How product teams operate, and why it doesn't work - John Cutler

If a leader digs too deeply into how you work, it's considered not being very strategic. There's so much pressure on leaders to be just acting, acting, acting, not thinking necessarily with AI and other things that are going on. And I think that that just creates a stigma. The macro climate at the moment is not friendly to continuous improvement. It's all about big swings. We don't have time to take small steps here. We need to do something bold. We need bold. We need X. We need all these things. Hey, it's the product experience, and I'm Randy Silver. If you follow product management on LinkedIn, then you already know John Cutler. He's got a brain the size of a planet, and he blogs prolifically about the best way to cut through the beautiful mess. It's always a joy to chat with him, and he sat down with me recently to talk about playing the game, the challenges that come up in organizations when we try to build and manage great products, and why it's just so weird and tough to do it well. But if someone's thriving at the game in the company, but you respect them, That's maybe a good signal to you. Like, is there something I need to learn from them? John, thank you so much for joining. It's great to have you back. It's been ages since we had you on the podcast. I think it was a pandemic podcast, something. It was way back. But now we're here. We're in person. Different kind of crisis in the world. Different crisis. Yeah. And we're in the flesh. Here we are. It's fantastic. And we had to come to Cleveland to make this happen. Yeah. Well, Cleveland came to us in some sense. There is that. So things have changed for you since last time. Yep. one or two companies ago, I think. So you're wearing the logo. So tell us about what you're doing at Dot Work these days. Yep. Well, I took stock of things and figured I would have fun in a startup. So I had met these folks from this company, Dot Work, and I liked what they were doing. And so I thought, let me give it a shot. Interestingly, I swore to myself I would not get involved in tools for anything close to product managers again. But? But. Yeah, I actually just started nerding out with the team when I wasn't working there. They kept reaching out and saying, what do you think of this Cutler? What do you think of that? And it was just fun to work with them. And it's obviously very out of character for you to nerd out about product management. Yeah, exactly. It's not like they didn't know how to lure me in to do those things. So, yeah, I like what they're doing. And, you know, it's in the strategy, goals, product team funding space. And then think about all the stuff that you might do above the team level. I mean, I think teams should use whatever tool they want. Basically, they should use it for ticketing or they should use their road or whatever roadmap tool works for them. But increasingly, you're seeing larger and larger companies, especially non digital product selling companies, try to embrace more product ways of working. And they just have fundamentally different scale challenges to take care of. So it's been a lot of fun. So one of the reasons we love talking to you is. you have a history of going out and just talking to tons of people getting a lot of insight as to how different people are working that's a lot of what you're doing with dot work as you as you're trying to figure out what to do now it's officially discovery instead just fun but yeah i mean i'm a method actor i did this at amplitude without talking i'm kind of into it and i like i would actually encourage people to think about that is that sometimes with product roles you can scratch a couple itches at once. It just doesn't need to be one itch. I like creating stuff. And so I still get to do that. I like going out there and talking to teams all the time and learning from them and just staying current. And then I also like doing product. And so my job now is to stay current, talk to teams and head up a product and create stuff. And so it's fun. So I feel like we're at a point in time now. There was a point in time where everyone was saying. well, we need to adopt a product model. We need to think about product, which they also said was agile. They said, okay, well, let's do it the Spotify way. Let's do it the SVPG way. Let's do it the Safeway, God forbid. Let's do it some other way. That's good food. I grew up in a town with a Safeway. So if you're from the States, you can get it. There is truth, but not that Safeway. There is everyone was saying, let's take an off the shelf model and try and implement it. And we've kind of seen the fallout from that now. And the things I have seen work best are companies where they may start with a model like that, but they're very intentional in their thought process. What is working for us? What is not working? What do we adopt and what do we change? But you're talking here at the conference about kind of why that's so hard for a lot of people. Why process is almost a dirty word. I think a lot of that is baked into the product mindset in a way. And I was reflecting a lot about this the last week or two where when I was an IC product manager, I just worked around my company. I didn't think everything was lame. And I say that in the way that you think about it like you're just wired. It's a feature, not a bug to go out there and obsess about. customers and excess about what they're doing. And you sort of get this attitude of a little bit, been there, done that, you know, it's a little cavalier, like cavalier PM thing. And I think that actually even bubbles up to some leaders too, where if a leader digs too deeply into how you work. it's considered not being very strategic. It's not really taking a hold of business. I mean, there's some great talks this morning where people were leaders at CPOs at companies, and they're talking about the intentional design of their teams, which was so heartening to hear. I think that in a lot of places, it's a bit of a bad word, especially in the current economic and political climate at the moment where everyone is just told to be into all the details and anything that smacks of. Care, concern, bureaucracy immediately is friction. We have to get rid of that. There's so much pressure on leaders to be just