John Cutler is Head of Product at Dotwork – a startup dedicated to transforming how teams collaborate and manage product development. He is also a prolific writer, including his wildly popular newsletter, The Beautiful Mess. John’s prior roles include supporting product teams at Toast as Senior Director, Product Enablement and Product Evangelist and Coach at Amplitude.

In today’s episode of Product Momentum, John joins Sean and Dan for an in-person conversation recorded at INDUSTRY, The Product Conference back in September. We caught up with John in between his day 2 keynote and re-entry into “startup survival mode.” During our chat, John reflects on organizational realities and ways of working, the notion of product people as game designers, and how that mindset highlights the importance of fun and dynamism in the workplace.

Here’s what we learned:

Organizational Realities and Ways of Working

A deep chasm lies between the way organizations communicate their ways of working and their actual practices, John says, highlighting the multiple realities that coexist within companies.

“I think in any socio-technical system, you tend to see different frames and perspectives,” he adds. “Companies are not rational places. I’ve been doing a lot of research [in this space], and I’ve learned that pirate ships, despite their reputation, are way more organized than your average company. And actually way more democratic too.

“View process and your ways of working as extensions of what you do for your customers,” he continues. It’s a perspective that encourages empathy and a customer-centric approach even in internal ways of working.

The Concept of Product People as Game Designers

During his keynote, John introduced the notion that product managers and their teams are essentially “game designers” responsible for creating engaging, dynamic experiences.

“I like the game design idea because everyone can relate to playing an amazing game and being in the zone with friends,” he offers. “When you experience a great restaurant, that’s service design. Enjoy an amazing vacation? That’s experience design. Ultimately, it’s not super-complex; people can relate.”

Applying this mindset to product development and team dynamics can make work more enjoyable and effective.

Importance of Fun and Engagement at Work

During the conversation, Sean suggests that “roughly 90% of the people you work with – if they could make the same salary doing something else – would actually do that something else.” The statement highlights the critical role of having fun and being engaged in your work that often makes the difference. John goes on to distinguish genuine engagement and dynamic work environments from the many superficial initiatives he often sees.

“I’m trying to decouple the sort of ‘corporate engagement industry’ from occasions where people find themselves ‘in the zone,’ a state of flow that goes beyond fun into a sort of dynamism in their environment.

Our conversation with John Cutler is the first of five that the team recorded at INDUSTRY: The Product Conference, on September 9-10. We’ll publish the additional in-person episodes over the next several weeks, including chats with Sahil Jain, Axel Sooriah, Shensi Ding, and Michelle Parsons. Great insights from outstanding product leaders!

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Sean Murray [00:00:09] Hey everyone, welcome to Product Momentum. I’m Sean Murray, Director of Product Management here at ITX.

Dan Sharp [00:00:15] And I’m Dan Sharp, a Product Manager at ITX. It’s our privilege to continue the product momentum journey. A platform that celebrates the thinkers and doers who are shaping the future of software development.

Sean Murray [00:00:25] Our goal is to introduce you to industry leaders, innovators, and practitioners, and bring you their insights, advice, and innovations. We talk with experts from product strategy, UX research and design, security, engineering, leadership, and more. We’ll discuss how their approaches to problems help empower teams and build trust. And we’ll explore trends, tools, and techniques that your team can use to deliver the software solutions your users need today. So tune in, stay curious, and join the conversation.

Dan Sharp [00:00:53] You can catch us on your favorite listening platform, or if you prefer the video experience, you can find all our latest episodes on the Product Momentum YouTube channel.

Sean Murray [00:01:01] And if you like what you hear, be sure to subscribe, like, comment, and share. That way, we can be sure to provide you with the best podcast experience.

Sean Murray [00:01:15] We could have just gone three hours with John Cutler. That was an amazing conversation. Tell me what you thought.

Dan Sharp [00:01:19] Yeah, we had a lot of fun. For me, one of the big takeaways was organizations, companies, they are both less organized and less democratic than your average pirate ship. So be careful. You might be made to walk the plank. We learned a lot about how, even as individual contributors, we can influence ways of working, make it more game-based, make it just more fun. More fun and enjoyable while we’re doing the hard stuff.

