Stop Being the Tin Man — Build an Octopus Organization, with Jana Werner
23 Sept 2026 · 56 min
In this episode of the Scaling Coach podcast, host Bill Gallagher interviews Jana Werner, an executive‑in‑residence at AWS and co‑author of The Octopus Organization. The conversation introduces the “Octopus Organization” as a metaphor for a decentralized, adaptive, and distributed‑intelligence model of work that contrasts with the traditional, hierarchical “Tin Man” (Taylorist) model. They explore why modern volatility, AI‑driven speed, and complex environments demand organizations that can learn quickly, empower autonomous “arms” (teams), and avoid the 300+ dysfunctions that plague rigid structures. The dialogue walks through a catalog of 36 anti‑patterns—such as the “super‑chicken” mindset, building a pedestal before solving the hardest problem, jargon‑filled communication, dependency hell, and the “shadow of the leader.” Jana and Bill discuss practical leadership habits: self‑awareness, recognizing micromanagement, delegation, perfectionism, and internal focus, and they highlight three pillars of effective octopus leaders—clarity, ownership, and curiosity. They stress the importance of psychological safety, generative conflict, and the practice of “leaders speak last.” The impact of AI is examined, noting that AI collapses delivery costs and accelerates change, requiring leaders to personally adopt AI tools, create slim central hubs for technology, and let edge teams experiment. Throughout, they share anecdotes about coaching, personal connection with team members, and the value of 360‑feedback and genuine curiosity about individuals. The episode also promotes Bill’s book Busy Is Broken and Jana’s book The Octopus Organization, directing listeners to resources for further learning.
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So I have a quick favor before we go. I'm in the middle of my doctoral research and I need some CEOs. Here's the question: is there a point where working more hours actually indicates a worse leader? Nobody's measured it before. I'm measuring it now. So if you're a CEO or president with at least 10 people in the business and 3 direct reports, it takes just a few minutes and your team answers a few anonymous questions. But what you get back is a report comparing how you rate yourself to how your team rates you. That gap is usually the interesting part. The link is scalingcoach.com/study. Again, scalingcoach.com/study. The link's also in the show notes. Help me out now, please. All right. What do we learn from octopus about running our organizations? The octopus organization is the subject. Maybe you've been noticing about it. Maybe you've noticed it in HBR. Maybe you've seen some press about it. The Octopus Organization is our topic today. It's really cool. Really excited about this. Wasn't on my radar. Boom, it's here. I'm so happy to have this conversation today. I think you're gonna dig it. Hey everybody, Bill Gallagher, scaling coach, host of this podcast. Bring our show to you every week. More than 700 episodes now as you hear this. So for 10 years now, we've been doing this. Talk to all kinds of authors, gurus, experts, everything to do with the world of growing your company. And I had some amazing people on. I think you're going to love our conversation today. Before we get into that, my own book is live and in the wild. Busy Is Broken. Busy Is Broken is about how you become the bottleneck in your business as the organization grows. The things that we see in the leaders that we work with, the research The history, how we got to this place, how busyness is a kind of an addiction that's a problem for us, and how after you build the business, how all of that. Anyway, busynessbroken.com. You can order the book now. Paperback, hardcover, Kindle, e-reader, audiobook. It's all there. Go get it. busynessbroken.com. And then if you'd like me to talk to your group, organization, company, etc. I'm booking as many conversations as I can now for Busy Is Broken. Anyway, it's out and available now, Amazon or wherever you get your book, or go to busyisbroken.com where there's some extras, including a validated assessment of your leadership and how you do it, including input from your peers and all that as part of my university PhD that's going alongside the book. Or better to say, the book actually— the PhD fills in some gaps in the research that the book doesn't address. address at this point. Anyway, uh, welcome to the show, Jana Werner.
Hey, thank you so much for having me.
Everybody, Jana is an executive in residence at Amazon, at AWS. Um, and they're working with companies about their stuff. And, and she coauthored this book, The Octopus Organization, uh, which is really cool. And, um, she's done all kinds of work across a range of like universities, organizations, Oxford, London School of Economics. The HBR tie-in, like on and on and on. And, um, her original, uh, PhD, Uncertainty Dynamics. So we're going to get into all of that now. Jana, so the octopus. Yeah. Octopus is interesting. I don't know a ton about it, but we know brilliant, adaptable. You have these arms, the arms actually think for themselves, like distributed, right? But then they're also sort of weird solitary things. They don't live forever. Uh, they can even eat themselves. Um, and I, uh, like, why is that a thing that CEOs should consider modeling?
Excellent question. Do you know they also can play the piano? You can teach them to play the piano, but that's maybe not really relevant for execs.
Jazz piano, classical?
Uh, I think they can do a range of mixes. So whatever you, whatever you fancy. Yeah, exactly. No, but they're really— they've got an absurd ability to adapt. They shape-shift, they change the texture of their skin, they have an unbelievable ability to learn. Even— they can even alter their RNA. So when they switch from cold to hot water, for example, they switch their chemical makeup within hours. But most importantly, they have 2/3 of their neurons in their arms, so their arms can act, operate, sense, and react independently. And in a world that's moving as fast as it is right now, all of my conversations, of course, with Fortune 500 execs are about AI, the speed of tech change, the volatility in the world. So this idea of being adaptive and decentralized, um, has really resonated with us. And yeah, no metaphor is perfect, and all the metaphors we've heard of, but we thought this is a nice idea to wrap it into this idea of distributed intelligence, fast learning, and Super wild adaptation.