acting, acting, acting, not thinking necessarily with AI and other things that are going on. And I think that that just creates a stigma around the idea of intentionally designing your org. It's good in theory, but I think ultimately for a lot of leaders, it's hard. And then for a lot of the PMs, a lot of them could just care less. they're like a heat seeking missile, you know, for whatever they're into. Do we still, I mean, I know we want, I think we want, but do you think that the idea of going for empowered teams is still, is that a safe word these days? Do people actually want that or do they just want micromanagement? I don't know. I think that just things like empowerment and high agency and those types of words just have lost a lot of meaning to me. I mean, if people were empowered. You wouldn't just go randomly lay off 30% of the people in your company and say, you just need A players in your company. Apparently, it wasn't that empowered to begin with, no matter what people talked about. So I think that there is a reckoning at the moment that people understand that a lot of companies are pretty transactional. They want teams to move fast and to have an impact. I don't know if this idea of empowerment carries the same weight in the current macro climate. I wish it did. And I was talking to someone this morning, you know, there's all this busting on agile stuff, but I almost feel that the agile stuff is too heretically communitarian. It's too, you're supposed to pair, you're supposed to be on a team, you're supposed to think about things being sustainable. The macro climate at the moment is not friendly to continuous improvement. It's all about big swings. It's we don't have time to take small steps here. We need to do something bold. We need bold. We need X. We need all these things. And so, you know, you've got me going now thinking about this empowerment thing. I just don't think it carries the way that it might have even a number of years ago because the lived experience of people out just navigating companies at the moment. But I have to say one thing, great thing about dot work is you also just meet leaders doing really cool things, amazing things. Like the heartening part about. I think, dealing and working with a lot of different companies and teams is you see these pockets of goodness. Is there a common thread for the pockets of goodness? I mean, typically, there is a leader who has created a sphere of trust and safety for the particular group. And two, there's a level of intentionality. But it's one thing to say that. It's another thing to put that into action. So I think the intentionality. And then the third thing, often it's just luck and things beyond their control. It's just the company happens to be in an upswing. Maybe the founders of the company deeply believe in something. So yeah, I can't say there's one definitive pattern, but it is, I would recommend to anyone who feels that their current company is not fun to be at. And there's a lot of people who feel that way right now. Just, you know, try to come to events and to conferences because it's so heartening. Like even being here, you just meet people, you see, well, all our problems are fairly similar, but ultimately there's these bright spots happening in lots of companies. And so it can actually be a good spark. One of the things that I've seen, and I know Matt LeMay talks about this, and he did a lot about it in his recent book, is there are people who are good at managing up, and there are people who are good at the process of doing everything the way we told them over the last number of years, this is what a good product team looks like. But ultimately, it's about those big swings. As I said, it's about you have to be delivering value. Otherwise, what is the point of all that process? You can do everything right, and it's the wrong time. The circumstances weren't right. The process isn't something that's definitively going to lead to success. We just happen to believe that if you use this basic approach, you're more likely to be successful. Yeah, and I think that's very hard for some people to process. I remember I was really heavily involved in music, and you'd read, there's this... Yeah, it has kind of a rude second part, but it's called gear X, you know, so it's like gears or something. And you read in this magazine about like how to set up your equipment to get a certain sound. And then you try to get it going in your studio. You just can't get that sound no matter what you try. But you're going through this cycle of to do a good job. You go through these cycles of trying to get the sound and trying to get things. And I think that for a lot of teams, it's hard for people to think we're doing the right things and then not getting these stellar results. And I think that that goes a lot into. Yeah, setting the right habits and then realizing there's a great we have a great customer. And I love what he said to his teams. He said he asks them at the end of the day to grade their efforts. So you come up with some impact that you thought you were going to produce. And then he says, OK, I want you to give a score yourself. But I love when he was talking to us about it. He told his team, he's like, look, if we're at a point five, we might as well flip coins. Right. But if we're one. we're lying to ourselves and i love that kind of idea it's like there's a healthy spot around like 0.7 or 0.8 and they graded it from zero to one where i know that we're taking risks and we're reflecting on our mistakes and i loved how his openness to the idea of it doesn't always work out the way you want it to work out um but it's the reflection and the habit that counts and then ultimately in the long term it's going to benefit the team i just love that that was a great example that makes sense okay so You gave me a preview of the talk you're doing here at Industry. And one of the things you said in it is the people who are good at this, they've figured out how to play the game. Yeah. And I'm not sure I like the word game in this, but I think you were intentional about using it. So can you talk a little bit about that? Yeah. The realization that I had, and it kind of hit me like a brick, was I was chatting with a leader. and they said you know my team's not very strategic and they don't seem to really be into it