Category: General

  • 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. 

  • Crafting Compelling Investor Update Emails: A Guide for Startup Founders

    Crafting Compelling Investor Update Emails: A Guide for Startup Founders

    Introduction

    Effective communication with investors is a cornerstone of successful startup management. A well-crafted investor update does more than report facts; it actively engages your backers in your journey. This guide explores how to structure updates that not only inform but also encourage active participation and acknowledgment of investors’ contributions.

    The Structure of an Effective Investor Update Email

    1. Greeting and Positive Opening

    Start with a personalized and upbeat opening to engage your investors from the outset.

    Example: “Hello Investors! As we embark on a new and exciting year, I’m thrilled to share our latest milestones and plans.”

    My example could be even better with: “Hello Alexis!” as I am more tempted to read when my first name is mentioned.

    2. Highlight Major Achievements

    Begin with key successes to demonstrate the positive impact of your investors’ support.

    Example: “This quarter, we’ve exceeded our targets, achieving record-breaking performance!”

    3. Key Metrics and Financial Performance

    Detail the financials and growth metrics to provide a clear picture of the company’s health.

    Example: “Our revenue surged to $X00,000 in Q4, marking a significant X0% growth from the previous quarter.”

    4. Operational Updates

    Share important updates regarding team expansions, strategic shifts, or infrastructure enhancements.

    Example: “We’re excited to welcome our new CTO, John Smith, who brings a wealth of experience to our tech team.”

    5. Challenges and Lowlights

    Be transparent about challenges, fostering an environment of trust and collaboration.

    Example: “We’re facing some challenges in optimizing our supply chain, which we’re actively addressing.”

    6. Product Updates

    Update on product developments, customer feedback, and market positioning.

    Example: “Our latest product iteration has been well-received, with significant improvements based on customer insights.”

    7. Future Plans and Goals

    Articulate your vision and objectives for the upcoming period.

    Example: “Looking ahead, our focus will be on scaling operations…”

    8. Engagement and Calls to Action

    This is crucial. Make specific requests of your investors, and include at least three actionable items, varying in commitment level. This approach increases the likelihood of engagement.

    Example: “To continue our momentum, we need your involvement. Here are three ways you can help: 1) Try our latest product and provide feedback, 2) Introduce us to potential partners in the XYZ industry, and 3) Share our recent press release in your network. Any of these actions would be immensely valuable.”

    9. Recognition of Contributors

    Acknowledge and thank investors who have made significant contributions. This not only shows gratitude but also motivates others to contribute.

    Example: “A special thanks to Jane Doe for her invaluable marketing insights, and to John Doe for facilitating key industry introductions last quarter. Your contributions have been pivotal to our success.”

    10. Closing and Appreciation

    Conclude with a sincere note of thanks, reinforcing the importance of their support.

    Example: “Your belief in our mission continues to be our driving force. Thank you for being with us on this exciting journey.”

    Conclusion

    An investor update is a strategic tool that goes beyond mere reporting – it’s about creating a collaborative and engaged investor community. By clearly articulating both the achievements and challenges, and by inviting specific actions and recognizing contributions, you foster a deeper connection with your investors. This not only keeps them informed but also actively involved in your startup’s journey towards success.

  • Beyond Top Ten: My Essential Non-Fiction Reads for Leadership and Personal Growth

    Beyond Top Ten: My Essential Non-Fiction Reads for Leadership and Personal Growth

    A few months ago, Kevin Fishner presented me with an intriguing challenge: to list my top non-fiction books. As simple as it sounds, this task quickly unfolded into a reflective journey through the pages that have shaped my understanding of leadership, personal growth, and organizational development. But how does one confine such a wealth of knowledge and inspiration to a mere top ten? The truth is, it’s not just about ranking books; it’s about recognizing the unique value each one brings to different stages of our journey and the varied challenges we face.

    In this list, you won’t find a conventional top ten. Instead, I offer a collection of books, each holding a special place in my library and my heart. These are books that have not only influenced my thoughts but have also been integral tools in my workshops with teams during my career and now at Pearlside. They are more than reads. They are experiences shared, lessons learned, and wisdom applied. From fostering an understanding of team dynamics with Patrick Lencioni’s insightful fables to navigating the complexities of global business using Erin Meyer’s ‘The Culture Map,’ each book has been a key in unlocking potential – both in myself and in the teams I’ve had the privilege to coach and guide.

