What differentiates the highest-performing product teams | John Cutler (The Beautiful Mess)

1. 0:00 – 5:50

   What is a product evangelist? John’s unique role at Amplitude

   1. JCJohn Cutler0:00

      Let's say you're a founder and you're trying to decide, "Should I invest more on processes or should I invest more on people?" The first thing is introspection. What do you believe in, really? What do you believe in and what do the people around you believe in? And how can you be a coherent leader? And you know what? You can't... You can nudge yourself a little bit away from your happy place, but you're not gonna go super far. You're not gonna go from, like, a process-driven, meritocratic XYZ person all the way to like a, "I'm going to start a collectivist company where everything is sort of a consensus decision to do" that. You're not gonna do that. But, like, I think it starts with self-awareness and then that's like, that's how people form their authentic leadership vibe, and then they flex a little bit and then they embrace other perspectives.

   2. LRLenny Rachitsky0:47

      (Instrumental music) Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. I interview world-class product leaders and growth experts to learn from their hard-won experiences building and scaling today's most successful companies. Today my guest is Jon Cutler. Jon is one of the most prolific, beloved and longtime writers and sharers of product wisdom online. And as you'll hear at the start of this episode, thanks to his really unique role at Amplitude, he's worked with a large percentage of product teams and product managers around the world. I've learned a lot from Jon's writings over the years and share his stuff often, and so it was a real honor to chat in-depth with Jon. I anticipated this would happen, and it happened. This ended up being the longest episode I've done yet and honestly we could have kept going for a lot longer. We chat about what differentiates the highest performing product teams from less well-performing product teams, what it takes to create real change within a company, why you should be skeptical of frameworks and tools that you read about online, why all underperforming teams fail in similar ways but high performing teams succeed in many different ways, and so much more. I am confident you will love this episode and I cannot wait for you to hear it. With that I bring you Jon Cutler after a short word from our wonderful sponsors. This episode is brought to you by Merge. Every product manager knows the pain of slowing product velocity when developers struggle to build and maintain integrations with other platforms. Merge's unified API can remove this blocker from your roadmap. With one API, your team can add over 150 HR, ATS, accounting, ticketing and CRM integrations right into your product. You can get your first integration into production in a matter of days and save countless weeks building custom integrations, letting you get back to building your core product. Merge's integrations speed up the product development process for companies like Ramp, Drata, and many other fast-growing and established companies, allowing them to test their features at scale without having to worry about a never-ending integrations roadmap. Save your engineers countless hours and expedite your sales cycle by making integration offerings your competitive advantage with Merge. Visit merge.dev/lenny to get started and integrate up to five customers for free. This episode is brought to you by Eppo. Eppo is a next generation A/B testing platform built by Airbnb alums for modern growth teams. Companies like Netlify, Contentful and Cameo rely on Eppo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth team stack. This leads to wasted time building internal tools or trying to run your experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved about our experimentation platform was being able to easily slice results by device, by country and by user stage. Eppo does all that and more, delivering results quickly, avoiding annoying prolonged analytic cycles, and helping you easily get to the root cause of any issue you discover. Eppo lets you go beyond basic click-through metrics and instead use your North Star metrics like activation, retention, subscriptions and payments. And Eppo supports tests on the front end, the back end, email marketing and even machine learning clients. Check out Eppo at GetEppo.com, GetE-P-P-O.com, and 10X your experiment velocity. Jon Cutler, welcome to the podcast.

   3. JCJohn Cutler4:21

      Yeah. Thanks for having me, Lenny.

   4. LRLenny Rachitsky4:23

      I kind of know you as Jon Cutler. I feel weird to call you just Jon.

   5. JCJohn Cutler4:27

      (laughs) .

   6. LRLenny Rachitsky4:27

      Do you find that to be true? And also do people call you Jon Cuttlefish because of your Twitter handle?