Sean Murray [00:01:45] Yeah, this cold open is going to walk the plank. Let’s go get it.

Dan Sharp [00:01:59] We are live today at Industry with John Cutler. Super excited for this conversation. John is the head of product at DotWork. He is also a prolific writer of product thinking. He’s on LinkedIn. He is the author of The Beautiful Mess. It is probably one of my favorite newsletters dealing with empowering product teams, but also the reality of working in human networks. So we’re really excited to have you today.

John Cutler [00:02:26] Awesome to be here.

Sean Murray [00:02:27] I’m going to embarrass Dan a little bit. He’s been talking about this particular podcast for like three months.

Dan Sharp [00:02:31] It’s like my Super Bowl.

John Cutler [00:02:33] I’m honored.

Dan Sharp [00:02:35] So, you know, you had a talk earlier about game design and ways of working. I am one of those product managers who maybe gets a little twitchy when people bring up process. Yes, I’m curious, what advice did you have for me to be able to turn kind of that external thinking about building good products and turning that inward for building good ways of working?

John Cutler [00:02:55] Yeah, I think that the first thing that comes to mind is acknowledging that you’re doing this for customers. That’s a good start, right? You’re thinking about your customer’s environment. You’re thinking about how your product influences their particular environment. You’ve got all the thinking there. So that’d be the first one. The second one is probably acknowledging just how much bad process we have and we’re surrounded by and how we check out at that. So that’s when in the talk I said that’s a feature not a bug. So I think the process resistance is a little bit like I’ve just seen so many of these things that we would never release that. We would never release quarterly planning to our customers. That’s probably a good question for people. That’s like, would you release how you work to your customer? And people are like, God, no, we would ever do that to our customers. So I think that that’s probably the first step is to think about it as an extension of what you do for customers. It’s probably good start.

Sean Murray [00:03:44] We talked that there is the communicated reality of the way of working versus the reality reality. Why is there this dissonance?

John Cutler [00:03:52] I mean, I think in any socio-technical system, you tend to see different, I just call them frames and perspectives. And I don’t even think it’s just those. There’s the idealized present. There’s real, real present. There’s idealized future. Oh, we’re going to adopt the product operating model. Everyone’s bought in. There’s the official now. And then there’s the real now. You know, the official now is not even quite as bureaucratic as the real now. Right. And then and also a lot of teams, they just. You know, go in and they do their own sort of their localized ways of working. So I just think you have to approach your company. There’s multiple realities going on at any given time. And so you need to be open to that. I would say you can extend that same thinking to customers, you know, anyone who sells an enterprise product. For example, we sell an enterprise. We have to remind ourselves that sometimes our champions literally have to be trained to be a salesperson for our particular product within the company. And then even then, there’s. A snarky security person who’s just had a bad track record with vendors. And then there’s the other person. And so, yeah, there’s multiple realities also with our products as well.

Dan Sharp [00:05:00] Right. So, yeah, I mean, I think your conversation, you know, when you’re doing the Q&A, you’re mentioning your self-awareness as a product and the journey of self-awareness. Like, you have my ideas, the best idea, there are no other ideas. And it’s right to the evolution of like, actually, other people have good ideas and they’re coming from your lens. I would love if you could just talk about that from building empathy towards the people you’re working with and stakeholders.

John Cutler [00:05:23] Yeah, I mean, I think I drew a pyramid once and it took a lot for me to. I was like, where am I in this? I’m definitely not at the top. But, you know, at the bottom is like complete lack of self-awareness. There’s no questioning why I do what I do. And then the next there is like, OK, oh, I’m self-aware. I do things for a reason, but I am right. And the whole world works like I know exactly how the world works. We could just keep on going up the stack from there. Like, oh, oh yeah, the people I work with, well, they’re wrong, but they have. They’re offering their views to the world. Of course, I’m right. And then then you’re like, well, they’re valor. You know, that’s the next level. And then you kind of working up to the top where you realize, wow, I am I’m so deep in my I’ve got my view. But other people have really valid views. In fact, I need to learn from them. I need to create the space for that thing. It’s easier said than done. As we discussed, you know, yeah, companies, companies are not rational places. The idea of rational economics started to just get deep is this idea that the rational firm. Yeah, it’s not. I’ve been doing a lot of research and pirate ships, for example, are way more organized than your average company. Like your average pirate ship, they’ve got quartermasters. You can fire the captain. You can it’s actually way more democratic than your. Average organization. You can you split the booty, I guess. You know, the plank is the exit. And you think about it, it’s it’s. They’re even more that than the average merchant marine. The average merchant Marine, but still merchant marine have these things going on. So, yeah, I think one thing people have to absolve themselves of is this idea that it’s called the “as if” problem. You think of your company as if it’s a thing like, oh, this is as if. It’s a sports team or as if, it’s whatever. We’re just not. I don’t know. You can’t fit your company in your head. It’s just this little mini-culture and you just have to roll with that.

