Category: Le Podcast – Season Four

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

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

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

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

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

    It sounds simple. It is not simplistic.

    Reboot’s bet: leadership is personal work

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

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

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

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

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

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

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

    A company built on diversity, not a single method

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

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

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

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

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

    Ali shared something that I’ve experienced myself.

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

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

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

    This is not soft. It’s operationally sound.

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

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

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

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

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

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

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

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

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

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

    Yet it makes perfect sense.

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

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

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

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

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

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

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

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

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

    References

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

    Here is the transcript of the episode

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

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

    Ali: Well, I guess I would say, 

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

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

    Ali: Yeah, 

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

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

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

    And I feel 

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

    Ali: Hmm. Thank you.

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

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

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

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

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

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

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

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

    I really like that that approach.

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

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

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

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

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

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

    Ali: yes. 

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

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

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

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

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

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

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

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

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

    Ali: Yeah. Yeah.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Alexis: Yeah.

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

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

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

    so,

    Ali: Yeah.

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

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

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

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

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

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

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

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

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

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

    Anyway. Totally hooked. Yeah.

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

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

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

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

    Ali: I know. Yeah.

    Yeah.

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

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

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

    hope for that. 

    Ali: said. 

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

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

    Alexis: Yeah.

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

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

     That was really fantastic.

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

    The horse picture is from Missi Köpf (on Pexel)

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

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

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

    Lisette Sutherland disagrees.

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

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

    Remote collaboration changes what becomes visible

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

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

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

    Two classic failure modes: rhythm and conflict

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

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

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

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

    Start with yourself, then build the agreement

    Lisette’s sequence is practical:

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

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

    Innovative models: fewer messages, more clarity

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

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

    That investment creates a capability the company can reuse.

    Face-to-face is a powerful accelerator

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

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

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

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

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

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

    Two experiments she’s excited about

    Lisette is currently exploring two formats:

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

    Where to follow Lisette

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

    collaborationsuperpowers.com/superkit

    Here’s the transcript

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

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

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

    Alexis: I love it.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Alexis: That’s well connected with

    working from anywhere

    and living from where

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

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

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

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

    Alexis:

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

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

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

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

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

    Lisette: sometimes .

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

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

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

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

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

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

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

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

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

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

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

    And I like your second point about,

    you don’t need to be friends.

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

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

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

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

    Yeah.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    really enjoying

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

    Lisette: 100.

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

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

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

    It’s just

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    in those terms.

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

    Jurgen is Jurgen Appelo

    moving motivators is one of the

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

    So a few things that,

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

    you are also the host of a podcast I love.

    That’s collaboration superpowers.

    Lisette: Yeah.

    Alexis: Yeah.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Alexis: Mm-hmm.

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

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

    Alexis: Hmm.

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

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

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

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

    Alexis: Yeah.

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

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

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

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

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

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

    Alexis: Mm-hmm.

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

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

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

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

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

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

    So those are two events I am really enjoying.

    Alexis: That’s fantastic excited about it.

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

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

    It’s super fun.

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

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

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

    Lisette: Was my honor. Thank ​you!

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

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

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

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

    Scaling happens in stages, and each stage changes the game

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

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

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

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

    Culture is not a poster, it is a lived reality

    Anne breaks culture down into four pillars:

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

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

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

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

    Build the people function earlier than you think

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

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

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

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

    Candidate experience is employer branding

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

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

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

    Lean performance management supports initiative

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

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

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

    On metrics, Anne makes a helpful distinction:

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

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

    One final reminder: take time to think

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

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

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

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

    Listen to the episode

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

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

    Anne Caron

    References

    Here is the transcript of the episode

    Alexis:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    Photo de Ales Maze sur Unsplash

  • Radical Product Thinking: A conversation with Radhika Dutt

    Radical Product Thinking: A conversation with Radhika Dutt

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

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

    From product diseases to a new mindset

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

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

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

    That question became Radical Product Thinking.

    Beyond “fail fast”: vision driven, hypothesis driven

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

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

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

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

    The Radical Product Thinking framework in five parts

    Radhika describes five components that work together:

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

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

    1) Product vision that is specific, not vague

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

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

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

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

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

    2) Strategy grounded in real pain points

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

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

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

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

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

    3) Prioritization as leadership at scale

    This is one of my favorite parts.

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

    Prioritization becomes a way to scale your intuition.

    Her tool is a simple but powerful map:

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

    This creates four quadrants:

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

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

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

    4) Execution and measurement without gaming the system

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

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

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

    5) Culture: purpose, autonomy, psychological safety

    Radhika defines culture through the conditions needed for innovation:

    • shared purpose
    • autonomy
    • psychological safety

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

    Her culture lens is very usable: two dimensions

    • fulfilling vs non fulfilling
    • urgent vs non urgent

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

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

    Then she delivers a beautiful shift:

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

    A mindset shift that changes the conversation

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

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

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

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

    Transcript

    00:00.00

    Alexis Monville

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

    00:21.93

    Radhika Dutt

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

    00:25.86

    Alexis Monville

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

    00:35.45

    Radhika Dutt

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

    01:48.68

    Alexis Monville

    Um.

