to observe their effect on group dynamics.
    • Virtual coworking sessions using Pomodoro: quick check-in, three focus sprints, short breaks, and a closing celebration. Simple accountability, strong results.

    Where to follow Lisette

    Lisette offers a Remote Working Success Kit, including a guide for a personal user manual, team agreement tips, and time zone guidance at:

    collaborationsuperpowers.com/superkit

    Here’s the transcript

    Alexis: [00:00:00] Welcome to Le Podcast on Emerging Leadership, I am Alexis Monville. Today we have a special treat for all of you who are navigating the complexities of remote work and leadership. We are joined by Lisette Sutherland. A pioneer in the realm of remote collaboration. She’s the force behind Collaboration Superpowers. a platform that equips people and companies to work together from anywhere. Lisette is also the author of the book work together anywhere. a comprehensive guide to thriving in a remote environment. And the book is now available in French, by the way. With her hands-on workshops and her own podcast, she’s been helping teams across the globe to connect and collaborate effectively no matter where they are.

    Hey, Lisette, how do you introduce yourself to someone you just met?

    Lisette: I try to keep it as simple as possible because nobody wants to hear a long story, so I always just say I help teams work better together remotely. I kind of leave it open and that way [00:01:00] if people wanna ask a little more, they can ask it from whatever angle they want to. And otherwise, if they look at me with dear eyes, I just kind of move on to the next subject and I and I ask about them.

    Alexis: I love it.

    Can you share a specific moment or experience that led you to specialize in remote work?

    Lisette: Yeah. I mean, it was a long series of small events, but really the, where it actually started was when I was living in Los Angeles almost 20 years ago, and I was working for a man who was building at that time an online project management tool. Now you have to remember, this is 20 years ago, and those tools were not available.

    Basecamp had just started, you know, Zoho was still a very popular tool on the market. I mean, it was really a while ago. So there’s not that many tools out there. So the tool was interesting in and of itself because it was just interesting. But. He had us all over to his living room one day and he sat us all down.

    He had like a, a pool. ’cause Los Angeles, so many [00:02:00] people have pools. So he had a swimming pool, so it was like a pool party. But he sat us all down and he started to explain his vision. And his vision was he wanted to end aging. So he wanted to stop aging. So his goal was he didn’t wanna die, so he was trying to figure out how to get longevity scientists collaborating together so that they could solve the problem of aging.

    And he realized that these scientists didn’t live in the same town. And so he needed to create a tool for them to collaborate and share data and solve this problem. And so I remember sitting in his living room and. My mind was blown, right? I was just like, what a wild idea. And I thought, well, why not? You know, like, why not?

    But the thing that happened was it got me thinking about what else could we do if location wasn’t an issue? So like, could we solve cancer? Could we, global warming? You know, so there’s a, there’s a bunch of things that played into it. One was [00:03:00] also that I had quit my job earlier, I worked for a, a big office and, I didn’t quite understand why I needed to quit the job.

    I just knew in my body that I needed to quit, and eventually I learned later that it was because the office was so ugly. I. And I was having an allergic reaction to just the gray walls and the cubicles, you know? So all of this sort of played into me getting interested in remote work and I just started asking people how they were working remotely, what they were doing.

    And you know, everything else followed in a long series of events, but it really all started with that weird conversation in that man’s living room.

    Alexis: That’s very interesting, that’s more than remote work, that’s really that idea of remote collaboration.

    Lisette: Exactly. I don’t care about remote work at all. For me, it’s way more exciting because what ended up happening after that conversation was my favorite band from when I was a teenager. I had met them because I’d been to so many shows, you know, but, and my favorite band called me to see if I could go on tour [00:04:00] with them now, because I was working for this man who was building an online project management tool.

    I was able to work from the van with my team during the day with a mobile router stuck onto the window of the van, and at night I was tour manager and I was selling merchandise and part of the band, and I, I was on tour with them for years doing this. And so the freedom that being able to work from anywhere offered me, changed my life in that way, right?

    I was all of a sudden I could work from anywhere. And so I started thinking like, what am I doing in Los Angeles? Like, I could go anywhere, like, why am I here? So, yeah, it’s yeah, it was bigger than remote work indeed.

    Alexis: That’s excellent. Are, you originally from los Angeles?

    Lisette: No, I have a weird history in terms of that. I grew up in Germany for the first 10 years of my life, and then went to the US for 25 years. So, consider myself American, my, my roots somehow where I grew up as American. But then 15 years ago, I moved to the Netherlands. [00:05:00] I’ve been in the Netherlands ever since.

    And now I have Dutch citizenship, so I’m never going back. But but yeah, so I I’m kind of a mix.

    Alexis: That’s well connected with

    working from anywhere

    and living from where

    you, feel that your, your place, your home is. That’s, that’s really cool.

    Lisette: And it opened me culturally also to understand how different cultures. So just to have an awareness of that so that that also helped

    Alexis: I can totally relate with that. when you are used to work with people on only from the same country, you you start to understand really well the interactions, the way they communicate. And suddenly when there’s someone from another country that don’t have exactly the same norms in term of communication, So when you get to work with people in a lot of different countries that change your perceptions of other people.

    Lisette: Yeah, indeed. And you never think it’s gonna be that big of a deal. I mean, I moved from the US to the Netherlands, so it didn’t seem like it was gonna be that huge [00:06:00] of a culture change. But it’s the little things, it’s all the details. yeah, never underestimate all the details. the

    Alexis:

    Can you recall a, a challenging remote work situation and how you navigated it?

    Lisette: In the early days, all the remote situations were challenging in that it was unusual. It, the internet connection wasn’t good everywhere and so, You know, I say like I was working from the van, but it was quite painful to try to really interact with the teams. For me, the most challenging remote work situations now, now that the tech is better, comes in the personalities of the people that I’m working with on teams.

    Right. So it’s the conflict, it’s the trying to understand somebody else that I think is where . Where it’s super challenging now, even for me at this time, is just really trying to navigate personalities and figuring out why people are the way that they are. Cause [00:07:00] I tend to be very judgmental and defensive, which are not good qualities and, and so it’s extra hard work when something happens to not have that knee jerk reaction.

    Of like, what the heck is going, you know, what the heck? You know, I, I really have to force myself into curiosity mode. So I think for me, that is the most challenging situation. I know it’s not a specific one, but I wrestle with it weekly,

    Alexis: I, like that you are self-aware enough to be able , to catch yourself,

    Lisette: sometimes .

    I’m not, I’m no angel. I’ll admit. I am no angel, but I am working on it,

    Alexis: do you have a real life example where poor communication led to a problem in, in the remote setting?

    Lisette: Yeah, for sure. I’m thinking back when I was on the Management 3.0 team and there there, the team changed quite a lot, people coming in and out. But there’s one a couple people on the [00:08:00] team, actually, there’s one person where they worked at a different rhythm. Than the rest of the team.

    Like they were just so much faster. I don’t know what happened. They were like on, on, I don’t know what it was. They were just like moving at a on freight train speed and the rhythm really threw everybody off and we were having a hard time communicating about it because you don’t wanna tell somebody to slow down like that doesn’t seem, you know, you’re like, you know, you’re too good.

    Because he was kind of taking every pieces of everybody’s jobs because he was just getting ’em all done, and everybody kind of felt like they’re, they’re getting stepped on. So that was a very challenging situation because we all wanted to applaud his enthusiasm, and yet we were all really annoyed by how like many things he was trying to take care of.

    So that was a difficult conversation. And then there was another one where the personalities just didn’t gel. And in that case, It prompted us to create a new section in our team agreement about [00:09:00] how we were gonna handle conflict as a team. Like when it comes up, what steps are we gonna take? Because what ended up happening was everybody was talking behind everybody’s back, and it’s online.

    So you’re just in all these private chats all day, you know, like whispering to everybody back and forth about what’s going on, and it just wasn’t helpful. And so eventually what we ended up doing is one, we brought in an outside facilitator to help facilitate the conversation because everybody was too close to it.

    And the other thing that was odd in that situation was we had a very flat structure. There was no boss, like there was no one in charge. And so when a situation like that arose, there was no manager to make decision. the We just had disagreements and nobody to make the, the top decision on like which way to go.

    And so we brought in an outside facilitator that just had no skin in the game, you know, they were just there to facilitate the conversation and that really helped. And from there we built our processes for the future. [00:10:00] But I have to be honest, we never ended up getting along. We just never liked each other, but I also learned that you don’t have to like each other to work well together.

    You can still work well together and not be friends That’s also okay.

    Alexis: But that’s a, good one about building your team agreements and, evolving your team agreements and maybe sometimes you need That’s okay. ,

    And I like your second point about,

    you don’t need to be friends.

    It’s a, it’s, it’s an interesting one about what are your expectations on, being on the team.

    And for some, people that’s definitely, befriending everybody, and it’s not necessarily helping them or helping the team. So it’s an interesting challenge.

    Lisette: Yeah. Yeah, it’s, it is weird because you have to be professional, but not, I mean, it’s great when you become friends. Some of my closest friends are people that I work with. Like, you know, forever, you know, Canadian Dave, I have worked with him since I was 22 years old and, you know, we’re still friends to this day and yeah.

    But I, I did learn you have to be professional, but you don’t have to be friends. It’s great [00:11:00] when it happens, but it’s not a requirement.

    Yeah.

    Alexis: That’s cool. Okay. so tell me, have you consulted for a company that’s successfully transitioned from the traditional setting to remote work?

    Lisette: I have never consulted really. So I’m not a consultant and I’ve made the distinction early on and I’m wrestling with it now because I’m wondering like maybe I should consult with people. What I have always done is give workshops . so I, what I have done is I go into a company and I give a workshop and we create a super action plan.

    Then usually in the companies that I work with, they’ve got an agile coach, or a Scrum master, somebody on their team that’s helping them integrate these new practices into their everyday work. Because I think with remote work, what it actually is in the end is a change management program, and so, I specialize in giving the workshops and seeding the information.

    And then there’s an agile coach usually, or a consultant already at [00:12:00] company that takes over, the or one of my facilitators, they also do consulting. So anytime a company wants me, to take them through the process, I hand them over to the experts of change management,, or the agile leadership sort of method.

    I don’t specialize in that, but I have interviewed and I have given workshops for hundreds of companies now, well, I wouldn’t say hundreds that have transferred from in-person to remote. That is a more recent phenomenon, but definitely dozens of companies now that have transitioned.

    Alexis: What are the things, the typical things that need to go through or they need to already understand, so it can work.

    Lisette: Yeah. One is I always start people off by saying you really need to start with yourself and creating for yourself a personal user manual for what it is that you need in order to be productive. Get really clear on that so that if you need to be around people, Make sure that you build that into your day or if you really, you know, if you’re not getting enough movement or [00:13:00] whatever your why is that you’re trying to work in this way, really be clear.

    From there, then I always, say, you’ve gotta build a team agreement, and everybody knows this. I’ve been saying it for since the beginning one, one of my first interviews was about creating team agreements and I was like, oh yeah, that seems like an obvious one, and I’ve been teaching it ever since. And yet I would say 85, 90% of all companies that come to my workshops have no team agreement in place. So creating a team agreement is the next thing. And then the other biggest thing that people are running into is communication overload. Too many meetings, too many emails, just the bombardment of information coming in, it’s not slowing down. is the problem, right? We’ve tried filters, we’ve tried flags, we’ve been priori, you know, priorities on the emails, the, the channels. it doesn’t stop the information from coming. And so that is, I would say that is the biggest challenge or one of the biggest challenges that people are struggling with now is when you’re together in the office, [00:14:00] you can kind of manage that information overload by proximity because you’re all together.

    But when you go hybrid especially, or just let’s just say remote flexible first. Let’s say flexible first. So however you’re working, that information overload with everybody in various locations has to be managed differently than we’re doing it now.

    Alexis: Have you observed, an innovative work model, recently that solved those kind of issues?

    Lisette: Yeah, indeed. And, the gold standard for this is WordPress because they’ve been working with their, they created a system, a blogging system called P two years ago and have actually eliminated email from the company pretty much. 15 years ago. And what essentially what they’ve done is every time a decision needs to get made, you know it ha it goes into sort of a sort of blog.

    Sort of post where others can add information to it. Maybe you want a loom video or a link or outside information, right? And everything sort of gets documented. [00:15:00] And over time what it’s done is it’s created an organizational blockchain of all their decisions that get made. And so instead of all these emails going back and forth or a meeting about why is this thing blue?

    They have a record of their organization and all their decisions that they can go back to so that they don’t have to reinvent the wheel all the time. So I find that a really innovative way because they found a way to document things in a, in a way that is useful. Otherwise, you know, it’s just information everywhere.

    So you’ve really gotta organize it. And then another innovative work model that I’ve seen is just a company that actually has, this is one that has recently transitioned from in-person to remote. A company in Germany, and they’re a huge company with thousands of people, and they have started to run hybrid PI planning sessions.

    So for those, I think I know your, your audience is very agile, so you’ll know the PI planning sessions, but these are basically [00:16:00] very large meetings of like a a hundred people. Are planning the next, let’s say two to three months, I think it’s maybe six, seven weeks. I’m not sure how many sprints they’re planning for, but they’re planning for like the next two to three months and they’re doing that all together.

    Usually you wanna do it in the same room with like a big whiteboard with sticky notes and everybody’s there together, but they’re doing it across three time zones, Malaysia, Canada, and Europe. So it’s like 12 hour difference. They’re doing it in a hybrid way, and so I’ve found that just the focus and the attention that they’re putting on that to make it happen, I find it very modern and refreshing.

    It’s not ideal and it’s very hard, but it’s a reality for many teams, right? Of course, you’d wanna do PI planning in the same room together. Of course you would want that, but the reality is you can’t. So then what? And so that’s the innovation there. I’m

    really enjoying

    Alexis: that’s very impressive. [00:17:00] How many people are there, are involved in those hybrid PI plannings.

    Lisette: 100.

    Alexis: Okay That’s quite a lot. Okay. I.

    Lisette: It’s quite a lot. And the, and the guy that did it, he really experimented with it in the beginning. What he did is he actually ran practice sessions with all of the teams before they did an actual PI planning session. And they just did it to get used to, how do you behave on the whiteboard? How is it gonna be used?

    How are we gonna communicate with each other as it’s happening? You know, like, let’s run through a demo together. So they did that. Then they actually ran the session and it’s working. I mean, it’s still painful, but the reality is that they can’t get everybody together.

    It’s just

    Alexis: Yeah, Okay. that’s a, that’s confronting the Brutal reality

    it’s, it’s usually a good idea. But yeah, those big room

    plannings are, when they are in person are, when they are in person and well facilitated, are usually really good. but [00:18:00] when you cannot do it. You need to find another big room and an online one can work.

    It’s interesting. I love the idea of the practice session,

    number of time when you start something and you make the assumption. Don’t ever make assumptions that everybody will be able to use the tools. I. And then you realize that they’re not able to connect, or they are, they don’t understand how to even create a sticky note, and you spend the first half hour to try to explain to people, while others are really frustrated by those people, that’s not really a good start.

    Lisette: Totally yeah, a dress rehearsal is, it was brilliant. It was really brilliant and you know, it took him so much time. , like he really spent a lot of time on this, however, now, they can now do PI planning sessions on a regular basis. You know, anybody new that comes in will be helped by the collective of people that are already working on this.

    And so what he did is he, you [00:19:00] know, he spent a considerable amount of time upfront to get them up and running, but now they’re up and running and they’re only gonna get better from here. Right? So the superpower that this company has now developed, I think was well worth any investment that they made into that.

    Alexis: could you share with us, an anecdote about a remote team building exercise that had really a significant impact?

    Lisette: Yeah, this is interesting. So this one was a hybrid experience that I had, but so I was working with the these people in person and remote, so it was a hybrid situation, but I was the only woman on an all male team, and. I don’t, I, you know, it never, it didn’t even occur to me. It wasn’t a thing, but it was just that I was the only one and it was so o like I was the, you know, so obvious.

    And I was the only American on a team of all Dutch men. So, there’s a lot of differences already and I haven’t naturally enthusiastic personality, and I don’t know whether that’s because I lived in America or it’s just, Who I was [00:20:00] from the start, I don’t know. But I was really trying to tone it down and keep a professional distance with everybody and, you know, just being sort of very professional and not letting my enthusiasm or sort of my natural humor come out.

    Also, my humor doesn’t come across as other Sometimes in languages know, I can really express myself better in English, I . So But I played moving motivators with one of the people at the office. I think he had seen it on my desk or he knew that I was, it was just in the beginning when I was first starting, to work with Jurgen and all of these things.

    And he saw moving motivators and we actually played a game of moving motivators together. And what happened from the game is it turned out that his primary motivator was relatedness, meaning that. He needed to be friends with the people that he worked with. That was really important to him, much more than anything that he was working on.

    And he had been trying to be friends with me and I was like shutting him down. And when I saw that [00:21:00] his big thing was relatedness, it was like this aha moment. And so it allowed me to let the guard down a bit. And we became friends and we’re still friends to this day. And I really, I think I owe it to that game because I didn’t realize he was trying to reach out.

    And so one of the, I guess to bring it back to remote one of the things that I think the context that we sometimes miss when we’re remote is is what people need in order to feel connected on a team. So I think that’s the thing that I learned from that is you really have to ask people what they need in order to feel connected.

    He needed friendship and I was just trying to fit in . So yeah, that, yeah, that was a, that was a mindblower, it was a game changer for me because now I think

    in those terms.

    Alexis: Yeah, I will put links, for the listeners.

    Jurgen is Jurgen Appelo

    moving motivators is one of the

    management 3. 0 [00:22:00] tools.

    So a few things that,

    I will put links to because. Those are really amazing things, and you are absolutely right that that connectedness, that sometimes we are able to build in person more easily, but not always, because you still need to be intentional about it, online, it’ll, you definitely need to be intentional. So using those kind of games, understand the motivations of others. That’s fantastic!

    you are also the host of a podcast I love.

    That’s collaboration superpowers.

    Lisette: Yeah.

    Alexis: Yeah.

    can you tell me about a story that on one of your podcasts that had really a significant impact on your understanding of remote work, remote collaboration.

    Lisette: I mean, there’s been so many. I do the podcasts in order to learn myself. That’s what I mean. I’ve never, I look back and I see how people use their podcast as a sales [00:23:00] tool, and I’m a little bit ashamed ’cause I’ve never even thought about it. Like, for me, the podcast was always a way of networking with people that I wanted to talk to.

    So I’m like looking back, like, how could I use this for, as like a, a sales funnel? But I, I just, it never even occurred to me, which is so silly. So you know, from the beginning I spoke with . These are all things I knew, but they were really reinforced ’cause I was speaking with experts in their field. So there was one Teo Haren, he’s a creativity expert from Sweden, and he wrote a book about why it’s important to change your place when you work.

    And I remember him saying like, if the best place for you to work is at the office, then you need to work at the office. He has yet to meet a hundred, you know, one person that says a hundred percent of the time all year round. The office is the best place to work. So he really solidified for me that it was important for people to change their place just for the sake of creativity and innovation.

    Right? Sitting in that same great cubicle every day was not innovative. So yeah, so that was a mindblower. [00:24:00] When I spoke with Phil Montero, I mentioned this earlier, Phil Montero was one of the leaders in this field way back in the day, and he was just too early. He was like way, way ahead of his time. But he’s the one that came up with the team agreement and in fact, I took it with his permission and ran with it.

    But he’s the one that said to me, you must have a team agreement. And this was reinforced recently by when I spoke with astronaut Paul Richards in January. I wanted to interview him about . Extreme remote collaboration, like remote, like what are, you know, they’re working from space, you know, we’re just talking about time zones between like here in New Zealand, right?

    Like space is different. And what he really said is astronauts train to have the right information at the right place at the right time. And a good example of this is in Houston at headquarters, all the channels are open. Everybody’s listening in on all the channels, right? So it’s just madness. It’s just you can hear and see everything.

    So it’s like having Microsoft Teams and Slacks and everything [00:25:00] open all at the same time, right? Madness. But they all have specific protocols about if you need to get attention in a particular place, or if you need to show somebody something in particular, that there is a protocol that you use and then all of a sudden that person is dialed in, right?

    And so it occurred to me that that is similar to what we need on remote teams. Or hybrid teams, I, I use them interchangeably is that we need intentional working is the superpower. That is the key to making it all work is, you know, there’s no one right method. There’s no one right tool. It’s all about being intentional about how you work together.

    That is the only way, if the astronauts left it to chance, it would be madness. And it’s the same for remote, you can’t leave it to chance.

    Alexis: that’s Very interesting. Once again, the intention is really key. So we spoke a lot about remote and hybrid. how important is face-to-face interaction in that age of hybrid remote work?

    Lisette: I think it’s really important, but I don’t say it’s [00:26:00] critical. I don’t say, I mean, it’s not necessary. You can do team building online. It’s possible. We’ve seen evidence of it in many different places. I have my own anecdotal e evidence that I can share. But face-to-face sure does. It sure does make things faster and it enhances it.

    So it sort of acts as, oh, I’m gonna forget the word. I wanna say enzyme, but it’s not an enzyme. It’s something, it’s, it makes things go faster. It it speeds it up. I can’t think of the word right now. So what I would say is, I mean, my experience with the Management 3.0 team was we worked together for four or five years before we ever got together in person because I was insistent that if anybody could build a remote team, I could do it.

    Right. Like what kind of what? What sad confidence that was. And then we got together in person and it changed the whole thing. Like we got an Airbnb in Portugal in Lisbon and the team went out one night and we just got . I mean, alcohol was [00:27:00] involved. We were very drunk and dancing in the streets of Lisbon and having the best time.

    And it changed the dynamic of the team. We were like a very close, tight-knit team after that, we had really shared something special with that and we’d laugh the whole night and the rest of the weekend. It was great. And from then on we met every six months and it only enhanced the bonds of the team. We were close before, but we were, we were different after.

    I must say it was really different, so now I really recommend that people do it. The thing is, is that I know you can build a a bond without it because I also worked with a woman for nine years. She was in California and I was in the Netherlands. We virtually coworked together for nine years and she was one of my closest friends.

    And so we did finally meet in person right before the pandemic for the first time. And it was fun because I knew, I knew her whole apartment because I’d worked with her for nine years. So I’d like had breakfast with her in the morning. I’d been to the bathroom when she put on her makeup. You know, like, you know, I’d seen, I’d been on [00:28:00] all the dates that she’s been on and the, I didn’t go on the dates with her, but you know, like I got to hear about all the dates that she’d been on.