    Join me as I share this curated list, a tapestry of narratives and insights that have been pivotal in my journey as a co-founder and leadership coach. Whether you are at the onset of your career, leading a startup, or steering an established organization, these books offer a compass to navigate the ever-evolving landscape of leadership and personal growth.

    In the realm of leadership and team development, certain books have transcended the role of mere guides, becoming instrumental tools in my workshops at Pearlside. These selected works offer theoretical insights and have proven to be practical in real-world applications. Let’s delve into these cornerstone books:

    1. The Five Dysfunctions of a Team by Patrick Lencioni: Lencioni’s captivating fable delves into the heart of team collaboration – or the lack thereof. In my workshops, this book serves as a mirror for teams to reflect on their own dynamics. Through its compelling narrative, it provides a framework for understanding and overcoming common obstacles to teamwork, turning theoretical concepts into tangible actions. I wrote a post reflecting on my experience with a leadership team here.
    2. The Advantage by Patrick Lencioni: Building on the themes of his previous work, this book offers a holistic view of organizational health. Our workshops explore Lencioni’s model as a roadmap to achieving business success through cultural coherence and leadership clarity. It’s a powerful guide for leaders seeking to cultivate a vibrant and productive workplace culture. I wrote about this here.
    3. The Culture Map by Erin Meyer: In today’s globalized business environment, understanding and navigating cultural differences is paramount. Meyer’s book is a key resource in our workshops for developing cultural intelligence. It equips leaders with the tools to effectively manage and lead across diverse cultural landscapes, enhancing global collaboration and empathy. I used again the Culture Map in a workshop just a few weeks ago.
    4. What Got You Here Won’t Get You There by Goldsmith Marshall: This book addresses the subtle nuances of personal growth and behavioral change essential for leadership advancement. In our sessions, we use Marshall’s insights to help leaders identify and rectify the small, yet impactful, habits that can hinder their progress, fostering a mindset geared towards continuous improvement. I explain how I conduct the workshop here.
    5. Understanding A3 Thinking by Durward K. Sobek II: A3 thinking is more than a problem-solving tool; it’s a methodology to foster critical thinking and communication. I love using the approach to structuring thought processes and decision-making, enabling leaders and teams to tackle complex challenges systematically.

    Reviewing the list, I realized that I used many other books in my workshops, books by Deming, Drucker, and Senge to name a few. It gives me ideas for more writing!

    Here is the alphabetical list of books:

    1. A Brief History of Time – Stephen Hawking
    2. A Business and Its Beliefs: The Ideas That Helped Build IBM – Thomas J. Watson Jr.
    3. A Little History of Philosophy (Little Histories) – Nigel Warburton
    4. American Icon: Alan Mulally and the Fight to Save Ford Motor Company – Bryce G. Hoffman
    5. An Everyone Culture: Becoming a Deliberately Developmental Organization – Robert Kegan
    6. Blink: The Power of Thinking Without Thinking – Malcolm Gladwell
    7. Built to Last: Successful Habits of Visionary Companies (Good to Great, 2) – James C. Collins
    8. Business Model Generation – Alexander Osterwalder
    9. Changing on the Job: Developing Leaders for a Complex World – Jennifer Garvey Berger
    10. Chimp Paradox: How Our Impulses and Emotions Can Determine Success and Happiness and How We Can Control Them – Steve Peters
    11. Collaboration by design: Your Field Guide for Creating More Value When Bringing People Together – Philippe Coullomb
    12. Competing Against Luck: The Story of Innovation and Customer Choice – Clayton M. Christensen
    13. Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration – Ed Catmull
    14. Delivering Happiness: A Path to Profits, Passion, and Purpose – Tony Hsieh
    15. Freedom, Inc.: Free Your Employees and Let Them Lead Your Business to Higher Productivity, Profits, and Growth – Brian M. Carney
    16. Good Authority: How to Become the Leader Your Team Is Waiting For – Jonathan Raymond
    17. Good to Great: Why Some Companies Make the Leap… and Others Don’t – James C. Collins
    18. Great by Choice: Uncertainty, Chaos, and Luck–Why Some Thrive Despite Them All (Good to Great, 5) – James C. Collins
    19. Homo Deus: A History of Tomorrow – Yuval Noah Harari
    20. How Not to Diet – Michael Greger
    21. How to Win Friends and Influence People – Dale Carnegie
    22. Humanocracy: Creating Organizations as Amazing as the People Inside Them – Gary Hamel
    23. I’m a Joke and So Are You: Reflections on Humour and Humanity – Robin Ince
    24. Immunity to Change: How to Overcome It and Unlock the Potential in Yourself and Your Organization (Leadership for the Common Good) – Robert Kegan
    25. Joy, Inc.: How We Built a Workplace People Love – Richard Sheridan
    26. L’art de devenir une équipe agile – Claude Aubry
    27. Lean Management: Mieux, plus vite, avec les mêmes personnes. – Pierre Pezziardi
    28. Legacy: What the All Blacks Can Teach Us About the Business of Life – James Kerr
    29. Leonardo da Vinci – Walter Isaacson
    30. Les mots sont des fenêtres (ou bien ce sont des murs): Introduction à la Communication Non Violente – Marshall B. Rosenberg
    31. Man’s Search for Meaning – Viktor E. Frankl
    32. Managing for Happiness: Games, Tools & Practices to Motivate Any Team – Jurgen Appelo
    33. Never Split the Difference: Negotiating As If Your Life Depended On It – Chris Voss
    34. Outliers: The Story of Success – Malcolm Gladwell
    35. Radical Candor: Be a Kickass Boss Without Losing Your Humanity – Kim Malone Scott
    36. Radical Product Thinking: The New Mindset for Innovating Smarter – R Dutt
    37. Reboot: Leadership and the Art of Growing Up – Jerry Colonna
    38. Reinventing Organizations: A Guide to Creating Organizations Inspired by the Next Stage of Human Consciousness – Frederic Laloux
    39. Search Inside Yourself: The Unexpected Path to Achieving Success, Happiness (And World Peace) – Chade-Meng Tan
    40. Shoe Dog: A Memoir by the Creator of Nike – Phil Knight
    41. Spiral Dynamics Integral: Learn to Master the Memetic Codes of Human Behavior – Don Edward Beck
    42. Stupid, Ugly, Unlucky and Rich: Spike’s Guide to Success – Richard St. John
    43. Surely You’re Joking, Mr. Feynman!: Adventures of a Curious Character – Richard P. Feynman
    44. **Talking to Strangers: What We Should Know About the People We Don’t Know** – Malcolm Gladwell
    45. Team Topologies: Organizing Business and Technology Teams for Fast Flow – Matthew Skelton
    46. The 4 Disciplines of Execution: Achieving Your Wildly Important Goals – Chris McChesney
    47. The Anatomy of Peace: Resolving the Heart of Conflict – The Arbinger Institute
    48. The Art of Gathering: How We Meet and Why It Matters – Priya Parker
    49. The Artist’s Way: A Spiritual Path to Higher Creativity – Julia Cameron
    50. The Autobiography of Malcolm X – Malcolm X
    51. The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever – Michael Bungay Stanier
    52. The Culture Map: Breaking Through the Invisible Boundaries of Global Business – Erin Meyer
    53. The Diamond Cutter: The Buddha on Managing Your Business and Your Life – Michael Roach
    54. The Dream Team Nightmare – Portia Tung
    55. The Fifth Discipline: The Art & Practice of The Learning Organization – Peter M. Senge
    56. The Five Dysfunctions of a Team: A Leadership Fable – Patrick Lencioni
    57. The Goal: A Process of Ongoing Improvement – Eliyahu M. Goldratt
    58. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers – Ben Horowitz
    59. The Happiness Advantage: The Seven Principles of Positive Psychology That Fuel Success and Performance at Work – Shawn Achor
    60. The Lean Manager: A Novel of Lean Transformation – Michael Ballé
    61. The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change – Camille Fournier
    62. The Meme Machine – Susan Blackmore
    63. The Phoenix Project: A Novel About IT, DevOps, and Helping Your Business Win – Gene Kim
    64. The Qualified Sales Leader: Proven Lessons from a Five Time CRO – John McMahon
    65. The Rider – Tim Krabbé
    66. The Righteous Mind: Why Good People Are Divided by Politics and Religion – Jonathan Haidt
    67. The Sketchnote Handbook: the illustrated guide to visual note taking – Mike Rohde
    68. The Soul of a New Machine – Tracy Kidder
    69. The Southwest Airlines Way – Jody Hoffer Gittell
    70. The Starfish and the Spider: The Unstoppable Power of Leaderless Organizations – Ori Brafman
    71. The Toyota Way: 14 Management Principles from the World’s Greatest Manufacturer – Jeffrey K. Liker
    72. Thinking In Systems: A Primer – Donella H. Meadows
    73. Thinking, Fast and Slow – Daniel Kahneman
    74. Training from the Back of the Room!: 65 Ways to Step Aside and Let Them Learn – Sharon L. Bowman
    75. Unflattening – Nick Sousanis
    76. Understanding A3 Thinking: A Critical Component of Toyota’s PDCA Management System – Durward K. Sobek II
    77. Visual Teams: Graphic Tools for Commitment, Innovation, and High Performance – David Sibbet
    78. When Breath Becomes Air – Paul Kalanithi
    79. When They Win, You Win: Being a Great Manager Is Simpler Than You Think – Russ Laraway
    80. Whiplash: How to Survive Our Faster Future – Joichi Ito
    81. Why I’m No Longer Talking to White People About Race – Reni Eddo-Lodge
    82. Why We Sleep: Unlocking the Power of Sleep and Dreams – Matthew Walker
    83. Work is Love Made Visible: A Collection of Essays About the Power of Finding Your Purpose From the World’s Greatest Thought Leaders (Frances Hesselbein Leadership Forum) – Frances Hesselbein
    84. Work Rules!: Insights from Inside Google That Will Transform How You Live and Lead – Laszlo Bock
    85. #Workout: Games, Tools & Practices to Engage People, Improve Work, and Delight Clients – Jurgen Appelo