   7. JCJohn Cutler4:32

      Yeah, Jon Cuttlefish. There is this... I learned yesterday there's a DJ, a famous DJ called John Cutler without the H. So-

   8. LRLenny Rachitsky4:39

      Hmm.

   9. JCJohn Cutler4:39

      ... I don't know if people are into house music, uh, to do that. Yeah, I think usually it just, like most Johns, it, like, forms into, like, Cutler or JC or something like that, so. But just Jon is good, yeah, for now, or Cuttlefish. You could just call me Cuttlefish. That'd be fine.

   10. LRLenny Rachitsky4:51

       You said that you actually... We were talking before this. You said you do some music. So, um, is that DJ actually you?

   11. JCJohn Cutler4:57

       No, (laughs) but that would be really funny. In fact, the person yesterday who reached out over Twitter said, like, "Dude, I don't know what you're doing now in your career, but I really like, like, your earlier work." But that would have been pretty cool to be John Cutler the DJ, though, because I wrote songs and, you know, played, you know, rock music and stuff, not- not like a house DJ, so.

   12. LRLenny Rachitsky5:15

       Okay, this could be the next phase of your career, which we'll talk a bit about. But let me just say that I am so incredibly excited for this conversation. I've been hoping to do this for a long time and now that you're between gigs, we finally found an opportunity to do this. And I just have a feeling this is going to be one of the longest episodes we've done because there's so much I want to ask you and there's so much interesting stuff that you've had access to and that- I think that you can share. So, uh, I hope you're ready for potentially a marathon of an episode.

   13. JCJohn Cutler5:40

       Sure. Yeah, I'm ready. This is exciting.

   14. LRLenny Rachitsky5:42

       (laughs)

   15. JCJohn Cutler5:42

       Hey, I'm on vacation now between jobs, so, like, this is, this is the highlight of my day. We could go all day if you want.

   16. LRLenny Rachitsky5:47

       All right. E- eight hours, let's do it.

   17. JCJohn Cutler5:49

       (laughs)

2. 5:50 – 17:28

   John’s reflections and feelings on leaving Amplitude

   1. JCJohn Cutler5:50

      .

   2. LRLenny Rachitsky5:50

      So I was thinking that we start with a little bit about this unique role that you had at Amplitude, which you just left after about four years, and what's most interesting about it is it gave you access to an incredible number of product teams and product managers, unlike anything else I've seen or any other role I've seen before.Could you just talk a little bit about this role that you had at Amplitude, and what it was like to work with so many product teams and so many product managers?

   3. JCJohn Cutler6:16

      Yeah, absolutely. So first off, you know, I, I remember almost specifically the day that Sanya from Amplitude reached out and was sort of floated this idea of this role to me. And I'm so grateful for Sanya and Justin, Matt Alhazerrr, Spencer, you know, the whole team. Because it was really, it was really kind of a weird role from the beginning. You know, they were starting to get more and more customers who were not traditional startups or kind of growth, you know, stage startups showing up, and they needed to figure out how to convey expertise and convey things to the broader product public in a way that would land with those companies, right? And so, you know, as I kind of, I guess, you know, kudos to them (laughs) for thinking this weird idea could work. So I'm really, really grateful for that. But yeah, my official title was Product Evangelist. I don't think that I super fit that role, but that was the, the title that we had. And basically, my job was to wake up every morning and do things that would overlap Amplitude the product, but then help up-level our customers, sort of up-level the broader product community. I e- I call them, like, current customers and future customers. That's how I woke up every day, that like I'm either talking to a current customer or I'm talking to a future customer, and th- you know, the, this product transformation's happening all around the world, just means it's a matter of time. Like eventually they'll become Amplitude customers, so I should just try to make them awesome and try to help them with different expertise. But my day-to-day was spent a lot advocating for different ways of working, doing coaching, doing workshops. Uh, I wrote the North Star Playbook, uh, in partnership with Jason, who, like, was a co-writer with that. We did a lot of one-to-one coaching sessions. I, I had these things called product therapy sessions when I would just wake up in the morning and just kinda soak in whatever problem (laughs) people were having for the day. And I, I did meet, you know, with hundreds and hundreds of people and, and did workshops for thousands and thousands of people and talks for more than that, you know, tens of thousands really in terms of the talks. So it was just a, yeah, crazy experience doing that. So it, the, the technical details is I pre- predominantly reported into marketing and product marketing, and then I did a stint actually where I was on our product team as we were sort of getting our education efforts, uh, going. Ultimately we moved that over to customer success and I went back to marketing. So though, that's the, you know, the, the technical side of it, I reported into marketing. But I do remember, you know, the day I arrived and probably a w- couple weeks later we had our all-hands, you know, annual kickoff, and there was a big presentation about our goal being the trusted expert. And that still resonates with me the whole time I was there, that like an evangelist is there to help up-level the world with trusted expertise. And in a product like analytics product, there's the product analytics, but then there's whole other ways of working that overlap that. So yeah, generally that was my role, is kind of a, is a crazy role for sure.