Sean Murray [00:07:13] The real reality. Yeah. Love that. You you gave everybody a new title today. So in your talk, you gave it a you said, I want to talk about that. But two years ago, Marty Cagan did the same thing. He told everybody, if you have the title of product owner, enjoy your promotion. You are all actually product managers and it like probably ownership is a function of product managers. And we lost that battle internal that we’re working on it. You gave everybody the title is game designer today. Yeah. So talk to us about why product people are game designers.

John Cutler [00:07:42] I just thought it would be fun to have fun these days. Yeah. Yeah. So I thought it’d be just interesting to just challenge people. The reason why I like the game design idea is everyone can relate to playing an amazing game and being in the zone with friends or doing something just like you can relate being in an awesome restaurant. Guess what? That’s service design. Right. Or you can really to have an amazing vacation. Guess what’s that’s an experience design. Or you can. End of life care. That can actually be an incredibly things. My son was in the NICU. That was an incredibly designed experience. How they helped us to be able to do these things. And so ultimately, I think people can relate. And that’s what I like about that thing. It’s one to you know, these words like a socio-technical system or it’s complex. That’s like 1% of people in the world. You have to acknowledge. This is like the super, not even super nerds, just super geeks about that stuff. Your average person is like, is my company easy to navigate? Right. And so I think that that’s an I like that that that lends the games. I think we can all relate to a great game. We can all really to that. And then like I said in the talk, a lot of debates happen internally about sort of the system versus individual tension. We feel especially a lot here in the United States. And that all sort of falls away when you accept that almost we’re surrounded by experiences that we shape that shape us that we’re bringing stuff. So then you don’t get caught up in that whole system-individual dichotomy, which a lot of people seem to argue about, you know, vocally or not. That’s going in a lot of people’s heads, so I think it also helps defeat that a bit.

Sean Murray [00:09:11] I want to touch on the importance of having fun. Yeah, work. One of my mentors actually told me that when you’re when you. Working with people in a work environment, you have to think that like 90 percent of the people that you’re working with, if they could make the same salary doing something else, they would choose that something else. Right. So like they if you need you have a responsibility to make work fun because not everybody is there doing exactly what they want to do. Right.

John Cutler [00:09:37] Wow I didn’t think of that.

Sean Murray [00:09:39] Yeah. Like me personally, I would be. I would go back to coaching university level rugby. That would be that. But there’s just no money in it. Right. You know, my kids need to eat.

John Cutler [00:09:49] And are you involved in scrum at all?

Sean Murray [00:09:52] Well, I get this question a lot because scrum is very different in that environment than in the work environment.

Dan Sharp [00:09:58] His teams end up very bruised when he gets in a scrum.

Sean Murray [00:10:00] Yeah, we can walk. We can work on proper form later. But but why is it so important to make sure that we’re having fun at work?