We've covered related things, not your topic, but related things in the past. One of our past guests, former commander of the US Special Forces, Stanley McChrystal, talked about how when it was all command and control, they couldn't keep up with the threat in some of the environments they were operating. Until they let go and let units operate on their own, they were falling behind.
Absolutely. And we are quoting him in our book, and we've already had an introduction by a colleague because we're moving in the same kind of worlds and have similar points of view. I fully agree. The challenge is that most organizations, unfortunately, are still based on this factory model that we inherited from Frederick Taylor and his friends. They're still working in this way of focusing on standardization, specialization, control through individual performance, compliance, predictable outcomes. And that usually means that you break work down, you turn it into lovely silos, you measure the individual. So it's the opposite of working together. And the idea is, of course, that it was designed to de-risk and be really efficient. But we don't have this kind of world anymore where we produce repeatable outcomes. We don't produce nails so much anymore. We do, but we're good at that. The world today really depends on building real genuine connections with customers, with your own people, with stakeholders, learning and things coming in from the environment. Work is so much less transactional, much more cross-disciplined. Customers have much more choice, so do employees. So we thought we need to get away from this rusting construct. We called it the Tin Man, like the Wizard of Oz. Yeah. And we said, replace it with this idea of an octopus organization. We deliberately used metaphors. even though every metaphor has their limit, but no company is ever perfectly Tin Man or octopus. And even when they are really advanced, we also saw companies snap back when a leader leaves or when something difficult happens. So we wanted to use some playful, fun metaphors and wrap it into that. But fully agree with Stanley McChrystal's point of view, his idea of pushing information into the organization until it's borderline illegal, I really loved. And the The idea of the commander's intent. So there's a lot of that in the book as well.
You know, it's funny, you're right in, right at the beginning, boom, we're like, okay, the structured environment. So we create these assembly lines, and we create processes, and we refine, and we refine, and refine. And that's great, right? It has a value. We, we can make nails, we can make hamburgers, we can make lots of things in a repeatable fashion. But then somebody comes in and says, wait, I don't want cheese on my hamburger. And you're like, oh no, now we have to redesign our system.
Yeah, exactly.
Or the materials come in a little bit different. And so our process breaks, the machinery doesn't work with it. And so there's that tension between refining, optimizing, and focusing, and then, but also being flexible. I think it's interesting you say that there's not like a perfect organization one side or the other. It's a mix of.
Yeah, absolutely. And we need to be able to manage both. And it's often difficult. We are not that ambidextrous. We're often good at the operations. And especially with AI coming in now, I speak to C-levels and they're talking. I had 2 CXOs in the same week say to me, my people aren't imaginative enough. They're really good at the operations part and they have to be. We were always safe. We never got really stretched in the other parts. But now we have to reimagine, rethink work. What can we do? What is out there that we could grasp an opportunity? My people can't do it. And I said to them, it's not your people who can't do it. We had coaching conversations and they're realizing it's how they're set up. They're set up to focus on operations. They're set up to break things down. They're set up to follow process. And so it's very hard for people who are kind of raised, born and raised, so to speak, in their work career in these environments, and these environments not allowing you to, to get things done, it's very hard to break out of that and, and then demand that your organization suddenly is creative and curious and, and creates things.
You know, it's interesting, like, I think there's a deep sort of personal psychology involved, right? Like the, and cultural reference. So I and Most of our listeners, probably viewers, um, many of the people that I work with, the primary audience are founder, entrepreneurial, a little bit of CEO, but as, as you start to go to more hired gun CEO and president, there's a lot more like desire more for rule and structure, but, but the CEO founder, they just love everything's just, you know, all the no rules matter or whatever. And, and, and, and then also different environments, right? Like, um, you might be German and maybe I've spent some time in Germany and I, and I'm like, uh, part of me loves the order of the environment. And then the other part of me is like, no, I just like, stop it. I like want to do whatever I want to do right now. Don't tell me what to do. Right.
Yeah. Yeah, it's really challenging. Of course, as companies grow, you require some sort of structure. And I work with startups really closely. I've actually been in a startup and helped it scale and got sold to HP. So I understand the spirit. I love the founder spirit. I love the entrepreneurial spirit. And indeed, I work for Amazon, and we consider ourselves the world's largest startup. So we're quite happy to operate like a group of islands that are a bit of a startup, and we accept that there's duplication. We'd rather have duplication than nobody trying something new. We always say 2 is greater than 0. Yeah. And so I absolutely value the spirit. I do strongly believe that even in large organizations, people have the spirit. I've been a practitioner. I lived, I worked, and I transformed and helped change large organizations. So I speak from having all the battle scars. I've made all the mistakes, definitely all of them, all of the ones that we laugh about. and write in the book and have a lot of empathy. I think the spirit is in people. And we know that 30 to 40 years of self-determination research and theory show us people want to take ownership. They want to have this ability to own something and to drive something. But it becomes harder when an organization calcifies. Every time one person makes a mistake, 99 others get punished by adding another process, We tell the story of the pigs and the chicken about approvals. We tell the joke that the pig and the chicken, they go down the road, and the chicken says to the pig, hey, let's open a restaurant. And the pig says, yeah, what shall we serve? And the chicken says, well, ham and eggs, of course. And then the pig says, well, you know, I got to be much more committed to that than you. And so, for anyone who didn't get the joke, obviously the ham, you know, from the pig. And so we tell the story that in many big organizations, you have all these chickens. They come to meetings, they want to lay their eggs by giving approval, sign They want to have opinions, but not enough pigs. And we say, maybe don't call them pigs, but we call them single-threaded leaders. This kind of entrepreneurial owner wakes up, goes to bed every night owning a problem and having the authority to pull it through the organization with a small team that's as independent as possible. We call dependencies defects at Amazon. So how can you free up that team? How can you have less chicken in your organization and generally free up the organization from the silos and all these— anti-patterns we talk about in the book, and that we help dismantle, so people can bring this entrepreneurial and startup spirit to their companies. Because that's exactly what's needed everywhere, and just focus outward, not inward, focus on the customer, trying things, being curious.