    The journey through these pages has been more than an academic exercise; it has been a voyage of personal and professional discovery. Each book on this list has left an indelible mark on my approach to leadership, team building, and personal growth. They have been companions and guides, challenging my perceptions, affirming my experiences, and inspiring new ways of thinking and leading. In my work at Pearlside, these books have informed our methodologies and helped shape the transformative experiences we strive to create for our clients.

    In sharing this list, I invite you to view these books not just as a collection of titles, but as a mosaic of knowledge, each piece offering unique insights relevant to different stages of your journey. Whether you are navigating the complexities of team dynamics, cultural diversity, personal growth, or organizational change, these books provide a wealth of wisdom to guide you.

    Call to Action:

    Now, I turn the page over to you. What are the books that have profoundly impacted your journey? Which titles resonate with your current challenges and aspirations? I encourage you to share your thoughts and recommendations in the comments. Let’s continue this conversation and enrich our collective journey with diverse perspectives and insights.


  • Pivoting Forward: The Birth of Our Vision

    Pivoting Forward: The Birth of Our Vision

    By Alexis Monville & Jeremie Benazra

    “Every new beginning comes from some other beginning’s end.” This ancient wisdom resonates deeply through the cycles of life, reminding us how impactful the understanding and embracing of endings is to welcome new chapters truly.

    So, what does it take to pause and reflect meaningfully at the closing of a chapter? Just writing a summary or takeaway? What is available currently to help us have a powerful insight to take to the next chapter? How is it related? What do we really leave behind or run away from? 

    In our individual interactions and experiences, we’ve been easily caught in the tapestry of human behavior. Time and again, we could notice a distinct pattern. While there’s an abundance of guidance on starting afresh, finding the new shiny thing, climbing the corporate ladder, or handling workplace conflicts, there needs to be more dialogue on a fundamental aspect of our professional journey: the ending.

    So, why would acknowledging the end be so vital? The essence of it is simple yet impactful. Proper closures lead to authentic new beginnings. A hasty or unclear conclusion can often leave behind a trail of unresolved feelings and doubts and hinder commitment to new ventures. In contrast, a well-navigated closure can usher in clarity, contentment, and renewed purpose.

