The John Cutler Hypothesis: Great Product Leaders Foster an Environment Where the Best Decisions Can Happen

John Cutler is the Product Evangelist at Amplitude, a product analytics platform that helps product managers. His career spans music, entrepreneurship, Product Management, and UX Research at such companies as ZenDesk, AdKeeper, and more. In this episode of the Product Science Podcast, we talk about what patterns John sees working with product teams on their process.

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Questions We Explore in This Episode

The John Cutler Hypothesis: Great Product Leaders Foster an Environment Where the Best Decisions Can Happen What is product analytics and how can it help your product development team? How do you analyze value and behavior over the customer lifetime? What can get in the way of using analytics to drive great decisions? What does John mean when he talks about the broader environments that teams operate in?

How did John go from getting hired to do MBA students’ homework to a career in product management? What did John learn from working during the first dotcom boom and bust? What happened with John’s bartending video game, Last Call? What did he learn about product management from driving a rickshaw? How did he transition from there into product management?

How did John’s experience show him how many different versions of product management are out there? How did his background as a UX researcher influence his approach? Are there regional differences in product management approaches? How does John work around different perspectives and vocabulary that can influence design? Why is it so important to start fresh?

What is the danger of assuming someone knows how to do something based on their resume? Why is it so important to look at the context around someone instead of writing them off as a poor performer? What is the difference in perspective between the days when people worked their entire career in one company and now? How can we learn to take a broader view of things? What is the right way to think about leadership in times of change?

Why does Holly shy away from the phrase “MVP”? How is the struggle for appropriate vocabulary not so unusual when you look at history? What is behind the anxiety that gets in the way of a solid product management approach? Do companies that are kicking ass spend a lot of time on theory?

Quotes From This Episode

If you're locking down a roadmap a year in advance of specific features, no amount of data that you have is going to make a difference. You've already committed to doing that thing. - John Cutler Click To Tweet They've gotten the theoretical angle, but they're missing that muscle from going through this loop over and over again. When experienced people try to relay little bits of wisdom there's no way it’s going to sink in. - John Cutler Click To Tweet When you're on a team that's kicking butt, you spend less time talking about theoreticals and you talk about what's happening right now. What does the data say? What did that customer say? What did we learn this week? - John Cutler Click To Tweet For a lot of PMs as well, depending on the organization, they're also slipping into this role of creating an environment where the best decisions can happen, - John Cutler Click To Tweet


Holly Hester-Reilly: Hi, and welcome to the Product Science Podcast, where we’re helping startup founders and product leaders build high growth products, teams, and companies through real conversations with people who have tried it and aren’t afraid to share lessons learned from their failures along the way. I’m your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.
Holly: I’m so happy this week on the Product Science Podcast to talk with John Cutler. John is currently … I believe your title is product evangelist.
John Cutler: That’s the best we’ve come up with so far, but yeah.
Holly: Yeah, at Amplitude. And he’s been writing and talking and thinking and coaching on products for quite some time. So, super excited to have him. John, welcome.
John: Yeah, thank you so much. I’m excited and you’ve been kicking butt with these podcasts.
Holly: Thank you.
John: Like, no effort that I have has started so well formed. So, you knocked out that season. And so, I’m in awe.
Holly: Thanks. You know what’s really fun as a product management coach? When someone tells you you’re doing something really well, and you get to tell them, “That’s because I applied my product management skills.”
John: Score, you did it.
Holly: It’s the best. So, tell us, for anybody who doesn’t know a bit about you, why don’t we start with what you’re doing these days? And then we’ll go back to how you got there.
John: Sure. So, I currently work at a company called Amplitude. Amplitude makes products that help people build better products. So, the product is most known now for analytics and specifically product oriented analytics. So, if you think about tools that you use to look at data, there’s tons of tools. And they target different parts of the customer journey, they target different types of questions. They often specialize in getting different sources of data that you can look at. So, they all have different specializations.
John: But Amplitude is laser focused on behavioral analytics, things that can help product managers and product development teams experiment and figure out the formula for lifetime value. So, how can you get people to really get value out of your product or offer the value to them, you don’t want to get people to do anything. Hopefully they’re getting value out of the product. But not just do that to hit a quarter goal or to drop people in through the top of the funnel. There’s all tools, there’s analytics tools for that. If you want to know how many people are dropping through the top of the funnel to get to your landing page, there’s pretty good tools for that. Amplitude does some of that. But we’re really focused on those long evolving relationships that customers have with products, and then how to tweak things to improve lifetime value.
John: So, that’s Amplitude. My role is product evangelist. That’s the best we’ve come up right now. There’s different types of product evangelists. Some evangelize products all day. I think Amplitude sells itself and I don’t really need to talk about Amplitude. What I actually focus on are the broader environments that teams operate in and how that might impact their ability to make use of a product like Amplitude.
John: And so, what we notice when we’re out there talking to prospects in the broader product community is that a great example is if you’re locking down a roadmap a year in advance of specific features, no amount of data that you have is going to make a difference. You’ve already committed to doing that thing. You haven’t committed towards an outcome or you haven’t taken a deeper look at what you’re doing. So, you could have an amazing analytics solution, or what we call product intelligence solution, but you would be stuck because the structure within your company isn’t aligned around working in the way that we imagine people working with our product.
John: So, that’s what I focus on. Mostly we have a lot of passionate people about our products, so I don’t really need to evangelize the product. But especially as we move into the enterprise and especially as we get these bigger and bigger customers, it becomes increasingly important to try to pick away at some of the other blockers to be more impact driven.