Well, look, if you, if you know, and, and because I know our audience are more comfortable with the creativity and the, and the, and, and maybe the complexity, A lot of people in our organizations are not. They're like, just tell me what to do. Tell me what my job is. Tell me what the rules are so that I can— and it's different kinds of people. I was talking to my brother who, you know, shares a little bit of that and his ex-wife, and she like did her job according to the policy for her like career, you know, like, yeah,
I think it gets trained out of people. You know, when we're kids, we ask up to 107 questions. Do you know how many questions we ask as adults? Up to 3. So this curiosity gets trained out of us. And I'm an optimist, and I believe in humans and people. And I believe that most people in organizations want to own something and do something good. Because you have these people that get bogged down in companies, and then they go home, and they have a hobby, and they bring everything. They are creative. They do something cool, be it the local chess club or the charity that they help with. Why can't they bring this excitement to work? Not because they don't want to, they have it in them. Yeah. It's the organization usually stifling that. And that's something I've seen. I've led teams that were put down, and they were the lowest-performing teams. And then you speak to these team members, they're all curious, interesting, lovely people, but your organization has put them down. And when you give them a bit of space and encouragement and support and rip away some of the shackles, it gets easier. And The same. I've spoken— you're right, Bill. I've spoken to the COO of an investment bank, and she said, my people don't want ownership. And then we took— I could have told her the answer, but after half an hour of a coaching conversation, she got herself to the realization there's no upside for them to take ownership. The first time they make a decision that's considered bad or wrong, it has what I learned in the English language, career-limiting consequences. So What's the point? For most people, either it's bad news or it's far too much work to do more than follow the process because the companies make it so hard to take any initiative, to own anything, to get resources and funding. So of course it's better to then just follow the process. That's the default then. But do you know the saying from Reed Hastings, the CEO, co-founder of Netflix, that we don't want to dummy-proof our organization so much that only dummies want to work there? So,
so
brilliant.
Like, how do you— and I, I think I hear this, really good to touch on the human, human side of it and the safety and the— because I come across entrepreneurs again and again, they were like, well, we're gonna get into that when I get the right team. Like, the team I have right now is not the right team. They don't have ownership, they don't have initiative, they don't— like, it's just not them. Like, I just need different people. Like, I, I really, I really question that again and again. Like, at a deep fundamental human level, I wonder if so often people don't show any initiative because every time they do, you just crush them. You tell them it's wrong or bad, or you, or you humiliate them, or like, you don't celebrate them. You don't allow for a little mistake. You don't. And you think about like, would you do that? Do you do that with your children? Like, um,
I
hope not. I think actually the sad answer is we do. Some of us, you see parents humiliating, pushing, constraining their kids in some ways. And then you end up with conformist kids who maybe make life easier for you in some regard, but don't make you proud.
I heard this story. I don't know if I can tell it properly. It's from my co-author, Phil. And he said, one of his former colleagues was on stage talking about skills and skilled people and who take initiative. Yeah. And then someone in the audience said to him, well, it's easy for you to say you are Amazon or you are Netflix. You've got all these good people. We have, to your point, Bill, we have all these average and bad and they're not good. And he answered, you know what? I hired your people and got out of their way. Yeah. It's like my favorite quote. It's, it's in all of us. And there's lots of, um, research even on sports teams where, for example, an average player— this person, there's a— this was a player in the 1990s, a basketball player, and he, um, I think he had a French name, I've forgotten his name now. But anyway, he had like very average stats, but every time he was put in a team, the team's performance went up. So we find from sports all the way to research and teams and companies, a group of average people will always outperform 1 or 2 really cool people. Do you know the story of the super chicken? Have you heard about that one?
No, tell me about the super chicken.
I need to tell you that because it fits nicely to the story. Um, there was a, there was a breeder who wanted to find out, um, how, how outperforming, um, how outperforming people or individuals work. And He thought, let's start with chicken because it's very easy to know if chicken are doing well by the number of eggs they lay. And so over several generations of chicken, he bred out and selected only the chicken that were super hardcore performers. So lots of egg layers. And then he had another flock of chicken and he just let them grow over their generations as they wished, average chicken.
Right.