    So I’d like seen her clothes and helped her pick out outfits and things, you know, like we had a real friendship as if we were hanging out together. it’s possible, it just takes a long time.

    Alexis: it’s very, very interesting to see the difference. the Airbnb aspect of it. I was on, That team, we had a Airbnb too. Cooking the meal together is making you close.

    That’s probably an experience that people need to live from time to time.

    Lisette: Yeah. Yeah. And it’s, you know, there’s just nothing like sharing a big pile of nachos together. and just hanging. It’s, there’s just nothing like that online yet. And yeah, I don’t believe in replacing that either. I think people were naturally like that

    Alexis: So, everything rosy, but do you have a, a real life experience when remote work, remote [00:29:00] collaboration fail?

    Lisette: We see it everywhere. It’s failing now, right? There’s all the return to office mandates that are happening now. So I would say we’re actually seeing remote failing on a mass scale at the moment because leaders are saying that productivity is down, people are disappearing, and culture is suffering.

    Alexis: Mm-hmm.

    Lisette: People feel less connected to the company now, and I, I can’t dispute that. I mean, the data shows that productivity is a bit down. You’re hearing stories of shenanigans, but that’s ’cause those are the fun stories to hear, right? The people that have two to three jobs, the, the people that are just, you know, they’ve got like a robot moving the key, the mouse so that it looks like they’re active.

    And I mean, I think we’re just seeing remote work fails everywhere in the moment. And because it’s not for everybody and if you wanna do it, you really have to set yourself up to do it well.

    Alexis: Hmm.

    Lisette: So, I mean, [00:30:00] yeah, I, I can’t dispute the data. People are, one is people are less connected to the companies, but I also think, you know, that’s somewhat the company’s responsibility also because we need to figure out like, what do people need in order to feel connected to the company?

    Alexis: Yeah, I have the, the feeling that it’s, We are blaming remote work for that lack of connection and lack of engagement. at the same time, when I look at the, the Gallup survey that they are doing for more than 20 years now, engagement was already low for a lot of companies. For a really long time. So,

    yes, we can blame remote work I’m not completely sure the, the, the reason is, is there, and the mandate to be back to the office will really help with that. So, i would encourage people to, to dig a little bit deeper than.

    Lisette: I totally agree. I’ve been saying, and I shouldn’t say that, I shouldn’t say this on a podcast, but Okay. I think that remote work is being used as a scapegoat for [00:31:00] poor management.

    Alexis: Yeah.

    Lisette: I think they’re blaming remote work, but actually it’s, it’s the way that we’re, it’s the way that we’re working. That’s not, that’s not working and it’s, but it has nothing to do with remote.

    It’s just that it’s highlighted by remote. You hide it can’t with remote weirdly enough.

    Alexis: I like that. so, can you tell us about an upcoming workshop or event you are particularly excited about?

    Lisette: Well, I’m experimenting with two new kinds of events, so we all, you know, we have the workshops about remote working. We’ve got one on hybrid and leadership and the work together anywhere is our flagship workshop. And those are all standard well-oiled machines at this point. Like we’ve given them thousands of times, like we know the, the right, the right stuff.

    It’s good. I’m experimenting now with something called an icebreakers playground. The point of this is to just play around with various icebreakers and various tools to understand their effect on group dynamics. [00:32:00] So for example, if you’re trying to get a group to get together and have, have big ideas, you want ’em to think outside the box, right?

    And do something new. Are there exercises that you can do remotely to warm a group up in that way

    Alexis: Mm-hmm.

    Lisette: Or, you know, like maybe it’s a new tool. And so I, I’ve called it the icebreakers playground because one, it’s experimental for me. I don’t know what’s gonna happen. And so, you know, in my designed workshop, I know exactly what’s happen.

    It’s been designed that way, but in the playground it’s really experimental. And so I’m very uncomfortable with the, the improv of it all because it never goes as planned. And yeah, it’s always a bit scary as a facilitator ’cause it never goes as planned. But it’s really fun to play around with all these different activities and exercises for just how to get to know each other and how to create a specific group dynamic.

    And then the second event that I’m working on is virtual coworking sessions. And what these sessions are, are basically[00:33:00] we use the Pomodoro technique. People show up, they say, what are you, what are you gonna get done over the next two hours? And then we, and we do like a quick icebreaker, what are you gonna get done?

    That just lasts less than 10 minutes. And then we do 30 minutes of focused work. We have the camera on and the sound off. Then we take a five minute break, we come back, do 30 more minutes, another five minute break, and then a third 30 minute session. And then we end by checking in with each other for what did you get done?

    How’s it going? And we do a little celebration and then we move on with our day. And they’re just, it’s amazing how much you get done with three 30 fo with 30 minute focus sessions. And it’s amazing how much more you focused when watching other people are there you. Sometimes I’m, you know, like my mind is, I have like monkey brain, right?

    It’s all over the place. And so I’m like, oh yeah, I could. I’m like, no, no, no. I, I’m doing this task. I’m focused here with this person. Oh, no, no, you know, no, no, I’m doing this task. [00:34:00] So it’s, it’s, and it’s really fun. They’re free you know, we’re just playing around with them just to get stuff done and see what it’s like to virtually co-work with each other, what comes up.

    So those are two events I am really enjoying.

    Alexis: That’s fantastic excited about it.

    I know that there’s some tasks that I really want to do. As soon as I start to work on it, I’m already procrastinating and I’m already finding new things to do or things to fix or, or let me do and then, and an hour pass. So I believe, I will go to, in one of the coworking session.

    Lisette: Good. Yeah, that’s exactly what these sessions are for. Like, if you’re at home alone, you know you need to do it. You don’t really have to do it though, right? Like if you don’t get it done, it’s not gonna hurt anything. But it’s, it’s exactly for tasks like that. So yeah, join us. Join us and have some accountability.

    It’s super fun.

    Alexis: That’s very cool. So where can our listeners follow you to get more real world tips on remote work or remote collaboration?

    Lisette: Well, what I’ve done [00:35:00] is I’ve put together I call it a super kit. It’s a remote working success kit and it has a guide for creating your personal user manual, how to set up a team agreement some time zone tips, and it’s got also the super cards, right? So if you’ve got like a PDF where you can print most popular. And you can get that at collaborationsuperpowers.com/superkit.

    Alexis: Excellent. Thank you very much, Lizette, for having joined the the podcast.

    Lisette: Was my honor. Thank ​you!

  • From Zero to 1,000: Building a Scalable Organization with Anne Caron

    From Zero to 1,000: Building a Scalable Organization with Anne Caron

    Startups move fast, until they don’t. Many teams discover too late that the real constraint isn’t product or funding. It’s the organization itself.

    In this episode, I spoke with Anne Caron, People Strategy consultant and former Google HR leader, about what it takes to build a company that can scale, without losing energy, clarity, and trust along the way. Anne is the author of From Zero to 1,000: The Organizational Playbook for Startups, and she brings a rare blend of experience from hypergrowth inside Google and years advising founders.

    Scaling happens in stages, and each stage changes the game

    Anne describes startup growth as five stages: 0–30, 30–75, 75–200, 200–500, 500–1,000 employees.

    Her analogy is memorable: startups grow like children. Parenting a toddler and parenting a teenager are not the same job, and neither is leading a 20-person startup versus a 300-person company.

    • 0–30: the Age of Innocence. Everything is informal. Decisions flow through founders. The risk is structuring too early and killing flexibility.
    • 30–75: Childhood. More autonomy, more roles, more layers. What worked becomes chaotic. Founders need to delegate and build first management foundations.
    • 75–200: Pre-adolescence. People want independence. Experts join. If founders keep control, turnover rises.
    • 200–500: Adolescence. You cannot control everything. You rely on the foundations you laid earlier.
    • 500–1,000: a new level of system. The HR function typically becomes a full strategic capability, often with a VP or CHRO.

    The point isn’t the exact numbers. The point is anticipation. If you wait for pain to force you to act, you will be late.

    Culture is not a poster, it is a lived reality

    Anne breaks culture down into four pillars:

    • Purpose: the origin story, why you exist
    • Mission: what you do now, and how it evolves
    • Vision: what you’re trying to build toward
    • Values: how work is really done inside the company

    Purpose, mission, and vision give direction. Values shape the day to day.

    A crucial warning: values must describe reality, not aspiration. If values don’t match lived experience, people will feel misled.

    Anne also points out something many leaders underestimate: founders influence most of the culture. Not through speeches, but through behavior. If a founder is always late, punctuality will never be a real value, no matter how often it appears on slides.

    Build the people function earlier than you think

    Anne argues that you don’t need HR on day one, but once you approach 30 employees, especially if growth is coming, you need to invest in the people function.

    Hypergrowth often starts around 30–50. Hiring takes time. Waiting until you “need a recruiter” means you are already behind.

    One practical solution Anne suggests: hire a more junior HR profile in-house, and pair them with a senior mentor who can help design what fits your context and culture.

    She also shares a clear threshold: if you are making more than 20 hires a year, it becomes more cost-effective to have an in-house recruiter rather than relying on agencies. Beyond cost, it creates internal learning and strengthens employer branding.

    Candidate experience is employer branding

    Anne makes a simple comparison: you don’t book a hotel based only on the hotel’s website. You check reviews.

    The same is true for hiring. Your reputation is shaped by candidates, including the ones you don’t hire.

    A positive, thoughtful candidate experience is rare, and it becomes a differentiator. People talk. On social media, negative experiences spread fast. Great experiences can create future opportunities, even with people you rejected today.

    Lean performance management supports initiative

    Anne’s view of performance management is broader than forms and ratings. Performance is the result of a system that enables people to do their job.

    That includes clarity, communication, tools for managers, and removing needless friction. It also means avoiding overly complex processes that slow down initiative.

    High performance often comes from empowerment, autonomy, and an environment that encourages people to take responsibility and make decisions.

    On metrics, Anne makes a helpful distinction:

    • KPIs are like a dashboard: they tell you when something is off.
    • OKRs can help drive initiatives, but they should not be used as a direct mechanism for compensation decisions.

    Both are indicators. The work is in how leaders interpret them and act on them.

    One final reminder: take time to think

    Anne closes with advice that sounds simple, and is often ignored:

    Many people issues can be resolved with reflection and common sense.
    Before creating a new process, look for the root cause: information, training, clarity, tools, leadership behavior.

    Processes do not prevent bad things from happening. Building the conditions for good work does.

    If you are scaling a company, this episode is an invitation to do the foundational work early. Not to copy what Google or Netflix did, but to define what fits your identity, your context, and your ambition.

    Listen to the episode

    You can listen to this episode on your favorite platform: AnchorSpotifyBreakerGoogleApple

    Take the time to think. Many people-related issues can be resolved with some reflection and common sense. Instead of setting up processes for every problem, try to address the root cause.

    Anne Caron

    References

    Here is the transcript of the episode

    Alexis:

    Welcome to Le Podcast on Emerging Leadership, I am Alexis Monville! In today’s episode, we have the privilege of hosting Anne Caron. An international speaker, author, and consultant, Anne brings a decade of experience as a senior HR executive from the tech giant, Google. In 2015, she channeled her expertise into her consulting practice, guiding founders in sculpting high-performing and positive organizations. Her deep-rooted experience with entrepreneurs led her to craft a unique methodology for startups, aiming to cultivate the right organizational structure and team dynamics. This methodology is beautifully encapsulated in her book, ‘From Zero to 1,000’. Today, we’ll be delving into Anne’s journey, her insights on building successful startups, and the essence of her book. Welcome, Anne!

    Anne:
    Thank you very much for having me, Alexis.

    Alexis:
    Could you give us a brief introduction about yourself?

    Anne:
    Certainly. I’m a people strategy expert, which means I focus on the human side of organizations. I’ve been doing this for the past eight years, supporting startups in building their people-oriented structures. Before that, I was with Google for 10 years. I joined in 2005 when the company had only 5,000 employees globally, and in Europe, there were 1,500. At that time, people recognized Google as a search engine, but few knew about its potential as an employer. I was hired to establish Google as a top employer in the region and to develop initiatives around talent attraction and sourcing strategies. By the time I left a decade later, the company had grown to 65,000 employees, presenting a whole new set of challenges.

    Anne:
    The challenges shifted from attracting talent to optimizing processes to handle the high volume of applications we received, which was in stark contrast to the situation a decade earlier.

    Anne:
    After those 10 years, I felt the need to return to a building phase, which led me back to the startup ecosystem to assist founders in structuring their organizations for growth.

    Alexis:
    What inspired you to delve into the world of startups and organizational development?

    Anne:
    I noticed a gap. Many startups prioritize product development, revenue, and capital raising but often neglect organizational structure until it’s too late. I saw a pressing need to support them early on, especially the founders and CEOs. While HR is essential, there’s more to people strategy than just the typical HR operations. Another motivation stemmed from my time at Google. While I learned a lot about creating a positive work culture, I noticed that as Google grew, many of its processes became similar to other large corporations. This lack of innovation was partly due to rapid growth, which often led to hiring individuals familiar with large-scale operations. These individuals would sometimes hastily implement processes they knew from other organizations without fully understanding Google’s unique culture and needs.

    Anne:
    This experience made me keen to study how we can consciously identify and define what an organization truly needs, rather than just replicating processes from other companies.

    Alexis:
    I noticed a glowing endorsement on the cover of your book from a former Senior Vice President of People Operations at Google. Can you share more about your shared experiences at Google? I particularly enjoyed his book “Work Rules!” as it highlighted practices at Google that seemed effective. Were there aspects that inspired you to think more proactively?

    Anne:
    Absolutely. I had the pleasure of working with him [Laszlo Bock] and found him to be an inspiring leader. His book provided valuable insights into the workings of a company that many startups admire. There are several books out there, like those about Google, Netflix, and Amazon, that describe how these companies achieved success. However, what worked for Google was tailored to its unique identity, shaped by its founders Larry and Sergey. While these examples are inspiring, they aren’t necessarily a one-size-fits-all playbook. Every company, like every individual, has its unique characteristics.

    Anne:
    When I began my consulting practice, my goal was to develop a methodology to help founders understand their identity, vision, and work culture. Towards the end of my time at Google, I noticed some discrepancies between the models we implemented and the company’s values. Initially, Google’s culture and values were incredibly strong and aligned.

    Alexis:
    That’s insightful. In your book, you discuss the different stages of a startup. Could you walk us through these stages and the unique challenges each presents?

    Anne:
    Certainly. I’ve defined five growth stages for startups, ranging from 0 to 1,000 employees. The last stage, from 500 to 1,000 employees, usually has its foundational elements in place. But starting with the first stage, from 0 to 30 employees, I refer to it as the “Age of Innocence.” I often compare a startup’s growth to the development of a child. The challenges and management strategies for a startup are akin to raising a child, and the issues faced at each stage differ significantly.

    Anne:
    Parenting a 10-year-old is different from parenting an 18-year-old. Similarly, I describe the stages of a startup’s growth. The first stage is like the baby phase. Everything is new and exciting. Everyone knows each other, and decisions are made collectively. If there’s a question, it’s directed to the founders. There’s a general feeling of excitement and commitment. It’s a positive time, though not without challenges. This phase is often remembered fondly, much like looking back at a baby’s early days. This is the “Age of Innocence.” The challenge here is that some founders, especially those from corporate backgrounds, try to structure too quickly. In this early stage, you don’t need many processes. Everything happens organically. Overstructuring can reduce the flexibility, which is a startup’s main competitive advantage. It’s essential to reflect on the organization’s identity, goals, and values. Often, founders are preoccupied with product development, revenue, and fundraising.

    Anne:
    The second stage is “Childhood,” when the startup begins to walk and gain some autonomy, typically between 30 to 75 employees. This is often during the Series A or B funding rounds. The focus shifts from survival to serving more customers. The informal culture that worked initially becomes chaotic and less effective. New roles emerge, and layers are added, creating a distance between the team and the founders. This can lead to confusion about priorities. Early joiners might feel discontented with the new layers, and some managers might not be suited for their roles. It’s crucial to build foundational structures and develop people management capabilities. Founders often struggle to delegate, which can slow down processes.

    Anne:
    From 75 to 150 employees, we enter the “Pre-adolescence” stage. There’s a desire for more independence and autonomy. As more experts join the team, it’s vital to delegate and allow them the space to make decisions and manage their teams. If not, it can lead to high turnover rates.

    Anne:
    From 200 to 500 employees, we enter the “Adolescence” phase. At this point, you can’t control everything anymore. It’s like having a teenager; you can’t dictate their every move. You have to trust that you’ve laid the right foundations from the start. As a CEO or founder, you can’t be on the ground with the teams, guiding them at every step. That’s why establishing a foundation early on is crucial. From 500 to 1,000 employees, you typically have a competent HR team in place, led by an HR VP or Chief HR Officer, who can strategize and plan for the next phases.

    Alexis:
    It’s interesting how you’ve related the growth stages to child development. Going back to what you mentioned about Google, due to rapid growth, there’s a tendency to hire people who’ve done it before, even if they just replicate what they know from previous roles. This might not align with the original vision of the company.

    Anne:
    It’s okay to hire experienced individuals, even if they don’t have startup experience. However, they need time to understand and absorb the essence of the organization. They should design strategies that fit the specific culture of the company. Moreover, they should be comfortable navigating ambiguity, which is common in startups.

    Alexis:
    In your book, you discuss three steps to building a positive and scalable organization. Could you delve into these steps?

    Anne:
    Certainly. The first step is defining who you are, what you’re doing, and where you’re going. Without this clarity, you can’t build anything substantial. The second step is defining your company culture, which will shape your business strategy and organizational design. There are four elements to company culture: purpose, mission, vision, and values. The purpose is your origin story, explaining what brought you to this point. The mission represents your current state, a moving target that evolves with the company. The vision is your end goal, describing the future you’re working towards.

    Anne:
    The three elements – purpose, mission, and vision – serve as the GPS of your organization. The mission acts as the vehicle, bridging the gap between the purpose and the vision. This GPS represents the overarching business strategy, which is typically broken down into ten, five, three, two, or one-year plans. These incremental steps lead you towards your ultimate goal. Without this framework, it’s challenging to have a cohesive business strategy and ensure everyone is aligned. The fourth element is the company’s values. These values determine how work is conducted within the organization. They should reflect the actual experience of working with you, not an aspirational version of who you wish you were. If these values are genuine and authentic, they’ll attract the right people. However, if they’re just aspirational, new hires might feel misled.

    Alexis:
    So, it’s about being true to who you are?

    Anne:
    Exactly. Eighty percent of a company’s culture stems from its founders. For instance, if a founder is habitually late to meetings, it’s unlikely that punctuality will be a practiced value, regardless of whether it’s listed as one. It’s essential for founders to approach this with honesty and humility. If a company claims to be innovative or empowering, these qualities should be evident in every aspect of the organization. Every process should encourage innovation and empower its people. This foundational step is crucial. Without it, you might end up merely copying others because you lack the essential elements to customize and design the right organization for you. The next step is building your people function. This involves hiring an HR team on time and establishing the basics before adding perks like TGIFs or bean bags. It’s about getting the essentials right first.

    Alexis:
    That makes sense. So, it’s about establishing a strong foundation and then building upon it?

    Anne:
    Precisely. If you don’t pay your employees on time, no amount of bean bags will make up for it. Once the basics are in place, you can introduce additional perks.

    Anne:
    Once the foundational values are established, you can begin to build systems that drive performance within teams. A significant part of this is equipping managers with the right tools and resources. However, the CEO and leadership team play a pivotal role in communication. While there are essential tools to facilitate this, my primary focus is on lean performance management. Overly complex processes can stifle initiative, and high performance often arises from taking initiative, making decisions, and feeling empowered.

    Alexis:
    So, the values serve as the foundation for subsequent steps, and everything built afterward should align with these values?

    Anne:
    Exactly. For your values to be genuinely lived and breathed, they need to be reflected in every process and policy. When these are in sync, both the values and the system are strengthened. If they’re not aligned, neither works effectively.

    Alexis:
    It’s clear that establishing these foundations early on is crucial, or there will be repercussions later on. Can you delve deeper into the creation of the people function? How does it align with the startup stages you previously outlined?

    Anne:
    In the early stages, I don’t necessarily recommend hiring a dedicated HR person. However, as you approach 30 employees, especially if you anticipate rapid growth, it becomes essential. Hypergrowth typically starts around 30 to 50 employees, and you’ll likely double or even triple in size within six to twelve months. Given the pace of this growth, you can’t wait until you have hiring needs to bring in recruiters. Recruiting takes time, and if you haven’t started early, you’re already behind. A good practice is to hire your first HR person around the 30-employee mark.

    Alexis:
    But what kind of HR profile should startups look for at that stage?

    Anne:
    That’s a challenge. At 30 employees, startups might not have the budget for a senior HR person, nor the scope of work to keep them engaged. Yet, they need the expertise of a senior HR professional to design and adapt policies and frameworks to their culture. A solution I’ve seen work well is to hire a junior HR person with a few years of experience and pair them with a more senior HR mentor. This mentor can guide them in designing processes tailored to the organization’s needs. Once you’re making more than 20 hires a year, it’s more cost-effective to have an in-house recruiter rather than relying on agencies. This approach also helps in building internal knowledge and focusing on employer branding.

    Alexis:
    That makes sense. So, it’s about balancing immediate needs with long-term growth and strategy.

    Anne:
    Precisely. With more than 20 hires in a year, having an in-house recruiter is a no-brainer.

    Alexis:
    So, when you’re building your employee experience, it starts from the moment you contact them or when they reach out to you, right?

    Anne:
    Exactly. Employer branding isn’t just about having an attractive career page on your website or showcasing photos of your office. Think about it like choosing a hotel for a vacation. Do you rely solely on the hotel’s website, or do you check reviews on Tripadvisor? It’s the experiences and opinions of those who’ve been there that matter most. This includes people who’ve interviewed with your company. Ensuring a positive recruiting experience can set you apart. It’s rare, but not complicated, to provide a memorable experience for candidates.

    Alexis:
    Absolutely. Those who interview with your company will share their experiences, and that feedback will shape your company’s reputation.

    Anne:
    With the prevalence of social media, negative experiences spread quickly. It’s rare to hear someone rave about a fantastic interview experience. To achieve that, you need to create a “wow” experience. I’ve written an article on LinkedIn called “The Cookie Effect” about creating such experiences. Even if you don’t hire someone now, if they speak highly of you, there might be opportunities in the future. It’s essential to leave a positive impression on everyone, even those you don’t hire.