Holly: Yeah, that’s awesome. It’s a very forward thinking approach for the business to invest in that.
John: Hopefully. These are all bets. Who knows, you know? There’s no silver bullet with these things. You’re always placing these bets. And as I get … I’m on a marketing team, and there’s so many parallels there with the types of bets that you make and having to understand things. And I tend to think too that if you take a couple steps back, customer success, marketing, sales, if the company is the product, then all of these different departments are also products or part of this experience. I think we overburden the word product a lot and sometimes beat people up with the word product. Like, you’ll see these companies and if you can call what you’re doing a product, then you’re CapEx, and people love you and you’re working on customer facing work. And if you can’t call what you’re doing a product, then you’re in the dark dungeons of the company.
John: But for lack of a better word, if the whole company is a product, then all of these departments are different parts of the experience and can influence the experience and lifetime value. So, I’m excited to work on a marketing team. It was a little disconcerting at first, but you know, I do my thing.
Holly: Yeah. Tell us more about how you got to doing that thing.
John: Man, it has been a crazy road. I will tell a couple little tidbits of stories of things that I’ve done. I was in New York for about 18 years, very distracted, dropped out of school twice. I had a side business doing the assignments for NYU MBA students. So, they were smart enough to hire people to do their homework. And then, also facilitate activities. So, I remember being in New Union Square or Saint Mark’s Place or something, and the team met me at the Starbucks there and I was facilitating this group of MBA students. And I was, I don’t know, 19 or something. And they were smart enough to pay someone to pay someone to come in and help them and do it.
John: So, I would do things like that. And then I got really into music, again, did a lot of touring and music. So, my 20s were a blur of getting very distracted by things. And I did have some fun gigs. I worked at ViaCom, Nickelodeon. I would produce their big upfront presentations, their annual ad upfronts. And that was fun. So, you got used to dealing with the CEO of the company and designers and people creating stuff and that was good. I worked in the PowerPoint sweatshops that they had in Manhattan at the time. Like, you would … You know, at Morgan Stanley or whatever, 24 hours a day there’s a room of 150 people doing PowerPoint and Excel and Word. And you were measured by how many keystrokes you used and the number of errors. And you could imagine some of these roadshow decks for investment banks have like two-point text on charts.
John: Or the other funny one is I remember one night where it was a rush job. And they have these slides that have like 600 logos on them, ecosystem type slides. And someone said, “Well, we could go and find them, or we could just send this to India.” And so, that night, I think we ran up like thousands of dollar bill or something. They were recreating logos, like 600 logos. The amount of money spent just for optics was at an all-time high. So, that was actually a real learning experience. You were like in the belly of the beast during the dot-com boom, the first dot-com boom, and the dot-com bust.
John: And they would always rename the companies after animals because they couldn’t expose the names of the company. But it would be something like Fish with a net capitalization of hundreds of millions of dollars will buy Barracuda. And any reasonable person who knew anything about the landscape of business would be like, “Oh yeah, they’re talking about Yahoo,” you know? You would know in two seconds.
John: So, actually, I spent years just playing music and trying my own little businesses and then reading massive roadshow documents at investment banks over time. So, that kind of teaches you some things too. Anyway, this is all in the mess of my 20s, music-
Holly: Wow, I’ve just got to say, that is one of … That is just random. That is like a drunkard’s walk through creativity and business and design and entrepreneurship.
John: There was all kinds of things. It was … We all go at our own pace for doing these things. I’ve found that I really wanted to create things and have … I had this bartending … I made a bartending CD-ROM game called Last Call. And Last Call was published by Schuster, but they didn’t think ahead of time to distribution. So, Kmart wouldn’t sell it because there was lewd dialogue, you know? Like, you’re in the bar and you have to serve these people. But at the end, you get to this Bacchanalia, you know, Bacchus is there. And there’s all this stuff. And it’s crazy things, like Tina Fey using a pseudonym to do non-union work was sitting there doing voiceovers for us. And Adam Felber from Wait, Wait, Don’t Tell Me. And just this fun community of people in New York making this CD-ROM game, and it was a complete flop because there was liquor and bad language in it. And so Walmart and Kmart wouldn’t carry it.
John: But I did get the rights to sell it online. And Simon Schuster’s like, “What is this person going to do with this website? Like, you’re going to sell stuff over the web?” And I thought, “Yeah, I’m going to get the rights to buy my own product at a real discount and then sell it.” So, I actually made a decent amount of money selling my own game direct to people all around the world. And I always say the joke that 15 years later this bar owner from Germany said … I’m not going to do accents because I’m terrible at it. But he’s basically saying, “I have a Win 95 machine in the back office that I have kept pristine with nothing downloaded on it so that I can run Last Call to teach bartenders.” And you hear these things.
John: So, anyways, so I got involved in these funny things. And this one real estate startup. And then of course, the market collapsed. And it was all sort of a mess, the touring, the music, and all those things. And so, then as I moved into my 30s, I kind of got my act together and did more consulting, did a number of product management things and ad tech and eCommerce and more consulting, UX research, product management and moved into there. I forgot one of the other jobs, I rode a bicycle taxi, those New York rickshaws.
Holly: Yes, yeah.
John: So, the funny thing about the rickshaws is that at that time … There’s a lesson in product here because we would always be downtown. And on a good night, you’d make $80. And then, Pierre comes in one day and says, “I’ve been in mid-town. And I’ve seen the light. If you go to mid-town, you can make $120 because of the theaters.” And everyone’s like, “Well, that’s really far. Are we going to go all the way to mid-town? What are you going to do?” And Pierre keeps coming back and making like $120. And it’s like, “This is $100. This is a lot.”