And after several generations, the super chicken had mostly pecked each other to death, whereas the average flock of chickens had produced lots and lots of eggs. So the idea that average— and I mean, chicken are not human, but the story is lovely, and it's actually supported by lots of actual human research to say that a bunch of average people, if you think they're average, will outperform if you give them the conditions as a leader. To your point, Bill, it's— It's leadership coming up with excuses about why their people don't perform, but they should really look at themselves, but with empathy. Yeah, I was a leader. I made lots of mistakes. Someone eventually was kind enough to tell me I was micromanaging the team. And luckily they told me and we could have humor. And I said, give me a little sign, pick your ear in a meeting when I start doing it or stuff like that. I've made all of these mistakes. So I don't speak from the ivory tower or the high horse of wisdom. But if leaders can listen and learn and be a bit more curious themselves, you can really turn this around. I have absolutely no doubt. I've done it, and others can do it. And your book—
Micromanagement, micromanagement, one of the 4 things that leaders do again and again that gets in the way in my book.
Yeah, what do you say? What do you— what advice do you give them?
Well, so delegation, micromanagement, perfectionism, and internal focus are the big things that I've seen again and again. And of course, you know, there are other— there are positive traits, but these are like the sins that I see the most. And I think the first thing is self-awareness, right? So what do I do? What does it look like? What do I do? We don't notice, right? Like we I look at myself in the mirror one way. I see myself in the world metaphorically. I look in the mirror in the camera right now and I see myself a particular way, but I don't notice the micromanager. I don't notice the person who refuses to delegate. I don't notice where I'm a perfectionist or where I'm too internally focused. I don't notice all those things all the time. So the first one is like the self-awareness. And then it's useful to notice like the why. Why do I do what I do? Think about like how, and with that knowledge, like realization, you can actually begin to imagine another way and, and try another way. But you think about all those kinds of patterns that we do, like we start those at a few years of age and then we just build on them our lives, right?
Absolutely.
Doesn't mean that we can't do something else, but it's, there's a lot of years practice.
It requires a bit of vulnerability. And like you say, actually seeking real true feedback and being curious about the feedback. And we write about— we have 36 anti-patterns, and one is the shadow of the leader. So we— in the UK, there's this saying, the fish stinks from the head. So the idea that— yeah, the idea that leaders set the tone of what's valuable, what's important,
Yes.
Whatever they set the tone of is what the organization will do. So if a leader is 5 minutes late every meeting, time isn't important. Or if a leader says adopt AI but actually doesn't do it themselves, OK, so it's not really important. So you're absolutely right. And we talk about every of the anti-patterns we deliver. We say, how, how, what's the opposite? What does an octopus leader do? And what are a few things you can start doing? So in leadership, we give some suggestions, asking people for 360 feedback, And this whole thing is not about, I think, changing. You are who you are. You're not going to change your character. You're not going to go from introvert to extrovert. But as you rightly say, Bill, these practical things of how we lead, there's definitely things you can learn. I've learned to step away from micromanaging. And it's not, it doesn't have to be scary. I think most leaders are scared they have to change who they are. But it's actually learning practically how to become better. It's like a To me, leadership is like being an Olympic athlete. You have to work at your emotional response, how you turn up, how you support people. It's an important job. It's a really, really important job. And I think you have to work hard at it every day of how you turn up and support your people.
Yeah, we've touched on a bunch of things. A couple of things I heard, one of them is this notion that there's more potential in your people than, than we touched on. And I coached a company a few years ago, fairly small in our, in the range of companies we coach. But, but, but good typical, like, but like $4.5 million is where I started with them, $4.5 million sales. And then we took them to $16 million and then through a sale of the business. Right. So it's a nice— if you think about a small company, like that's a nice growth and then a nice little exit for the, for the owner of the company. But when I first started working with him, one of the things he said to me is like, I don't know, my people, it's the wrong team. I don't like— I can't get more out of them. them. I don't understand. I don't know how to motivate them. And, and I remember one day really clearly, I spent, I had some extra time. So I spent some time interviewing one-on-one, some of the people in their offices. And, uh, and then I came back to him at the end of the day before we went to drinks and dinner. And I said, so tell me about your people. Like which, what do they want? What are they up to? And he didn't really know. And I said, okay, well, let me, let me give you some hints. Who wants to buy a house? Who is ready to start a family? Who has never left the United States on a trip? Who, like, wants to go back to college? So all these things were people in, in his team, and he didn't know any of them.
Yeah.
And, and perfectly defensible in his world. He's like, you know, asking people their personal things, it just feels intrusive. Like, I'm like, no. Like, yes, there's a degree of like, you don't want to ask who they're dating and why and everything about every little detail. Like, there's a, there's an art to that, but, but to know them as like a human being. So he spent some time, he figured out, and then he could connect the dots with them. Like, I, like, I want you to step up here because I'm helping you buy that house, right? And that turned out to be like fundamental to the thing that people started to step up. Now, A couple of them actually left. That's okay. They, you know, it was a bad fit or like they didn't want to play that game or whatever. But the rest of the people and overall, like we went through that growth and that eventual sale of the business. So, I think there's a lot to be said with like getting into and helping your people level up because they are kind of the access to that flexibility, right?
Absolutely.
They're the arms that like you can't Control on your own. Maybe you shouldn't try.
Shouldn't. Yeah, the ownership— where I've seen that done really well, and I learned, was, um, really, really brilliant and capable managers, managing directors, leaders of, um, large-scale hotels or hotel chains. They are senior leaders, but they know absolutely everyone. They know the personnel who cleans the rooms, the chefs, the the bellboys, and they know everyone, even though they are the most senior leader of maybe one hotel, one big famous hotel or a chain. And they connect with the people, they know their staff, and they're interested versus other hotels and managing directors who aren't. And you see a big difference of how the staff then carries the love to the customer and the personal care and all that. So that's probably the closest example I've seen that resonated and that Impressed me a lot.