John Cutler [00:10:06] Yeah, I mean, I think that well, first of all, some games are agonizing. They’re not even like fun in the traditional sense. They’re just you’re just engaged. You’re thinking about it. But yeah, I guess my thought was I mean there’s the sort of corporate engagement industry and I’m trying to decouple from that with this particular message where it’s things like people should be engaged. And you should run an engagement survey. And there’s this myth, this sort of empty thing of engagement or even autonomy, mastery and purpose, which you could say that also defines some good game design ideas. I would even go beyond fun just imagining that we there are things we can do to create more dynamicism in this environment and laughter. And most importantly, just have not people just ruminating on the the easy stuff that’s just the low hanging stuff. Yeah, they just get some people’s mind to do that. And I think, you know, a good example for folks would be if you if you ask them on a particularly hard day, you what happened that day and like, well, I was kind of doing this and it was so obvious that their day was super frenetic. OK, they were never really in the zone. They were never, really, you engaged just in the moment. And I think that that’s just just from a business sense that feels like a colossal waste. But then just also in the creativity you get from people. And that’s one of the things that guided the talk that I told that story of, you know, my people aren’t strategic and like your CEO makes second grade level slides that say that the strategy is to make money. It’s like the most non-strategy thing. Like, why in this environment are we talking to each other that we’re like fifth grade, second grade strategy when people leave work and they’re like. Oh, I’m going to start this crusade. I have my these alliances. I’m doing this. Well, we’re going to mine ore and then we’re gonna turn the ore into, you know, Trojan horse. And then we are going to do this. Like, they’re obviously decent at thinking. These are like smart people. And so thinking about how to create environments where people can be smart. Just they’re smart cells. They’re smart, curious cells seems like a like a good. It’s win, win, win, win, win for customers and for company for you and your community just seems like a good idea.

Dan Sharp [00:12:18] Yeah, it’s like an empowerment there. So I’m curious. You’ve been doing a lot of research, you know, going out to talk to organizations, you’re seeing their five pillars, seeing their triangle of strategic destiny. And then going in talking about how they actually are working on a daily level amongst the different levels. So kind of what have you been seeing? What are the big takeaways? Any aha moments?

John Cutler [00:12:41] I mean, the current climate is rough. For sure. People are scared. They’re not surfacing information. This is not a moment of continuous improvement out in the corporate world at the moment. It’s sort of big swings. It’s we don’t have time for that type of thinking, which is the reality at the moment in a lot of companies. So I’m definitely seeing that. But also, you know, you see the march of time and the analogy that I use is. You know, there’s these different waves. 2008 was agile and 2012 was scaled agile. Then 2014, 15, 16, maybe DevOps. And then there was product 1.0, where you’d have POs and PMs in the same company. And then and then then they jump back into platforms. And then they were realizing you can’t operate on a monolith. Like you can have any of this empowerment unless you start decoupling what you’re doing from an architectural standpoint. Then it tips into a little bit of design thinking. Then it goes into this. And then you’re in product 2.0. And you’re thinking. And so there is a kind of general march of time that’s just happening regardless. So you notice that as well, like it would be crazy. Well, I’ll talk to five large retailers and you could give and take a little bit. But frankly, also, the people are just traveling between these companies. It’s almost like a mono company. We always think about companies, but it is community, the community of tech. You can’t view a company in isolation as an ecosystem because it is the ecosystem of the people working in that community and especially in certain domains. It’s like people are going between all the major retailers in the United States or all the banks in the thing. You look at their resumes, it just moved around it. So it’s kind of like companies grafted onto large communities of people. So you see these trends. You know, they’re all somewhat in a similar space of a certain type of company. You certainly see companies lagging. You know there are companies operating like it’s 2002. That happens. But look, if you’re a bank and operating like its 2014 and all the other banks are operating like, it’s 2013, 14 and 15. Right there in the middle of the bell curve. Well, you don’t need to be a neo bank at that point because I mean, might get disrupted by a neo bank. But for the most part, you’re just just in your camp. You’re in your class, the class of 2015.

Sean Murray [00:14:41] You said something really relatable in the in your talk about not having like the pro level Miro license. So you’ve got like a six gig gig forge with like, you know, thousands of frames on it. Going to talking to these companies and now you’re working in this kind of like startup mode. What are some of the lessons that you’ve learned that you kind of tried to apply at your at this? Like, you know.