and i was talking to someone from the team and he goes home on the weekends and plays one of the hardest strategy games in the world with like 10 other people and he's involved in these open source projects and he's also a musician he's like yeah i just don't happen to bring my strategy to work like i'm i'm into these games and so i started to latch into this idea of games And the important thing that there's game as the political game to be played. I'm playing the game of the company. I've learned how to navigate this game. I can play this game. And then there's the game designer part, which is what my talk is really about. So actually, there's one slide where I say, you know, playing the game of a company is learning how to navigate the politics of it and hopefully thriving, but just hopefully just surviving cases. But a co-design game is a little bit like D&D or when you get people together, like there's some rules, but you co-create the game together. And that analogy just sort of stuck with me as I talk to all these leaders because I keep wondering, I'll ask them questions like, that's an interesting game you set up. And you could see a smile on their face like, yeah, it is a little bit of a game, but not in the game kind of way, just like you did. Not in the, I'm creating a political game to play. They're like, I have made it kind of fun to work here. I have made it engaging to work here. And so then I started to use this analogy of the game more and more. So let's stick with the analogy for a minute. When you play a game, there is winning and losing. You said it's thriving and surviving. But how do you define or what are you noticing people as? What are the good elements? What is the success criteria in these games? Well, I sit down with my seven-year-old and we play games. And a lot of it's not about winning or losing. A lot of it about is playing together. And so I think that there's... There are intrinsic and extrinsic rewards in a work environment. And then I think that for a lot of people, like for example, in a lot of great games, you become more experienced over time. So part of the reward is you can feel yourself getting smart. You can feel yourself building your skills to do it. A lot of great games have a compelling story. It's like the strategy of your company. And so you just get more enthralled in the story. You do that. A lot of great games... reduce the amount of non-value-add thrashing you do in your brain. So whenever you're a product manager and you see teams that don't have any sort of prioritization or strategy in their company, all these PMs are spending half their day just trying to mind read. That's playing the game. I'm playing this weird mind reading game in my company. But what they really want is they want someone to kind of structure a lightweight game. with some rules, some idea of what it means to win, like some idea of what it means to play together. And I don't know, I just started to think like, what is it about the fact that people can go home and play a strategy game for 20 hours at another level compared to their company and then walk in on a Monday morning and it's like they're at like a third grade level brain. And it's probably because the environment in many places we work are not nearly as compelling. is the games that we play so okay i'm going to torture a metaphor so just bear with me on this one and unfortunately they're both it's two separate military things coming into one so we've got the the ooda loop at the observatory side next and i think what you're saying with the game is it really helps you to orient and understand What is the board that you're on? What is relevant? What is not relevant? What is a good path to go down? And ideally, not just for you, but for the organization as a whole. But then you've got the other side of, and I can't remember the name of the computer, but in war games, that goes through the whole thing. And at the end, it says, you know, a curious game. There's no way to win. I mean, you can, yeah, you can say there is this existential game of working in companies and that ultimately you can't win. I don't know. I think more relatively. You just meet people who are happier in their environments. And I think one of the common things that we framed in our culture, at least, is your happy environment because of some, like we're so uncomfortable, at least in the United States, with the idea that we are also part of our environment and the system that's around us. We're so individualistic. And the thing that struck me is you go to a great restaurant and you feel good. Someone designed that restaurant. Someone made it or you're playing a game that's amazing. Someone designed that game. Like we are somehow so comfortable with the idea of designed experiences and designed environments and design things outside of work. But it feels uncomfortable to leaders. They're like, well, you know, I mean, it's up for everyone in this company to individually figure out if they're thriving in this particular environment. And I just don't, I don't know, I just don't buy it. I mean, because when you see leaders and you see the people that work in certain environments just be more charged and. positively charged in what they're doing you think like okay there's something here i'll go with the the production aspect of this and not the factory production but you know putting on a show or sports team either one it's when it's working you can feel the energy from each other you everyone's working whether you're the lighting person whether you're the the musician or the singer or the dancer or whether you're the athlete when it's working yeah it feels special yeah yeah Well, you see, and I think that that's that. One thing that I found was interesting is I sort of do this test with different leaders about when they start to feel dirty with the idea of making a game. And so when I say, do you design incentives? Yes. Do you design the onboarding of your new employees? Yes. Do you design your job ladders? Yes. Do you design your meetings? Yes. Do you design the frameworks that you use? I don't know do you design the process that you use suddenly like their eyes become no no I don't did I don't do that so it's just also kind of funny how I'll probably get into that a little bit of the talk where we were uncomfortable