I walked around a factory with one of our clients, a small factory in the United States, so that, um, in, uh, the Southwest. And as I walked around, I realized the president of the company knew like a lot about all the people, hundreds of people. And we went in, he's like, oh, Jana, how are you? And like, how's your kids and what's going on? And like, he just had a like deep, and these people like delivered for him. Like they cared about him and, and probably more than any policy or anything else, like going around and kind of feeling the people, connecting with them, like was deep in his DNA. And I, I, I watched it and I admired it. I'm like, God, that's really great. You know?
And it's, yeah, it's wonderful if people do it. It's, it's really beautiful if they do it. Not everyone's comfortable with that. And I think you can learn it a little bit. this warmth and connection, you can learn it. I do think on a broader level, we talk in the book, we talk about 3 themes: clarity, ownership, and curiosity. And we've seen the leaders that operate really well, many of them are this personal. But what all of those leaders do that are really good is they create clarity. So they provide context to their people. They create a mission or a purpose that people can buy into. To your point, they know their people. But they also create some other emotional connections that's about the purpose of the organization. Why are we doing this work? So an emotional connection to that. They share their values, they live their values. They also promote people based on the values. So they don't say one thing and then actually promote for something opposite, which we see in some companies. They use their values for decision-making. And they create continuous clarity, what's important, what isn't. And that gives them the context for this decentralized action and ownership because people are like, ah, this is why I'm here. This is what's important. This is what I should look at. This is the context I have. And then I can actually move faster and be more adaptable because you can switch everyone on because they have this clarity of context.
You know, I think like that business, there's, there's a lot there. So like just pausing to appreciate people. I, I tend to be like an overthinker and I live in my own world. I'm, I'm introvert and self-absorbed and lots of things like that. Um, and, but I also know how to do it. So I know that about myself, but I also know how to do the other. So I'm at dinner last night and a friend of mine is sharing about her life and her work and things like that. And I start to notice a pattern and, and I, and I'm listening to her speak and, uh, see her across the table and And I like, I just started to be in love with who she is as a human being, like to allow myself to appreciate her, to appreciate like, this is, oh, I start to notice a thread about her, all of her work and that kind of thing, like something deep about her. And I, and I, and I like, I let it, I kind of see it. And I allowed myself to be in love with it. I don't mean in a weird way. My wife was sitting right next to her. And, uh, and I'm like, I just— and then after a minute, I, I called it out and I said, I just, I just noticed how proud you are to be of service to, in service of people and things that really matter, that impact our world and that kind of thing, and how you pour yourself into that and you give yourself over to doing that work in service of something, all these different areas and topics. Um, that she's worked in over her career. And then she became like very emotional in the moment. She cried, you know, and because somebody saw her, right? And named it, right? Like, and I think all of us, like there's things that we aspire to that we hold important and beautiful. And when you notice that about people, like you bring out the best in them. Absolutely.
Yeah, I couldn't agree more. And I think this curiosity of leaders to listen, listen with curiosity. Most of us listen with the desire to form a response. But this idea to just listen and really understand where someone's coming from and seeing them, I think, is invaluable. So there's lots of, there's lots of learnings in here. It's hard. I mean, I, when I was a younger leader, I worked very much on the thing, on the problem to solve. I was very transactional, time-driven, output-driven. Yeah. It takes some wisdom and experience and a bit of comfort to be vulnerable and to be curious and to be okay not seen as perfect. It takes time and also being okay Kind of being kind to yourself, say you won't always lead perfectly, but you can try every day.
You know, I, it's, uh, I, I've been fired more than once, uh, for saying something a little too clearly. Um,
yeah, career-limiting consequences.
Career-limiting. I had a, I had a CEO hired me to work with a team. And he wanted to grow his company, wanted to pass it on to the next generation, that kind of thing. It has since done that. But so he brings me in, he has 2 complaints about his team, that the team is, they're late on everything and they're passive. And they're not really leaders, they're a little passive. And now this is a company that grew to over $500 million in sales, a lot of people, operations in multiple countries. Does a good product in the world. And I worked with one of the divisions for many years, but I worked with him very briefly because after coming in and after a little bit of delay, I visited one of their meetings and, and the meeting started late. He was one of the last people to show up. We started 25 minutes late, I want to say. And, and then he like just talked. And he had a lot of notes and prepared information. He's very prepared, very smart. He talked at people for like 2 hours, and then now we're overtime. And then he asked if anybody had anything to answer. And then he asked me for feedback on how their meeting went, because I'm a coach, right? And so I said, well, I gave a little bit of feedback to the whole team broadly. And then I said, we could talk more in your office afterwards. in his office and I said, listen, do you remember why you invited me here to work with you, a 1-year contract? And he said he couldn't remember in the moment too well, but I refreshed him. Like, remember, it was because they were late and passive. And I thought I had good news to deliver here. I thought this was going to go well. I didn't realize it was going to be my last conversation. And he said, yeah, yeah, yeah. And I said, okay, well, It's you. It's all you. And he's like, what are you talking about? I said, well, listen, you show up late and it's not the first time. And so, you teach them late is okay. And then you talk at them forever and ever and ever. And you're the first and last person to talk and you teach them to be passive. So, you're teaching them late and passive is okay. And if you're not going to change or work on your behavior, your patterns, then nothing will change in those things. And that's really good news because it's very easy to work on yourself, very hard to work on other people. And, and he's, he's like, oh, that's very interesting. And then he told somebody to cancel my contract.