    During one of our personal explorations, we chanced upon Daphne Rose Kingma’s remarkable book, “Coming Apart: Why Relationships End and How to Live Through the Ending of Yours.” While its primary focus was on personal relationships, the depth of its insights is undeniable. Like passing through a door, which place are we going away from, what does passing the door mean for us, and where to?

    From Daphne’s work, we can understand that we look for a new identity once a personal achievement is completed. Seeking new relationships and new horizons is our way to find new personal tasks to complete for this new identity to take shape. So, what do we want to step away from, and what are we really seeking for? Since our workplaces’ perception is established with the relationship we entertain, how can we use this treasure trove of wisdom in the domain of professional life?

    The challenge was evident. Adapting a deeply personal narrative to the structured realm of professions isn’t straightforward. But our shared mission is clear: to equip individuals with the insights and tools to transition through career endings with grace, insight, and resilience.

    And so, our guide, “Pivoting Forward: Understanding Career Endings and Preparing for New Beginnings,” came to life. More than just a reinterpretation of Kingma’s work, it’s our sincere attempt to bridge the personal with the professional, recognizing that our careers, akin to our personal relationships, form an integral part of who we are and see ourselves.

    In “Pivoting Forward,” we offer an insightful compass to help navigate the intricate journey of closing a meaningful chapter. We believe that with the appropriate perspectives and insights, every conclusion can pave the way for a brighter, more aligned future.

    In wrapping up, every groundbreaking vision sprouts from keen observation, empathy, and a desire to effect change. “Pivoting Forward” is a testament to this belief. Through this guide, we hope to shine a light on one of life’s most underrepresented yet profound transitions, offering a hand to those on the brink of a new professional dawn.

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    • Reflecting on Rhythms and Relationships: Insights from Kent Beck at Plato Elevate

      Reflecting on Rhythms and Relationships: Insights from Kent Beck at Plato Elevate

      On November 8, 2023, Kent Beck, an influential software engineering figure and the Agile Manifesto’s original signer, delivered a profound session at the Plato Elevate conference in San Francisco. His talk, titled “What I Learned about Coaching in the Back of an Ambulance,” offered a journey through his illustrious career and the evolution of his coaching philosophy.

      In the early ’80s, Beck’s time at Tektronix Labs was pivotal, shaped significantly by his mentorship with Ward Cunningham. Cunningham, known for inventing the wiki, instilled in Beck the rhythms of engineering and a burgeoning belief in pair programming. The scarcity of terminals meant sharing one, which led Beck through an organic learning progression—from observing to correcting, suggesting, and finally, taking the lead. This experience laid the groundwork for his later methodologies.

      Fast-forwarding to 2011, Beck faced a humbling moment, considering himself the “worst programmer” at Facebook. This prompted a shift towards coaching, where he dedicated himself to mastering various techniques. Beck shared an anecdote about employing the ‘mirroring technique,’ which involves repeating a person’s last word to spur their thought process. This method, often used in negotiations, proved to be a powerful tool in coaching, revealing the strength in simplicity and active listening.

      However, the pressure of keeping all these techniques top of mind led to an incident that found Beck in the back of an ambulance, momentarily robbed of his speech. This experience was a catalyst for change. He emerged with a renewed approach to coaching: to be fully present and authentic. Beck emphasized the importance of preparing for each session with the intent to deliver unequivocal value, helping individuals transition from good to great.

      Kent Beck’s journey is a testament to the continuous process of learning, adapting, and evolving. His latest endeavors, including his book “Tidy First,” reflect his ongoing commitment to refinement and excellence in software engineering and coaching.

      For those intrigued by Beck’s wisdom, his presentation on “Tidy First” is available for further exploration on InfoQ, shedding light on the intricacies of refactoring and clean code.

      In a rapidly evolving world, Beck’s reflections at Plato Elevate remind us of the timeless value found in mentorship, the iterative nature of skill acquisition, and the courage to adapt our approaches for the betterment of ourselves and those we aim to uplift.

    • The Story Behind “Pearlside”: Redefining Leadership for a Sustainable Future

      The Story Behind “Pearlside”: Redefining Leadership for a Sustainable Future

      The Pearl Perspective

      When you hear the word “sand,” what comes to mind? For some, it’s the tiny grain that can jam the gears of a well-oiled machine. For others, it’s the beginning of something beautiful—a pearl. At Pearlside, we choose to see the pearl.