John: And then, another person comes in and says, “I’ve been doing what Pierre has been doing. But I have a minimum price of $40. I don’t take a ride for less than $40 in mid-town, and I’m making $200.” Then everyone’s adapting like, “Oh, okay, you’ve got to use minimum pricing. You’ve got to do these things.” And then before you know it, years later, a good night working in mid-town in Times Square, it’s $300 or $400 cash, which is pretty decent to ride your bike around all day.
John: And then you’d always get these funny things. Like, this one time these investment bankers, six guys jump on. And then they say, “You can’t take six people, can you?” It’s a bicycle, so you can move a bicycle.” And then I said, “Well, yes, I think I can do it. Will you each pay me $10 per block? That’s the bet.” And they all said, “Yeah, yeah, whatever.” So, that’s $60 a block. And then we went from Union Square all the way up to Grand Central, so that’s 14 to 42, you do the math, $60 per block. So, that was crazy.
Holly: Wow, yeah.
John: And they paid, of course. So, that was the funniest part of it. So anyway, these are stories about … To anyone listening who has had a messed up background that you feel embarrassed to tell the world about, I am just unleashing right now. Just let the freak flag fly. Everyone gets into product at their own time. You can drop out of school, you can do whatever, and you get into this at your own time and find your groove at your own time.
Holly: I can hear that sort of feeling about it in you. But I also think, I don’t know about you, but I know plenty of people who’ve let their freak flag fly in their 20s, and it didn’t involve any MBAs or making video games with Tina Fey. Like, how did you do that? That sounds like a really stellar version of that winding path.
John: Yeah, I mean, but I’m not talking about all the years I was completely bored too. I mean, there’s selection bias, right? There’s probably a whole year that I was like, “I’m going to make this album in my basement and go to the bank and stuff.” So, if I said that, if I was like, “Yeah, I spent two years going to the bank every night and trying to make an album in my basement,” you’d be like, “I have a friend, Jack, like that.” So, always select the best stories and then you’ll be in good shape.
Holly: Yeah, that’s a really good lesson. I like that lesson too. Yeah. So, somewhere along the way, you discovered, apparently, that you had a skill at understanding business and at doing creative things and whatnot. So, how many years were you working in product management before you joined Amplitude?
John: You know, that was kind of interesting because at the time, I remember working at a startup called RichFX that did eCommerce stuff. And at that point, no one was even the product manager, you know? A friend said, “Hey, we’ve got to get someone to come in and kind of unravel this or do this thing.” And it’s funny because that startup, I think, like Stephen Frieder now heads up all the sales at Adobe, all these people went on to do all these particular things. But at that startup at the time, we were just sort of figuring it out.
John: And so, I think that in a couple of these roles, it was friends or people you know say, “I think we’ve got that kind of complex thing that we need someone to think about.” And it wasn’t even really full formed at doing that. And then when I got involved in ad tech, I was involved in an ad tech company that burned really hot and then it wasn’t burning hot anymore. So, you can raise money for anything, especially if you’re really well connected and you’re passionate and you have a really, really strong vision.
John: So, I worked at an ad tech startup called AdKeeper. And the whole idea of AdKeeper was that you were going to put a little button on ads and that people actually love ads, so they were going to click on that K button and it would keep the ad in your keeper. And then, if you could keep your ad in your keeper, you could go back and interact with the ads later.
John: So, you’d find things like … And then, here’s the stroke of genius or madness or whatever. So, Scott Kurnit, I love Scott, he’s great. So, Scott says, “This is a network problem. We’re going to extend to the top advertisers in the world. They can use our technology for free for the first year.” And so, we had Ford, Kmart, like massive, massive, massive brands. And if you’ve done ad tech, you know that actually getting a button on a thing is a lot harder than you think it is. Like, that was the problem. This was super complex ecosystem to do it. But I admire Scott’s guts with all this.
John: But I started in an ad role there. And Charles who worked there went onto Jet and then Jet did Jet’s thing. So, all kinds of people who did these things, Barry Engel worked there. All kinds of New York people that I knew. But even then at that point, Sarah Doody who does the UX thing, she does UX classes, so we were all there. And again, it’s like, had we fully figured out what product is the way that I think about it right now, probably not. And even I remember when that didn’t work out and interviewing at Stack Overflow and different things, you’d do these interviews for product management roles. And it was just so varied at the time. So, what I would say is that it’s not like I … I mean, you were at MediaMath, right?
Holly: Yes.
John: Maybe around the same year.
Holly: Yeah, I was going to ask you what year that was.
John: Yeah, maybe you had a vision of what product management was there. But anyway, my point was that this all … A couple of these jobs touched on what I think about product management is today. But they were either white space filling or there was … It was more sort of communicate to the engineers focused, or it was any of these things.
Holly: Makes it hard to answer, right? Hard to answer all [crosstalk 00:18:29]-
John: Exactly.
Holly: yeah.
John: So, I’m going through those things. And that kind of brought me up. I worked at a company here in Santa Barbara called AppFolio. And that was when I was a UX researcher, much more sort of had figured its crap out. And that was, we had product roles and I started to get into it. So, it’s been a journey even from my own figuring out. Zendesk had its own version of what product was. And now at Amplitude, I talk to hundreds of teams. And even there, it kind of varies. I think there’s common threads between all of these things, but that’s been my … My path is not like five verifiable wins out of five successive companies.