    Alexis:
    That’s a great perspective. I’ll link to your article in our broadcast. You mentioned building a performance management system and also brought up OKRs. Are these two concepts connected?

    Anne:
    Yes, OKRs are related to performance management. But in essence, everything ties back to performance management. Performance is about accomplishing tasks, and performance management is about creating a system that enables people to do their job effectively. Everything we’ve discussed, from defining culture to ensuring employees don’t have logistical concerns, contributes to performance. Many factors, both internal and external to the company, influence an individual’s performance.

    Alexis:
    So, on one side, we have metrics showing how your business is running, and on the other side, we have new initiatives measured or driven by OKRs?

    Anne:
    Exactly. KPIs are like your car dashboard, providing a quick summary of essential metrics. They show you when there’s an issue, like low oil or gas levels. However, neither KPIs nor OKRs should be used solely to make decisions on salary or development. They are indicators that inform us and help us make decisions and manage people.

    Alexis:
    That’s insightful. As we wrap up our discussion, what’s one piece of advice you’d like to leave our listeners with?

    Anne:
    Take the time to think. Many people-related issues can be resolved with some reflection and common sense. Instead of setting up processes for every problem, try to address the root cause. Processes won’t prevent bad things from happening. Often, issues arise because someone wasn’t informed, trained, or equipped properly. Addressing these human aspects can be more effective than relying on processes.

    Alexis:
    Where can our listeners connect with you and learn more about your work?

    Anne:
    I’m active on LinkedIn, where I regularly post articles and reflections. They can also reach out to me through my website and learn more from my book. I’m always open to having a chat.

    Alexis:
    Thank you, Anne, for sharing your invaluable insights and experiences with us today. Your journey and the methodology you’ve developed are truly inspiring for founders and leaders aiming to build positive and high-performing organizations. To our listeners, if you wish to dive deeper into Anne’s approach and learn more about her work, I highly recommend her book ‘From Zero to 1,000’. It’s a treasure trove of wisdom for anyone in the startup ecosystem. Thank you for joining us on Le Podcast on Emerging Leadership. Until next time, keep leading and keep inspiring!

    Anne:
    Thank you for having me. It was a pleasure.

    Photo de Ales Maze sur Unsplash

  • Radical Product Thinking: A conversation with Radhika Dutt

    Radical Product Thinking: A conversation with Radhika Dutt

    In this episode, I had the pleasure to talk with Radhika Dutt, author of Radical Product Thinking: The New Mindset for Innovating Smarter.

    Radhika has lived the full spectrum: engineering, startups, big organizations, and years of learning the hard way. What makes her work so compelling is how clearly she names the patterns many teams fall into, and how practical her framework is for escaping them.

    From product diseases to a new mindset

    Radhika starts with a story from her first startup, where the team caught what she calls Hero Syndrome. Their ambition was real, but their vision was vague: “revolutionize wireless.” It sounded exciting, but it did not tell anyone whose world they were changing, what problem they were solving, or what “success” would look like.

    Over time, she kept seeing similar patterns across organizations: teams moving fast, doing a lot, and still feeling stuck. In 2017, she asked a simple question:

    Are we all doomed to learning product leadership through trial and error, or can we build products systematically and avoid these predictable traps?

    That question became Radical Product Thinking.

    Beyond “fail fast”: vision driven, hypothesis driven

    Radhika challenges a common Silicon Valley assumption: that the best way to build products is endless iteration and pivoting.

    Iteration can hide a painful truth. Most teams can only afford a small number of pivots before they run out of money or momentum. When teams keep trying random directions, they lose the sense that they are learning. The work becomes demoralizing.

    Radhika links this iteration led mentality to the venture capital model: fail fast, learn fast, move on. That model can produce unicorns, but it is not proof that it is the best way to build products. Survivor bias is not a method.

    Her alternative is not “don’t iterate.” It is: build with clarity. Define the change you want. Make hypotheses. Plan actions. Measure whether it works. Learn in a way that preserves momentum.

    The Radical Product Thinking framework in five parts

    Radhika describes five components that work together:

    1. Product vision
    2. Strategy
    3. Prioritization
    4. Hypothesis driven execution and measurement
    5. Culture

    It is a full system. Not a workshop artifact you file away.

    1) Product vision that is specific, not vague

    A powerful moment in the conversation is when Radhika reframes vision.

    A “good vision” is often taught as broad and grand: disrupt an industry, revolutionize a technology.

    In Radical Product Thinking, a good vision is detailed. It answers:

    • Who are you trying to help
    • What problem do they have and what do they do today
    • Why is the status quo unacceptable
    • When will you know you have arrived
    • How will you bring that end state to life

    This level of clarity changes everything. It makes alignment possible. It gives teams a real target.

    2) Strategy grounded in real pain points

    Radhika then introduces a mnemonic for strategy: RDCL, like “radical.”

    • R: Real pain point
    • D: Design of the solution
    • C: Capabilities required underneath
    • L: Logistics: delivery, business model, training, partners, operations

    This last part, logistics, is often skipped. Many teams act as if the business model can be bolted on later. Radhika insists it must be part of the strategy from the start.

    A crucial detail: a pain point is real only if it is validated, meaning verified plus valued.

    Verified: you observed it.
    Valued: people are willing to give something up for it to be solved.

    3) Prioritization as leadership at scale

    This is one of my favorite parts.

    Radhika reframes leadership: it is not telling people the top three priorities. It is enabling people to make good tradeoffs when you are not in the room.

    Prioritization becomes a way to scale your intuition.

    Her tool is a simple but powerful map:

    • Y axis: vision fit
    • X axis: survival fit

    This creates four quadrants:

    • good for vision and survival
    • investing in the vision
    • taking on vision debt
    • neither

    A key idea is naming vision debt when you take it on. Saying it out loud protects trust. It signals that you are not abandoning the vision. You are making a conscious tradeoff.

    Radhika also highlights the usefulness of a survival statement: what does “survival” mean right now for this product? Cash, stakeholder support, time, credibility. Make it explicit, so decisions become less political and more objective.

    4) Execution and measurement without gaming the system

    Radhika makes a thoughtful critique of how OKRs are often used.

    The goal of execution and measurement is to test whether strategy is working. That requires hypotheses and metrics tied to the assumptions inside your strategy.

    When measurement becomes an exam, people optimize for looking good. That invites sandbagging and metric manipulation. Radhika advocates for a more collaborative approach: measure to learn, not to prove.

    5) Culture: purpose, autonomy, psychological safety

    Radhika defines culture through the conditions needed for innovation:

    • shared purpose
    • autonomy
    • psychological safety

    Purpose and autonomy are reinforced by earlier parts of the framework. Psychological safety is about reducing politics and creating conditions for meaningful work.

    Her culture lens is very usable: two dimensions

    • fulfilling vs non fulfilling
    • urgent vs non urgent

    The goal is to maximize the quadrant of fulfilling, non urgent work and minimize the other three:

    • fulfilling but urgent: heroism
    • not fulfilling but urgent: organizational cactus
    • not fulfilling, not urgent: the soul sucking quadrant

    Then she delivers a beautiful shift:

    Your organization itself can be treated as a product that serves employees.
    You can define pain points, craft strategies, test hypotheses, measure improvements, and refine culture over time.

    A mindset shift that changes the conversation

    What I took from this episode is not just a framework. It is a shift in how you lead:

    • from iteration without direction to vision with hypotheses
    • from top down prioritization to tradeoffs people can make themselves
    • from measuring to judge to measuring to learn
    • from “culture happens” to culture as something you can design and improve

    If you care about building products that matter, and building teams that can sustain innovation, this conversation will give you both language and tools.

    If you’re interested in learning more about Radical Product Thinking, you can find her book in bookstores or visit her blog at radicalproduct.com. Join us for our next episode as we continue exploring the fascinating intersection of leadership, innovation, and the future of work. Until then, keep leading the change.

    Transcript

    00:00.00

    Alexis Monville

    Welcome to the podcast on emerging leadership. I’m Alexis Monville. Today we are thrilled to have with us Radhika Dutt. Radhika is an innovation and program product management expert. She is the author of the book “Radical Product Thinking: The New Mindset for Innovating Smarter”. Radhika has worked globally across diverse sectors, from startups to giants. Welcome, Radhika.

    00:21.93

    Radhika Dutt

    Thank you. Thank you for having me and I’m so excited to be here with you today.

    00:25.86

    Alexis Monville

    Thank you, Radhika. Could you please introduce yourself to our audience and share a bit about your background and the work you do.

    00:35.45

    Radhika Dutt

    Sure, so my background is that I started out as an engineer. I studied engineering at MIT and I became an entrepreneur soon after. My first startup was called Lobby 7 and we started this with a group of co-founders. There were five of us in total and we started it while we were still in our dorms at MIT. My whole experience has been through entrepreneurship and then working at larger companies and making mistakes along the way. For example, my first startup Lobby 7 was where we caught the “Hero Syndrome”. What I mean by that is our tagline and vision statement was to “revolutionize wireless” and our tagline was “enlightened wireless”. If you ask me now what does that mean, what did you mean by “revolutionizing wireless”, I’m really not sure. All we knew was we wanted to be big. That was all that mattered and that is “Hero Syndrome”. So that was the first “product disease” I caught and along the way there were other product diseases that we caught.

    01:48.68

    Alexis Monville

    Um.

    01:59.93

    Radhika Dutt

    I’ve worked in different organizations and kept seeing product diseases. Over time, as I learned from these product diseases and learned to do better, I then watched other people make these mistakes and had to watch them suffer through it. The burning question for me in 2017, after almost twenty years of experience, was: Is it that we’re all doomed to learning from trial and error or is there a way we can learn to build products systematically so that we can avoid these product diseases? That’s how “Radical Product Thinking” was born.

    02:37.48

    Alexis Monville

    Wow, excellent. I’m glad you’re touching on the product diseases, that’s really something that is interesting. In “Radical Product Thinking”, you’re describing the approach, but you really start to say it’s really a mindset change. I believe there’s an exchange between Alice and the Cheshire Cat in Alice in Wonderland that is inspiring that and making it easier to understand. Can you tell me more about that mindset change?

    03:12.24

    Radhika Dutt

    Yes, so the mindset change we need is moving away from the belief that the best way to build products is through iteration. This Silicon Valley mentality of trying different things and putting them on the market to see what works has led us to continually pivot and iterate until we find something that works. However, this mindset disguises the fact that a team can typically only afford 2 to 3 pivots before they run out of money or momentum. Teams lose momentum as they begin to feel they don’t know what they’re doing. They’re just trying different things, and it can become demoralizing when they don’t feel they’re making progress.

    03:50.30

    Alexis Monville

    Go on.

    04:06.38

    Radhika Dutt

    Teams need to feel they’ve learned something and have a clear next step. This iteration-led mindset needs to change. We need to become more vision-driven. We need more clarity on the problem we’re solving, our set of hypotheses, our planned actions, and how we will test if it’s working. We need a more systematic approach. It sounds obvious, but then one might wonder how we ended up with this iteration-led mentality. The answer is that it’s baked into the venture capital (VC) business model.

    Venture capitalists invest in multiple startups, needing only one to succeed big for a return on investment. In fact, they want startups to fail fast so they’re not continually investing in something that’s not going anywhere. This “fail fast, learn fast” mentality originated from the VC model.

    05:23.17

    Alexis Monville

    Yes?

    05:37.14

    Radhika Dutt

    While this VC model has led to some unicorns, it doesn’t mean it’s the best way to build products. It’s more survivor bias than a proven method. Entrepreneurs need to realize that world-changing products often come from a more systematic and deliberate approach.

    06:06.21

    Alexis Monville

    So what would be the pillars of the Radical Product Thinking philosophy when looking at this?

    06:14.91

    Radhika Dutt

    The first pillar is seeing your product as a mechanism for creating the change you want. Until now, we’ve thought about a product as a physical or digital thing and its success as the end goal. We need to start with clarity on the change we want to bring about before we build the product.

    The second pillar is that your product is only successful if it creates that change.

    The third pillar is the idea that you can build your product systematically. In other words, you can engineer the change you want to bring about by starting with a clear vision of the end state. This vision then translates into strategy, priorities, hypothesis-driven execution and measurement, and culture. These five elements – vision, strategy, prioritization, hypothesis-driven execution and measurement, and culture – make up the Radical Product Thinking framework.

    07:50.41

    Radhika Dutt

    This step-by-step framework allows you to create visionary products systematically.

    07:56.59

    Alexis Monville

    To clarify, could you tell us more about the first element of the framework – product vision? When I hear “vision,” I’m tempted to think of grand visions and ambitions that aren’t really grounded in reality, but I believe that’s not what you’re referring to.

    08:17.91

    Radhika Dutt

    Exactly. We have to discard much of what we’ve learned about what constitutes a good vision. We’ve been taught that a good vision is broad, such as revolutionizing wireless or disrupting a particular industry. But in the Radical Product Thinking approach, a good vision is detailed and answers the who, what, why, when, and how questions.

    By this, I mean: whose world are you trying to change, and it’s not everyone’s world. What exactly is the problem and what’s the solution they’re using today? Why is the status quo unacceptable? When will we know that we’ve arrived, or in other words, what does the end state look like when this problem is solved? And finally, how are we going to bring this about with our product?

    Let me give an example to make it clear. The Radical Product Thinking format gives you a fill-in-the-blank statement to help you answer these questions. Here’s an example of a vision statement for a startup I had many years ago:

    “Today, when amateur wine drinkers want to find wines that they’re likely to enjoy, they have to pick attractive-looking wine bottles at the wine store or try wines that are on sale. This is unacceptable because it’s hard to learn about wines this way and leads to many disappointments. We envision a world where finding wines you like is as easy as finding movies you like on Netflix. We’re bringing about this world through a recommendations algorithm that matches wines to your taste palette and an operational setup that delivers these wines to your table.”

    11:07.18

    Alexis Monville

    That’s a product vision. It’s not grand, but it’s very clear about the problem and the change it will create for wine enthusiasts.

    11:27.86

    Radhika Dutt

    Exactly. This vision isn’t about changing the world for everyone. It can be for a very specific group of people. The clarity it brings is such that even if I hadn’t told you anything about my startup, by the end of the vision statement, you knew exactly what we were doing and why we were doing it.

    11:49.55

    Alexis Monville

    Absolutely. So next up in the framework is strategy. Could you tell us a bit more about that?

    12:00.23

    Radhika Dutt

    Yes, let’s discuss the problems we face today with strategy. Most company strategies I see usually read something like this: “We’re going to build XYZ in terms of a feature set or products. This will require an investment of X million, and we’re planning to launch it in these markets. The expected return will be such and such.” This type of strategy is quite vague, I’d say. So, what does a good product strategy look like instead? The mnemonic is RDCL, standing for Radical, where we ground it in the real pain points. The word ‘real’ is emphasized because we want to distinguish it from the imaginary pain points.

    Firstly, we must ask the question, “What makes someone come to the product?” This question then leads to the ‘D’ in RDCL, which stands for Design. What is our solution to the pain that brings people to the product?

    The ‘C’ stands for Capabilities. This involves asking, “What’s the underlying engine that powers this solution?”

    Finally, ‘L’ stands for Logistics. This involves asking, “What is the business model? How are we going to support this product? What training is required?” All these questions about how we will deliver the solution to the customer are often overlooked. When we build products, we usually say, “Okay, first we’ll build a product and then we’ll attach a business model at the end.” Without thinking about it comprehensively, which is what we want to avoid with this question ‘L’. Let me walk through an example of how this RDCL comes together. If I go back to the wine example…

    13:53.21

    Alexis Monville

    Sure…

    14:03.10

    Alexis Monville

    Yes, please do.

    14:11.84

    Radhika Dutt

    Our startup likely had a real pain point. People were coming to this product because if they wanted to learn about and try wines, they didn’t want to read magazines that used language that felt intimidating. They wanted to learn in an easy and fun way, and find wines that they liked. That’s the real pain point that drew someone to the product.

    The design aspect comes in when I consider that I can’t ask you questions about your tastes by asking things like, “Alexis, how much tannin would you like in your wine and how much acidity would you prefer?” Those types of questions are difficult for most people to understand and answer clearly, right?

    15:01.47

    Alexis Monville

    Yes, those are expert questions. Not many people would know how to answer them, maybe just 1% of people would be able to answer them with absolute certainty.

    15:10.76

    Radhika Dutt

    Exactly, so we ask questions that are much simpler. For example, I can infer how much tannin you might like based on how you prefer your tea or coffee. If you like it black, you probably enjoy more tannins than if you take your coffee with milk and sugar. Similarly, by assessing which fruits you prefer in a fruit salad, I can gauge how much acidity you enjoy on your palate. We can construct a quiz based on all of this. That’s the design.

    The capabilities then involve mapping this to a set of wines. We have to create a database that correlates wine varietals, among other things, to such tastes. Then there’s logistics, where we consider our business model. We could charge a business model where you buy one wine at a time. But what we came up with was a subscription model, creating wine courses where you progress through the courses by tasting different wines and learning along the way.

    These are examples of how this all comes together. I’ll give you another example of logistics – we didn’t have an inventory of wines we were supplying. So, we had to collaborate with partners who prioritized customer service.

    16:41.12

    Radhika Dutt

    We had to find stores that had their inventory and could implement this model using our approach. That’s another example of logistics. So, that’s a comprehensive Radical strategy.

    16:48.15

    Alexis Monville

    I’d like to revisit real pain points. When you say real pain points and not imagined, does that mean you’ve verified that your users actually consider these as genuine pain points? How do you go about doing that?

    17:13.60

    Radhika Dutt

    That’s a great question, and it’s often where we stumble as product people or in innovation in general. We often assume that a pain point is real because we think it is. The formula for determining whether a pain point is real is that you must validate it. Validated equals verified plus valued. What this means is, ‘verified’ is when you’ve personally observed that someone has this issue. This could involve conducting user interviews or going out into the field to watch people in action to discern if they truly have this pain point.

    But even when I mention user interviews, we can’t directly ask, “Is this a pain point for you?” People usually aim to please you and are likely to give you the answer they think you’re hoping to hear. A good user interview is one where you ask questions that seem neutral, but from which you can ascertain the pain point.

    The second component, ‘valued’, is about whether someone is willing to give up something or invest something in exchange for having that problem solved.

    18:24.57

    Alexis Monville

    I see…

    18:39.73

    Radhika Dutt

    For instance, even with a free service like Facebook, people are willing to invest their time into it, so there is some sort of an exchange. They’re willing to give up their privacy. We can discuss the ethics of this separately, but the question of verified plus valued is crucial in determining if the pain point you’re trying to address is real.

    19:06.48

    Alexis Monville

    Absolutely, I understand. I really like the question, it’s very useful. Moving on to prioritization, could you talk about its importance and how it’s effectively implemented?

    19:18.54

    Radhika Dutt

    Yes, one of the things that often happens is that we work on a vision, and that vision often gets filed away for posterity. It’s like, “Okay, we’re done with that exercise. Let’s proceed with our everyday tasks now.” But prioritization is where we can bring that vision into our everyday decisions. This is incredibly important for leadership.

    We often think that good leadership is about telling our teams what the top three priorities are. However, what I’ve come to realize is that good leadership is about being able to scale your thinking, enabling every person to understand your rationale for the trade-offs you’re making. This way, you don’t have to be in every meeting, but people know exactly what the right trade-offs are to make. That is what good leadership is.

    So how do you do that? A lot of your rationale as a leader comes from years of experience and it’s often intuitive; you just know what the right trade-off to make in a given moment is.

    20:31.70

    Radhika Dutt

    The hardest thing for leaders is to communicate your intuition. In the Radical Product Thinking way, the way you do that is by recognizing that when we make these trade-offs, we’re really balancing the long-term against the short term. It’s the yin and yang of long-term versus short term.

    In engineering terms, this yin and yang gets converted into an X and a Y axis. Your Y axis represents whether something is a good vision fit or not, and the X-axis represents whether something is good for survival or not. So now you have this X and Y of long-term versus short-term considerations.

    21:09.21

    Radhika Dutt

    Things that are good for the vision and good for survival are, of course, the easy decisions. But if we always just focus on these easy decisions, then we’re still being quite shortsighted. Sometimes we need to do things that are investing in the vision. This quadrant is where it’s good for the vision in the long term, but in the short term, it’s not helping you survive.

    An example of investing in the vision could be spending three months refactoring code, or taking the time to do some user research.

    21:31.23

    Alexis Monville

    I see…

    21:44.92

    Radhika Dutt

    Your customers might not see immediate benefits, but it’s essential to do for the long run. That’s an example of investing in the vision. The opposite of that, by the way, is taking on vision debt. Vision debt is where something is good for survival, but it’s not helpful for the long-term vision. An example of this is if your customer says, “If you build this custom feature for me, then I will sign the contract.” If you keep doing this, it adds lots of vision debt.

    22:21.17

    Radhika Dutt

    Over time, you may end up with what I call obsessive sales disorder. This is not to say that any of these quadrants are bad per se, but we have to be really mindful about how we’re making these trade-offs. As a leader, when you decide that you need to take on this vision debt, one of the most important things is even recognizing and telling your team that, “Look, I understand that we need to win this deal. We’re taking on vision debt.” By acknowledging that it’s vision debt, you’re not making the team feel like this is a top-down loss of confidence in the vision. At least your team feels like you understand the trade-off now.

    23:10.56

    Alexis Monville

    Excellent. You even discuss in the book the idea of a survival statement. You can have a product vision statement, but you can also have a survival statement to help the team understand what you mean by survival at that moment in time.

    23:28.63

    Radhika Dutt

    Right, exactly. When we chart vision versus survival, one of the goals is to make these decisions less contentious. Instead of “I think we should do this” versus “No, I think we should do this,” when you plot vision versus survival, it makes the discussion more objective. Are we not aligned on where this fits on the vision fit, or are we not aligned on how this is helping us survive or making survival harder?

    We’ve defined the vision with a lot of clarity, answering the who, what, why, when, and how, but similarly, we should define what it means to survive. For a startup, survival might mean financial survival—I need the money to survive. If I don’t bring in the money, either through fundraising or winning a deal, my product is going to die because of financial survival.