That's a shame.
But somebody tells you next day, like, I don't want to do that. But I think it's really good news because it's depressing. When you find out it's your fault. But it's also very empowering because you can work on you.
Absolutely. And you need to have the maturity to accept that. And you're right, this, this space where a leader talks all the time and doesn't listen, it's also pointless. Why do you hire all these smart people? The companies that do this well, they have constructive conflict, emergent thinking, they have generative conversations, genuine connection. They then quickly execute on ideas, and it's okay that they're not perfect. They want to learn. It's okay to— it's not embarrassing. It's okay to make mistakes. That's the culture you want. And at Amazon, we say leaders speak last. So we often do this, that we have conversations and give feedback on an idea, and the leader, most senior leader in the organization in the meeting will speak last because of exactly this. We want leaders to be curious and enable generative conflict and creative abrasion and not not just provide their opinions or points of view? What's the point? What do you have people for if you don't make them work at their best?
It's a really good question. A lot of companies are like that. You see everybody competing to be the smartest person in the room. I'm like, stop it. Why don't you be curious?
Yeah, it's exhausting to try and be the smartest person. And nowadays it gets harder and harder to be the smartest person in the room. And you want to actually— why do you pay and buy in really smart people if you want to be the smartest in the room? All the leaders that are brilliant at what they do that I interviewed for the book, that's Benedetto Vigna, CEO of Ferrari, Indra Nooyi, former CEO of PepsiCo and now board member at Amazon, the CEO of London Stock Exchange, Dame Julia Hoggett, all of these leaders had one thing in common. They were incredibly humble. If you had met them in the street, you wouldn't know they're CEOs of such companies. They're humble and they're relentlessly curious.
So what are these anti-patterns? You've referenced that a couple times.
Yeah, so anti-patterns, we found— Phil was the international CEO of McDonald's, so he delivered change across 120 countries. I can't even believe how he did that and brought together 120 countries. And I've worked in large organizations, and we see again and again that there's these kind of reflexes or go-to ways of doing things that you just learn in organizations. That seem kind of right at the moment, but actually don't make things better or even make things worse. And so we call them anti-patterns, anything from using jargon. Like, we've had this company that says, we want to be an AI-forward, data-enabled, customer-centric organization that leverages its global synergies, blah, blah, blah. You're like, I'm half asleep. I also don't know what it means to leverage my corporate synergies on a Wednesday afternoon. It makes no sense. And we all use this jargon sometimes because we are in an in-group or it's shorthand, but it creates no clarity for people. And it's much harder to say things plainly. Then you have anti-patterns, how you create silos in organizations. You have anti-patterns around these best players, around the shadow of the leader, the failure culture that we create. So we kind of, we grouped them. We found about 300 dysfunctions of organizations in this world. It hits this crazy volatile fast-moving world with a Tin Man way of operating. And, and this crash between the world and how they operate creates more than 300 dysfunctions, more now with AI on the rise. And so we group them into 36 anti-patterns, and, and we, we explain how does a Tin Man organization act, how does an octopus organization act in, in contrast, and what are 3 to 5 things you can do. Because We've read so many management and leadership and business books that say you need to become agile, you need to become product-centric, but how? And so we, we wanted to add— we are both practitioners— we wanted to add some practical things that people can do today. Doesn't have to take a crazy transformation, it doesn't have to take like turning everything upside down. Little things you can start doing, breaking one habit, one anti-pattern at a time.
And can you give us a taste of a couple of them? Like, what are some good juicy ones?
Yeah, one I really like right now in the world of tech change is about— we learned this from Astro Teller. He's the CEO of Alphabet X's Moonshot Labs. We interviewed him. And he said, Jana, if you wanted to get a monkey on a pedestal to recite Shakespeare, where do you start? We were like, where are you going with this, Astrid? Basically, the anti-pattern is that when people finally get a project set up, an initiative, they got money, resources, what they will do is they want to try and show progress. They will create something, they will try and put it in the PowerPoint to their bosses or show they're doing something. But often they don't solve the hardest problems first. If you want to get a monkey to recite Shakespeare on a pedestal, you don't start building the pedestal. if you will never find out if the monkey can actually speak. So Astro said to us, tackle the hardest problem of your projects first, because then you know if you can get there or not. And actually, if you can't and you prove this really fast, then you can free your resources for the next better, more important thing. And we see many companies, this anti-pattern that they build a pedestal, they try and show progress, there are zombie projects that go on and on. And they never get the monkey to talk. So that's a really good anti-pattern, especially now in AI. You want to try something and learn fast. There's many others. We talk about the crazy failure is not allowed. We talk about the lack of psychological safety and interviewed Amy Edmondson. We talked about the lack of diverse teams that don't have enough creative abrasion. We talked about the shadow of the leader that, to your point, you just gave a great example of a shadow of a leader turning up late, never letting anyone speak. There's many in there that apply to the organization. Fetishizing process. So you add processes, layers over layers, the dependency hell of teams. How do you get out of dependency hell? What about these annual crazy budgets that are dead on arrival? That's what the CFO told us. Our budget, we know even when I get it, it's dead on arrival. You can't do annual planning anymore. So there's a lot of things in there that's the typical. When we share them, usually we get a giggle, a laugh, or rolling eyes. Because they're just, uh, they're just recognized by many, um, organizations that do these things. And we're trying to help, help organizations to get out of those.