and I think leaders are uncomfortable because it feels a little big brother it feels like I don't want to design this environment I feel bad designing the environment for people but I actually think that leaders need to embrace that and yeah i've just found when i'm chatting with people if i frame it as a game and something fun and something and they can all relate to what a good game feels like you know good games have achievable goals they have the right amount of difficulty they have a social component you can self-identify they've got a good story we can all relate to what a good game feels like and so i think it almost takes the stigma off of are you this a plus leader to do it so i think that's my experience In the preview you gave me, there were a bunch of things that you said were specific things that you talked about. The rules, the mechanisms, and so on. Talk a little bit about the things that we should be conscious of while we're thinking about our environments and being intentional about them. Yeah, so, yeah, I think that the key word is intentionality. And so when I chat with leaders about it, I mean, the agenda of a meeting is a design thing. You've made choices that, in theory, I think the grounding element is behavior. So when you're designing a game, I actually, my first tech job was I had a video game company. So I designed this game and it wasn't great. So in retrospect, I would have designed it differently. But you do think about the behavior of the players and you think about it. So the way that I try to get to all the different parts is what impacts the behavior of people in your environment? And you start to think like, yeah, the rituals is pretty heavy word, but it is, you know, what do you celebrate? When do you meet? What are the agendas you have? What are the artifacts you use? And it's kind of funny with software development. Like if you went to, say you went to an artist shop or a luthier or something like that, and you walked in and they had terrible tools and everything was messed up and it was dirty and they had priceless guitars sitting getting smashed or they were trying to build stuff. You'd be like, this is an uncomfortable place to work. But if you go to your average tech company and you kind of look at Slack and like try to ask people what's in their brain, they're like, oh my God, it's a bunch of Google docs and I can't think about it. And the reason I'm mentioning that to answer that question is it's how it's the words you use yeah um it's the models that you encourage people to talk about uh it's the dashboards that you create they have like a certain element of uh framing the game that you play it's kind of funny you call it the balanced scorecard but it's a scorecard and i think a lot of those things again in isolation i mean i could just keep listing those things i i think one thing that leaders vastly underestimate is just there's a rhythm i call it in my talk i say checkpoints where in most games you hit this checkpoint where you get to kind of clean the slate a little bit if you make the checkpoint you get there you keep your points you do everything you get to launch into the level again and you do something so those intentional rituals where you close the loop yeah are so important and i think the idea that you only do that once a quarter or you do it in a very performative qbr process or you're not really close like nothing was shipped Everyone's talking about all the points they're getting done or whatever. And you ask, well, did anything ship? No. To do that. So that's another thing. Anyway, I'm blasting you with different ideas. But it's pretty much all of it. It could probably seem overwhelming if you frame it that way. But I think the other thing, too, is to flip the perspective. You are playing the game in your company. And there's parts that feel like that kind of swarmy political game. But then there's the other thing. It's what you are participating in. I think one phenomenon that happens, which is really weird to me, is... A lot of the global things that happen in the company, because people are afraid of being criticized or because so many people are involved, get washed down to the most bland, mediocre middle. It's like the teams have all these vibrant things. And then whoever finance, like we're doing annual planning. And like, it's almost intentionally lame and bland. It's so bland and so unopinionated. And you notice this in the companies that have maybe more opinionated founders who are like, I really care about this quirky thing at this level. Like I really care about maybe a certain document we write or I care about that. The amazing effect it can have on the whole org because instead of ending up with the kind of bland corporate ease. At the upper level where nothing really makes sense, everyone just does what they can do to just get out of those meetings. It's like they're not meaningful to people. You're just asked to guess. You're just you don't do anything. Imagine if you could turn those into things that were actually really valuable and effective for people. It could change the game for a lot of companies. This episode is brought to you by Bolt.new, a product manager's secret weapon to bring ideas to life in record time. You're being asked to do more with less and your team is busy crunching away on 1,000 different priorities. But with Bolt, you don't have to wait. 