    24:42.56

    Radhika Dutt

    However, let’s say I’m in a big company. Maybe my company has money in the bank, so what kills my product is not necessarily financial survival, but it might be stakeholder support. Maybe if my bosses don’t approve of my product, then that’s going to kill my product, and so survival might be pleasing stakeholders. Writing a survival statement is really helpful to acknowledge what the short term means and to make these objective trade-offs.

    25:09.80

    Alexis Monville: It’s often difficult to balance the long-term and short-term aspects of a product. Now let’s discuss execution and measurement. How does it fit into the Radical Product Thinking framework? It felt a bit like you were making a case against the use, or maybe more accurately, the misuse of OKRs. Tell me more about that.

    25:34.38

    Radhika Dutt: Before we challenge OKRs directly, let’s discuss what we’re trying to achieve with execution and measurement. The goal is to determine if our vision and strategy are working. Execution and measurement are about creating a set of hypotheses for each element of the RDCL so that we can understand what our hypothesis is and how we’ll measure its success. Now, if we consider OKRs, they set a number of goals, like hitting 20,000 signups by the end of this quarter or increasing revenues by 20%. The philosophy around OKRs is about setting big, lofty goals that are challenging to achieve. But you have to step back and ask if they’re really helping measure if the strategy is working.

    26:51.88

    Alexis Monville: Right.

    27:05.18

    Radhika Dutt: As a product manager, I have all the data behind the product. If you ask me to prove that I’m meeting my goals using my product statistics, I have a lot of flexibility in showing that I am meeting those goals. However, what you really want to know is not whether I’m meeting those goals, but how the product is doing. Is the strategy working? Do we need to change our strategy? This requires a more collaborative approach. OKRs, on the other hand, don’t feel collaborative. They’re like an end-of-the-year exam. You either pass or fail, and the incentive is to show that you have passed. This misaligns leadership’s incentives with employees’ incentives. Instead, we want a collaborative environment where employees are encouraged to share what’s working, what’s not, and what hypotheses we’re observing. Maybe we need a new approach. That’s why, as I illustrate in the book, instead of OKRs, we need a collaborative approach to create hypotheses derived from our strategy and metrics for measuring whether it’s working or not.

    28:45.34

    Alexis Monville: I’d say there’s a misuse of OKRs. What you described could exactly be OKRs if implemented properly at a team or product level. Certainly not for individuals and not linked to their compensation, as that would skew the system entirely.

    29:12.14

    Radhika Dutt: I agree with you. Traditionally, people have wanted to use OKRs because vision statements were too vague, like “revolutionizing wireless.” OKRs were intended to provide a clearer narrative of the impact we’re trying to have. But expressing this solely in numbers can lead to sandbagging, where ambitious people set their goals lower for fear of failure.

    30:06.78

    Radhika Dutt: We definitely should not create OKRs for personal goals or for product teams because that leads to manipulations of statistics. Even at a company level, if we don’t implement OKRs properly, there’s a temptation to sandbag and avoid personal responsibility.

    30:42.78

    Radhika Dutt: If we don’t handle it right, there’s a fear of appearing as if one’s department has failed.

    30:47.59

    Alexis Monville: That transitions us nicely to culture, the last part of the framework. Can you tell us more about what you mean by culture and why it’s important?

    31:02.36

    Radhika Dutt: For innovation to thrive, we need a culture where people have a shared sense of purpose, autonomy, and psychological safety. The first two are covered by other elements of radical product thinking. The shared purpose comes from the vision, while autonomy comes from helping people understand how to make trade-offs. The last piece, psychological safety, is about creating a team culture where people feel they’re doing meaningful work, not distracted by company politics.

    32:17.78

    Radhika Dutt: It’s important to consider how employees perceive company culture because it might be different from your intentions. Think about culture on two dimensions: is work fulfilling or not, and is work urgent or not? When work is fulfilling and not urgent, that’s the most wonderful time at work.

    33:05.26

    Alexis Monville

    Yeah, that’s what I call the impact and satisfaction and that’s always what I’m trying to drive. It’s to get to that quadrant of having an impact and I’m really satisfied by by the work I’m doing to get to that Impact. 

    33:26.68

    Radhika Dutt: We want to maximize that quadrant of fulfilling, non-urgent work, and minimize others. One such quadrant is heroism, where work is fulfilling but urgent. Too much of this can be exhausting. The next quadrant is organizational cactus, where work is not fulfilling but urgent, like paperwork. The last quadrant is what I call the soul-sucking quadrant, where work is neither fulfilling nor urgent, such as feeling unfairly treated or unvalued at work.

    35:54.99

    Radhika Dutt: A good culture maximizes meaningful work and minimizes the other three quadrants. To create such a culture, we can use the elements of radical product thinking. Define the pain points that lead to time in the bad quadrants, then work on a strategy with hypotheses and measurements. Over time, you can measure whether your culture is improving and whether your team is gelling better.

    36:22.81

    Alexis Monville

    I Really love it because then we can use the framework to improve the culture of the organization really consider the organization itself as a product that will serve the employees to help them do their best work I Really love that.

    36:45.60

    Radhika Dutt: Exactly, your organization itself is a product that serves your employees. You have a vision for that change, and culture becomes your product, your mechanism for creating that change.

    37:24.61

    Radhika Dutt: It’s about making better products and making the world better by creating those changes.

    37:29.11

    Radhika Dutt: Alexis, thank you for having me on this podcast. In terms of how people can reach me, there’s the Radical Product Thinking book, which is in bookstores. They can also learn more on the blog at radicalproduct.com. I always love to hear how people are applying the Radical Product Thinking approach to create change in the world. You’re welcome to reach out to me on LinkedIn to share how you’re applying Radical Product Thinking.

    38:53.71

    Alexis Monville: Radhika, thank you so much for joining us today on this podcast and for sharing your invaluable insights on radical product thinking. To our listeners, you can find a transcript of this episode, our references, and more episodes at emergingleadership.network. Join us next time as we continue our exploration into leadership, innovation, and the future of work. Thank you, until then, keep leading the change.

    39:32.32

    Radhika Dutt: Thank you.

    Photo de Ricardo Gomez Angel sur Unsplash

  • How the Cloud Threatens Open Source and what we can do about it: A Conversation with Daniel Riek

    How the Cloud Threatens Open Source and what we can do about it: A Conversation with Daniel Riek

    Open source is everywhere. It powers the cloud. It powers our phones. It powers most of the modern software stack.

    So why does it feel like we are losing control?

    In this episode, I’m joined by Daniel Riek, who works on special projects and strategy with the CTO at Red Hat. Daniel has spent most of his career in the open source space, from startups to large scale product leadership, and he brings a sharp perspective on what changes when open source meets the cloud.

    Open source is about freedom and sovereignty

    Daniel prefers the term free software: not free as in cost, but free as in freedom.

    Freedom to understand how software works, change it, improve it, redistribute it, and collaborate. In other words, sovereignty: the ability to control the technology that increasingly defines our lives.

    And that is not a niche concern anymore.

    Software is embedded in the physical world: connected devices, home automation, infrastructure, products, services, everything. As software becomes more central, the question becomes simple: who controls it?

    The cloud is a powerful paradigm

    Daniel defines the cloud as more than infrastructure. It is a paradigm built around three promises:

    • Developer velocity: teams can keep building without stopping for underlying dependencies
    • Operational excellence: best practices are embedded so systems stay reliable
    • Elasticity: you scale up and down dynamically and pay for what you use

    From the outside, it looks perfect.

    So why does it create a threat for open source?

    The core tension: open code, closed operations

    The cloud is built on open source. Linux, Kubernetes, containers, virtualization, databases, libraries: open source is the foundation.

    But the differentiator in the cloud is not only the code.

    The differentiator is how you run it.

    Operationalizing software at scale requires know how: security, reliability, performance, upgrades, incident response, compliance, cost controls. Cloud providers turn that expertise into a proprietary advantage.

    That is the turning point.

    You can have open source software, but if you cannot operate it at the same level, your freedom becomes theoretical. The control shifts from the code to the service.

    The same pattern shows up in everyday life. Many people do not run their own mail servers anymore because operating them securely is too complex. A small inconvenience is often a symptom of a bigger shift: the operational layer becomes the lock in layer.

    Abstraction on abstraction and the distance from the underlying system

    Cloud native development encourages abstraction. You do not want every team, or every project, to reinvent databases, messaging, identity, security, and operational tooling.

    So abstractions pile up. Abstraction on abstraction on abstraction.

    The benefit is speed.

    The cost is distance:

    • distance from what is running
    • distance from how it is configured
    • distance from how it is secured
    • distance from how to debug it when it fails

    And when those abstractions are proprietary services, the distance becomes dependency.

    The downward spiral: open source built on proprietary foundations

    Daniel makes a strong point: the cloud era can push open source into a downward spiral.

    Open source projects want to focus on their core mission, not on running everything underneath. But if the operational layer is proprietary, projects face a dilemma:

    • depend on proprietary black box services, undermining sovereignty
    • or run everything themselves, which creates a disadvantage in speed and effort

    Daniel uses GitHub as a revealing example.

    Git is open source. GitHub is a service built on top of Git. The glue, integrations, and differentiators are proprietary. Many open source projects depend on it for collaboration, issues, CI, and now AI assisted workflows.

    That does not make GitHub “bad”. It makes it a clear illustration of dependency in the cloud era.

    What we can do: expand open source to include operation

    Daniel’s proposal is direct:

    Open source must expand beyond “code in a repository” to include operationalizing the code.

    That means:

    • making “running it” part of the project’s scope, not an afterthought
    • enabling others to build on services, not only on libraries
    • creating a virtuous cycle of contribution at the service level, not only at the code level

    Not every project will do this the same way. But the direction matters.

    Decentralization as a counterweight

    The cloud tends to centralize. Centralization increases dependency. Dependency increases power concentration.

    So Daniel highlights decentralization as a key counterweight.

    He points to Mastodon as an example: open source software, with a federated model where many instances can exist and interoperate. The project includes operation as part of its reality, not only as code.

    The broader lesson is not “everyone should use Mastodon”. The lesson is that decentralization is a viable pattern when centralized platforms become too controlling.

    The leadership skills the cloud era demands

    Daniel is careful here: some of this is prediction, not finished history.

    But the direction is clear. Open source in the cloud era requires leaders who can:

    • understand dependencies and their long term cost
    • reason about centralization versus decentralization
    • think in terms of sovereignty, control, and sustainability
    • distinguish software, product, and service
    • align principles with strategy, not convenience alone

    There is also a more personal layer: conviction.

    Where do you keep your principles even when convenience pulls the other way? Where is the line? What tradeoffs are you willing to accept, and which ones create unacceptable dependency?

    A moving landscape, not a fixed answer

    Daniel ends with a reminder: the tech industry moves in cycles. Centralization and decentralization swing like a pendulum. Costs, crises, and new constraints reshape decisions. Edge computing is one example of a decentralizing force driven by physics, latency, and reality.

    Leadership means staying aware, staying honest, and making choices that mix strategy, principles, and immediate needs.

    Listen to the episode:

    You can listen to this episode on your favorite platform: Anchor, Spotify, Breaker, Google, Apple

    Here is the transcript of the episode:

    00:00.00

    Alexis Monville

    Welcome to the podcast on emerging leadership. I’m Alexis Monville. Today we are joined by Daniel Riek, who works on special projects and strategy at Red Hat. His previous roles include leading Red Hat’s AI Center of Excellence, managing cross-product integration engineering, leading Red Hat Enterprise Linux Product Management, and multiple startups, including ID-Pro, one of Europe’s first open-source service providers. Daniel has spent most of his career in the open-source space, and today we will discuss the future of open source in the cloud era and how individuals and leaders can support open source and ensure that it remains accessible and open. For those who may not be familiar with the term, Daniel, could you explain what open source is and why it’s important?

    00:54.35

    Daniel Riek

    Of course. I actually prefer the term “free software,” which is not about free as in no cost. It’s about free as in freedom. Free software allows you to change the software, understand how it works, improve it, and redistribute changed versions of the software. “Open source” is basically just a marketing term for the same thing. Often we refer to free and open-source software (FOSS) to combine them. I use them largely synonymously. The point is that it’s about empowering the people who use software and giving them the right to understand the software, adapt it to their needs, improve it, redistribute, and collaborate on the software. It’s really about sovereignty in technology. It’s about controlling the technology that defines your life.

    01:56.11

    Alexis Monville

    Okay, really interesting. In a very interesting talk at FOSDEM, you’ve spoken about the challenges facing open source in the Cloud Era. Could you tell us more about these challenges and why they are important for those in the tech industry to be aware of? Why should people outside of the tech industry care?

    02:19.16

    Daniel Riek

    Right. Free software is about empowering you to control the technology. As everyone is probably aware, more and more of our life is defined by software. An example I often use is a connected mousetrap I have in my basement, which does a very traditional task. It’s a mousetrap, but now it’s connected to the internet. It talks to my local Wi-Fi network and then talks to a cloud server and then notifies an app on my phone when it did what it does, which has a huge advantage. It avoids me finding things weeks later in the basement, so it’s really useful, and I bought that mousetrap, which is a very physical, very mechanical thing, because of that software feature. My light switches in my house are all small microcontrollers. They’re all small computers running software and talk to each other and, through some home automation, talk to the internet. So everything in our world is defined by software. Basically, everyone is exposed to that to some degree. Every business is definitely exposed to that, and more and more businesses differentiate through software features in their internal organization, in their customer interactions, and progressively even in their product. So everything is software, and logic is done in software. Our interactions with the world are with software. Because we control our physical world with software, the software complexity is approaching the complexity of the physical world. It’s no surprise there.

    04:24.70

    Daniel Riek

    And part of that of course is that things need to be always connected it means that there’s more and more software and a paradigm that really came along with that expansion and you can argue about cause and effect. But, you know, I think they just co-evolved is the concept of Cloud computing which I would define as the mixture of an operational paradigm – how do you run your software – and the underlying Infrastructure. That’s optimized for developer velocity so you can keep building software without having to stop for things that are underlying dependencies, whether that is infrastructure like a computer you need to run on, a network connection or a service like a database. You compose your software and you try not to stop for underlying infrastructure or have your developers stop for underlying infrastructure, so developer velocities. The second part is operational excellence. You want because if your business or your world or your house depends on software running, you don’t want to have any kind of operational fragility. You want your software always to run and you want the best practices that are common in whatever one does. You want that to be applied to how your software runs. Because if, even if you cannot have a positive differentiation from optimizing things because you’re just doing something that’s very mundane like running a web service or something, you still would have a disadvantage if you weren’t doing it as well as your competitor, right? So you want the operational excellence, the best practices embedded in how your stuff is run, how your underlying services and infrastructure is run, and lastly, you want elasticity which means that you can increase or decrease your usage dynamically at any time. So if you have, for example, a sale, a new product launch, and you expect a lot of traffic, you want the ability of your services to scale up, and then when you don’t need that anymore, you don’t want to keep paying for services you don’t need anymore. That’s what we call elasticity, so things can grow and can reduce as needed. And that is really what Cloud is about. It’s a paradigm that gives you a software architecture and infrastructure that supports maximizing developer velocity so you never have to stop when you create your own stuff. It embeds the operational excellence best practices, and it’s elastic. And yeah, most people know someone like Amazon or Google or Microsoft or in Asia, Alibaba, and you know there are big cloud vendors, IBM is a cloud vendor, Oracle is a cloud vendor, so these are companies that provide that kind of infrastructure, and there are many smaller ones. Even people running their own data center want to run them in this paradigm. So the goal is to support modern software and your dependencies by running yourself in the cloud paradigm.

    07:56.46

    Alexis Monville

    Yeah, so Daniel, if everything around us is defined by software, and we have that great capability of the cloud that is, as you said, optimized for developer velocity, we have operational excellence so things can continue to run always, and we have elasticity, so we don’t pay for what we don’t need, so we pay only for what we need, and we can increase our capacity. That’s absolutely perfect. So why are there challenges for open source?

    08:27.14

    Daniel Riek

    Yeah, that’s really interesting. So first of all, everything that people do in the cloud nowadays is built on top of open source. All the major clouds use open source. They’re usually based on Linux as the operating system. Open source virtualization technology that’s in Linux like KVM, or container concepts like Podman and Docker, and orchestration tools like Kubernetes. So, it’s a lot of open source in there. The place where open source is successful right now is the common base of what I call “code assets” – software program code that sits in a repository or is a binary that you can take and run when you need it, and that’s what most of the cloud vendors use. It’s what the cloud services are built on the highest. So, if you have a database in there, that has usually for most, a strong open source base. Even most of what any user does nowadays is built on the foundation of open source code. People build their own business differentiation in software. For example, let’s stick with the example if I build this control stack for my connected mousetrap, right? There’s a lot of open source in there, both on the device itself, some of the pieces in the microcontroller, our open source libraries. You can basically assume that because it’s most of the common underlying software, the middleware that they use to talk through the internet is based on open source. The parts on your mobile phone also include open source libraries, and you can verify that if you go to your mobile phone settings, you will find somewhere the open-source licenses that they have to list.

    Now, the issue is that when you operationalize software, and in fact, operationalizing open source software, is the biggest differentiator for any kind of cloud vendor or people who provide software as a service. Even in some cases, they take the same open source code that’s publicly available, but they know how to run it with that operational excellence, and that becomes suddenly a proprietary differentiator. It includes knowing how to make it scale, how to run it, how to configure it securely, and how to keep it secure against attacks, which is a common problem. Software gets attacked directly or through supply chain issues, and if you don’t have the right process in place, and you download random open source software from the internet, there’s a risk in that. So, the cloud providers have these processes nailed down, and taking open source software and actually running it as cloud-grade enterprise-grade software is suddenly a proprietary thing. That obviously creates a conflict because now the point of open-source software of “I want to empower people to be in control of their technology, I want to provide freedom” is running up against the problem of actually running the software now being a proprietary feature.

    12:20.95

    Alexis Monville

    Okay, so the point of open source was that freedom and that control and if you have a software that is open source, but if you don’t know how it’s run, then you don’t have that freedom and you don’t have that control anymore. So that’s the problem. So what can you do about it?

    12:40.66

    Daniel Riek

    So that’s the first problem. There’s another problem that is kind of a second-degree problem, but I want to mention it. The first one becomes very obvious as soon as you try to do this. It’s a common discussion in the open-source industry or business. Even people who do a lot of open source, for example, don’t run their own mail servers anymore because of the complexities of running it securely, keeping it operational, protecting it. Or even being able to get your mail accepted by other services, the way to use it is not as free as the underlying code anymore. That becomes pretty obvious that, “oh, I have this open-source software, but I don’t know how to run it or at least not as securely as you know at that scale or as well as performant as efficiently.” But the other problem then compounds that because, if you do cloud-native development right, the point is of cloud is to abstract from underlying complexity, so you can focus on the core way you want to differentiate. If you’re a business, you want to implement your business differentiation in software and all the things that are not differentiating for you that are just the requirements that you have that you know like a database. Most businesses just need the database, and having a better database probably is not going to help you sell more of your product in most cases, right? So, you want to focus on your application that uses the database. You don’t want to spend your time on figuring out how to run the database. The same is true for an open-source project. If I’m doing an open-source project, I want to focus on the core of my project. Let’s say it’s Home Assistant, home automation software. I want to focus on making that better, not on how to run the underlying database or message bus or whatnot. So, what happens is that people start building abstractions on top of abstractions on top of abstractions, and that creates a distance from the underlying open-source software.

    14:08.24

    Alexis Monville

    Yeah, that’s why I gave up on running my own mail server when all my emails were going nowhere. I gave up and used the service, and then some of them were finally reaching their destination.

    14:18.80

    Daniel Riek

    Right, exactly. And that sounds like a small problem, but it’s a symptom of the bigger problem, which is really that people are building abstractions on top of abstractions on top of abstractions, and they start to lose sight of the underlying open-source software. So, it becomes really hard to know what is running where, how it’s configured, and how it’s secured. And when something goes wrong, it’s really hard to debug because there are so many layers of abstractions that could be the problem. So, that’s really the second-degree problem.

    15:40.35:

    Daniel Riek

    I want to figure out how to do the best home automation. I don’t want to have to figure out how to run the underlying service to provide that. And because those services in the cloud are run as a proprietary concept, you, as an open source project, have two choices: either you start depending on proprietary black box services that you can’t look into and you can’t control, or you have to run all of it on your own. And that creates a fundamental disadvantage for open source projects when they try to develop in a cloud-native way. It means they benefit from all the greatness of the cloud paradigm, where they either have to do it themselves and figure out the operational excellence or depend on a proprietary service, and thereby undermine the whole point of open source even when they create code. And that creates a downward spiral of open source value when open source development itself starts depending on proprietary approaches. A great example here is GitHub, right? Most open source projects use GitHub, which is an awesome service that gives you management for your source code, collaboration issue management, CI management, more and more integrations, now an AI bot that helps you write code. It’s built on open source software, right? It’s in the name. Git is an open source project created by Linus Torvalds, the same person who created Linux. But the service itself, the glue code, all the differentiation, everything that makes it such a great tool other than the core open source code underneath Git, everything else is proprietary. So the moment you use GitHub, you have built this kind of proprietary dependency in any open source code. And it’s not just GitHub; it’s actually owned by Microsoft, so for people who have a long history in open source, Microsoft was always anti-open source. They called open source a cancer back in the day, and they were very anti-open source. Now, most open source projects, at least in their ongoing practice, depend on the Microsoft service to keep building and managing their source code.

    18:18.30

    Alexis Monville

    Yeah, Dependency is an interesting challenge for open source. So if we want to escape that downward spiral that you mentioned, what can we do about it?

    18:32.46

    Daniel Riek

    So ultimately, on a high level, I think that open source needs to expand the concept of open source from code – you know, code in a repository and the code license – to include operationalizing the code. That means two things, right? One is like, and it’s not going to be the same for every open source project, but ultimately, open source projects should include in the project charter running their software as a service or as part of a service. And with the goal to enable other open source projects to then build on that service in a cloud-native model so that you create the same kind of development approach that you have in the proprietary world, where people can aggregate existing services and come together and create this you know, it creates an exponential growth rate, right? Because you can build on top of all the things that other people have done which in open source, you do that kind of at the code level, you reuse libraries. But if applicable, I should be able to reuse an existing service and then create a virtuous cycle of open source. It’s what we call this contribution cycle where people come together and contribute to open source projects to bring them forward to expand that to a similar cloud-native concept of things running and then other things aggregating beyond just the code in a repository.