John Cutler [00:15:02] Oh, startups are like chaos; talk about pirate ships. Startups with pirate ships without the quartermaster, you know, to do it. It’s just a world apart. I mean, that’s the thing about context. I mean in a startup, it’s just do or die every day. You just have to it’s 10 o’clock. You got to write that doc. You better get back to the customer. You got do it and it is actually helpful, though, because you see that, you know, in larger companies. Are you learning faster than your ship or shifting faster than you learn? And in a large a lot of companies, I think product-minded people sometimes just don’t accept the reality of the situation. They’re like, oh, my company, they could be more product focused. We got to do this discovery. We got do this. We got a label every problem. And I’m like, no, not really. You’re 10 years behind the other banks in the thing. And there’s not a lot a rocket science in what you do. You could literally go and throw darts at other companies and copy what they do. You don’t need to reinvent the problem unless you’re a unique kind of bank, unless you do that. And they are learning. They have learned faster than they ship. Their problem is they’re just not shipping fast enough. The thing I’ve observed is this the inflection point is so hard to measure. So let’s say that you’re learning faster than you ship. And so you’ve been investing a lot and just being able to get the flow going. These companies stay in that flow mode a lot longer, not thinking about, are we learning? So they are. In other words, the inflection point from learning faster, than you ship or shipping faster than, you learn is way faster than you think. So that’s the that’s, the argument for product practices. So it would be a mistake to just be like. Well, we’re not going to do that because we just need to ship right now. It would just be that. Wow, we need to play catch up. So the strategy from a pure product standpoint is we got to catch up and that means that we gotta move fast, but we’re still doing discovery. We’re still the things that the customers, because if you don’t work that muscle, then you end up in this kind of trough of disillusionment that you see these large companies go through where they did the flow. They did the DevOps thing. They did a skilled agile thing. And then one day they realized it’s not enough. Oh, now we’ve got to spend the next three years kind of trying to figure out this new thing, instead of just kind of gradually. Easing in the practices as they were working.

Sean Murray [00:17:12] You brought up learning and that was actually one of the first conversations that we had when we walked into INDUSTRY on the second day. We talked with somebody about, you know, the quote that we got was like, she’s asking her team, like, what are you going to learn over the next eight months? So how do we get away from learning? How do we kind of like pull that? How do you pull that need back to our teams to say like, Hey, not only do we have to focus on what we have do, but what are we learning in the process?

John Cutler [00:17:37] I think a lot of this is just tempo. And so what I mean by that is that a lot, you see a lot of these companies that are just saying like, we are now doing continuous discovery. They just sort of forget the continuous part of it. They’re like, how we’re doing this thing. And we brought in these people and we’re and so I think, I think you just have to work it into the day to day rituals and the, and the analogy that I use is a lot of times people think this is just this one zero shift for a company. It really isn’t. All the product companies that people idolize who have these product leaders…on Lenny’s podcast. They go into meetings and spend 70% of the time about deliveries and dates and stuff too. That’s the reality. I know people, those companies, that’s what they do, but the reality is they also spend 30% talking about the outcomes and they talk about the next thing and they pressure test the ideas or you have a designer and engineer on a team saying this hasn’t passed the bar of evidence to actually work on it. That’s what the real world looks like in those companies. Not this like highly choreographed song and dance. To do these things. And so I think it is about the, like, what would we observe? The behaviors we would observe if a team was doing that. So obviously there would be time spent with customers. I worked at a company where we would like hands off of keyboards for one week designers, engineers and PMs leave in a van to go out and see customers. And that was normalized in that thing. So probably those engineers in that one week did more customer time than in a lot of companies do in a whole year. And that was the, that was just the behavior. That was the habit.

Dan Sharp [00:19:04] Yeah. So it’s a building up, like building that muscle and making habit, right? We were talking, you know, in previous episode about how, like with, you know change management, how it’s so easy to fall back on your existing patterns, existing knowledge, right. When things get stressful. Yeah. So I’m curious, you know, as for individual contributors, right, how can they kind of influence some of the more thoughtful processes, more thoughtful ways of working?

John Cutler [00:19:33] You can do a lot locally as a PM. Jeez. It depends on the company though. I mean, if they’re heavily into some standardized approach, you can’t. But imagine you could tons of stuff. The team can just get away with it. Yeah. Is like, as long as you’re just doing the thing and, and whatever, let’s just, they say, let’s just say story points or something like someone’s asked for story points, just make them up. Like don’t use them. You just, just fill in the form, play the game.

Dan Sharp [00:19:58] We call that “who’s line is it anyway” planning? Where the points don’t matter.