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So one of them is what you were just talking about with finance is interesting because I've been in lots of companies where they have very strict finance rules about project-based funding and Apex and Opex and things like that. and it i did realize a certain point i would have to work with finest to change the rules of the game yeah to create an environment where the teams can succeed so that's one part of the other part is you were talking about the the environment as a whole yeah and you know famously we celebrate some really crappy behavior and crappy leadership. Yeah. You know, we want to go back to like a kitchen metaphor. You know, Gordon Ramsey's got one hell of a temper on him. He is celebrated. So most of the famous chefs have gotten into trouble for creating bad environments over time. Maybe not most, but quite a few. If you are someone in a company, you know, most product managers are middle management. And then you get up to a certain level. But if the environment is not great. whether it is finance has rigid rules or whether it is bad behavior how much can we do to change the game finance is a great example because anytime i talk to someone in finance and just explain it over a drink like after work or whatever they're so understanding oh yeah and so the funny thing i think that's a great example of i think that the finance game with product is more changeable than we think If you really try to really empathize with their particular situation. Yeah, because there's rules to the game they're playing. There are actually accounting rules to the particular game that they're playing. But if you, the funny thing is chatting with someone in finance sort of explaining product and they said, John, I understand. We literally buy companies as a bet that they're going to produce an outcome. Like we don't buy, we didn't do that M&A to buy a project. We bought a stream of revenue. We bought. people we bought asked like we think in terms of assets and capital to do this and so what i found with the finance folks is that a lot of product people come with pretty monolithic purist ideas of it there isn't a question about whether you're going to fund projects or products it's more like what is your mechanism for funding products at different stages right um oh when you have a product that's been around for a while where you're just eking out the last tiny percentage points of that product you might fund it in a different way You have to build models. And this is the finance product game is one that can be co-designed and it's totally worth the leverage to be able to do it. So I think that people should imagine that they're not beholden to like finance doesn't want to lead the company astray. No one wants to do that. Now, the second part, I think about just crappy environments. I think that, well, first of all, a lot of the companies. It's funny. There's one or two companies that get celebrated a lot for being amazing product companies. And then any friend out there has worked at is like, that was like the hardest and worst three to five years of my life. It's like incredibly difficult to work there. People are extremely difficult. And so one thing first is to a lot of the companies people idolize are sort of crappy places to work at. But I think it has a lot to do with localized spheres of things being good. I think that. Ultimately, our experiences of companies are fairly local. And as product operations people and things, we tend to be glue people fitting it all together. But most of the people in the company, their experience is rather local. And I think that the takeaway that leaders can have there are other folks is even in the midst of just normal corporate yes, I guess, it's still possible to create boundaries of trust among people. And so I think that's where I would focus. So, John, a lot of times when we talk about getting started with something like this, people want a framework. They want something specific. So I know you can't go away and just design an entire game at once. And as you said, co-design can be really important. So do you have any practical tips for people to think about as they do? tomorrow what should they start thinking about yeah so i think that first of all there's a lot of stuff to pull from behavior design a lot of games are basically behavior design and the great thing about behavior design although it sounds very dirty again i'm putting on my u.s hat right which is that sounds like you're manipulating people there's a lot of stuff in behavior design and the first thing that you do in behavior design and this is where i would start thinking about it is what behaviors do we, it sounds simple, but it's like, what behaviors do we want more of than less of? And what I've found in the product sphere is there's so much talk about empowerment and curiosity in words, but then when I ask people, what does that look like? What does it look like when someone is data-driven? What does it look like when someone is empowered? Like, describe what's going to happen tomorrow. What are some of these behaviors that exist? People are a little bit terrifying, right? And if we want to be reductious, what are your KRs for that? uh yeah exactly so right they're gonna like empowerment okay and a lot of times when you ask people for outcomes it's pretty bland it's what everyone else wants and when you ask for these sort of mean what do people want in their lives it's like agency empowerment and so i think the first thing to think about as your team is get specific with behaviors and that just is a great discussion and so i'll give you an example if someone says um we want to be more data driven That could mean a million things for a million different teams. What would it look like? And so what I think is positive about that is then you start working into some of these game design aspects of it. So you would think, okay, right now, to us, being data-driven is at least tying the loop back on something, at least having some hypothesis of some of the metrics that might move because of something that we delivered, and then holding ourselves into some ritual. Okay, so that gives you a sense, the behavior sense that you're looking for. And then you have to start thinking about like, well, what are the mechanisms that we need to make that easier? Before starting making, how are you going to make it harder? Think to yourself, how can we just do that more naturally? So this is an example where you start in behavior design frameworks that goes a lot deeper into this. I'm just simplifying. But you'd sort of ask like, well, what's getting in the way of that behavior? Is it competency? No, no, actually. A ninth grader, a high school student in the United States could pretty much solve this problem of defining the metrics. It's not that. Is it accessibility? Okay, yeah, there is a fair amount of copy and paste. Actually, the metrics aren't very accessible. Okay, so that's the second thing. Then the next thing is, is there social reinforcement? Well, no, not really. We've been asking the people to just write these into docs and we never talk. There's no social reinforcement over what's happening. the fourth thing that you might say