    20:13.76

    Alexis Monville

    Wow, okay, what’s the first step to do that?

    20:17.17

    Daniel Riek

    I think that depends a little bit. There are different approaches for different projects that will be taken, and there are a bunch of ongoing things. I think one key point is starting with awareness right? We need open source projects to be aware of the problems, aware of the dependencies. I think we need to get a push towards decentralization, and that’s an interesting topic, right? Part of the problem, part of the benefit of the cloud that how people consume it today kind of co-evolves with increasing centralization. So people move to the same thing, which is part, like, it increases the benefit for keeping things proprietary for that centralized entity, and increases these dependencies on very few entities. So a decentralized approach automatically counters that, and we’ve seen that in a different space, right? Like if you look at the Twitter situation, a lot of people have decided that Twitter, for this or that reason, isn’t a great platform anymore. It’s too centralized, and many people don’t agree with the approach of the previous or current ownership, and whatever. I don’t want to get into that issue. The structure is the point though, is people have a problem with this one centralized platform being the one place where everyone comes together, having to submit to their rules, and not being able to have sovereignty over your own content. And the answer that kind of is a front answer right now interesting is a project called Mastodon, which is an open source project with a decentralized approach, right? Where everyone can run their own social media instance of Mastodon. It is the true open source project. It already has this concept of running it as part of the project, and there are many people, you know? So, it’s not just code in a repository, the people involved in the project themselves are also running instances of it, and everyone can go and run it. It’s easy to run because it’s part of the project. And then you just connect, you negotiate with others to connect to them so you create a decentralized social network of people running their own instances of Mastodon. So that’s a great example of an open source project that has cloud-native operationization as part of the content. I’m sure it could be improved but it you know it obviously is working to some degree because a lot of people are now using Mastodon, and it’s evolving fast to be an alternative to centralized social media platforms.

    23:19.10

    Daniel Riek

    So that’s a great example, right? It comes down to expanding the project scope to include operationalizing, so running the software as a service, and a decentralized approach, which means that many people can run it and you somehow bring that together to create a joint benefit and growth and collaboration on top of that.

    23:44.79

    Alexis Monville

    So awareness of dependencies, running your project as a service, and thinking of decentralization. So avoid that effect of centralization that will put you in that trap of building things proprietary. Okay, that sounds like something people can do. The question would be, next, why they are not all doing it, but Mastodon is a good example. So, let’s go with that. What are, from your perspective, the key leadership traits and skills needed to succeed in open source in that cloud era and to make that happen?

    24:31.19

    Daniel Riek

    That’s a hard one, right? Because now I’m looking at a crystal ball, and it’s very much like it’s my opinion, not an experience because it’s an ongoing struggle, and you know, it’s generating like open source as a concept for code at rest has one, right? It’s the standard base for everything. So it’s in it has proven that it’s the most efficient way of creating and maintaining the underlying common code that everyone needs but that no one can actually differentiate on. And we all have also proven that you can professionalize that and create businesses around that without compromising the underlying concept. I work at Red Hat as you know, and with me and that’s what Red Hat does. Red Hat has a subscription business model that is fully compliant with the concept of open source. Ultimately, selling the similar to how cloud is kind of about the embedded best practices. Red Hat’s business model is the best practice of maintaining enterprise-grade open source and increasing cloud-grade open source code for business users. A huge benefit for everyone, right? It benefits everyone because it’s complying with the open source model and contributing back. It is also collaborative with everyone else in the space, usually. Reddit does not solve problems on its own. It’s always in collaboration, even with competitors because it’s this common underlying base, right? So that works really well, and that’s proven, call it: The normative power of the factual that is working in the software industry.

    26:35.12

    Daniel Riek

    And, you know, that doesn’t mean that there is no proprietary software, but that’s usually kind of close to the customer use case, you know. Ultimately, what customers implement themselves usually, they keep proprietary because that’s their business differentiation. But soon as you get like one or two levels down, you get into common services. And I think, to my predictions, that model can be expanded to services right with a decentralized approach. And I think a key leadership really like it’s understanding the benefit of open source and ultimately like, I have kind of two minds there, right? But in my private life, it’s something like a conviction that I want to be in charge of my own technology. And I want to be, so I use open source even when it’s not necessarily convenient, right? That if you go into the business side, I have a more utilitarian view on that, right? I want to do open source so it benefits me. And I think, so I think not going to be sustainable, so you have to find a synergy where open source is really useful for you, which aspects of it are critical for you, think strategically, think about your dependencies, and how you want to have control and sustainability and sovereignty so that you don’t get into dependencies that harm your business. Then, focus on those areas. I think that is the key leadership skill that people need to develop, but it’s not the same for traditional open source for code at rest. It’s just about adapting it to not accept, for example, for cloud services, the things that you wouldn’t accept for code at rest.

    28:54.20

    Alexis Monville

    I like what you said about conviction, and some people are saying you don’t want to leave your principles behind for convenience reasons. But the line is probably blurry and there’s probably a limit that you cannot overpass and that’s interesting to be aware of that too.

    29:23.62

    Daniel Riek

    And yeah, and I mean, we always, if you look at the cycles in the tech industry, it’s always a little bit of pendulum swinging back and forth between concepts, right? You always have, for example, a trend to centralization, like the mainframe. Then we had the PC, then we got the cloud, which turned back into centralization. Some people say it’s just a reinvention of the mainframe, right? Like it’s a black box service running on someone else’s leased hardware that you pay by the hour. It’s really convenient, and I use it for certain things. I use traditional data center approaches for other things still, but in the cloud-native mindset. But sometimes it’s better to buy the hardware and not run pay by the hour because you’re always utilizing it. So you have to, and I think we see right now, we had a huge expansion, there is an economic crisis going on, and we see a lot of people reconsidering that, going into cost control mode and suddenly reducing their cloud spend or even rediscovering their data center. We have other trends like edge, which comes from software defining the world. Now software needs to move closer to the data sources and interaction points. The classic example is a self-driving car. A self-driving car needs to take decisions locally because if it has to ask the cloud, it will fail to brake in time. So it has to take the decision locally, so you need local compute power. So suddenly, you need a decentralized approach there, and so it comes back to leadership, looking at the trends and the requirements honestly, reconsidering decisions, reconsidering the trends, and making your own choices informed by a mix of strategy and principles and immediate needs.

    31:38.37

    Alexis Monville

    And among those are an understanding of dependencies, an understanding of centralization, decentralization, and that understanding of the difference between software or product and the service itself. It’s really fantastic, Daniel. Thank you so much for joining us today and sharing your insights on the future of free and open-source software on the cloud. Your experience and expertise in this field are truly valuable and inspiring to emerging leaders in the tech industry and everywhere else. Thank you, Daniel.

    32:18.59

    Daniel Riek

    Thank you, Alexis.

    Photo by Taylor Van Riper / Unsplash

  • The best framework to grow yourself as a leader

    The best framework to grow yourself as a leader

    This is Le Podcast on Emerging Leadership. Today’s episode is a little different.

    For this recording, OpenAI is the host. Just for today. The regular host shared the BEPS framework with OpenAI and asked for questions to ask.

    Emma Monville impersonated OpenAI for the recording.

    Now that this is clarified, let’s continue.

    The BEPS framework: four axes of leadership growth

    BEPS is a framework designed to help leaders and managers broaden their impact. It maps leadership responsibilities across four axes:

    Business
    Understanding the business and the ecosystem your organization operates in. It includes developing a clear vision and understanding the reasons behind your solutions, products, features, and services.

    Execution
    Delivering work and achieving results.

    People
    Hiring, growing people, managing performance, and self improvement.

    System
    Understanding the system formed by people, organization, processes, and tools, and removing obstacles to great work.

    The framework is simple on purpose. It creates a shared map to talk about where a leader invests time, what they neglect, and how they can grow.

    Why BEPS exists

    Alexis created BEPS while helping teams move from a function based organization to cross functional teams.

    In that shift, managers started questioning their role. Many saw management as primarily about pushing execution, often through micromanagement. BEPS helped them turn around and see the full space of leadership: business clarity, people growth, and system improvement, not only delivery.

    The common trap: execution everywhere

    In Alexis’s experience, most leaders overinvest in Execution and underinvest in everything else.

    Sometimes it looks productive: more tasks, more activity, more tracking, more pressure.

    But without Business understanding, you can deliver the wrong thing. Without People focus, you burn out or lose talent. Without System work, you keep fighting the same friction again and again.

    The framework makes this imbalance visible.

    BEPS as a self improvement tool

    The simplest way to use BEPS is personal reflection.

    Look at your past week and ask: how much time did I spend on each axis?

    Then do it again for several weeks. Patterns show up quickly. Not all weeks are the same, so Alexis recommends looking at a longer period, and recognizing that some activities have a cadence. For example, career conversations may happen monthly or quarterly, not weekly.

    The point is not perfect balance every week. The point is awareness, then deliberate adjustment.

    BEPS to assess a team or organization

    BEPS also works at a team level.

    If a team’s priorities are entirely framed as activity and delivery, the framework invites better questions:

    • What do we know about our business and our ecosystem?
    • How do we know we are building the right thing?
    • How do we grow and retain people?
    • What are we improving in the system to make delivery sustainable?

    A healthy set of priorities touches all four axes. If everything sits in one axis, blind spots are likely.

    Why System must be separate from Execution

    Alexis explains why he does not merge System into Operations.

    When System and Execution are mixed, people tend to default to Execution and neglect improvement. BEPS keeps System visible.

    Alexis connects this to Deming’s idea: a bad system will beat good people every time.

    How BEPS relates to other leadership models

    BEPS is not meant to replace other frameworks. It is a map that helps leaders locate their growth edges.

    Alexis mentions:

    • Servant leadership, especially when managers shift away from micromanagement and toward enabling teams
    • broader models like Strategy People Operations, where BEPS adds clarity by separating System from Execution
    • habits and practices that can be used to grow along each axis

    How the framework evolved

    BEPS did not start as BEPS.

    It started with three axes: Business, Execution, System.

    The People axis came later.

    Alexis shares this openly and explains why: early on, the teams he worked with associated people practices with bureaucracy and box ticking. He wanted first to shift how they saw the organization and the system. Then, when the time was right, People became the fourth axis.

    The two qualities behind the framework

    To use BEPS well, Alexis highlights two key qualities:

    • curiosity: learning, listening, exploring beyond your default area
    • humility: accepting you do not know everything, and being willing to adjust

    Together, they create the conditions for real growth across all four axes.

    OpenAI

    Alexis, how would you describe your role to someone you just met?

    Alexis

    I am the Chief of Staff to the CTO at Red Hat, an enterprise software company with an open source development model.

    OpenAI

    What inspired you to develop the BEPS framework?

    Alexis

    I was really looking for something that would be able to help people get out of the corner of the room they were stuck in. I was trying to help teams. I was trying to mentor people and help them see the full spectrum of their role, and they seemed to be blocked somewhere, stuck somewhere in the corner of the room. So for me, the BEPS Framework represented an opportunity to help them turn around and see all the available space for them to grow themselves and grow their organization or teams.

    OpenAI

    How did you develop the four axes of the BEPS framework (Business, Execution, People, and System)?

    Alexis

    It all started with working with a team and especially the managers of the team we were trying to really transform the organization from an organization that was built by functions. So you had product management, engineering, quality assurance, and support. All those organizations should work together to develop a product, but they were a little bit fighting with each other, trying to justify their lack of results. We were trying to change the organization and build cross-functional teams. The managers were wondering what their roles would be because they saw their roles as really focused on one aspect of the work, not looking at all the other axis. So, showing them the four axes was a way to tell them: Oh, okay, there’s more to my role than just micromanaging the people already doing the work.

    OpenAI

    In your experience, which of the four axes do leaders and managers often neglect or underinvest in?

    Alexis

    It’s really interesting because I believe the axis people love to be involved in is Execution, and they usually neglect all the others. So. It’s not necessarily one of them. It’s more all of them except execution. And they focused on execution, but in the wrong way. I’ve seen people already focused on really doing their work but forgetting about everything else. I’ve seen managers focused on getting people to do work, do work, do work, do work, do work, do more activities, and more work, more work, more work, and really micromanaging the activities but not looking at the other axes and not looking at the impact of that work and missing the whole point.

    OpenAI

    How can the BEPS framework be used by leaders, either individual contributors or managers?

    Alexis

    I believe a framework is first of all a self-improvement tool. It’s really, looking at it and reflect on what are your contributions. One way to do it is simply to look at your past week and reflect on how much time did you spend on each axis. If you look at the definition of the axis, what do you know about the business axis for example? What do you know about the industry you are in? What do you know about your competitors? What do you know about your partners? What do you know about your own business? Do you know how your company is making money? Do you know what are the really important forces at play there? Ah and if you have all the answers. That’s great. You can use all your knowledge about that business axis to improve on the three other ones. If you know nothing, there’s probably an opportunity for you to develop and an opportunity for you and your team to grow, work with your peers on so on and so on. So, first of all, a self-reflection tool that can help you be more effective.

    OpenAI

    Can you give an example of a situation where the BEPS framework helped a leader or team to be more effective?

    Alexis

    That’s really interesting because, in many mentoring sessions I did, people were usually a little bit stuck on execution. They wanted to get to the next promotion. In a way, they wanted to get to the next level. But they were missing the point about how to get there. The BEPS framework was an interesting tool to show them: Okay, where are you already working on? What are you really working on? And for example, if I pick the system axis for example, what are you doing to really improve the processes and the way the organization is set up? A lot of time, the leaders put that responsibility on their manager. Asking them: Really? That’s only on your manager to improve the organization, the system, and the processes. You have no role in that, and of course, by asking a few questions, they realized that they could do many things. They were the ones dealing with that system on a day-to-day basis, providing the experience to people. So that was a way for them to realize that they could be more effective. We can go to the other axes and have the same kind of conversation. So. It’s really an opportunity for people to see other aspects of their roles, other facets of their roles.

    OpenAI

    How can the BEPS framework be used to assess the focus and priorities of a team or organization?

    Alexis

    Yeah, it’s definitely that!  Where do you put your focus on? How do you define your priorities, and if your priorities are to deliver a list of activities and to tick all the boxes I’m asking you? Okay, but what do you know about your business? How do you improve your knowledge about your business? How do you know you are right? How do you know you are wrong? How do you know you’re developing the right things to serve your customers or users of your product or services? How do you help your people grow? How do you keep them in the company? Keep them engaged. So, If you look at the priorities of a team or an organization, there should be something on all of the axes. If everything is focused on one, you’re probably missing the point. So that’s a great tool to look at how people define their focus and priorities and help them reconsider, then move things away from their default axis.

    OpenAI

    How do the four axes of the BEPS framework relate to other common frameworks or models of leadership and management, such as servant leadership or the seven habits of highly effective people?

    Alexis

    Oh yeah, that’s a really great question. I was looking for a framework that is simple enough to explain and will cover all aspects without being too simple. For example, I’ve heard many times that the only framework you need to have is Strategy People Organization. No, Strategy People Operations more exactly. But you’re missing the point there because strategy, I can say, okay, that’s my Business axis. People, Okay, that’s my people axis. But Operations is Execution and System; usually, when you mix the two, people focus on the execution. They forget about improving the system, and as William Edwards Deming said: a bad system will beat good people each time. So you really want to have all those axes together.

    If I consider Servant Leadership, it’s a really interesting one because basically, the managers I was helping when we changed the organization from functions to cross-functional teams with people in charge end to end of delivering something, the managers were looking for a new role because they were not supposed to micro-manage people and focus only on execution. So their role was already moving to that servant leadership role, so we helped them see that, and we used some of the servant leadership principles to help them reconsider their role, and it really worked well. And, of course, the 7 habits are well-known for many people, so that’s also simple training to have simple things to do, which helped them realize that they were not really working on the other axes. So, we use the other frameworks to help people grow on the four axes. BEPS is a simple way to help people discover all the facets of their roles and responsibilities.

    A bad system will beat a good person every time.

    William Edwards Deming

    OpenAI

    Can you share any tips or best practices for how leaders and managers can effectively balance their time and focus across the four axes of the BEPS framework?

    Alexis

    The first one is knowing what we are doing—knowing what you are doing and where you invest your time. So if all your time is focused only on one axis or you’re imbalanced, that’s a problem. But how do you know that? You only know that when you can track where you invest your time during the week, and you can do that in several weeks to have a good balance. So, of course, not all the weeks are exactly the same. Let’s say you’re doing that for four weeks, and you look at all the different aspects of your work, and each Friday, you take some time and tag. You say, okay that was really business, that was more execution, that was more already working in the system, that was more already working on the people, and so on and so on. You look at how balanced or imbalanced you are, and maybe you reconsider how you will invest your time in the following week or following weeks. I believe that’s this way. Ah, you can really have a better picture or a better balance. Of course, the things that you will probably do, and let’s say every month or quarter, you need to do that for a longer period to have a good picture of your balance or imbalance. For the people aspect, growing people or managing their careers, that’s maybe not a conversation you have every week. That’s maybe a conversation you have monthly or even sometimes quarterly only, so there’s a cadence to find and a balance to find on a quarter. That would be a good setup.

    OpenAI

    How has the BEPS framework evolved or changed since you first developed it?

    Alexis

    The beginning of the framework, and I’m a little bit ashamed of that. To be honest, there were only three axes. That was Execution, of course, and there were the business and the system axes. I really wanted people to connect their knowledge of the business with the execution, with the day-to-day work. I was focused on improving the system so you could see what was missing. And that’s why I’m ashamed of it. There was just a small missing piece. I forgot that people were maybe an interesting aspect of that framework. So, of course, I added that later. But just as an excuse for that, to try to justify me a little bit. The people I was working with really saw all the HR things as really bureaucratic and just ticking-the-box exercises, and I didn’t want to fight that battle upfront as a starting point. I already wanted them to reconsider the organization and all the processes involved first. So we started with those three axes, and then we added the people axis when it was the right time to do it.

    OpenAI

    In your opinion, what are the key qualities or characteristics that a leader or manager should possess to be successful using the BEPS framework?

    Alexis

    There are probably two qualities or two characteristics. It’s curiosity and humidity. I believe the two are really needed. You need to be curious. You need to learn to listen to others, and you need humility to reconsider things and accept that you don’t know everything. You probably don’t know how wrong you are or how right you are. Until you really see all the perspectives of the people of an organization. So Yeah, I would say curiosity and humility are the key qualities.

    OpenAI

    Alexis, you are the Chief of Staff to the CTO at Red Hat. Thank you for joining me today.

    Alexis

    Thanks for having me!

  • Invest in Open Source with Joseph Jacks

    Invest in Open Source with Joseph Jacks

    Over the last years, we moved from innovating in secret labs to innovating in the open.

    Open source has become a key way to shape standards, accelerate adoption, and build software ecosystems that compound over time. In this episode, I’m joined by Joseph Jacks, founder and General Partner of OSS Capital, a fund focused exclusively on early-stage commercial open source companies.

    Joseph’s perspective is clear: open source companies are not just proprietary software companies with a different license. They are a different species, across many dimensions.

    What Joseph does, in plain words

    Joseph invests in entrepreneurs building companies around open source technology.

    He explains open source as a licensing approach that gives anyone permission to use, download, modify, and participate around a piece of software. Many people interpret that as “free”, but the more important dynamic is permissionless participation and the ecosystem it enables.

    OSS Capital operates in private equity, specifically venture capital: investing in startups early, building a portfolio, and holding investments for a long time rather than trading.

    Why start OSS Capital

    Joseph came to venture after being an entrepreneur and working inside an early open source company. Along the way, he noticed two things.

    First, many venture firms describe their focus in vague terms. If you survey funds, the message often sounds like: “we invest in great people building great companies.” Joseph found that lack of focus confusing.

    Second, he developed conviction that open source companies are categorically different from proprietary software companies. Not in one way, but in many.

    The combination of those observations led him to build a fund with a clear mandate: commercial open source, early stage, focused thesis.

    Investing in projects before teams

    One of the most distinctive ideas in this episode is Joseph’s approach to sourcing.

    He says he does not spend his days meeting founders in pitch cycles. In most cases, OSS Capital starts differently:

    • develop a point of view on a market and where disruption is happening
    • identify a specific open source project that stands out
    • contact the creator of the project only after conviction is built

    This flips the typical VC dynamic. Instead of being pitch-driven, it is thesis-driven.

    A large part of the work is separating signal from noise. Joseph describes a data-driven diligence approach using public signals in the open source world, including what can be learned from GitHub and ecosystem traction.

    It resembles, in his words, some of the initial diligence patterns of public-market investors, even though venture holds are long-term.

    From project to company

    When OSS Capital invests, it is often at the earliest stage, sometimes when the company is being incorporated.

    Joseph describes early help in several areas:

    • team formation and early hiring
    • shaping a business plan and monetization strategy
    • understanding competitive dynamics and ecosystems
    • facilitating knowledge transfer through co-investors and advisors

    He emphasizes a network effect: bringing experienced builders of open source companies into rounds and relationships, so founders can learn directly from people who have already navigated the same terrain.

    Why commercial open source can be more capital efficient

    Joseph addresses a claim on the OSS Capital site: commercial open source companies being more capital efficient.

    His core argument starts on product development.

    Open source can accelerate feedback loops and improvement because the project is built in the open. More people test, adopt, contribute, and stress the technology earlier. That can reduce the cost and time needed to reach maturity compared to building privately.

    Then there is go-to-market.

    By the time an enterprise buyer is involved, the company may already have internal users and advocates. That changes the sales dynamic: adoption can pre-exist the sales conversation, lowering friction.

    Joseph also shares a longer-running hypothesis: some open source companies historically raised more money than they needed to reach key milestones. One part of his mission is to help open source companies be understood and built in ways that improve capital efficiency.

    Will open source keep growing

    Joseph is strongly biased toward “yes.”

    He points to a simple dependency claim: most professional software engineers rely heavily on open source, to the point that without it, modern software development would grind to a halt.

    He also makes a motivation argument.

    People often ask why engineers contribute without being paid. Joseph frames this through intrinsic motivation: contributing because it helps others, because it helps learning, and because it sustains the system that contributors themselves depend on. That intrinsic engine keeps the flywheel turning, even alongside extrinsic incentives.

    The leadership trait that matters most

    When I ask Joseph about leaders he admires, he answers: humility.