You know, I love planning. I love processes. And yet, you know, the minute you, um, create a plan, it's obsolete. And then the next moment it's obsolete. And then even if you're infinitely wise, it, it's a complex universe, right? Like, and something changes. And, and then you create, so you create a plan and you build a process and then you find out it doesn't work right. Or something's missing or you didn't have that. And there's elements that aren't even in the process that are dynamic and affecting it. And then everything's breaking down anyway, because of entropy and like, you know, on and on and on.
Yeah. We like the systems thinking too.
But there is value in the planning. There is value in the thing, isn't there?
Yeah, I think the practice of planning is not a bad one. I do think it teaches you to think about consequences. I also think it helps to build contingencies and plan ahead because it allows you to take better risk. We always see risk lately as downside and we try and manage it away. We've unlearned this idea from 100 years ago that risk is actually also opportunity and planning around that and taking those risks and taking the opportunity is helpful. It just becomes difficult when it becomes an obsession and when planning then leads to an implementation of the plan without thinking what's happening in the world and being thoughtful and flexible and curious about that as well. That's where the risk is. And in fact, I do see planning horizons largely become much smaller and shorter. At Amazon, we used to do 3- and 1-year plans. In some of the hardcore tech-forward parts of the organization, That doesn't work anymore. We have to plan on much shorter timescales, but still plan.
Shorter, shorter, shorter, but with some broad notion of where we want to be in the long run or what things look like. We're going to come back to AI in just a minute and the implications for AI and what it's doing. But I think it's interesting. You reminded me of a couple of young women who worked for me early in their careers, later in my career. But a few years ago still. And they came in and they were all excited about this new initiative and they did all these elaborate plans and all these structures and things like that. They were going into this big plan for this big breakthrough. We were going to 10x this business. And there really was great thinking and they're both very smart and they've both gone on to interesting things in their career. But I'm like, okay, but there's a million ways this could break and go wrong. And they were so sure of themselves. No, we've thought of
That's naive.
I'm like, oh, you're so young and sweet. Like everything? Like it's an infinite universe. We don't even know everything. You can't possibly think of everything like that. Who knows? And you're going to show up and then the power won't be there. Or the competitor next to you came with the almost exact same thing. Or, you know, a meteor strikes the building. I don't know. Like, you know, something, things are going to happen. And indeed they did.
Absolutely. I'm with you. We are— I like what you talked about, and implied we are systems thinkers as well. We think organizations aren't complicated like a jet engine where you can replace a part, or like the Tin Man in The Wizard of Oz where you can replace an arm. We think they're complex. You can't foresee everything. There's ripple effects from one change to another. I've led large-scale transformation programs top-down. It doesn't work that way. For example, we looked at, if you wanted to set up agentic workflows in a company that has never operated like that, it takes more than 250 things you have to change from rewriting your legal frameworks to allow agents to do things to how you compensate your managers all the way to the tech. You can't foresee all these 250 changes in a top-down plan. You have to learn your way through that iteratively. I fully subscribe to what you say, complex system thinking and iterating and learning your way through that. Everything else is slightly naive, I would say, with care.
When I was very young and trying to drive a big part of the business at Sprint, I, I had a lot of control over certain things: the, the design and marketing of our products and services, the marketing spend, the pricing, things like that. I had lots of control. But I had very little control over most of the people and the technology and things like that. So I would go out and I'd be like, okay, we're going to do this. We're going to change the price. We're going to put this, we're going to name it this. We're going to sell it like this. And then people would be like, yeah, but you haven't thought about this and this and that and then whatever. And I was very, very young and I'm like, yeah, no, that's your, that's your job. Like you go think about it. It doesn't mean I'm not going to do it. I'm going to do all these things. That's why we're talking now. You now need to go, go figure it out, like figure out how to do it. And, and I realized I didn't do it. So I did it successfully from a business standpoint, but not so successfully from a personal relationship standpoint, because I just knew that I could do things that created problems for people that ultimately had good business outcomes, but I would just create a mess and then they'd have to like deal with it. And right, because look, a lot of times, especially as your organization grows, you, you have direct control over not very much. But, but it can ripple out and affect a lot of people. And, and so my mistake was I didn't do it with enough, like, diplomacy and tact and relationship building. I just I like dropped little bombs on things that had good business outcomes, but made people's lives— I didn't do it so nicely. But I think there's something useful there in thinking about like how we do that and kind of let it, 'cause you can't, I can't conceive of and plan and build a whatever. And then who knows what will actually happen. And the bigger it is, the more complex it's gonna be. Yeah. Right, like on and on and on. Yeah.
Takes learning though. It takes— it's okay. I— we all make these mistakes and it takes a while to learn. And you sometimes you have to take a beeline and not go with the head through the wall and that you pick your battles and are thoughtful which ones are worth picking and which ones aren't. That's wisdom of age and experience.
All right. So big takeaways, AI undeniably important.
Yes.