in thinking of the game dynamics is is there replayability and then then you'll ask that and they'll say oh no no there isn't we spent six months deciding on the metrics to track and then everyone is so terrified to change them so the game you think that is a game like you want a replayable game you want to be able to walk in and say i don't think this metric is tracking what we think it's tracking and then be able to play the game again not be stuck with the metric for a long time so it sounds very simple but starting with behaviors imagining the behaviors that you'd love to see more of and then just start backing up and saying is it you know is it a competency accessibility issue or just people cognitively overloaded the number of teams that say we we would love to do this and everyone nods their head and then i say okay what are you going to stop doing to make any room in your brain to leave that like oh stop something You're like, yeah, maybe it's the, you know, 40-hour quarterly planning prep that you do that no one has an MPS of minus 20 that you pay $4 million a quarter for and staff salaries for. Oh, yeah, maybe that would be a good place to start to make that. So, you know, and I think the other point is to ask yourself what makes a great game. When you've played a great game, like those things like replayability, the right amount of challenge, the story. I'm not talking about the types of games that are extractive. There's a lot of games that. you know, basically dopamine hits for kids. I stumbled into my kid and he'd like found this one Sonic the Hedgehog game on my iPad that's basically like you sit there and you go like this and it just pops like a coin at you. And I'm not talking about that type of game. Just think about the really enthralling games and replayability and the social proof and all that stuff. And I think that those, I would say that those are your, that's your kind of levers that you have to encourage some of these. You're inspiring a whole bunch of interesting thoughts, but there's the app type games, which is a very controlled environment, but people fudge with them all the time because they're looking for the Easter eggs or they're looking, how can I play this differently? Can I go into explore mode or am I speed run mode or am I kill all the zombies? And those are interesting things. Corporate speed running. But then you've also got like Monopoly, which has been around forever. But I don't know anyone who plays it with the rules that come with it. Everyone has their own local rules about what do you do with community chess and jail and things like that. And the rules there just might be the affordances with the pieces and the board. So there's kind of affordances in the particular environment. There's an environment. But the physics of the game, you can change based on mutual agreement. And then there's sports as well. Baseball put in the pitch clock in the last year, and it made it a much more enjoyable thing. Basketball's got the three-point shot. It's got where the arc is. All these things change. The height of the basket has changed. Things like that, they change to make it a better game. Just because it's played that way doesn't mean it always has to be. And you can talk about what is the environment we're in and how are we interpreting it and doing it here. If people can get over the cynicism, I think that the cynicism about... This stuff gets so quickly equated to process and the bureaucracy of a company and the stuff that people see as the kind of unfortunate side effect of working at a company. And then the real mindset shift is to think to yourself, like, wow, it's like, why? It's funny. You'll see companies invest millions of dollars in DevEx, like developer experience, because you can relate to it. You know, it's like, oh, these are the tools that people use. Of course, the tool should work. and then in the kind of cognitive environments that a lot of pms inhabit it's just a badge of honor it's like well you you've chosen this job therefore you must suffer in in this in this thing when i look at it and i was like that's kind of stupid like you would never you'd never be a producer on a film that had a vision for a film and then say like Oh, yeah, I just want to run. I want to shoot fireworks off the whole time and have people like leaving the set at random times. And like, imagine you wouldn't be able to function as a creative human being if you did that. But we throw people into these environments that are just so and I don't think AI is going to help. It's more like all it's doing is speeding up more of the reactivity. It's like, oh, my God, I'm going to think about six things at the same time and hit browsers with all these questions. you still got to process it in your brain and let it simmer and sit for it to make any difference so yeah i don't um i don't feel cognitively better after a day with ai i feel worse like i've had to protect more of my actual cycles which is is a sign it's an important sign to pay attention to Okay, I suspect AI may come into the next answer as well, the next question anyway. Is there anything that people should avoid? You talked earlier about do you intentionally, do you set performance goals or incentive goals and bonus goals? There are things there that, you know, take into the logical extreme can lead to really poor behaviors or unintended consequences. So what should we be conscious to avoid as we start this? You know the best way is to talk about this with the team, and I think it might be called It's a liberating structure, which is this kind of facilitation. And I think that there's something called TRIZ, T-R-I-Z. And I think the whole idea of TRIZ is you say to a team, if we were going to design this environment to have the absolute worst effects, what would we do? And it's a great game because then people start, and people are a little nervous at first. You're like, no, no, no, just like, I'm going to start a... weed whacker in this room like that's obviously going to screw us up right and everyone laughs and then people start throwing out these wild ideas but then people start to say things like yeah we would uh randomly send them slack messages at all hours of the night and ask them to be to try to answer and then there's a little silence in the room and so the one i