    He observes that people who have accomplished a lot are often surprisingly humble. They separate what they built from who they are. That humility, combined with self-awareness, makes collaboration and problem-solving easier. It is also a trait he says he is still working on himself.

    Closing thought

    This conversation connects investing, ecosystems, and leadership in a useful way.

    Open source changes how technology is built, how trust is earned, and how companies can grow. And behind the models and the markets, Joseph brings the discussion back to something very human: humility, and the ability to keep learning in public.

    Listen to the episode:

    You can listen to this episode on your favorite platform: Anchor, Spotify, Breaker, Google, Apple

    Here is the transcript of the episode:

    Alexis

    This is Le Podcast on Emerging Leadership. I am Alexis Monville. Over the last years, people have moved from innovating in secret labs to innovating in the open, and open-source became the way to define industry standards. Today, I am pleased to have Joseph Jacks on the podcast to explore the open-source world. Joseph is the founder and General Partner of OSS Capital, a fund that exclusively focuses on early-stage commercial open source companies.

    Hey Joseph, how would you describe your role to someone you just met?

    Joseph

    Well, I invest in entrepreneurs building companies around open source technology, and if you don’t understand or if you’ve never heard of open source. It’s basically a way of licensing a piece of software a piece of technology in a way that anyone can use or download or modify or really participate in the commercial opportunities around that technology and so it kind of gives you this permissionless dynamic a lot of people think of that as free. Free to use, free to modify.

    Alexis

    Interesting so investing in entrepreneurs, how does it work. Are you doing that by yourself?

    Joseph

    That’s essentially what I do. I have a venture capital fund. There’s a part of the world called private equity. So there’s public equity. A lot of people might be familiar with public stocks like if you look at Apple or Microsoft or Walmart or whatever public company that’s kind of called public equity and you can buy and sell shares of those companies as an individual retail investor in whatever country you happen to be living in. You have a few dollars sitting around and then there’s the world of private equity where private companies manage their businesses without the scrutiny and regulation of being a publicly traded company. So private companies operate with a lot less public oversight and government oversight but at the same time, they really produce, I believe, the vast majority of innovation and economic breakthroughs in the world. And so in the technology industry, there’s a part of the private company sector called startups and you know there’s a lot of different definitions for the word startup and sort of what that means. But startups essentially refer it to a group of people could be one person building some type of technology that solves a critical problem. An interesting problem for the world and addresses some critical pain points, could be around automation, could be around giving people more insights into some information or data, making some business processes more efficient, a lot of different things. And there’s a specific type of startup that I focus on investing in and it’s a startup where the creator Is focused initially on building an open source technology of some kind and so typically is a project that is built towards addressing some problem for developers and or is built in the open transparently and allows people to see the technology in its entirety. You can read basically the entire ingredients and source code around that technology if you’re interested and want to you can actually modify and change that technology yourself.

    Joseph

    For example, if you’re a consumer of an early product that might launch on Kickstarter or maybe a big company. Maybe a new Apple product or something and you wanted to be able to contribute and change and modify that product or technology in some kind of way. It would really be either impossible or very very difficult to do that unless that technology was open source. The interesting thing about the startups that I invest in through my fund which is basically a venture capital fund. We invest money on behalf of others, limited partners. It’s really all of my money and also other people’s money that I manage and basically, our fund makes investment decisions in early-stage startups that basically fit our investment thesis and so. Going back to our investment thesis, we basically identify and develop a point of view around open source technologies that we think can really be the basis for overtime very large and impactful businesses.

    Alexis

    So tell me about the pivotal moment that led you to start OSS capital?

    Joseph

    Well, I was previously an entrepreneur for a number of years I started a couple of startups that really resemble our thesis and there were companies building a business, building a commercial opportunity. For the founders and investors of those businesses as well as the ecosystems they were operating in around some open source technology of some kind and so I developed a pretty strong understanding of this approach for a few years just as an entrepreneur. And I also got to know a bunch of people in the venture capital industry and in that kind of category of asset management and a lot of the observations that I developed around that motivated me to start OSS capital and so specifically what I learned there were a few structural things that I learned about venture capital. The main ones is that venture capitalists, very few of them have a clear focus mandates. In other words, if you were to survey maybe the top ones or even maybe the top 50 capital funds, they really just, the extent to which you can get a sense of their focus boils down to “we like to invest in great people building great companies” and so it’s really difficult to get a sense of what they actually focus on. At least from my standpoint that’s one aspect I was always kind of confused by. When you learn about open source in the context of building a product or a business it’s really the fundamental thing. It’s kind of you’re building the entire product or business around some core open source technology. What I developed as a point of view over many years from working at pretty early open source company called Talend which originally started in France and worked at a couple of other companies after that were fully proprietary software businesses is, and I developed the point of view that though those companies were different kind of they’re just like a different species of company right? There’s sort of unique on their own, on a lot of different dimensions. Not just one dimension but many many dimensions and those observations really stuck with me and so the combination of first noticing that there was very little focus in venture capital as an issue and then that combined with there’s really kind of No one types of technology companies. There’s ones that are just a fully proprietary technology behind the scenes and you’re commercializing and monetizing that somehow as compared to a sort of a type of company where the core technology behind the company is an open source project of some kind is a very different kind of company. I really started to believe and just that belief kind of continued to intensify over the years that building a commercial open source companies or open core orientiented companies and we really have to kind of invent new language to really describe why these companies are very different in many different aspects but basically those observations, the fact that I felt, and I still really largely feel that venture capital has very little focus and then being that open source companies are really fundamentally different and maybe they deserve their own unique kind of focused structure, really motivated me to start out as capital. I guess the one piece that gave me the confidence to do it was I felt at the time and maybe I feel this slightly less. So now I still probably feel this a little bit but maybe a healthy dose. I felt extremely unqualified to try to basically, solve this problem in a way that would require basically starting my own venture fund and going out and raising money from people and making investments and proving out the thesis. Until I noticed that no one else was really doing it. I had sort of made some assumptions that other people might jump into this and build a fund focused exclusively on investing in open source founders. But after getting to know a bunch of folks in the venture world, it quickly became apparent that was most likely not going to happen, not because people didn’t feel like it was a good idea. Good idea or not but really that required a very deep amount of conviction and belief that open source companies are sort of categorically different, qualitatively different and could actually grow into a large meaningful category on their own over time right? And so this is like 2017 2018 kind of timeframe. So yeah, that’s basically why I started the fund and yeah been a fun journey since then.

    Alexis

    Yeah, then I can imagine. It’s different If you’re a fund and you want to invest in IP and you don’t you don’t have any Ip or not the way that people think about Ip in the more traditional way. So it’s of course a default focus and I like the fact that draw really focus on something or gone he wanted to say something.

    Joseph

    Yeah, that’s true.

    Ah, no, no, no I think you’re exactly right? it requires a change in mindset and to revisiting a lot of previous assumptions and points of view on on how intellectual property works for sure.

    Alexis

    Um, so tell me what you are looking for when you meet with startup founders.

    Joseph

    Well, I don’t meet with any startup founders. Really I mean I focus exclusively on this world of open source technology and it’s interesting like most of our investments I would actually say probably 95% of our investments have been made by developing point of view. And then secondarily developing a thesis around a project that exists in the world and then sort of a none step contacting the creator of the project introducing ourselves. And telling them that we really like what they’re doing really a lot of the hard work and probably most of the hard work is in developing conviction that the person or the people the team behind creating the project are also the right people to start a company that you know can raise millions of dollars and go and potentially build a large business and so we spend a lot of time investigating whether the creators of the project can also be potentially great founders of building a company. And a lot of the time we don’t believe that’s true and we just don’t invest. But sometimes when the stars align then we invest. It’s quite different from the traditional venture capital approach where you’re sort of getting pitches all day and you’re sitting through pitch meetings and you’re taking introductions or whatever like we’ve certainly been introduced to a handful of people and we made some investments that way but I would say the vast majority of the time is we’re really just looking at a lot of data in the open source world developing a point of view about which markets are getting disrupted over others. And which categories can be created at what points in time we’re looking at changes in the software industry, the rates of growth in different areas like new categories that exist that didn’t exist before and we really start to kind of understand does open source have an advantage in a particular area for whatever reason and if it does the really interesting thing about open source is there’s so many implementations it’s kind of this cambrian explosion of implementations and approaches that starts to happen. Once it’s pretty clear something could work. Have a lot of people really trying to work on proving that out in the open source world. So a big part of our job is really just trying to understand from separating all the signal and the noise what stands out. What’s actually really interesting from a growth standpoint, from an engineering quality standpoint. There’s a lot of things that you can determine and understand by really just looking at Github and looking at the data. That is publicly available really to anyone and so it’s actually extremely fascinating doing what we do as a private seed stage venture capital investor has a lot of similarities to the way hedge funds manage public equity investments, at least in terms of the way they do some of the initial diligence I would certainly say it’s very different terms of how we hold the investments. We hold them for a very long time and we never we’re not selling and trading in and out of them like hedge funds, but the data-driven aspect is very intensely prominent in the way we actually, basically develop an investment thesis and a point of view about specific investment.

    Alexis

    Yeah, it’s’s really interesting to see that. Of course, it’s building the open so you can do the due diligence by yourself. So How do you help those project people to go from the project to building a company.

    Joseph

    Well a lot of the time I would say almost all the time when we lead or are the co-lead of a round we are involved when the company is incorporated or we actually help incorporate the company. And so it’s pretty much at the very earliest of the stages like when the project is at a point where the creators have decided and they’re interested in building a business around the open source technology and they appreciate that the purpose of that business is to invest and continue to grow the open source technology and just really continue to do what they’ve been doing the main things that we are helpful with when we make an investment are kind of multifaceted but I’d say the main things would be the formation of the team of the people that basically comprise the company and join the company. The formation of an understanding of a business plan and a monetization strategy whether that’s executed immediately or over time over the course of many years. We help a lot with thinking about competitive market dynamics understanding the broader ecosystem understanding kind of how the ecosystems coming together. A lot of people would maybe say this is the main contribution that we bring is we really make sure that it’s not only on an advisory basis. But a co-investment basis that other really great individuals who’ve built hugely successful open source companies from the last thirty you know 15 20 30 years actually come along the journey with us. It’s not that we like to be alone and we don’t mind being alone and we have a lot of you know, very high conviction in pretty much every investment that we make but, we really want to create a mechanism for doing knowledge transfer. We talked about this a couple of days ago but we have this kind of network of people that join us as angel investors in rounds a lot of them are our investors in our fund a lot of them are just advisors to companies that we’ve worked with. And they’re really great people I mean they’re individuals who basically from the idea stage and as founders built really amazing companies like Red Hat, Confluent, Github, Mongodb, Elastic, many really great open source companies that you think of today. A lot of those people can be really valuable and helpful, partners to new founders that are really just trying to figure out a lot of things that they’re encountering for the first time but other people may have already developed different points of view and and have encountered in the past already. So we really try to do this kind of knowledge transfer process where bringing other people onboard as co-investors as Angels and as advisors in really any kind of capacity really just to help these founders that we work with be more successful in whatever they’re dealing with whether it’s like hiring or building their community in a certain way or, even raising their next round of funding or should they raise the next round of funding. You know the different points of view on different other investors just a lot of different topics and so. Those are the kinds of things that we tend to help with early On. Because the companies are so early they’re all sort of facing similar challenges around like how to how to manage the growth of their communities, how to make their first or 10 hires, how to think about Market dynamics and their business Model. We tend to kind of cross-pollinate a lot of the ideas across the portfolio and also connect the founders with each other so they can kind of learn from each other as well and it’s actually reasonably easy to do that because all the companies are, kind of somewhat somewhat homogenous and similar and at least in terms of their fundamental structure. They’re all building companies and businesses around some core open source projects. They tend to learn from each other pretty pretty rapidly.

    Alexis

    Oh yeah I love that idea of leveraging the the power of the community to really build other companies I like that I read on your website that commercial open source software companies are 50% more capital efficient. Did I read that correctly? How would you explain that?

    Joseph

    Yeah, that’s something that we put up on our website. Actually our website currently today I think today’s June Thirtieth 2022 I think it’s the same website, we’ve actually had on on the internet since September Twenty Eighteen so we’re we’re actually pushing out a brand new website pretty soon I wouldn’t say that to correct the statements on the website. I think they’re all pretty accurate. Still 50% I think is low as a rough estimate. There’s a reason why I really deeply believe that open source businesses, commercial open source businesses are more capital efficient than other types of businesses and really the main reason is the following. So like if you think about a company that is building a totally proprietary product in isolation, in a cave, or in a closet or whatever metaphor you want to use. The energy required to build that product is a function of how much time and resources you need to invest in order to get that product delivered to the market or into some state where you can actually start seeing adoption and and typically you’ll really see a couple of a couple of things like the cost for doing that will either be subsidized by the individuals behind that technology themselves so they’ll sort of be self-funding that it will be through other sources of financing. You might have to raise money to sort of build that initial technology and prove that out or or another company could be funding it somehow you could be doing it nights and weekends on the side but by the time you launch something you kind of typically already spent a lot of time and energy into building that out. So it really just is is a lot more expensive to do that. With open source, it’s very very very different. The open source you have this kind of idea, you start building in the open from the beginning a lot of projects don’t quite do this and they they build in private and they have a lot of engineering cycles invested before sort of quote unquote flipping the switch on a repository and making it public. I Guess from that standpoint you could say that they’re very similar I mean you still have to make the investment in building out the project and building out the technology but with with open source because you have this dynamic where the project can actually benefit from an accelerated feedback input from many more people than possible if it was built in private and it was sort of a closed Beta and you had a wait list or whatever. It just makes the product and the technology better at a faster rate and as a consequence it reduces the cost to bring the technology to a state of stability and maturity and development velocity really that would otherwise be possible with a proprietary approach and so as a result by the time that we invest in a company around an open source technology. Most of the cases show that the project already has, a sort of an equivalent amount of adoption testing QA, development and really contribution from a lot of people that otherwise you’d have to kind of raise many millions of dollars to produce if you were building a fully proprietary technology company and that’s just on the research and development sort of core technology side of things if you look at customer acquisition and revenue and building a business. Lot of the things that we’ve seen as well are that capital efficiencies are even greater in in that area. So with open source projects, you have this developer community that could use the technology in a lot of different ways, and in many different flexible contexts and lots of use cases. They could be building out and by the time you sort of navigate to a buyer inside of maybe an enterprise organization an it or a line of business or a CTO organization, a lot of the time they might actually already be users of your technology and they might already be advocates and they could in fact, they could just survey their developer community and sort of recognize wow we’re actually already using your technology and everyone loves it. So by the time that we want to start negotiating a contract or you know understand what your product or your services were already sold like there’s no need to sell us and at that point it starts to become much easier and the friction starts to to drop dramatically for the startup or for the company wants to sell something that thing efficiently and sell it with the least amount of friction possible and so instead of the old way of selling software. This is actually not necessarily the old way I think this is actually largely still how it works in sort of proprietary saas world is you have a lot of customer acquisition dollar spent to just get in front of the customer and get users and get adoption and then you have another big wave of dollars spent to convert those um those users into paying customers and so that’s why I think we have in in this kind of saas category we have all these terms like viral coefficients and all the conversion rate heuristics. All these different things that are really optimized around. Okay, you’ve spent a certain amount of dollars to just get the adoption wheel flywheel going and then you have another amount of dollars that you spend to figure out how to convert those users and I’m not saying all those things go away completely. Obviously you still have to invest time and energy and sort of navigating how to convert all of your of your adoption into a business of some kind, fractionally or marginally speaking. But with open source has a sort of phenomena that helps not just with distribution and marketing. It also helps with quality of the product, innovation rate of the product, trust of the product and so many other things. I believe the 50% capital efficiency percentage that you’re that you’re pointing to on the website there is pretty low and in fact, I think that percentage amount was actually referring to something a little bit more specific and so I can kind of explain what it is in like 30 seconds or so but it’s basically pointing to there’s a cohort of open source businesses in the last kind of first years that reached 100M or more in revenue what I was referring to in that percentage was that on average those businesses went out and raised I believe about a quarter of a billion dollars to reach that level of revenue.

    Joseph

    Meaning that they went out and raised a seed round a series a, series b, a series c, and in some cases a series d to reach a 100M revenue business and I would argue and and this is a long-running hypothesis that we’re actively testing with OSS Capital.

    Alexis

    I Get this.

    Joseph

    And hopefully, we’ll see what the data looks like in the next 5 years or something, but I would argue that in all, not some all of those cases, those companies raised too much money that they did not need to raise in order to reach the same outcomes and the same revenue milestones, in, in fact, the same amount of time. So, as a result, you can say those companies were overfunded or they raised money unnecessarily, however, you want to express that is basically part of our mission with OSS Capital is to change a few things about the way open source businesses are built so that they can be better understood from a fundamental standpoint and basically run more capital efficiently.

    Alexis

    So based on all that we can expect that we will have more people creating open source software in the future right? Do you see that really growing?

    Joseph

    Well, this is an interesting question There’s a lot of research and reports that I can point to, maybe you can include them in the show notes, that show the rate of open source. Some people point to it as declining, some people point to it as growing. tend to be very biased in thinking that the rate of open source is only expanding and growing. One proxy for that would be looking at Github’s data. They’re going to reach something like 100M registered users pretty soon I think when Microsoft acquired them in 2018, they were around 30M users. So they’ve grown quite a lot over the last few years. It’s not to say that every registered account on Github is someone creating open source I don’t think that’s true. It’s probably a fraction of that 100M that we’re about to see on GitHub actually creating open source projects, but one thing that I do think is true in a broader sense is more humans are becoming aware of the fact that sort of the highest leverage and the most impactful professional career. You can pursue is in software development, software engineering and more specifically building software products and I believe that building software products will over time become more and more automated and humans will need to learn fewer technologies and fewer languages to build complex innovative products, but I do not subscribe to the point of view that the ai is going to be writing all the code for us I do not believe that is true, and so I think more people, more humans will need to learn how to program and write code for computers because with the way computers are currently built, we need to express very precise instructions to that computer in order for the computer to do what we want it to do and I don’t believe that the the Ai models today can generate the level of precision and nuance needed to build complex software products that do very arbitrarily complex things for humans whether it’s infrastructure software, database, software application, software what have you? there are too many wide encompassing aspects of the technology stack that need to be fine-tuned and tweaked and implemented using code and software largely stitched together, managed, or written by hand via humans and so as a result I can only be most confident in the fact that as the software and that sort of this digital technology career starts to become more compelling and interesting to more people because this is really where the highest leverage and the highest compensation is in in the tech industry, more people will realize in order to be the most differentiated you really have to learn. You have to learn how computers speak and as a result you have to learn how to program and I think as that happens if you look at all of the software engineers today, all the professional software engineers, there’s a lot of debate we can do around this but like I think largely speaking most people would agree, there’s somewhere in the order of 20 or 30M software engineers in the world like professional software engineers. Some people say 50M, so let’s say it’s somewhere between 30 and 50M. I would argue, and I think most people would agree that 99.9 of all of those software engineers heavily heavily depend on open source, and it’s not a question of how much they depend on open source. It’s really they fundamentally depend on open source like without open source technology and tools and infrastructure. They would not be able to do their jobs period like that. They would not be productive like imagine as a developer that you went to your computer, and instead of using millions of projects that exist, that you can readily access on the internet for free and pull together in your application to be productive and build something for the World. You had to write your own custom compiler from Scratch. You had to write your own programming language from scratch. You had to write your own application server from Scratch. You had to write your own development framework from Scratch. You know you had to write your own networking stack from scratch and your own database runtime from scratch and a long list of things. You would never get anything done. It would take you decades of your life to get anything done if you were very talented in the modern world, and so I think that there there’s this. There’s this leverage that exists with open source that is unquantifiable and immeasurable, and as a result, software engineers really greatly appreciate that. And they continue to participate in that movement. This is an interesting kind of Phenomena that non-technical people. People who do not code or do not understand how computers work. They just don’t understand how it works. A lot of time when I’m talking to our investors who, in a lot of cases, are non-technical institutions or other individuals and they do that. They’re not familiar with open source. They’ll often ask this question. Why is it that humans continue to invest so much of their time in this open source thing when they’re not getting paid and they don’t have any economic benefit and. It’s kind of interesting that people ask this question because it’s very revealing of the lack of appreciation for, how much benefit and Leverage engineers get from helping other engineers. Right? There’s this really interesting tribal aspect where engineers are very motivated to help other engineers and the way that they do that most efficiently and effectively is by contributing to open source and sharing their project and sharing their their insights with others. And that just perpetuates the growth of this community and so I think as more people come into the tech industry and appreciate that software engineering is the highest leverage discipline.Then they become software engineers. They realize that the only way they can continue to benefit from all the things that come with that is to really contribute to open source and to give back to that community. I think that just continues to expand the flywheel of open source and it continues to accelerate the fundamentals. Another aspect that people don’t really appreciate is there’s really two types of motivations in the world. There’s motivation to do something for an extrinsic reward sort of like an extrinsic motivation I’m doing something to get paid some monetary or some measurable reward. Or you’re doing something intrinsically you have you have this intrinsic motivation you’re doing it out of the goodness of your heart or in order to learn something new or to have a good feeling about participating in some positive system and that’s really what open source is all about people do it for the intrinsic reason that helping others sort of overrides all the other motivations. And they want to do that specifically because they’ve benefited from all these infrastructure that already exists and so I think it’s kind of a counterintuitive thing. It’s a little bit difficult for non-technical people to understand. But I think it’s pretty profound and I believe that’s the the kind of the main reason open source will continue to grow and be be a huge force. Overtime in the future and actually furthermore I have a much more kind of aggressive point of view around this which is that I think open source will not only just continue its current pace. But as people realize more how powerful this approach is for building technology I think that we’re going to see open source disrupt and transform pretty much every category in the at a minimum, the digital technology world which is all of software all of consumer applications, pretty much anything digital that you can imagine.

    Alexis

    Wow that this is really impactful and speaking about intrinsic motivation, changing the world is a good one. I love it. Joseph, you worked with a lot of leaders among those who you admire what’s the one trait that stands out to you.