Profoundly powerful. Companies are doing it, struggling with it, worrying about it. Individuals and companies are freaked out or excited or both. They're doing it in a lot of different ways. What do you see? What's important? What are the implications? Give us your thoughts from the frame of the Octopus organization.
Well, we see that the rise of AI is creating or putting a few norms that we build our organizations on, undermining those norms. So for example, change, we built organizations on a notion when change was expensive, difficult to do. So we managed the resources, whether it be people or time and money. We planned, we worked slowly through that, the big projects. But with AI now, the delivery cost converges towards zero. At Amazon, if we now decide between building one or another prototype, we simply build both. And we do it fast. You can now build things in 5 days, but then the approvals still take 5 months. So, our organizations lag behind that speed because they're set up for a different time. And the other thing, of course, is the tech change is so, so, so fast. We always talked about fast tech change in the past, but this is a whole new dimension. If all AI development stopped today, it will still take 5 years for companies to catch up on what even is available today, let alone the accelerating speed of what we get. So those 2 things really are making or putting challenge on traditional organizations that are more Tin Men and less octopus. And what we see work really well is where leaders genuinely engage with the technology, their boards, their executives, not just give a decree and say, you go and do it, but who actually themselves form habits and learn how to use the technology and not just a basic use, because most companies use or leaders use it on a basic level and then it's not really productive. If you only ever write a prompt and get a response and you don't create context and you don't refine and you don't give background on yourself, all these good things, if you don't try out your first agents yourself, it doesn't work. If the leaders get it, they suddenly demand different things from their organizations. As a leader who knew a process takes 2 to 4 months. And because of, with his own experience of AI, he now demands his team to give this response in 5 days because he knows it's possible. So that drives true change in an organization. Leaders walking the walk, talking the talk is one really good thing I see. And the other is give a slim center of centralization where you make the technology available. And then allow people to use it and innovate on the edges and bring the good stuff on the edges back into the center through that slim—
There's my cheesy radio. This is so— I just love what you're saying here.
Thank you.
Get it in your seat as the leader, as the C-suite, be using, adopting, learning, applying. And then give tools to people and let them do things like let the octopus arm behave on its own. Stop trying to get those 2 things. If I had nothing more to say about AI for all of our clients, and I look at all the companies that we're seeing, those 2 things make a massive difference. You don't want just like one big initiative. It's going to fail. Um,
100%. Yeah. There's lots of nuance in that. Um, But absolutely, those are 2 big things. There's a lot you can talk about— your data, how you use your data, governance, how you need to update all of that. But yeah, leadership and making the capability available is really, really helpful.
Pardon my old cheesy radio cowbell and air horn, but I just, I think so, so important. Like, if you as a, as a senior leader in the company are not using AI pretty much every hour of the day at this point, then you have your own homework to do, right? And, and go beyond a few basic queries with chat. Install and, and let Cowork do some scheduled tasks for you. Build something agentic. Start to integrate things, get multi-threaded things, try things across different platforms. Like, Be integrated to every part of your life and find a way. It's a fundamental technology, like kind of the personal computer showing up. It's gotta like get in your core. You need to be literate. And then let your people like iterate, explain, experiment with things in every department at every level, right? You're gonna find things.
Yeah, absolutely. Couldn't have said it better. So a lot to do there and a lot of habit to be built and And reimagine, not just automate what you have, reimagine and give people time and chance to reimagine, but also do things across the top where you go end to end. People need to bottom up learn and do things, but then you get lots of duplication as well and not true reimagination. So also as a leader, cut through the top, go end to end, find a value stream, a bigger problem to solve, and reimagine it. Don't just Recreated in AI.
Jana Werner, The Octopus Organization. You can find it on Amazon. You can also go— there's the link on the screen. We'll put it in the show notes. theoctopusorganization.com. That's the place to go read more, get the tools, resources, see about their work, that kind of thing. Um, you'll find all that. It's been a great conversation. I've enjoyed this thoroughly. I love this idea about allowing some complex, adaptive, independent work across the organization and becoming that kind of a flexible thing. Doesn't mean don't ever plan or don't do any work on process, but allow for that flexibility in the face of all that. It's really brilliant. Thank you so much.
Thank you so much for having me.
Uh, also a reminder, my book is out now. Get it on Amazon or wherever you buy your books in every form that you'd like. You want to hear me talk it to you? That's there. You want to read it on your device? That's there. You want the physical copy? That's there. Um, and then you can go to our website, busynessbroken.com. There's also a validated assessment of your leadership. You can get some feedback from your subordinates on what it is. Get— see the other side, the part of the mirror you don't see, reveal your blind spots. Then you go to work on it, and that can only lead to good things. Thanks again, everyone, for watching, for listening. 700 shows and more, wherever you're getting this now. Like, subscribe, all those kinds of things. Thanks, Bill. It's such a pleasure to have this show every week and to talk to you all. And I love getting the feedback. So drop us a line, let me know what you got out of it, how you applied it. I love hearing those examples. We've been doing this for a long time and reached over a million people now. And it is really lovely to hear back from people on the things that you're getting. So thanks again for watching, for listening. Until next time, keep scaling. Thanks for listening today. One last thing. If anything in this episode hit home, my book digs into it further. Busy Is Broken: Do Less, Scale More. It's all about how to stop drowning in work and build a business and a team that scales without you. Available right now with content samples at busyisbroken.com. Go grab it. Be less busy.