      Why? Because we believe in the transformative power of perspective. Just as an oyster turns a grain of sand into a valuable gem, we help design and build sustainable and high-impact teams and organizations. These organizations are not just efficient; they are places where people are highly satisfied and engaged. They are environments where individuals can turn challenges into opportunities, much like an oyster transforms a grain of sand into a pearl.

      The Anagram of Leadership

      You might have noticed that “Pearlside” is an anagram of “leadership”—well, almost. While it’s not a perfect match, it’s close enough to make you think. And that’s intentional. At Pearlside, we don’t chase after perfection; we embrace the beauty of imperfection. We accept failure as a stepping stone towards success and view it as an opportunity to learn, adapt, and grow.

      The Iterative Journey

      In today’s rapidly evolving landscape, clinging to outdated models of leadership is not just ineffective; it’s detrimental. That’s why we’re committed to redefining the concept of leadership to make it more inclusive, sustainable, and impactful for the modern world.

      We understand that this is a journey, not a destination. It’s an iterative process that requires ongoing learning and growth. We are collectively committed to this journey, not just for ourselves but for everyone around us. Through practical experience and hands-on opportunities, we aim to facilitate growth for individuals and organizations alike.

      The Ultimate Goal

      Our ultimate goal is to transform the way leadership is understood and practiced. We want to create a world where leadership is not about authority but about empowering others, not about individual achievements, but about collective impact; not about maintaining the status quo, but about driving meaningful change.

      Conclusion

      So, the next time you find yourself faced with a grain of sand—a challenge or obstacle—remember that it’s all a matter of perspective. Will you let it jam your gears, or will you transform it into a pearl? At Pearlside, we’re in the business of creating pearls. And we invite you to join us on this transformative journey.

    • 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)

    • New Experiment for Effective Meetings: Discovery One-on-One

      New Experiment for Effective Meetings: Discovery One-on-One

      Hello,

      Ever struggled with breaking the ice in meetings with new colleagues or clients? I’m excited to share a unique approach from our book, “I am a Software Engineer and I am in Charge,” that transforms these encounters.

      🎯 Introducing: Discovery One-on-One

      🤔 What Is It?

      This is a structured yet flexible approach to prepare and drive effective meetings with people you’re not yet familiar with.

      🌟 Why Use It?

      Building a strong relationship is crucial for effective collaboration. This method ensures that your first meeting lays a solid foundation for future interactions.

      👣 How It Works

      1️⃣ Prepare Your Board: Create a simple board with three columns: To Do, In Progress, Done.

      2️⃣ Set the Agenda: Use sticky notes for each topic: Ice Breaker, Professional Background, Experience, 3 Wishes, and a wild card (???).

      3️⃣ Ice Breaker: Start with light, engaging questions to ease into the meeting.

      4️⃣ Share Backgrounds: Discuss your professional journeys.

      5️⃣ Discuss Relevant Experiences: Tailor this part to your specific context.

      6️⃣ 3 Wishes: End with a creative question about transforming work or the workplace.

      7️⃣ Wild Card: Allow space for any additional topics they might want to discuss.

      📝 Note: This approach is adaptable. Feel free to tailor it to suit the context of your meeting.

      🔄 Why It Matters

      First impressions count. A Discovery One-on-One ensures your first meeting is not just productive but also enjoyable, setting the stage for a great working relationship.

      📚 Curious to learn more? This is just one of the many practices we delve into. Check out the experiment: Discovery One-on-one.

      👇 Have you tried a structured approach in your one-on-ones? How did it go? Share your experiences!

    • The Essence of Leadership: Insights from Agile Tour Bordeaux

      The Essence of Leadership: Insights from Agile Tour Bordeaux

      At the recent Agile Tour Bordeaux conference, attendees had a unique opportunity on Friday afternoon: a segment dedicated solely to exploring ideas through open space technology. Within this dynamic framework, I had the privilege of conducting a workshop that probed the nature of leadership. The high participation and engagement from attendees made this discussion exceptionally enriching.

      What is Leadership?

      Our session began with a straightforward question: “What is leadership?” Participants around the table shared their perspectives, leading to a myriad of words and phrases, such as “Action,” “Vision,” “Authenticity,” “Inspiration,” and “Curiosity.” As we revisited these initial descriptors, we added depth and texture. Words highlighted in green on our workshop sheet further clarified and enriched our initial understanding.