John: I’m always, jealous, you know? These kids come out of Stanford or whatever, and they’ve got X Company on their resume, Y Company, Z Company, and they’re 26 years old. And they can basically be hired anywhere. There is a whole other path to get into this, which is you work at companies, not quite figured it out. No one’s figured it out. Then you all get older together and you’re all wiser and you all start hiring each other. And then you all figure it out. But those companies are messed up. And then you go to the next set of companies. And you all hire each other again. And you’re all learning. And I’ve been doing this for a while now, so I’m still kind of figuring it out.
Holly: Yeah. I love that. I was thinking, I can’t think of … I don’t think I’ve had anyone on the podcast that fits that other version of graduates from school, has all these top companies on their resume now. This could be a selection bias on my side of who I invite, but almost everybody has some form of winding path. One question in there that would help piece together my view of the world is what year did you move to Santa Barbara?
John: It’s about six or seven years ago.
Holly: Okay. So, it’s 2019 as we record this, so it was around-
John: Yeah, 2012. I mean, real estate collapsed 2008. Then there was that startup and that startup, and that job and that job. And it was before then, and it was those things. I don’t know. It’s been … Yeah, so I think AdKeeper maybe was around 2010 or something.
Holly: AdKeeper was after the crash?
John: Yeah. That was … Was it? I might be-
Holly: Because you were like, “Well, you could raise money for everything.” And I was going to be like, “Unless it’s 2008. In 2008, you couldn’t raise money for anything.”
John: It must have been beforehand then, now that I’m thinking about it. Yeah, anyway, that’s how bad my memory is of the 2000s.
Holly: Yeah, I totally get it. I totally get it.
John: I will not Google it. You know that feeling when now we’re so clued in that when you have a question, you look for a screen?
Holly: Yes.
John: And I just found myself being there like, it becomes your memory.
Holly: It does.
John: So, we’re outsourcing our memory to Google. And so, I found myself instantly like, “I’m going to go and check the computer now and find out when AdKeeper was,” but I’m not, now we’re chatting.
Holly: Yeah. There are podcast hosts who will do that live. I thought about it. And then I was like, “No, I’d get too distracted.” But I’m curious, I think one piece in there that I’m sure our listeners would also love to hear more about is … I don’t know what you feel comfortable talking about, but I’m curious about what flavor of product management you experienced at Zendesk.
Holly: And to give you a little more context as to why, when I first came across your writing, it was probably about three years ago around when I started my H2R Product Science. And one of the things that your writing helped me learn was how many … I mean, I’d already started to learn how many different versions of product management exist in the world. But your writing helped me learn that even more because you had enough of an audience that people would respond with questions and you would see how different articles resonated differently. And they weren’t necessarily the same questions I had or the same things that resonated for me in terms of whether it was a novel and exciting thing or how it applied to the companies I had been at. And it helped me sort of see, “Oh, there’s all these other practitioners of product management.”
John: And if you’ve been in New York or in the Bay area, you’ve worked at even two, three, or four companies, it’s not been until I’ve really started to interact, probably even at Amplitude with this many teams that it truly kind of settles in about how wide these roles are. And I always need to catch myself on Twitter or other things about … I become much more curious. I end a lot more statements with a question, you know? I’m really trying to think about what it means in that particular environment, what the context is, because I think what happens is, especially in cities or even groups of friends or groups of coworkers, it has this kind of effect that folds in on itself that you build in these visions of doing it.
John: And so, an example would be where I was surprised is I walked in to do a Facebook interview once. And at a certain point, they’re like, “Well, here’s a marker. Could you just start kind of drawing that out?” And I actually said to them, “My preference at this point would be to collaborate with the designer, because I’m confident about my thing.” And then, they looked at me like, “Huh, you know? I don’t get that. You don’t want to just go out and draw this thing?” And I’m like, “I could draw it, but these are just my ideas. How would I facilitate an environment that we could …”
John: And so, remember, I had been in an environment as a UX researcher where we co-designed everything. Like, you wouldn’t … Even UX wouldn’t come in with the done product. We would work on it together. And so, that was like a big mirror. I had never been in that environment. So, even then, that’s an example of how Facebook has its way, and then everyone who’s worked in Facebook goes into a couple of sort of companies. So, they all kind of take a little bit of that going there. And if you’re in another environment, great example in Germany, there’s a company called Zing. And a set of companies in Germany with a lot of really interesting product leaders. And I can tell that there’s a kind of German vibe that has sprung from those particular companies where there’s been a cross-pollination of people in those companies.
John: So, yes, absolutely this is not just … It’s hard to put the thing in the box. Specifically about Zendesk, I mean, how would I describe that culture? It was an output from how the company was founded. You had a little bit of Northern European … There’s two things in Copenhagen, or I think it started in Copenhagen or some place, I’m forgetting now. But one is, people are very, very direct with each other. And two, there’s a design influence, you know? There’s an idea of simplicity and design in doing those things.
John: So, it started up there and I think they briefly went to Boston and then they ended up in the Bay area. And so, drop that into a Bay area where for all the best of the world that’s going on theoretically in Silicon Valley, it can be highly political in other ways. You have people who’ve worked at the same set of companies are just doing the rounds at different places. I met someone the other day who’s like, “My strategy is to work one year at the company and get out because they’re all messed up. I’ve been doing this for eight years, I’m vested in eight companies. I don’t really need to work, but I just go where the technology’s cool and that’s what I’m going to do because the Bay area’s messed up and it’s a meat grinder and everyone is all into themself. Highly individualistic culture, not my game. I’m going to play it for all it’s worth.”