    Joseph

    I would say the main trait that stands out to me is humility. Um people who have accomplished a lot and are extremely successful at what they do tend to have humility and it’s one thing that I’ve noticed. And that has really stood out to me and something that I’m still personally working on. I can definitely have a lot of arrogance and hubris a lot of times. So developing humility I think is a really important attribute that I really admire and it’s actually something that is easy to forget like when you’re really trying to identify the absolute best people in whatever area that you’re looking into and you’re trying to find the best insights and the most skilled people who have just a level of depth that is hard to express, because it’s kind of experiential or some individual has accomplished some massive outcome or built something really huge. I would say the vast majority of the time people who have accomplished really huge things if you really sit down with them and get to know them. They’re very humble and in fact, they’re so humble that they sort of look back at everything that they’ve built and they think, they almost think very little of it. They sort of think I learned a lot from that but I don’t think that’s what defines me as a human and it’s an interesting quality that I appreciate a lot. Probably the main quality. The reason I’m so interested in this is I’d say there some leaders who don’t have that quality where they may actually be very accomplished and may be extremely good at what they do, but they don’t have this humility that comes with a level of self-awareness that becomes very valuable in conversations when you’re partnering with them or you’re collaborating with them or you’re trying to solve a problem and that’s probably the number one thing that I pay attention to these days.

    Alexis

    Excellent, Really really beautiful and inspiring. Thank you very much Joseph for having joined the podcast today.

    Joseph

    Thank you Alexis for having me.

    Photo by Ian Schneider on Unsplash

  • Collaboration by Design with Philippe Coullomb and Charles Collingwood-Boots

    Collaboration by Design with Philippe Coullomb and Charles Collingwood-Boots

    The challenges facing humanity are growing in complexity.

    Collaboration is one of the ways we can respond: by bringing diverse minds together and designing conditions where they can actually work through complex problems.

    In this episode, I speak with Philippe Coullomb and Charles Collingwood-Boots, co-authors of the book Collaboration by Design. They both describe their work in a similar way: designing how individuals and organizations come together to solve or navigate complex problems. Often through workshops, sometimes through smaller conversations that help people make sense of complexity.

    From a client booklet to a 360-page book

    The origin story of the book is practical.

    They were approached by a client in Singapore who wanted a training. Philippe and Charles designed it, and created a participant deliverable: a booklet of around 100 pages. People in their network saw it and reacted with a clear message: “This is what we need. There isn’t much written about the practice.”

    So they decided to turn it into a book. What they thought would take a few weeks became a year. The booklet grew into a 360-page publication, expanded topic by topic, until they forced themselves to stop adding.

    Charles adds an important point: people often saw a “simple workshop” but did not understand the depth of intent and practice behind it. The book is, in part, a way to codify that depth.

    The iceberg of facilitation

    One of the most useful images in the conversation is the iceberg.

    What we see in a workshop (facilitator, group, activities) is the tip.

    Below the surface is what makes the visible part meaningful and seamless: the sponsor work, the design work, the political and relational work, and the careful choices that prevent predictable failure modes.

    That is why Philippe and Charles resist the idea that “the facilitation in the room” is the most important part. It matters, but it depends on what happened before.

    Sponsor engagement is not optional

    For Philippe, the first critical step is sponsor selection.

    You need the right group of sponsors who represent enough perspectives and carry enough leadership to co-design the session. Selecting them is not trivial.

    Then comes the engagement work: a series of conversations that clarify context, objectives, and constraints. Mechanically it sounds simple. In practice it is tricky, because those conversations surface contradictions, ambiguities, and stakeholder dynamics that sponsors may ignore or hope to avoid.

    As Philippe puts it: whatever you identify, you must make explicit and address. If you bury it, you will pay for it later.

    Context setting is part of the craft

    Once the workshop begins, Charles places primacy on participant engagement.

    The goal is to create the conditions that allow people to explore, challenge, ask questions, and make sense together. That starts with context setting: participants need to understand why they are there, what the sponsors expect from them, what the journey is, and what role the facilitator will play.

    This is also where facilitation includes coaching sponsors. Sponsors do not always know how to open a workshop well. Helping them find the right posture and tone is part of the job.

    A workshop can feel dull for simple reasons: people are unsure what they are doing, activities feel disconnected, and no one explains why the perspectives in the room matter. Context setting fixes that.

    Virtual is similar, but harder

    Both Philippe and Charles are clear: the core principles stay the same online.

    Sponsorship still matters.
    Design still matters.
    The right questions still matter.

    But virtual collaboration often loses intensity. It takes more effort, more time, and often a larger delivery team than people assume. Philippe challenges a common belief: that digital delivery should be leaner than physical delivery. In his experience, it is not.

    There is also the relationship to content. In person, the physical act of drawing on a whiteboard makes iteration easy and creates shared energy. Online tools can approximate that, but the dynamic changes, and adoption becomes a real hurdle.

    Charles adds a sharp design point: you cannot design a virtual workshop the same way you design an in-person one. Energy, attention, and cognitive load are different. Online also creates more barriers to engagement: camera off, mute on, side distractions. Modules and activities need to be adapted to that reality.

    Hybrid is the hard mode

    Hybrid workshops introduce another layer of complexity.

    Charles calls it plainly: hybrid is very, very challenging. Tech becomes central, not peripheral. You need reliable audio, video, and collaboration tooling that supports cross-platform engagement, not two separate experiences.

    Philippe adds a vivid example: even a delivery team of seven collaboration professionals (five together, one remote, one remote) naturally formed “5 + 1 + 1.” The on-site group did not put enough effort into the digital channels, because their in-room collaboration felt easier. If that happens among experts, imagine what happens across multiple participant groups.

    The takeaway is simple: the technology may exist, but most clients underestimate what it takes to set it up well at scale.

    Space is a facilitation lever, not logistics

    When we speak about collaboration, we often reduce space to logistics.

    Philippe and Charles argue the opposite. Space is part of the design. It shapes the quality of attention, the mood, and the seriousness of the work.

    Charles describes space as an enabler of both effectiveness and experience. Philippe highlights a common client trap: putting space in the same bucket as catering and transport. But you cannot lock people in a windowless hotel room and expect them to invent an exciting future.

    There are universal attributes that matter: daylight, plants, space, line of sight. And then there is the next level: choosing a location and a space that is meaningful for the purpose of the workshop, so the environment reinforces the intent. When you have that alignment, the event gains wholeness.

    The workshop is a moment, not the end

    A workshop is not a purpose in itself. It serves something else.

    Charles describes facilitation as walking a tightrope between the plan and the reality of the participant group. A great facilitator is not executing a script. They are responding to a living system: sensing energy, listening closely, and adapting in real time.

    This is where the delivery team becomes essential. If the agenda needs reshaping, you need support to pivot fast.

    And after the workshop, the real question becomes: who will do what with what emerged?

    Philippe describes two categories of follow-through:

    • tangible outcomes: decisions, artifacts, documents that enable action
    • intangible outcomes: momentum, alignment, leadership energy, relationships that need to be nurtured

    Some sponsors will naturally leverage the workshop’s potential. Some will not. Part of the facilitator’s responsibility is to assess that and help sponsors maximize the value created.

    Closing thought

    This episode is a reminder that meaningful collaboration is designed.

    It is not only a workshop agenda. It is sponsor selection, context setting, facilitation craft, space as an enabler, and thoughtful follow-through that turns a moment into momentum.

    Here is the link to find the book Collaboration by Design. The book is available in English and French.

    Listen to the episode:

    You can listen to this episode on your favorite platform: AnchorSpotifyBreakerGoogleApple

    Here is the transcript of the episode:

    Alexis

    This is Le Podcast on Emerging Leadership, I am Alexis Monville. The challenges facing humanity are growing in complexity. Collaboration is offering us to tackle more complexity by getting diverse minds to work together. How to gather people to facilitate successful collaborations?

    Philippe Coullomb and Charles Collingwood-Boots design the way individuals come together to create innovative and sustainable outcomes to address complex issues.

    Alexis

    Hello Philip and Charles. That’s great to have you on the show.

    Philippe

    Hello.

    Charles

    It’s great to be here.

    Alexis

    So Philip. Ah, let’s start with you. What is your role and how would you describe it to someone. You just met.

    Philippe

    If I only I knew after all these years. I sort of defined myself as a collaborative designer. So in a nutshell my role is to design Collaborative Journeys to solve complex problems or make complex decisions in a multi-stakeholder context and most of the time it takes the form of workshops but not only.

    Alexis

    Thank you. Your turn Charles same question: What is your role and how would you describe it to someone you just met?

    Charles

    So I don’t know whether it’s a good thing or a bad thing but I have the same challenge as Philippe but if I come from a so similar background the way I describe my role is: I design the way individuals and organizations come together to solve or navigate complex problems and just like Philippe a lot of the time that involves workshops but sometimes it’s designing simple conversations to make sense of complex problems.

    Alexis

    it’s really interesting, I’m excited about that conversation! Can you tell me what was the pivotal moment that led you to write the book collaboration by design?

    Philippe

    It’s actually a funny story. We got approached by a client in Singapore who wanted a training so we designed the training and we thought that we needed deliverable for the training. And that it would be great if the deliverable was co-written with the participants. So we produced a sort of booklet or 100 pages booklet ah primarily aiming for the participants to that training and then everyone else in our in our network who saw that booklet. Said look. It’s amazing. We really need something like that. There’s nothing written about the practice, could you make that available and while we couldn’t because this was a client artifact we thought okay we have something pretty good. Let’s put in a few weeks of work to make it a little bit better and let’s turn that into a book. And then of course Charles and I being who we are we thought it was a few weeks and it ended up being a year. We turned a hundred pages booklet into a 360 pages book and every time we would touch a topic we would come with a list of 10 things we believed, that had to be described or illustrated and then we went on and on and on until someday we thought, Okay we have to stop here. We cannot keep adding so initially it started from basically making a prototype and people around us loving it and asking us for more.

    Alexis

    That’s really beautiful. That’s really serving the needs of people!

    Charles

    And maybe just add on to that. People often didn’t fully understand the way that we did things and the intent behind it so to some extent it was about trying to codify what people saw as a simple workshop. But in a way that really drew out the depth of practice and procedure that sat behind it.

    Alexis

    Excellent. So when I think of facilitating successful collaborations I picture the facilitation that happened during the gathering would you say it is the most important aspect.

    Philippe

    You want a good child.

    Charles

    Yeah, So my perspective it’s one part of it and certainly a great deal of emphasis needs to be placed on the Workshop. You know the manifestation of all the work but certainly it’s not I wouldn’t say the most important. For me, It’s the process leading up to it. It’s the work with the sponsor or the owner of the problem or indeed the solution that you’re trying to work towards and really unpacking with them and facilitating the process by which they come to understand the problem. And then starting to design from there. So The facilitation at the front of the room is an aspect but I wouldn’t say it’s the most important.

    Philippe

    To build on that at the beginning of the Book, we take the analogy of the iceberg and I think it’s quite telling what you see, the part of the workshop that you see which is a facilitator a group and a set of activities is on the visible side, the tip of the iceberg. And under that is a lot of pre-work and a lot of background work to make the experience meaningful and the delivery seamless.

    Alexis

    So, what happens before the gathering is really important. You spoke about engaging the sponsors. Can you tell us a little bit about what it means? What are you doing when you are engaging the sponsors?

    Philippe

    Yeah, sure. The first thing is to select the sponsors and make sure that you’re working with the right group of people that represent enough perspective that together show enough leadership so that you have the right conversation partners to co-design the session.

    Philippe

    And that’s not a small task selecting the right group. When you have them, the process is both quite straightforward and quite complex. Quite straightforward because all you can do is have a series of conversations so you schedule a number of conversations through which you will unpack the context clarify the objectives and then progressively develop convictions on what to do and how to do it in the workshop and quite complex because through those conversations you usually uncover a whole lot of contradictions ambiguities, complex stakeholder dynamics that either the client is not aware of or is aware of but closing a blind eye on and you cannot afford to just bury that under the carpet. Whatever you identify you have to address you have to make explicit and then address, otherwise you’ll pay the price later so that’s it, a straightforward process in terms of mechanics but conversations that are quite tricky.

    Alexis

    And that’s what will really change the dynamic during the gathering. So, when I read the book, to be honest, I realized some of the things that happened to me during some workshops or meetings, clearly, I realized that it was linked to that preparation before the meeting. So during the gathering now that you’ve engaged the sponsors and you designed the gathering. What is really important to you?

    Charles

    Obviously through that preparation you’ve developed an understanding of the client of the problem and enough of an understanding around the content to navigate the conversation. But for me, the primacy is engagement with the participant group. Creating the right conditions at the start of the workshop that enable an open conversation. A freedom for the participants to explore to challenge to ask questions to make sense. For me, it’s important to really set the right context up front and your position as part of that group in navigating and facilitating them through the journey that you’ve set out in the agenda.

    Alexis

    So setting the context that’s part of what the facilitator will do and part of what the sponsors will do.

    Charles

    Correct. Your role as a facilitator in that moment in that time needs to be clear. People need to understand what they can expect of you. The role that you will part play and you need to establish yourself in that position across the course of the workshop. But equally the drivers behind the workshop the work that they’re doing the expectation of the sponsors on the participant group to engage in the best way possible to get the best outcome is a key part to so setting that conversation or the dialogue up front with the sponsors and the group is all part of setting the right scene or creating the right conditions for participants to engage because we’ve all been through those workshops where it’s a very sort of dull and dreary experience where you’re not really sure what you’re there to do and.

    Charles

    Sometimes the activities are a little bit disconnected or you’re not too sure what they’re about, so enabling the participants to be confident in the journey that they’re about to embark on even if it’s a little bit unknown and confident in you as a facilitator to lead that and why they’re there. And why their perspective is important.

    Philippe

    And the even for the part that is on the Sponsor’s Shoulder. We do have a role to play. It’s not always natural for the sponsors to know how to properly set the context for such a workshop. So we need to coach them through that, to make sure that they adopt the right posture and convey the right messages sometimes it will be evident to them sometimes not and we need to check if it is and if it’s not we need to help them find the right tone.

    Alexis

    Okay, that’s simple, I Love it. With the pandemic, a lot of things had to happen remotely virtually and when I picture facilitation or collaboration I think of people in your room. What are the main principles to observe when you design and facilitate a virtual gathering? What are the things that are changing with all the things that are the same? Philip, do you want to start?

    Philippe

    Well, I’m not I’m not sure I want to because I’m not a huge fan of virtual collaboration. But I guess like all of us have done, I’ve done a fair bit and I think what doesn’t change is the absolute imperative to get the sponsorship right and to get the design right. So, however, you deliver the experience, making sure that you’re looking into the right questions in the right way is an imperative and you follow the exact same process to achieve that. The main difference is in the intensity of the experience and in the interaction with the content. I didn’t experience yet the same intensity of interactions between participants digitally and it takes a lot more effort to get to intense interactions aid thought and time to get to intense interactions digitally than it takes physically so you need to take that into account when planning the time scheduling the time of your different activities and sizing the delivery team it does take work we have for whatever reason that image that a digital delivery should be leaner than a physical delivery and I don’t think it is and content-wise there’s a completely different way to relate to content to relate to ideas.

    Philippe

    So in the physical world, we have whiteboards and there’s this sort of physical connection to the idea and we draw something It’s extremely easy to iterate. Everyone’s engaged. You can feed from everyone’s energy. This doesn’t happen online and again the digital collaboration tools like Mural, Google Jamboard all of these, offer the possibility to collaborate on the same objects and, but the dynamic is slightly different so you need to take that into account again in your design and of course, there’s the adoption of the tools that can be a real nightmare. No one needs an explanation to grab a marker and use a whiteboard. The adoption of a Mural board as simple as it may seem to some of us can can be a big huddle to others.

    Alexis

    Oh yes.

    Charles

    The big thing from my experience is you cannot design a virtual workshop through the same means as you would an in-person workshop. The demands of  energy of mind space are completely different in person than it is virtually. in addition, there’s a hundred, here’s a myriad of more barriers that people can create for themselves that create a limitation to engage. The simple act of putting yourself on a mute or taking your camera off. All these things create a distraction from each other in the content in the workshop. So the way you design needs to be very different the activities modules or tasks that you put in place need to be different. They don’t have the same effect in person as they do virtual. Now I would guess sort of one of the upsides of covid is the fact that the tools at our disposal are getting much better. And they’re becoming more effective in driving greater engagement on participants through these workshops and some of the micro improvements in the tools themselves and the functionality are getting better. So, much like Philippe I will take an in-person workshop over virtual any day. However, the nature of our work and I guess the nature of work more broadly sees a more distributed participant group quite often and the demand from the client or the expectation for the client is for us to support a virtual session. So we need to lean into it more we need to develop a greater skill around virtual but also hybrid workshops. You know where you have some virtual and some in-person that’s at a whole another layer of challenge and complexity. But yeah, again, more for us to learn and adapt our craft in pursuit of meaningful collaboration in multiple contexts.

    Alexis

    Tell me more about that hybrid setup where people are either joining in the room or joining remotely I Assume that with some people coming back to the office and some wanting to stay home it will happen more often and what other things to take into account when it’s hybrid?

    Charles

    I guess the first thing is it’s really hard. It is very very challenging. So that my experience is the role of technology in support of cross-platform engagement. The platform I mean those virtually in those in the room. The way you design and configure the discussions needs to be carefully considered, it is very easy just to default well those online are one group or have one type of discussion and those in the room have a different one. To ensure that you get a cross-pollination of thinking and perspective you need to weave the two together. A lot of the time that’s enabled by good tech that you have in the room. So either the polycom multi-directional mics and cameras to support in breakout in the room and virtual breakout discussion. There’s sort of different bots or sort of sort of mobile virtual participant devices that you can get these days but again the technical support and prowess required to manage that it is really important because otherwise there’s isn’t another potential fault or fault line in the work that can really derail the conversation and make things more distracting they need to be.

    Philippe

    I would totally emphasize the point on tech, you can totally have 4 people in a room and 1 person remote that completely works. But then if you have a workshop of 50 people and you have 10 groups like that in parallel. What is the technological ability of the client or the event to have ah ten spaces in a row a seamless audio input seamless audio output seamless video inputs seamless video outputs and seamless and digital collaboration boards. So, the technology exists but the setup it takes for thirty fifty or one hundred people to collaborate effectively in an hybrid mode. Most clients are not willing to put in the price. The main challenge is the continuity or the integrity of the experience. People in the room are in a different energy from people at home. they do not feed from the group they do not get that sense of momentum they do not feed from that and I have an example that illustrates that I did a session, I think maybe was 2 three weeks ago and it was just at the level of the team we were a team of seven delivering the session. 5 team members were colocated in Italy and I was the lead facilitator from Malaysia and the graphic facilitator was in the UK so team of 7 but in reality, we really felt that it was 5 plus one plus one the 5 people in the room delivering the workshop had a quality of collaboration that did not extend to the other two that were in different locations and even worse because they had that quality of on-site collaboration. They were not putting as much effort as they should have in the digital communication challenge channels that we had put in place with the Uk and with Malaysia so this is at the level of a team of professionals who are experts at collaboration. So imagine if you replicate that in 5 7 ten groups in parallel with people who are not professionals of collaboration.

    Alexis

    Yeah, I can totally empathize with that I remember switching from one team to the other and one team was already at ease with all the electronic tools and they were already. They had a way of working when they were using chat channel for the team, using that as a back channel for all their conversation within the room when the meeting happened. I switched to a team where the habits of that team were really different. They were using one on one back Channels. And so I knew there was something happening. because I could see their face changing and they could see people speaking about things that had not been discussed before and it took me some time to realize that just that habit of having one on one back Channel using text messages or chat was really hurting the dynamic of the team and it took me really a long time to realize that, so I can imagine just the use of the technology or the ability to use it could be a big problem to deal with.

    Philippe

    Yeah.

    Alexis

    I really wanted to cover that part of hybrid or remote meetings because that’s part of our reality as Charles mentioned but I agree with both of you I would prefer for in-person interactions all the time. I agree with that dynamic. Do you believe that companies will realize that and invest more in off-sites to get to the perfect space to ensure a good collaboration. Do you feel the space is also important when you are in person?

    Charles

    Ah, 100%! I think the space is a key facilitation lever that needs to be designed just as much as the agenda because it enables meaningful effectiveness and pleasant experience for those in the room. To the point around do I think clients or organizations are looking will revert back to in-person I think so not necessarily because they understand the value of in-person collaboration. But. Simple fact that as a community as a society. We’ve been so disconnected from each other this simple act of being in the room which was once probably overlooked, people will understand just how good it is having human interaction human connection, so I do think that’s going to be a key consideration and the speed at which our clients sort of go. Yes let’s all be in the one room together and we’ll fly people out or invest it in that way. I think that’s good. We’re gonna see a return to that. That being said, the fact that we’ve been collaborating virtually inverted commas in collaborating engaging virtually effectively across covid people who see it as equally as a means to just work continue to work that way. So yeah I think there’s a balance. We need to strike there.

    Philippe

    And regarding space. Yeah, of course, I couldn’t agree more with what Charles said and I think one of the things that makes it particularly challenging is that for us space is part of the design exercise. So we know how much choosing and setting up the right space for the job is absolutely essential often in the head of our clients space falls in the logistics bucket so it will fall in the same type of consideration as scattering as transport and so on so they usually don’t instinctively realize that space matters and that no you cannot ask people to look themselves up in a windowless room of an average hotel in the suburbs of a city and then from that place invent an exciting future for the next five years there’s a profound dissonance and while it seems obvious to us, it’s not always obvious to our clients. So there is a challenge for us to help the clients realize that space is in service of the business intent as is in service of the objectives of the session.

    Alexis

    Yeah, it’s interesting it reminded me, I had the chance to organize a gathering of something like 300 people in Boston and I was lucky to work with someone in the event teams that was really engaged in trying to make the experience really good and she found a space that was incredible because it was at the top of the building and the room had windows on both sides and the first person who entered the room said but how will we present anything? But she she used the screen that was a LED screen so we had a perfect presentation, perfect visibility of the content in a room with window all around. That was absolutely an amazing experience and compared to all the things we had before in those ballrooms in hotels where you are in the dark for the full day that was absolutely amazing. So it’s an interesting small thing about space to dig into. 

    Philippe

    And actually to build on that, of course, there are some universal minimum attributes that you would want from a space for workshops. You want a lot of daylight you want plants, you want space, you want line of sight so you can always see through the entire room and feel the energy through the entire room. Those attributes regardless of what you’re going to do you want people to be at their best create a space that’s conducive of that. But then the next layer and we seldom have that opportunity. But when we do. It’s absolutely amazing is First, you define the objectives and the high-level design and then you find a space that is meaningful in relation to the design and then the space becomes that and it’s when I say space. It’s space and location the choice of the city or the choice of the neighborhood or the country or the type of building. Then everything about the space is in service of the intention and that’s when you have a sense your event starts getting a sense of wholeness where everything speaks and everything about as you experience where you are what you eat What you see what you feel is in service of ah of a specific goal And when you have that luxury. It’s just amazing.