      Creating Conditions for Emergent Leadership

      A prominent theme that emerged was that of emergent leadership. Instead of appointing leaders based on traditional criteria or hierarchies, emergent leadership is about crafting conditions for leadership traits to manifest organically. Such environments, characterized by trust, autonomy, and collaboration, enable individuals to shine, exhibiting leadership qualities that may go unnoticed in more structured settings.

      Developing Leadership Skills: A Continuous Journey

      When we surfaced how to develop our leadership skills, there was a consensus: practice and aiding others are paramount. This sentiment strongly resonated with the Agile Manifesto’s opening lines, “We are uncovering better ways of developing software by doing it and helping others do it.” Given that we were at an Agile event, this alignment was fitting and heartening.

      Leadership: An Invitation, Not an Obligation

      Leadership, as we discussed, is an invitation, not an imposition. While the allure of leadership might be strong for many, it’s paramount to recognize it as a choice. Some might opt not to embrace leadership roles, and that is perfectly valid. True leadership acknowledges individual preferences, understanding that everyone carves their unique path.

      Gratitude and Reflections

      I want to express my deep gratitude to the organizers of Agile Tour Bordeaux. Attending the event as a participant was a refreshing and enlightening experience. The seamless organization, the diversity of ideas, and the vibrancy of discussions were truly commendable.

      Conclusion

      The Agile Tour Bordeaux was more than just a conference; it was a journey of discovery and introspection. Our leadership workshop, nestled within the open space segment, bore testament to the eclectic mix of ideas and perspectives present. Leadership, as we discerned, transcends titles or authority; it’s about fostering environments where everyone can step up, lead, and make a lasting impact.

    • Cultivating a Global Culture: Lessons from Canva

      Cultivating a Global Culture: Lessons from Canva

      📣 Have you ever wondered how some companies manage to preserve their culture while expanding on a global scale?

      🔗 I came across an insightful article that delves into this very question, looking at how Canva—yes, the design platform we all love—has successfully maintained a unified culture while spanning across continents.

      🌟 Key Takeaways:
      1️⃣ Culture isn’t just an ‘HR Thing’: Canva places culture at the core of their acquisition strategy, ensuring both product and team alignment.
      2️⃣ Autonomy & Integration: Canva adopts a thoughtful approach to incorporating new teams, allowing for strategic autonomy and gradual integration.
      3️⃣ The Role of Physical Spaces: Whether it’s a co-working space or a campus, the choice of workspace reflects and nurtures the company culture.
      4️⃣ Connection Beyond Proximity: Canva’s transition to remote work during the pandemic led to creative strategies, like “sacred lunch hours,” to keep the company culture alive.

      🤔 These insights could be particularly relevant for startups and scaling businesses looking to maintain their core values while expanding. And yes, it’s directly linked to the quality of leadership at all levels.

      👉 Here’s the article from Raconteur for a deeper dive!

      ✅ As we are working on launching a leadership development program designed to serve everyone regardless of their role, understanding the dynamics of culture is more critical than ever.

      💬 Would love to hear your thoughts! How important is organizational culture in your leadership journey?

    • The Origins of the BEPS Navigator

      The Origins of the BEPS Navigator

      Navigating the bustling corridors of a 300-strong cloud infrastructure team, I witnessed firsthand the complexities and challenges of a large-scale software development setup. The traditional organization with its neatly partitioned functions – product management, software engineering, quality assurance, and the like – seemed efficient on paper, but it was far from optimal.

      We brought together leaders from all functions to form a leadership team in a transformative move. With shared goals as our north star, we dreamt of a novel organization model: small cross-functional teams, each dedicated to delivering a distinct section of our product. These weren’t just any teams. Imagine having a dedicated team for ‘compute,’ another for ‘storage,’ and yet another for ‘networking.’ (Yes, the reality was a bit more complex than that!)

      To bridge the gap between our product managers and the teams, we introduced the ‘User Advocate,’ responsible for ensuring clarity in the team’s direction. Alongside them, we introduced the ‘Team Catalyst,’ a role committed to fostering collaboration among team members.