would leave people to think about the end when i was going to answer your question i was going to do an internal triz in my head which is like if you wanted to guarantee Like, first of all, there's some companies that do actually handle, there is one famous company and she described it and everyone knows this company, but there's a service designer there. And she had a great description of the company. She's like, this is globally pathological, locally generative. Basically saying that this, like at higher levels of this company, it is absolute dog eat dog world. It's a highly uncomfortable place to be. But on a local level, it's more generative and they're really doing great work. to be able to do that. So I think one mistake is to take, you know, if you said that I challenged people the other day, they said, well, psychological safety is a big predictor of success. I'm like, but you just listened, you just told me about six podcasts with companies that I know are not terribly psychologically safe at the moment. So like success at what success in your life, like success about people being happy, success at telling people how to do their job or, or buying, you know, buying server farms or something like that. I don't know how we got into this, but I was thinking about, yeah, when we did with the Triss thing, I think people actually intuitively sort of understand those things. But I think with the game stuff, the biggest thing is the worst thing is for people to check out. Okay. And meaning that if you give people just a perverse game, the problem is you won't hear about it after a while. People just, humans are incredibly adaptive. And if you have a company that's messed up. People will push back a little bit. The people who hate it will leave. And the people who remain there will come to some level of peace about the situation and you won't hear about it. So I'd say that the biggest anti-pattern is believing that because people aren't like telling you about it, that that means that there's not a problem. So I think that's kind of the biggest macro level problem or meta problem. That's... Terrifying. Yeah. I'm sorry, just stuck in my head is you were talking about Triz and there's an alternate approach that I love. And Roshi Probin's been on the podcast and talked about it. Her approach was a game she'd play with her team, which was every once in a while sitting down saying, if we were to write a Black Mirror episode about using our product, what would the plot be? That's awesome. I love those types of, but that's a good example of, this is also my like workshop principle. it's kind of incredible i'll go to a team and they say we can't prioritize anything this place sucks we can't make any decisions and you take people out of that context and and the leaders will say i might not have the right eight players working on this or i don't know we don't have the highest leverage people and you just change the frame a little bit and then you see people's creativity come alive like they are not cognitive this is the thing about behavior design so many of the problems and and i think we don't especially in our industry, like some of the thought leaders don't really help with this thing. So many of the problems we've persuaded ourselves are, we just don't have the smart enough people in this particular situation. And then if there's still a problem, it's like, well, we don't have a good enough leader. So it's either blame the leader or blame the people or both. And yet take them out of context. And these are like pretty bright, vibrant, cool people. I spent some time with a company a while back and they were trying to write a business case for a portal. and it wasn't working, and I've been asked to help them with that. And part of the problem was we had 15 people in the room for three days, and we were trying to do it, and part of the problem was the company had an identical portal aimed at the same user group, and they were trying to build two portals for this one customer profile. And the question was, why? But they were so stuck in the context of, well, Team A is doing this, and Team B is doing this, and never the twins shall meet. We have to keep them separate. And we finally got them to ask the question, and we got the leaders back in the room, and they said, well, have you written the business here? So we said, yeah, we've cracked it. This is what it is. But the real question is, do you have to prioritize, is it portal A or portal B, or should we just put one portal for this? And they finally said, well, when you put it that way, but it took me as a consultant, as an outsider in this case, to help seed it and change the context. Well, companies are, there's a great theory called the garbage can theory, which is that basically, it challenges a lot of notions of the like logical corporation they just say like corporations are just bringing people their solutions looking for problems yeah not not the other way you know they're just people thrown into this environment i was doing some research for for i didn't include this part but it's really funny because uh what is it steve jobs said you know i'd rather be a pirate than in the navy yeah well pirate ships have some of the most calculated games Absolutely. You can fire the captain. There's like a quartermaster. You could do that. You sign up to the thing that's actually has a democratic, like your average pirate ship is a lot more like designed than your average corporation. It was actually a very empowered team with its own rules. Yeah, not the Navy. I mean, granted, I understand probably like the level of bureaucracy in the Navy is higher, but we have this impression of like, I don't know, companies as these. you know, rational entities and stuff. And they're really not. They're just throwing together a bunch of people in a weird environment. So I'm not trying to be cynical about it, but you have to, I think you have to, the thing I've been asked, telling people a lot, thinking about the game thing too, and I leave people with this thought is a lot of people, there's a great book by William Ury called Getting the Yes with Yourself, which is a lot of navigating these environments is negotiating with yourself. And one of the interesting parts of that, I thought, extending that idea, was that if you're in a company, trust