John: So, let that be the lesson for people that there’s more layers to this about product culture than Marty Cagan’s description of product management, although I really appreciate that description. There’s regional cultures, there’s country cultures, there’s network effects, ranging from how people have moved around jobs. And then there’s the cultures of companies, the culture of the engineering counterparts and those things. All those things mash together to make it really fascinating. I mean, that’s why I wake up every morning because it’s not as simple … If it was just as simple as, “I need to teach you these things,” that would get pretty boring pretty quickly for me.
Holly: Yeah, me too. I love hearing about all the different versions you’ve seen. And similarly, I love how you mentioned what you probably learned the most when you started at Amplitude and started talking to this huge array. And I think it was similar for me, you know? I had found niches that worked for me, but when I started my own consulting and training company and I started doing discovery and trying to talk to as many different people and find out about all the different ways it works, I just feel like my entire world view has shifted because of the vast range of versions of this that are out there. And now it’s at the point where I have to just be like, “Well, what does that word mean to you? What do you mean by that?”
John: Yeah, shared languages … I mean, a lot of the activities I’m doing, lately what I do is I start from a clean slate and let the team design and co-design, like share mental models that help them with shared understanding. So, I don’t put my names on things. I start the team thinking like, “Hey, I think we all agree here that having a one page snapshot of these things, these foods, these Xs would be helpful for the team, these bets. Let’s just call them bets, okay? Make whatever you want out of the bet. But let’s design what this … Like, what are our needs? And what needs would need to be met by looking at this one pager?”
John: Now, it would be very easy for me to go in there with a canvas and a one pager. I’ve seen a million canvases for one pagers. There’s so many of them that I just reinvent canvases of them just for fun, which a lot of people are doing. But I step back and I sort of say, “What are your needs? What needs to be met?” And the fascinating thing I find is that even less experienced people are able to get 95% of the way there. They intuit and they understand from a theoretical angle what their needs are, the information they need. And when you strip away the words, they’re actually pretty good at starting fresh.
John: So, they have a lot of baggage from the community often, or other things about how things should be. Now, what they’re missing are … They’ve gotten the theoretical angle, but they’re missing that muscle from having gone through this loop over and over and over and over again. And this is the problem when experienced people try to relay little bits of wisdom. There’s no way that that little bit of wisdom is going to sink in. It’s encapsulated 10 years of going through that loop over and over. And just saying some, “Well, you’ve got to learn faster,” no one knows what learn faster means.
John: Now, the crazy thing is, maybe in college they studied science or whatever and they absolutely know what learning faster means. They just haven’t applied it into this mess of things that we call product development. So, I think that, I mean, it’s a kind of round about way of talking about this, but shared language is super important. Coming up with your own vocabulary can sometimes be really, really important.
John: And then, also, I think not passing too much judgment on people about this idea of a linear maturity scale, it’s really not like that. Like, it’s more of a system of understanding that they’re practicing over time. And so, it’s very easy as a VP or a practitioner or someone who’s done this for a long time to make really snap judgements on where people are at. And when you peel away the layers, there’s a lot more interesting things. A lot of these enterprises that I talk to … Someone said it best the other day, they’re like, “Well, this company brought in six digital native executives and nothing has happened.”
John: I thought, “Wow, okay. What do you mean by digital native executive? What does that mean?” “Well, they worked at this company, you know? They were VP at this company in that thing.” I said, “Okay, they’ve got that. Have they ever pressed deploy? Have they ever been there in this standup trying to understand all these quirky people?” We go to their LinkedIn profile. No, it was McKinsey, it was this, it was this and this. And before they knew it, they were VP and they were doing this thing.
John: Okay, so they’ve worked at those companies, but they don’t have the muscle. I need to coach you to coach them because you can’t assume that they’ve got this all figured out because of their resume or because they’re a VP. And similarly, you can’t … Don’t assume that you know it all. They know how to navigate this organization way, way, way better than you do. So, there’s skills that you just don’t assume that because they haven’t pressed deploy that they don’t know anything. They know tons of things.
John: So, I have these conversations a lot, which is just about kind of stepping out of our biases, I guess, to try to figure it out. This is … It’s a fascinating topic.
Holly: I think it’s also stepping out of our angle on the world.
John: Yep.
Holly: You know? It’s the biases, I mean it is that, but the biases that come from the experiences that anyone individual of us have had and what we think is generalizable. Like, most of us, we overgeneralize, right? It’s a human nature. it’s like a proven thing that we do that, you know?
John: Yeah.
Holly: Our brains like to do that, it makes the world easier to process. But we forget and think that everyone else’s experience is probably somewhat like ours. And you know.
John: Huge issue with this when someone’s like, “We just need to execute,” or, “It’s just a hiring problem.” I mean, I’m definitely biased. You can see in my writing. If someone comes and says, “Person X is just a poor performer,” almost as an intrinsic response to that, I will look at the broader system around that and I’ll be like, “I’m almost positive that this is not 80% because this person is having trouble doing X.”
John: Now, I’m biased, so sometimes it is the person. Like, sometimes the person hasn’t been trained up or it’s another person, you know? There’s many reasons to it, but I think I’ve been doing this long enough that my gut response is always, “Let’s step back, let’s map this system out. And let’s understand what’s going on,” because it’s so easy … I guess that’s our fundamental attribution bias, right? Like, your problems are system problems. And all the people making your life miserable, it’s them.