      However, our forward-looking vision encountered unexpected pushback, predominantly from the intermediate managers. They felt threatened, viewing their roles as narrowly confined to execution. This pivotal insight sparked my epiphany, leading to the creation of the BEPS navigator. It was designed to guide their transition towards a more encompassing, servant-leadership stance. Let’s delve deeper:

      • Business: It’s more than profit and loss sheets or market dynamics. It’s about comprehending the realm within which the organization functions within. Leaders should discern why their products or services exist in the first place and be able to articulate a clear and compelling vision.
      • Execution: While execution remains a critical facet, it’s not the sole responsibility. Leaders are not just schedulers or task distributors. They are the driving force ensuring the team delivers effectively.
      • People: Leaders wear multiple hats – they hire, they nurture, they manage performance. But above all, they invest in self-improvement, knowing that leadership is an ever-evolving journey.
      • System: W. Edwards Deming‘s words ring especially true here: “A Bad System Will Beat a Good Person Every Time.” Understanding the intertwined network of people, processes, tools, and organizations is vital. But leaders also hold the torch to illuminate and obliterate obstacles, ensuring their teams can function seamlessly.

      Amidst apprehensions and pushbacks, our leadership team clung to these axes, or as we initially called it, “the axes.” The shift was transformational. Our teams moved faster, silos crumbled, and products reached customers quicker.

      However, transitions are rarely smooth. Some managers couldn’t align with the new vision, some engineers misjudged the roles of User Advocate and Team Catalyst. But with every hiccup, the navigator provided a guiding light.

      In subsequent roles, I wielded the BEPS navigator in coaching and mentoring, helping leaders discern underexplored areas of their roles. Its simplicity is its brilliance – four overarching categories that can be tailored and deepened based on context. It’s not a tool for benchmarking or comparison but a mirror for introspection. Remember, balancing the axes doesn’t mean equal emphasis on all; it’s about investing energy where it’s most needed at a given time.

      The anecdote of managers fearing obsolescence in the face of transformation underscores a vital lesson. Leadership is not about controlling a system but understanding and molding it, ensuring everyone within can flourish.

    • The Myth of “Startup Culture”

      The Myth of “Startup Culture”

      The term “startup culture” is often thrown around in the business world, conjuring images of casual dress codes, open office spaces, and a relentless drive for innovation. However, after delving into the operations of various startups, like Freetrade, it becomes evident that there isn’t a one-size-fits-all “startup culture.” Instead, the culture of a startup is what its founders make of it. If they’re intentional, they can craft a unique, thriving environment. If not, they risk falling into the trap of replicating the corporate world they once sought to disrupt.

      The Illusion of a Unified Startup Culture

      Drawing from the Freetrade example in the Raconteur’s article, it’s clear that startup culture is not about pool tables or artisan coffee counters. It’s about the values, beliefs, and practices the founders and early team members embed into the company’s DNA. For instance, Freetrade’s CEO, Adam Dodds, emphasizes comfort and output over strict dress codes, reflecting his belief in prioritizing employee well-being and productivity over superficial norms.

      The Risk of Unintentionality

      Startups that don’t intentionally define their culture face a significant risk. As they grow and bring in experienced professionals from various backgrounds, especially from large corporations, they might find themselves in an environment lacking clear cultural direction. Their natural inclination would be to implement what they know best, often importing practices from the corporate world. While these practices might be efficient, they might not always align with the startup’s original vision or values.

      Intentionality in Crafting Culture

      Being intentional about company culture means actively defining and nurturing the values you want your startup to embody. It’s about creating an environment where every team member understands and aligns with the company’s values, from the newest intern to the most seasoned professional.

      When founders are clear about their startup’s culture and values, they can collaborate more effectively with experienced professionals. Instead of allowing a “copy-paste” approach from the corporate world, they can guide these professionals to implement practices that resonate with the startup’s ethos. This synergy can lead to innovative solutions that combine startups’ agility with established corporations’ expertise.

      Conclusion

      While there’s no monolithic “startup culture,” founders have the power to shape their startups’ culture actively. By being intentional about their values and guiding principles, they can ensure that their company remains true to its vision, even as it grows and evolves. As startups like Freetrade have shown, when culture is approached intentionally, it becomes a powerful tool for innovation, growth, and long-term success.