    Alexis

    Wow! So that’s totally different than going back to the office and having a meeting. Okay, perfect. So let’s say we did it. We engaged the sponsors properly. We designed the perfect agenda we find the perfect location the perfect space. The gathering is done. Ah so we’re done or what’s next?

    Charles

    Well then we begin? So the workshop itself is almost like walking a tightrope between what you plan to do and the reality of that plan in the face of the participant group. There’s only so much you can develop ah in terms of insight or perspective. The real test is when the people you’re designing for engage with that agenda and sometimes the agenda fits well and the conversation goes just as you had imagined only it’s more richer and has greater depth because of the different perspectives that are being fed in. Other times, not so many other times what you thought to believe what you thought to be true isn’t and you need to adjust and pivot as you go, so your connection to the content your connection to the agenda your connection to the energy needs to be extremely close. you need to sense What’s going on, you need to feel what’s going on. You need to listen and all the while it’s this balancing of that tightrope between what you had planned to do, what you’re hearing and what potential impact or shift that might need to happen. Sometimes it’s a small thing you change the language in some assignments or some activities other times it requires a reshuffling or reshaping of the agenda itself. So the facilitation isn’t just a simple act of following a script. The agenda it’s being acutely present in the group in what’s being said and constantly testing and refining as you go and my perspective is That’s what really differentiates between a workshop that has an agenda and you’re simply executing on the agenda and a workshop that is responding to the living system or the living participant group and as a result gets the right outcome based on on the desire and ambition that emerges from the group. So it’s it’s it’s never over even when it’s all you know everyone sort of had their celebratory drinks and head off into the world wherever they might be going to.. There’s always sort of more to be done because the reality is the workshop is just a moment in time and something needs to happen. With all the hard work and content that emerges from those workshops. So yeah, the preparation is just that it prepares you for the moment. But your role as a facilitator is a demanding one if you do it well, but also very rewarding one in the end.

    Philippe

    And that’s when having a team take all its meaning because to be able to do what Charles is saying you need to be supported by a team that has the agility to pivot. if the changes you make are marginal you might be fine on your own. But if you’re realizing that you need an entire shift of the agenda. There’s not a chance you can do that without a team and that also explains why and again it takes time to convince sponsors about that, why your workshop for 40 participants can have a team of 4, 5, 6 because you’re basically you’re buying the creativity and the agility to pivot and respond to everything you sense from the group.

    Alexis

    Excellent and what comes after the gathering you mentioned just before the booklet that was the origin of the book. So I assume that there’s something important that comes after the workshop after the gathering.

    Philippe

    Well, the workshop is never a purpose in itself. A workshop is in service of something else. So you have to ask your question. Do you have to ask yourself the question, how do I feed back the outcome of the workshop into whatever is coming next. Usually what’s coming next is some form of action because the outcome of the workshop needs to be implemented. It can be part of a project a program part of a strategic direction but actions have to be taken so at the end of the workshop. You  simply ask yourself. Who is going to do what with what came out and as a result, what are the most useful artifacts that we need to produce to enable them to facilitate their work going forward sometimes it’s going to be super sleek things with a communications purpose. Sometimes it’s going to be pretty rough documents because they’re going to be iterated the next day by the same people, but it’s all a matter of creating what’s the most useful that’s for the outcome part for documenting the outcome part then, of course, there’s also the same way we’ve been working responses to prepare them to the session. We need to work on responses to help them fully leverage the potential they’ve created so of course part of that potential is tangible outcomes. We made the decisions x y z we produced outcome x y z and of course, this is valuable. But there’s also questions around leadership momentum alignments more intangible outcomes and these need to be nurtured by the sponsors and again some sponsors will do that naturally some will not. You need to assess that as a facilitator. And if they don’t do that. Naturally, you need to find ways to help them. Um, help them do it in the best possible way to maximize the value for them.

    Alexis

    Philippe Coullomb and Charles Collingwood-Boots are the authors of the fantastic book Collaboration by Design. I highly recommend to all of you. Thank you Charles and Philip for having joined me today on the podcast and having written that book. Thank you.

    Philippe

    Thank you very much.

    Charles

    Thank you very much.

  • The Path to Purpose with Ashley Freeman

    The Path to Purpose with Ashley Freeman

    Some conversations leave you with a simple feeling: clarity.

    In this episode of Le Podcast on Emerging Leadership, I speak with Ashley Freeman, founder of Flourishing Work, about purpose, trust, and the kind of leadership that helps people grow.

    Ashley’s story begins in medical research, where she experienced both great and not so great bosses. That contrast sparked a question that stayed with her: what makes good leaders good?

    She went on to study leadership formally, but the real turning point came when she became a people leader for the first time. That is when she saw theory become practice, and practice create results: teams flourishing and business outcomes improving together. Within six months, she knew what she wanted to do for the rest of her life: lead, and help others learn how to lead.

    Leadership is taking care of people

    Ashley anchors her view of leadership in a definition she aligns with Simon Sinek: leadership is taking care of people.

    The best leaders she experienced invested in her development and offered opportunities before she felt ready. One example stayed with her: as an administrative assistant, she was invited into meetings and projects far beyond her job description. Not by accident, but by intention. The goal was growth.

    That is also why Ashley insists leadership is not about title. You don’t need direct reports to lead. You can take care of people in any role.

    Continuous learning, made real

    Ashley keeps learning in a very concrete way: she runs a book discussion club every Saturday morning.

    It started early in the pandemic with two participants. It grew. It then found a steady rhythm with a core group of five to seven people who still meet regularly. The club is not only about reading. It becomes a space to analyze concepts, apply them to real life, and hold each other accountable.

    As I told Ashley, one of the most surprising parts of a book club is realizing you did not read the same book as the others. People notice different things, keep different quotes, interpret ideas through their own experience. The discussion doubles the learning.

    And there’s a second effect: when a group is counting on you, you actually read.

    Personal brand and trust

    Ashley also works with leaders on personal brand, and she frames it in a grounded way: everyone has a brand, whether they manage it or not.

    Your brand is what you are known for. It’s the blank in the sentence: “What a ___ they are.”

    The useful part is this: you can influence that blank through choices and touchpoints. Which meetings are you in. What topics you show up for. What people hear you speak about. How you introduce yourself. How others introduce you.

    And yes, it connects to trust.

    Ashley’s point is not about forcing sameness. It’s about clarity: when you are clear about what you value, you attract people who can trust you because they understand what you stand for. You can be very different and still share core values such as respect. That shared core makes trust easier.

    Difference, conflict, and better work

    Ashley is also a Myers-Briggs practitioner and uses personality work with teams. She finds it especially useful because teams constantly do two things: take in information and make decisions.

    When teams are very similar, they move fast and enjoy each other, but share blind spots. When teams are diverse in preferences, they can experience conflict and misunderstanding. Ashley’s approach is to help each side see the value the other brings.

    Efficiency without relationships creates friction over time.
    Empathy without outcomes creates a different kind of frustration.

    The work is not to make people identical. The work is to build appreciation for why the difference matters, and how the combination creates better results.

    The book: finding your career purpose

    Ashley’s upcoming book is called The Path to Your Career Purpose.

    She shares two beliefs behind it:

    1. everyone has a career purpose, a unique combination of passions and talents
    2. everyone deserves good leaders when they reach their dream job

    The book is about moving from where you are today toward work that is both practical and meaningful. Ashley is careful not to dismiss the need to pay bills and provide for family. Her point is that both can be true: stability and purpose.

    And she connects it back to leadership: if we help people reach purposeful work, we also need environments where they can flourish once they get there.

    Closing thought

    Ashley’s definition stays with me: leadership is taking care of people.

    Not as a slogan. As a practice: development, opportunity, clarity of values, continuous learning, and the courage to work with difference instead of avoiding it.

    Listen to the episode here:

    Here is the transcript of the episode

    Alexis

    Hey Ashley, how would you describe your role to someone you just met.

    Ashley

    I Am the owner and founder of Flourishing Work which is a company based here in the US that provides facilitation and coaching services to leaders of all walks of life.

    Alexis

    Okay, okay, but tell me more What was the pivotal moment that led you to fund flourishing work.

    Ashley

    Oh great question. So my background is in medical research supporting the efforts of academic medical researchers and through that experience, I like everyone had good and not-so-great bosses and it just gave me a real passion for wanting to understand what makes good leaders good and what makes those leaders that aren’t as great. You know that way as well. And so  I ended up getting an MBA in leadership to really understand and study this topic further and it. But it was really when I started managing a team for the first time when I became a people leader for the first time that everything completely changed for me so I was able to see that the lessons we were learning in the classroom and the theory could actually be put into practice and do some amazing things to help the team really flourish and the business outcomes to match that level of productivity and that was it that when I about six months into being a people leader I said this is what I want to do the rest of my life I not only want to lead but also, more importantly, share how to lead and not just lead people literally but also just interpersonal skills like navigating difficult conversations. For example, I just wanted the rest of my life to be able to coach and teach people on those topics and it’s the best job in the world.

    Alexis

    Okay, okay, okay so you are a leader yourself. You worked with a lot of leader. So among those you admire? What’s the one trait that stands out to you.

    Ashley

    When I think about what a leader is I align with one of my favorite authors Simon Sinek’s definition which is taking care of people. So the best leaders that I ever had who led me were very invested in my development and giving me opportunities really before I even felt ready for them and made sure that I was okay and that I understood what my role was and that’s it. It’s It’s just taking care of people and that’s why I say you know in my opinion you don’t have to have direct reports to be a leader you can lead anyone. That’s definitely what stands out is that they just take care of their people regardless of who they are.

    Alexis

    Okay, okay, so that’s that’s really important because the taking care of people is something that you described if I understand well as growing them helping them to grow and identifying opportunities that help they believe you be good for that. That’s something around those lines.

    Ashley

    Yes, the best boss that I ever had brought me into a lot of meetings and projects that were well outside my Immediate job description. I was actually just an administrative assistant at that time and I say just because you know those projects and those meetings had nothing to do with organizing his calendar and booking his travel and some of the things that I was directly responsible for and yet he brought me into these opportunities for the express purpose of helping me to grow and I will never forget that.

    Alexis

    So really an important! How did you decide to develop yourself as a leader what was the one action you have in mind that was really, the One action you take you’ve taken in the past to develop yourself?

    Ashley

    Oh, that’s a good question I think I have kind of a vague answer to that because for me I really wanted to understand the theory behind what I knew who a good leader was and who a not so good leader was but I didn’t understand why. And for me, I really wanted to understand the principles behind what made good leaders good and so for me and in my case, it really was a lot of studying so I read dozens of books I still to this day lead a book club every Saturday morning I never stop learning. I just wanted to have that knowledge so that I could then apply it because I didn’t know what to do without that knowledge.

    Alexis

    I need to I need to ask a follow-up question on one thing you just said a book club a book discussion club every Saturday morning tell me more. Why are you doing that and I guess it will inspire people to do the same.

    Ashley

    Absolutely, you don’t have to have any experience I certainly didn’t it started in the very beginning of the pandemic and we just picked a book and set out some dates and when it was over. We didn’t want to stop and ah you know the first one I only had 2 participants and then the group grew significantly so we had probably I would say too many maybe eleven or twelve something like that, which was a little bit difficult on the virtual mechanism to really have that space to have discussion. It was just a few too many people. So then we found our stride in the third book and hit around say five or seven people and that group. That core group has been meeting ever since then which as of today what is that about None ars and two months and so why do we do that I mean it’s you know every to know that we have this core group of friends and colleagues every week that we can. We can learn together but more than that we’re we’re not just reading a book. It. It certainly provides enrichment beyond what you might read in a book itself. But more than that we become like I said friends and colleagues and we can really guide each other through the process of growing together and. Implementing and understanding analyzing some of the concepts from the book into our everyday lives and even hold each other accountable to improve our lives and our work.

    Alexis

    I love it. I definitely love it reminded me you know that the one book discussion club I went to and I that was one of the first ones so I was really really taking notes about the book to be sure that I will really have something to discuss and really really precise in all what I was doing and then the first person starts to speak and I’m thinking to myself: “it seems we didn’t read the same book”. And it was really fascinating the things that were already standing out for that person were totally different from me and I was looking at my notes and I was thinking that’s quite crazy. That’s really incredible. Of course, there were some commonalities. There were some things that we had in common but there were a lot of things.

    Ashley

    Um, yes.

    Alexis

    So That thought that I did not even saw that or look at that in for me, it was not really as important so I learned a ton just doing that just showing what you think is important. Showing how you articulate those learnings and listening to the others and you say Wow That’s the next level! That’s something yes and you remember the book and the learnings probably the book crazy well in doing that. That’s also that’s what’s really cool.

    Ashley

    Um, it’s I totally agree. It’s an incredibly enriching experience. It’s almost doubling the learning and the content that you’re taking in and even more than that you know that these people are counting on you to read this book. So you read a lot more books than you actually might otherwise because you know that you have that dedicated time so can’t recommend it enough when I first started I thought they were for I thought book clubs were for kids but ah here I am None years later still doing it every week

    Alexis

    Ah, I read on ah on your website that you are helping people on their personal brand.

    Can you tell me more about that or about that idea of personal brand.

    Ashley

    Absolutely you know we all have one. We all have a brand whether we’re managing it or not whether you’re a leader or not whether you work or not whatever you do you have some sort of brand which is sort of how you come across to other people. And what you’re known for if you will and the work that I do in that particular area is around managing one’s brand because you have a lot of control over how people think about you and it’s It’s such a gift to know that because it.

    Ashley

    It can seem like well we can’t you know control Other people’s thoughts or whatever. But when you think about it. You really do have so many opportunities and touch points and ah places where you put information about yourself or meetings you attend or so many opportunities when you really think about it. To showcase what you want to be known for which can bring all kinds of opportunities from either promotions or even just getting into the right groups of people whether it’s colleagues or in your personal or professional life who have the same values as you. Ah, so so one of the things As an example, you let’s say you’re in sales but you really want to be known more for marketing Well which meetings are you included on and not included on. Are you. Are you in the marketing meetings If not, you probably want to get in on them because people can’t read your mind. Um, you have to showcase what you want to be known for. Are you on the emails on that topic if not how can you be copied on them or you know how do people introduce you. Or what do they talk about when you’re not in the room if they say oh everybody was talking about you the other day. They just said what a blank you are well whatever the blank is that’s your brand and I just love that the blank doesn’t have to stay where it is. It can be whatever you want. Um, and there are so many opportunities to manage that.

    Alexis

    It’s interesting. Do you believe that when people know what their brand is it helped them to develop trust with people around them?

    Ashley

    I do and the reason why is because when we’re clear on what we stand for and what we value what we like and what we don’t like we naturally attract people who have those similar values and just to be clear I’m not advocating against diversity ah particularly of thought in this case because I think that that’s incredibly enriching. Um, but to develop. Trust you can you can have someone who’s very different than you but yet you both really value something like let’s say respect.

    Ashley

    And so you can you can develop a level of trust with them because you know that about each other whereas if you weren’t making that clear or you weren’t even sure yourself kind of what your brand was or what you care about then it’s pretty hard to find other people who share those same values.

    Alexis

    So showing who you are and being clear about the values that are important to you That’s building that trust, building that relationship at the at a deeper level in a way.

    Ashley

    Yes, yes, much deeper than you know we have the same job title or we live in the same neighborhood. It’s much more… It’s much deeper than that. It’s we we we care about the same things even though we may disagree on many other things. Ah, the core of who we are and what we care about is very similar and almost ironically I guess that actually opens up the opportunity to get to know people who are very different than you or who you might not naturally think that you would get along with or want to work with and yet you realize that. At the core you actually do value the same things and it becomes much easier to build trust that way.

    Alexis

    You mentioned diversity and the way you talk about the topic reminded me of a quote from Lincoln and I will paraphrase because I don’t remember it exactly but it’s something along those lines. It’s I don’t like that man much. I need to get to know him better.

    Ashley

    Yes I love that yes I want to jump up and clap I absolutely love that mentality I think you know I see it a lot in the personality work that I do I’m a Myers-briggs practitioner and there’s actually it’s not just something that I’m personally interested in the research shows that I’ve seen anyway that when you have that that completely different perspective on the same team working together your work product is better.

    Alexis

    Yeah I used MBTI before and other kinds of personality profile tools with teams and it’s really incredible to see that with some teams I worked with everybody was nearly on the same side of the of the disk or the quadrant or things like that and in other teamsm It was very very well-balanced.

    Alexis

    And you can see the result on what the team is able to do definitely. It’s quite incredible. You are using MBTI with teams.

    Ashley

    Oh yes, I think any personality assessment is very helpful because it’s it helps you understand yourself and how you’re different or similar to others and those insights are incredibly valuable. That particular one I find works best with teams because it looks at how clearly you prefer different ways of taking in information and making decisions about that information or coming to conclusions about it and if you think about those things taking in information and making decisions with that information is that not what teams do all the time and so it really sort of gets to the core..

    Alexis

    Um, yeah.

    Ashley

    You know where we get conflict in teams and to your point without fail when I have a team that is more similar of thought and personality type. They have the same blinds spots they get along great. They enjoy each other’s company and they get things done very quickly because they all agree on everything but they also have the same blind spots and so when you have the team that is less similar. They tend to come to me because they’re having either communication or conflict issues and when we break it down. It’s really a very touching moment really in this corporate setting where you wouldn’t expect it to be touching. But once we get all of the personalities sort of up on the screen and we start to just see the bigger picture of how we’re different and how we need each other. You just see the light bulb go on where it’s not just oh I don’t like that person because they’re not like me or they don’t think like me or they’re always so annoying you start to realize not only why they’re like that. But how much you need that different perspective to do better work. It’s really cool. It’s a very cool moment.

    Alexis

    So when you have those people in the room when you help people collaborate or work with each other I can imagine that it can become really intense and could even reveal conflict. How do you handle conflicts and how do you help the conversation move forward?

    Ashley

    Yeah, it. So from that perspective it really comes down to helping both sides see the value that the other one is bringing. So for example with in this particular context with Myers-briggs I’ll often see a dichotomy between those who are very efficient and effective versus those who are very people oriented and empathetic.Not to say that we can’t be both It’s just for whatever reason I am coaching clients tend to go into those buckets and so with the ones that are very efficient and effective. Once we start looking at the yes that’s incredibly important and what a gift that strength is because you know the rest of us would never get anything done without you. Thank you at the same Time. Um. Listening is really important and developing those relationships actually becomes more efficient and effective in the long term because those people that you’ve built relationships with and that you’ve listened to really carefully want to work with you and go out of their way to work with you and trust you to your point earlier. Um. You know, whereas on the other side. Maybe if they’re really focused on building relationships and listening to people and being empathetic and if that’s their strength then they may not get as much work done as their colleagues would like them to and then they get this perception of something you know back to our point about personal brand. Maybe it’s a brand of they I don’t know aren’t effective or so. Whatever the brand is and it’s in those conversations. Ah, where you start to see that that person is not just ineffective or hard driving or whatever the perception is it’s when you start to see what their strengths are and why you need them that it’s not necessarily that you just love working with them because they’re so different than you but you start to get an appreciation for why you need that other perspective to get the job done Better. It’s in the combination that we succeed not in the collective blind spots where it’s more comfortable and more fun to be.

    Alexis

    Yeah, that’s really exciting because that gives a sense of where you are going how do you interact with people. When you when you are coaching them or when you are facilitating conversations. So I am I really like the way you are framing all that you have something very exciting coming I need to speak about that so you worked on the book for the last two years something like that right.

    Ashley

    Yeah, one year and a half!

    Alexis

    And so the book is coming ready right now.

    Ashley

    Um, it is we are hoping to target a mid-July publication date.

    Alexis

    Excellent. So tell us more about the book.

    Ashley

    Absolutely And I’ll tell you in the frame of putting the pieces together that we’ve talked about and how it translates into why I care about this topic because it’s a little bit different than what we’ve been discussing and the way that pieces tied together is that the book is About. It’s called the path to your career purpose. So finding purpose in one’s work is something I’m very passionate about the way that connects to what we were talking about earlier in terms of leadership and coaching and facilitation is that. I have a couple of beliefs one is that I believe we all have a career purpose something and what I mean by that is we have a set of unique passions. Things that we’re very passionate about doing. And also a unique set of talents or skills that we have sort of our tools in our toolkit to carry out those passions in the world and that no 2 people have the same combination of those 2 things. So It’s very one of my passions is bring whatever that is for any individual on the planet out into the world because what I’ve seen in my work is that too many people are doing work that just provides for the family or pays the bills and that’s very important I’m not diminishing the importance of that. But what I’ve found in my journey is that you can do both. You can pay the bills you can provide for your family. You can you know build the lifestyle that you need and want to have and do work that is incredibly fulfilling and so that’s that’s what the book teaches the reader to do is go from wherever you are today to living a life of the fulfilling work that I would call you what you were meant to do

    Ashley

    And again back to the connection to what we were talking about so that was one belief the second belief I have is that we all deserve to have good leaders waiting for us when we get to whatever that dream job is and in the book I talk about you’ll have many dream jobs over the course of your career. They’re just kind of one point along the journey. But when you get there. Whatever that is whether that’s being a stay-at-home parent. That’s a job whether that’s working in a corporate setting whether that’s nonprofit whatever that is for you retirement. Whatever your job is um I just think that we all deserve to have good leaders there who will help bring out the best in us and so that’s how those pieces connect is that I’m bringing out what these unique gifts and passions are out of people through this book and then and then I’m teaching workshops and doing executive and leadership coaching to help people become those leaders and again I don’t define that as having direct reports just taking care of other people. So when you get to that dream job using the methodology in my book. You have the supportive environment that you need to flourish in your work which is the name of my company.

    Alexis

    I Love it. So the okay the book is on my reading list. That’s absolutely critical so you convinced me I Love the energy I Love the passion about that and I understand way better now where you are saying a leader is someone who takes care of people I Love it.

    Alexis

    Thank you very much Ashley for joining the podcast today.

    Ashley

    Absolutely, it’s been my pleasure.