   4. LRLenny Rachitsky9:16

      That is wild. You're basically a, like a free product coach for product teams. You just come in and help them up-level the way they build product. And then Amplitude becomes like, you know, you'll need to figure out how to work with data, Amplitude can help you be more data informed. I imagine that's kind of the general idea.

   5. JCJohn Cutler9:30

      Yeah. It's funny, I joke with our professional services team. I mean, so if you're a SaaS company, I think sometimes you have a professional services team. At Amplitude especially, the way that we saw that is, like, companies put money in and that sort of creates skin in the game. Th- they're, they're really paying you less for the professional services and more for the accountability and the access to the expertise. So I would joke with Jenna, uh, from that team that like maybe we should have monetized all these workshops, you know-

   6. LRLenny Rachitsky9:57

      Hmm.

   7. JCJohn Cutler9:57

      ... like I know Gib and other people, you know, they're charging like a good chunk for North Star workshops, and here we were just kind of doing them for free. So ultimately maybe there was another strategy there, but that we did those generally for free. And sometimes I kind of stuck my foot in it, you know, in the middle of the pandemic at one point we're like, "What are we gonna do? We can't travel for workshops." And I would put in my newsletter, "Hey, anyone want a workshop?" And then suddenly, you know, our sales team we had to grapple with like, "What are we gonna do with these 120 leads?" Like how are we gonna work with them? (laughs) So like, i- it caused like, it was funny having to deal with it. But yeah, in general this is a unique role. I would definitely consider SaaS companies think about a role like this, but it's really nuanced. We can share some links later as I reflected on what we did right and wrong. But ultimately I think you shouldn't rely on individual people. You should think of evangelists as almost like concentric circles of your community and some people who just happen to have more expertise. Look, our internal team's amazing, like Ibrahim and Justin and Abby and when Sanya was at the company and just, like, everyone's an advocate. Everyone's a potential evangelist. It's just that there's only so many hours in the day. So you could think of your community as just these concentric circles of evangelists and advocates. It's just like how you design it, right, (laughs) that does it. So yeah, recommended, it's a little tricky, but yeah, it's a, was a cool move to do.

   8. LRLenny Rachitsky11:19

      That sounds like a future post, how to do this in a different way.

   9. JCJohn Cutler11:21

      Yeah. (laughs)

   10. LRLenny Rachitsky11:21

       Where they don't have a Jon Cutler in place. Uh, you said you worked with hundreds of teams. Maybe just give us some numbers roughly like how many companies have you worked with, how many product managers do you think you've spoken to in this career?

   11. JCJohn Cutler11:32

       Oh, geez.

   12. LRLenny Rachitsky11:33

       This phase of your career.

   13. JCJohn Cutler11:34

       So I think I did it recent... there's might have been over the four years, maybe 800 one-on-ones-

   14. LRLenny Rachitsky11:42

       Oh my god.