Holly: Yeah. You just summed up all the things that make me uncomfortable with the world today. I know so many people that assume that everyone owns their own problems, you know? And I’m on the other end of the spectrum. Somehow, I think I ended up with an unusually diverse set of exposure to different people in my young adulthood. And I don’t want to say childhood, but youth, you know? Like, during my youth. And so, I just got to a point where at this point, I walk around and I see people and I think, “What system led them to that place?” Not like, “What did they do?” And then I’m just like, “Oh my god, our systems are so, so bad.”
John: Well, I think someone reached out to me the other day and they’re like … They were talking about some enterprise and they said, “A 10 minute conversation will make your head explode,” you know? Like, there’s so much low hanging fruit, apparent low hanging fruit in these large companies. But then, I realized my dad worked for 30 plus years at the same organization or more. He came to the United States, and a lot of people don’t like the International Monetary Fund, but he worked at the International Monetary Fund. And he worked there from when he was probably 27 to when he was 67, 65.
John: And so, you talk to my dad and he’ll be like, “Yeah, that was a bad decade. Things weren’t good that decade.” Not like, “Last quarter sucked,” or whatever. And in some ways the IMF is bureaucracy, like that’s exactly what it is. There’s no better … for positive or negative, it’s the world’s … It’s as bureaucratic as you can get. Although, they’ve gotten a lot better at some things, actually. And so, that was really helpful looking at that, you know?
John: We become extremely, maybe for better, as far as I know, we become extremely impatient in assuming that there’s this kind of, “Oh, it’s just all messed up. It’s never going to get worked out. This thing is so backwards.” But I think I was relating that to these enterprises, where you talk to John Smart or these folks who’ve done these large scale transformations and he’s like, “Yeah, 24 months, 12-24 months things start to really improve. And it is possible. You need to get by and you do those things.”
John: So, then the next person, the next CEO of the 17-person startup that’s like, “I can’t figure this out,” you’re like, “It’s been a quarter.” You’re like, “You’re 17 people and it’s taken you a quarter or two and you can’t get your head out of whatever.” And then here’s Barclays and it’s been 12-18 months where these people who really know how to … Just much healthier approaches to change and have shifted and improved the lives of thousands of people, people working there, their customers and stuff.
John: So, I think it’s all very relative as we look into these companies and these systems. And it’s important to step back from your own personal experiences with the last company to think about change especially.
Holly: Yeah. And I think that change management, and I mean, I kind of don’t like that term because I don’t really feel like anyone should be thinking they’re the one managing the change. But leadership during times of change, coaching change, things like that, I think is an under-discussed area of product management. Really, we’re all involved in that. And if we work at a company that is doing any level of success, even if it starts as a company that’s full of people who are already following modern best practices for product management, it’s not going to stay that way forever because if it grows, it’s going to start bringing in people who haven’t been in that world, and those people are going to need help with that change.
John: Yep. And I see this a lot too in these product transformations within companies that the leadership and advocacy and evangelism that wedges product into that situation and gets going is not necessarily the same leadership and approach that is going to work once product thinking has started to spread across the environment.
John: So, I’m encountering a lot of environments now where engineering and design are actually expressing a lot of angst about the style of product. But then you ask them, “Well, what was going on eight years ago?” “There was nothing.” “Well, then what was happening five years ago?” “We finally started to get in this, VP a product, and you got these things going, and they started the alignment going, they started all that.” “And how did you feel about it then?” “It was great then.” Now, what’s the problem now? And what actually has happened is they’ve changed. The other people have stayed the same. They’ve become much more eager about impact. They’ve become much more … They don’t like the mini-CEOs.
John: The mini-CEO might have been actually the perfect model for when that was the only type of person that could get anything done in that organization initially when there’s a lot of tension. And now, they’re sitting there and saying, “Who is this person? Who’s this grandstander? Why are they taking all the credit for things? We’ve got to have different types of … We don’t even need a product manger on our team right now because we’re essentially doing it.” So, that’s the kind of evolution that I see that there’s these, it was all good in the moment. But someone said it the other day, “All traction involves detraction.”
John: So, just the very nature of something working often sets up a new environment where what worked before might not work in this new environment. So, I don’t know. I find that really interesting.
Holly: Yeah, I find that really interesting too. I think, I was going to ask you to tell me your definition of mini-CEO. But I think your followup description of how they felt about that person did tell us.
John: I usually describe it as relative to the people who are using that particular word because, yeah, I started a long thread about it. I’ve learned now to just ask the question. And then I can just sit back and then learn from people what they’re doing. But this mini-CEO thing is a really interesting example where some people use it in a really positive light, have really positive experiences with a CEO, create space for what’s going to go on and puts a goal on the horizon and makes it possible for the team to work that way. And then people who have a bad connotation, they’re thinking that this person has aspirations to run it all, you know? They’re power hungry or they’re trying to move up the hierarchy or doing that. So, it’s all a very relative statement.
John: I’m big into words. And usually if a word does not move you forward after a while, it’s not that I hate it or like it, I just don’t use it because it’s not usable.
Holly: Yeah. No, I’ve done that too.
John: I don’t get a lot out of using those words because it’s not helpful.
Holly: Yeah, I think my version of that, that would probably be interesting to some people is that I very much shy away from using the phrase MVP anymore.
John: That’s a great example, yeah.
Holly: Yeah, because it’s the same kind of thing where it’s just like, I have just encountered so much completely opposing sort of feelings and views and understandings around it that it was just like, “This is … We are spending so much time trying to come to a shared understanding of this word. Let’s just pick a new word and make our own definition and drop the baggage.”