your gut and look around and say, who is thriving here and do I respect them? Now, if all the people who are thriving in the company are people that fundamentally don't match your way of looking at the world or whatever, then you have to ask yourself that question. Maybe thriving is not. the goal in that company. It's hard to find a job. Maybe you want to survive. But if someone's thriving at the game in the company, but you respect them to do that, that's maybe a good signal to you. Like, is there something I need to learn from them? Is there some way that I need to develop? And so you can always like turn this game thing back to thinking about yourself where you're playing your own game in the company's game. And part of that's negotiating with yourself and then your vision of what it means to participate in these environments. And so the example here would be, I said that to someone and they said, Well, I can't I can't all the people who are thriving here are psychopaths. I was like, do you want to be a psychopath? No. Well, when you've answered your own question, like, like, I guess I guess you you want to set up your own game here. You don't want to participate in that particular game. So yeah, we could take that pretty far. But anyway, thoughts. John, that was fantastic. I really enjoyed this conversation. It's fascinating. We obviously could go all day and probably would, but we've got a conference to attend. Yeah, let's go. Let's hit it. Hey, Lily, I've been hearing a lot about product managers struggling with AI. Are you hearing that too? Absolutely. Everyone's talking about it, but many are still trying to use AI in a way that adds real value, just like IBM's recent report, which found 76% of companies aren't seeing the benefit. Exactly. Which is why it's awesome that our friends at Mind the Product are providing AI training courses designed specifically for product people. These are live online workshops happening this November and December. You'll join other product pros to learn how to identify real use cases for AI, integrate it responsibly, and make smarter product decisions. One of the things I love about the Mind the Product training is that it's taught by real practicing product people who understand you and your context deeply. So if you want the best trainers to give you or your team the right framework for adopting AI, head to mindtheproduct.com forward slash AI classes. That's mindtheproduct.com forward slash AI classes. Spots fill up fast, so don't wait. To get a 10% discount, use MTP Pod Train 10. The product experience hosts are me, Lily Smith, host by night and chief product officer by day. And me, Randy Silver, also host by night. And I spend my days working with product and leadership teams, helping their teams to do amazing work. Luron Pratt is our producer and Luke Smith is our editor.

In this episode of The Product Experience, host Randy Silver sits down with product veteran John Cutler to explore why creating great products remains one of the hardest things organisations do. They dive into why so many companies adopt off‑the‑shelf models (“Spotify”, “SAFe”, etc) and still struggle, and how the secret often lies not in what you build but how you build it—specifically the game you design for how you work.

John shares his game metaphor for organisational design: how to see your team and company as playing two games — the political organisational game and the design‑game you craft for how you work. You’ll hear why behaviours matter more than titles and tools, why checkpoints and rituals matter more than frameworks, and how you can start tomorrow to define the behaviours you want, identify what’s blocking them, and change the rules of the game.

Chapters
00:00 — The stigma around “how you work”
00:54 — Introducing John Cutler (again)
01:25 — What John’s building at Dotwork
02:46 — From fun to formal: doing discovery at scale
04:04 — Why process became a bad word
05:10 — The “cavalier PM” mindset
06:28 — Empowered teams vs. harsh realities
08:00 — What great pockets of practice have in common
09:03 — Managing up vs. doing the right thing
10:24 — Playing the game vs. designing the game
11:20 — What makes a great internal game
12:33 — Defining success: thriving, surviving, progressing
13:46 — Environmental design: why leaders hesitate
15:10 — Making intentional design less intimidating
16:42 — Tools, rituals, and the power of checkpoints
18:23 — The behaviour design playbook
20:41 — Removing blockers: access, repetition, reflection
22:12 — Replayability and the value of feedback loops
23:29 — Fixing the finance game
25:20 — Creating local spheres of trust
26:27 — Starting with behaviours, not frameworks
28:01 — Diagnosing blockers with behaviour design
29:53 — Identifying anti-patterns with TRIZ
31:08 — The myth of corporate rationality
33:19 — When no complaints doesn’t mean no problems
34:13 — Closing thoughts: are you playing the right game?

Key takeaways
— Intentionally designing how you work (process, rituals, environment) is as important as designing what you build. John argues that the latter often gets all the attention while the former is treated as a dirty word.
— Use the metaphor of a game: good games have clear goals, balanced difficulty, feedback loops, social interaction, story‑elements. When companies design their internal work like this, teams perform better. 
— Focus on behaviours not just tools or frameworks. What exactly does “empowered team” or “data‑driven” look like? Define the behaviours, identify blockers (competence, access, social reinforcement).
— Don’t assume that “no complaints = all good”. Organisations often get worse by stealth through people adapting or checking out. The absence of noise isn’t proof of health.
— Your personal radar counts: look around who is thriving in your company, and ask if you respect them. That may tell you if the “game” being played is one you want to join.
— Behaviour design and process design require constraint and ritual. Without checkpoints, loops close, or feedback cycles, the system decays.
— Macro headwinds (economics, AI, speed) mean continuous small improvements are under pressure; yet the fundamentals of “how we work” still matter.
— The relationship with support functions (like finance) can be changed: treat it as co‑designing the game, not battling a monolith.