    01:59.93

    Radhika Dutt

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

    02:37.48

    Alexis Monville

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

    03:12.24

    Radhika Dutt

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

    03:50.30

    Alexis Monville

    Go on.

    04:06.38

    Radhika Dutt

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

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

    05:23.17

    Alexis Monville

    Yes?

    05:37.14

    Radhika Dutt

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

    06:06.21

    Alexis Monville

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

    06:14.91

    Radhika Dutt

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

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

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

    07:50.41

    Radhika Dutt

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

    07:56.59

    Alexis Monville

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

    08:17.91

    Radhika Dutt

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

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

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

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

    11:07.18

    Alexis Monville

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

    11:27.86

    Radhika Dutt

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

    11:49.55

    Alexis Monville

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

    12:00.23

    Radhika Dutt

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

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

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

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

    13:53.21

    Alexis Monville

    Sure…

    14:03.10

    Alexis Monville

    Yes, please do.

    14:11.84

    Radhika Dutt

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

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

    15:01.47

    Alexis Monville

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

    15:10.76

    Radhika Dutt

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

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

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

    16:41.12

    Radhika Dutt

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

    16:48.15

    Alexis Monville

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

    17:13.60

    Radhika Dutt

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

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

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

    18:24.57

    Alexis Monville

    I see…

    18:39.73

    Radhika Dutt

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

    19:06.48

    Alexis Monville

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

    19:18.54

    Radhika Dutt

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

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

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

    20:31.70

    Radhika Dutt

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

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

    21:09.21

    Radhika Dutt

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

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

    21:31.23

    Alexis Monville

    I see…

    21:44.92

    Radhika Dutt

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

    22:21.17

    Radhika Dutt

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

    23:10.56

    Alexis Monville

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

    23:28.63

    Radhika Dutt

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

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

    24:42.56

    Radhika Dutt

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

    25:09.80

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

    25:34.38

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

    26:51.88

    Alexis Monville: Right.

    27:05.18

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

    28:45.34

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

    29:12.14

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

    30:06.78

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

    30:42.78

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

    30:47.59

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

    31:02.36

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

    32:17.78

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

    33:05.26

    Alexis Monville

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

    33:26.68

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

    35:54.99

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

    36:22.81

    Alexis Monville

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

    36:45.60

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

    37:24.61

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

    37:29.11

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

    38:53.71

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

    39:32.32

    Radhika Dutt: Thank you.

    Photo de Ricardo Gomez Angel sur Unsplash

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

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

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

    So why does it feel like we are losing control?

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

    Open source is about freedom and sovereignty

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

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

    And that is not a niche concern anymore.

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

    The cloud is a powerful paradigm

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

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

    From the outside, it looks perfect.

    So why does it create a threat for open source?

    The core tension: open code, closed operations

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

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

    The differentiator is how you run it.

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

    That is the turning point.

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

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

    Abstraction on abstraction and the distance from the underlying system

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

    So abstractions pile up. Abstraction on abstraction on abstraction.

    The benefit is speed.

    The cost is distance:

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

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

    The downward spiral: open source built on proprietary foundations

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

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

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

    Daniel uses GitHub as a revealing example.

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

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

    What we can do: expand open source to include operation

    Daniel’s proposal is direct:

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

    That means:

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

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

    Decentralization as a counterweight

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

    So Daniel highlights decentralization as a key counterweight.

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

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

    The leadership skills the cloud era demands

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

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

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

    There is also a more personal layer: conviction.

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

    A moving landscape, not a fixed answer

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

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

    Listen to the episode:

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

    Here is the transcript of the episode:

    00:00.00

    Alexis Monville

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

    00:54.35

    Daniel Riek

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

    01:56.11

    Alexis Monville

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

    02:19.16

    Daniel Riek

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

    04:24.70

    Daniel Riek

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

    07:56.46

    Alexis Monville

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

    08:27.14

    Daniel Riek

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

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

    12:20.95

    Alexis Monville

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

    12:40.66

    Daniel Riek

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

    14:08.24

    Alexis Monville

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

    14:18.80

    Daniel Riek

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

    15:40.35:

    Daniel Riek

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

    18:18.30

    Alexis Monville

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

    18:32.46

    Daniel Riek

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

    20:13.76

    Alexis Monville

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

    20:17.17

    Daniel Riek

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

    23:19.10

    Daniel Riek

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

    23:44.79

    Alexis Monville

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

    24:31.19

    Daniel Riek

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

    26:35.12

    Daniel Riek

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

    28:54.20

    Alexis Monville

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

    29:23.62

    Daniel Riek

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

    31:38.37

    Alexis Monville

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

    32:18.59

    Daniel Riek

    Thank you, Alexis.

    Photo by Taylor Van Riper / Unsplash