John: It’s so funny because I guarantee that probably like 1880s or I don’t know, maybe there was a famine in France, but whenever the Belle Époque was because I took a class called La Belle Époque, so I know it existed, I just forget when it was. So, La Belle Époque, there’s all these artists and stuff running around France. I guarantee at that point, there was a word that described a really cool coffee house where art was happening, like [foreign language 00:41:51], like there’s some word like that, but about La Belle Époque that described this kind of intangible spark. And then probably everyone was really excited to use it. And I guarantee eight years into the La Belle Époque, people were saying, “Don’t use that word. The coffee houses aren’t like that anymore. It’s been co-opted now by the bourgeoisie, you know? Like, we can’t use it anymore. We’ve got to have a new word that describes the new way that our coffee houses are happening.
John: And so, I think it’s just … You know, I wrote this post called The Way of Ways, and everything is just like this. And once you see it, and this goes back though to … There’s so much talking, how are you doing … Like, what are you doing? What are you doing week in, week out. And what I’ve noticed at the end of the day is a lot of these … This is where technical practices, and I have so much admiration for the engineering leaders who kind of create the momentum here. Half the anxiety with product managers and all these things is that the ability to have a resilient technology that can accommodate some of these changes in learning and not shipping every day or every hour, but just at the right cadence to learn that you need to learn without overwhelming that team.
John: So, what you see is this wicked cycle, like when you don’t have love on that side to create a resilient architecture and resilient things, you find all these silver bullets which then make it even harder for them to do what they want, which then causes more silver bullets, which means you play more Tetris. And then before you know it, no amount of reading Marty Cagan posts or talking about MVPs or doing whatever will work. Yet, we’re all sitting around with our thumbs under our knees because we’ve created the mess that now is causing nothing to be able to happen. So, product is often unconsciously complicit in the degradation or entropy of their whole system that they have at their companies.
John: And then there’s this finger pointing game that goes on. But the reason I’m bringing that up is that there’s a lot of talk stemming from just impatience and anxiety about our jobs. But when you’re on a team that’s just going to work and kicking butt, you spend a lot less time talking about theoreticals and you talk about what’s happening right now. What does the information say? What does the data say? What did that customer say? What did we learn this week? That’s why we don’t see as many blog posts from the companies that are kicking ass.
Holly: Yes, I love how you … I love so many of the things you just said, but the end statement there went exactly to a conversation I was having with my team earlier today about the way that knowledge gets spread on the internet and how a post having 5,000 likes doesn’t mean it’s actually a deep and useful post. And sometimes the deep and useful post has 10 likes. And that if you only learn product management through medium, you might be in trouble. It depends on who you follow. And I’m like-
John: Yeah, and that’s the thing. And these companies that are doing well, I’d say that there’s just fewer chronic issues, all the same acute challenges, all the same difficult conversations. And there’s just … I spoke to Ryan Singer yesterday for the podcast that I’m doing. But he was just describing this kind of, it’s hard work, but it’s not work that’s throwing off a lot of noise, you know? And I think that that’s the difference. Like, you need that cycle built up where you’re working hard, but not blowing things up all the time. And that’s how you kind of know that things … But back to these things about these posts and how you’re working, that’s the muscle that you build in these, that you do over and over again.
John: And my recommendation to people is talk to people who are doing that. And they might not have time to talk about it. They don’t have the luxury of a job like mine where I get to talk about it. They don’t have time to go to conferences necessarily, but you have to reach out to those people and just take their organization in context and say, “Well, can you just talk me through the last four weeks? Don’t tell me about your theory of product management because that’s kind of easy. I mean, I’m excited about that. We can talk about that later with dessert or after we have shots or something. But for right now, just talk me through your last four weeks. What does the day in, day out look like?” And that can be helpful.
Holly: Yeah. And that in some ways is coming back to how our conversation started where there’s the mess of all the things that happened in your 20s, but when you shared the gold nugget stories, that’s what people enjoy and learn from. I think that people learn … I mean, I think I know, one of my favorite books and podcast guests that I had is Shane Snow’s Dream Teams. And he talks a lot about the power of story. And it reminds me, I think tying back to what you were saying, to me, product management … In many ways, I think there’s two overarching buckets of skill in it. One is knowing, learning, figuring out, etc., how to make the best decision for the product. Like, what is the best decision and how do we make it? And the other is all of the work that’s involved in actually getting the company to make that decision. So, crossing that gap between, “This is the decision we should make,” and, “Well, we made that decision.”
John: Yeah. And I think too, for a lot of PMs as well, depending on the organization, they’re also slipping into this role of creating an environment where the best decisions can happen, you know? And I think that that’s … So, there may be even three angles to that. Like, the decisions that you … Like, the theoretically best decision, then the question of how do we create an environment where the theoretically best decision can happen? And then there’s the … Which in a way is your second thing. It’s kind of like when you … Like, the organization making that decision or coming to those things. Sometimes it’s not a … You don’t have all the information, right? Like, you need to partner with other people to do that.
John: But yeah, I think bringing it back, I think that’s the one thing with all these quirky experiences that if you’re sitting in a van with six smelly dudes and driving across the country so many times playing Xbox or something, you value the connections between people and how to be really … how to bring people along for the ride. And then of course, there were fist fights and stuff. So, you see how bad it can be, and then you see how good it can be. And then you … I don’t know. I’m not trying to … That’s a stretch connection, but you just reminded me as we talked about at the end of the day it’s about relationships, very close relationships with people. And that’s how I got to that from your statement that it’s not necessarily your decision in a vacuum.