John Cutler [00:20:00] Yeah. And so, so I think that there’s that element of like, you can do a lot locally with your team to think about, you know, I think one problem with a lot of PMs is that they get just caught in this kind of Wrangler den parent mode. And that doesn’t work either. You can’t be like the den parent of this team. And that’s, first of all, it’s belittling that team, but it’s learned helplessness for everyone involved. Yeah. And, and, you know, Oh, we’ve got to protect these engineers. We’ve got to do that. So I think sometimes it’s about. Just working out that minimally. So I use this minimally viable consistency at different levels of the company, but you could think for your, your org, like what are, what are the rituals that really matter? How can you do that? So you can sort of be a mini game designer on your team. And I mentioned in the thing, the part is the co-design part, which is if it’s just you, like, ah, I have product manager have decided the new way you’re going to work. That’s not fun. No one wants to co-Design.

Dan Sharp [00:20:48] That’s how you walk the plank.

John Cutler [00:20:49] Yeah. That’s done in your pirate ship life. That’s. Yeah.

Sean Murray [00:20:53] The founder of this podcast says that, uh, leadership is the art of create the art of possibility and the, and that management is the art or predictability. So I think kind of you saying, take on that leadership role within your own team. Right. Predictable what?

Sean Murray [00:21:11] That’s the question. Stuff. No, I always do that. People have all say do ratio of this or predictability. This or this. I was predictable. What? What do you want? And they’re just like predictable. We just need to be predictable. Predictable what? Like predictably awesome or predictive mediocre or w you know, say I could say anything and do it. Does that mean that pounces the say do ratio to be able to do it? And that was the, another inspiration for this game thing is you have a lot of power as a PM to create the mini game locally and then, and how it works. And what I mean by that is, is that, you know, if you set up this thing, but that was my critique of things like scrum. It’s a, it’s a game, but a lot of the rules and the mechanics are just weird. Right. And it doesn’t work necessarily. Like the whole idea of, for example, a sprint goal was meant to be this catalyzing goal that would allow people to treat it as a little variable scope. This outcome-oriented thing, the slice, get this into production. The whole idea of the sprint is to close the loop. You should ship stuff. And if you can’t ship at the end of the two weeks, do less. I remember talking to Ron Jeffries and he said, if a two week sprint doesn’t work, you have to do a one week sprint. If a one-week sprint, you’d have to do a two day sprint. And if a day sprint doesn’t work, do a one day sprint and actually in a company, we started doing one day sprints. You walk in that one. This is a better game. You walk in that morning, you have a discussion and that’s it. Like we’re going to be shipping at the end of the day, so you better size this thing down. To be in production by the end of the day. And so that’s an example of like applying the same kind of thinking that you could on your team. If you think of it as a systems thinker, you could think, okay, this game’s not working.

Sean Murray [00:22:50] This has been, incredible. thank you so much.

John Cutler [00:22:53] Yeah, my pleasure.

Sean Murray [00:22:54] What’s the next thing that’s coming up for you? What’s next?

John Cutler [00:22:58] I am in startup mode at the moment. It’s long, long, long hours in addition to this. Yeah. Like last night, it was writing out a proposal for a customer. Yeah. It’s I’m just in survival mode at the moment and startup mode and still can write, ship it every week or one or two a week or one, two or three a week. And then that’s it for me. Just. Surviving. All right.

Sean Murray [00:23:24] That’s the first literally surviving. That is what’s next for me. Thank you for making time to be an industry in the middle of the survival mode. Last thing we always ask is like, what are you reading right now? What are you encouraging everybody to read right now.

Dan Sharp [00:23:38] It doesn’t have to be business.

John Cutler [00:23:39] I’m reading this book about I think the title is how to think like a pirate. Hence the thing or how to ends. I’m learning about pirates. That’s what he’s doing. Yeah. Because it’s it’s fun. And I’m I’m liking the pirate now. What did you find? So that’s what I’m into.

Dan Sharp [00:23:57] We’ll look for the Jolly Roger. Extra media.

John Cutler [00:23:59] Next year’s industry.

Dan Sharp [00:24:02] Yes. All right. Well, thank you so much. It’s been great.

Speaker 2 [00:24:10] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get. So please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the ranking so that we can help other listeners move, touch, and inspire the world just like you’re doing. Thanks, everyone. We’ll see you next episode.