Holly: Yeah, no, I mean, I totally agree. And I think to me, that’s an assumption I made in my head as you were telling the story about your 20s was that you must be good at relationships because I don’t know-
John: Relationships until I get … What I learned about that is that it’s relationships until … We can end with this because this is what I would say at the end is that one thing I’ve definitely learned in the last year or two is that we’re all wired for different things. And so, one thing I noticed is that when I’m able to detach, if you have skin in the game, if you have a horse in the race and you’re asked to facilitate at the same time and help this environment going, certain people can do that well, certain people not so well.
John: And so, what I realized is that I had strengths and weaknesses. But one weakness for me was I very much believe in this idea of an environment and helping other people do those things to the extent that I’m super passionate about it. That’s really what’s important to me. But often for product you can get stuck between what are your needs? What do you want to see happen? And then your desire to facilitate an environment and help other people do it.
John: And so, one of the interesting twists for me in this particular role is I get to focus full-time on just helping other people do it without having skin in the game. And you said, “Oh, you must be good with people.” And what I noticed is that I’m actually great with people when I’m in a full on help mode. But when I’m kind of internal in the belly of the beast in the organization and I’m just like, “Everyone, can’t you see it? Can’t you see what’s going on?” You know? So, it must be like the therapist who has the dysfunctional family, but they can go out and help other people, right?
Holly: Yes.
John: So, it’s struggling with that thing. So, yeah, I’d leave folks with that, you’ve got to find your groove with it. And then, also as a PM, you have to be very deliberate about when you’ve got a horse in the race and you believe in things and when you want to try to act as a facilitator, because people see through that in two seconds. Like, if you’re juggling the hats you’re wearing inexpertly, people will immediately zero in on one, you won’t be as effective.
John: So, I see a lot of product managers for some reason being like a scrum master and running the retrospectives and stuff, which I’m like, “Why are you doing that?” Find someone else so you can be a participant. You’re a team member. Like, go to therapy together. Get someone else to facilitate that meeting for you. How can you facilitate it while also having skin in the game and also your own needs? What environment you can create where you can express your own needs. So, I’d leave folks thinking about that, about what are your needs? As well as what are your desires for the environment that you’re in and helping other people too?
Holly: Yeah. And I imagine it goes without saying, but you’re probably in the best situation if you can have those all be aligned so that your needs and the environment’s needs are met the same way.
John: Totally, yeah. I think that maybe one part I was getting at too is that one of the toughest things to understand is if your need is for a healthy collective environment where people are all bought in. So, often people associate that the product manager has their idea that their need is to have their idea met. So, the problem that I used to have is I would be advocating passionately for continuous improvement, but then people would be like, “Is that for you? What relationship do you have to that idea?”
John: And so, I know this is kind of meta to think about, but if in your … I always tell to product managers, if you have a choice between having a horse in the race and everyone in your organization being like, “That’s the person who wants us to do OKRs.” Or the people think, “Oh, John’s that person who’s really passionate about us coming up with our own experiments about ways of working,” and then working on that stuff. I actually tell people, if you’re going to commit to have a horse in the race, you’ve got to be ready for that challenge. But consider also that you’re just one person in this. And if you’re passionate about a healthier organization, be passionate for that, because once you get pigeon holed for being the MVP person or the OKR person or the whatever person, it makes it a lot harder for you to enact change.
John: So, I know that’s kind of meta, meta, second things, you know? You have your needs, but your needs are for a healthy environment. Be really deliberate about what you advocate for because you’ve only got so many bullets. I’m not into bullets thing because of all the shooting stuff. You only have so many spells to cast.
Holly: I would [inaudible] too. Yeah. So, you only have so many spells to cast and you’ve got to be careful. So, we will end it with that. How can people find you if they’d like to learn more or follow you?
John: Twitter’s good, you know? I have an 18-month-old who doesn’t sleep. And so, Twitter is a reasonable method, way to get in touch with me. You can email me. I guess connect in on LinkedIn would be good. I’d be happy for people to … My email is So, if you have questions, you can email me. When I’m at my desk, which means during the day, I think in terms of my job, you can email me there. Twitter is a good way to just sort of shoot the shit and figure things out and DM me on Twitter.
Holly: Yeah, awesome. And it’s @Cuttlefish?
John: Yeah, I’m a little hard to … Yeah. Yeah, I would mention that, @JohnCuttlefish. And I recently released … I took all the things off of Medium, put them on my own blog too called That’s my blog. And it’s bare bones. You’ll see it’s like 400 posts in one big list, 430 posts in one big list. So, you could read that. I am kind of hitting that roadblock where I’m finding myself not being able to get back to people because I’m kind of overwhelmed, maybe because of all the writing or the Twitter stuff. So, I’m trying to be more deliberate. Maybe in the future, I might create like a Slack community. I’m just trying to think about ways to communicate with people and not let them down. So, I’d say Twitter is a good way, but anyway. So, this is a challenge I’m having.
Holly: That’s okay. Well, this is where they can go if they haven’t already been following you.
John: Yep.
Holly: And hear more about your thoughts. Awesome. Thank you so much, John. I really appreciate it. I’m sure our listeners will as well. And-
John: Yeah, it was a little bit of a vision quest, but we’ll get there. I had the coffee, kid was up all last night. So yeah, we’re going to … Yeah.
Holly: Man, okay, awesome.
John: Power to all the weirdos and let your freak flag fly and you’ll be good. All right, talk to you soon.
Holly: Yes. All right, have a good one. Bye.
John: Bye.
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