   15. JCJohn Cutler11:42

       ... individual leader one-on-ones. I'm thinking it was at the peak it was in one year was 150 workshops and then overlapped in the next year between 200. So but mo- mo- mostly the average maybe let's say 3 or 400 workshops, 100 a year. It's heavy. Like and then, and then there was these just general, like, conference talks and other things that we're doing. Um, I, I tried to total, I exported all my Google Calendar invites and tried to categorize (laughs) all of 'em at some point. But, um, but, but really also you have to think about it is that what we did with the North Star Playbook...It was truly a team effort at Amplitude, like we started to have our s- our, I think it was Sonya who needed to like, we had three days to go in to close a customer and they were looking for us for trusted expertise. And she pulled together this workshop and she came up with these three games of product, which is a really tricky and cool way to describe like how your North Star, you know, inputs and North Star should be, and it started this ball rolling. And then they wrote a blog post about it, so if you search North Star you get to Sonya's post. It's an amazing post. And then our CSM started to learn how to do it, and then we were like, "We should write a playbook for it." And then it got to the point where if you go on LinkedIn, you know, people are like, "We used," uh, and I made a whole point of saying we did not invent this thing. (laughs) But people will say, "We use Amplitude's North Star framework," and I have to always chime in like, "No, we did not invent that thing. You should go to Sean, or you should go to any of these people who've done it in the past." But yeah, the whole point is that a lot of this stuff was evolved over time. It wasn't just some snap marketing campaign to do it. Same thing on our retention playbooks and engagement playbooks, like when I arrived at Amplitude people would send pictures of those playbooks sitting on their desks, and people thought, "Oh, it's just this piece of marketing content. How do they pull it together?" I- I did some research and our CS team developed a 110-page bulk of research from working directly with customers around retention and engagement, then we had a PM and a great content writer, Archuna, zero in and kind of like make it palatable, then we did art for it. So it didn't just magically appear. (laughs) People think that these, these artifacts that Amplitude has just magically appeared, but they were just, you know, it's a company filled with passionate experts at these things and, and it was like tested, iterated, tested, iterated, expanded, tested, put into motion, put into practice, and that's how you create these kind of franchise, like cornerstone pieces of content for your company. You don't just snap your fingers one day, (laughs) you know? So anyway, I wanted to point that out, huge group effort for all these things.

   16. LRLenny Rachitsky14:22

       How does it feel to have left Amplitude at this point? I imagine you're going through some rollercoaster of emotions.

   17. JCJohn Cutler14:26

       Oh, geez. Um, well, an immense amount of gratitude, definitely. I mentioned that. Uh, wonderful people, uh, wonderful customers, and just imagine, like if you're a product nerd, you know, one day you're with Amazon, like one day you're with IKEA, one day you're with Lego, one day you're with Intercom, then you're with a two-person startup, and then you're with like Figma, and (laughs) like. So, uh, so really like once in a lifetime experience to be able to do that. In fact, if I'd been a paid consultant, I never would have been able to do that. Another thing too is that there's this sort of selection bias, like if you're a consultant people come to you to work with you, but often I just had to talk to whatever team wanted access to expertise at Amplitude, not necessarily me, so I didn't get to dictate, a lot of times, the conversation. It's like, "Shit, I'm not doing a very good job here." Like, "This person thinks in a very different way than me (laughs) to do that." So yeah, a lot of gratitude. I would say it got really heavy a lot, in the sense that my son was born, three months later I start the job, and then the pandemic kicks in, and every day you're like absorbing just the tension from teams. You know, you're meeting leaders who are about to leave five days later, you know, you're p- meeting people who are trying to save their team from, you know, the pandemic imploding everything (laughs) they're doing. So there was, you know, you, yeah, I d- I joke about the product therapy thing but, uh, it, I would finish the day at 2:00 or 3:00 and then have to do another one, or you know, wake up at 5:00 to do an EMEA workshop, 5:00 to 7:00 it'd be two in workshop, then take a break then do another two-hour workshop, and then talk to a leader about how everything's gonna explode, and then another leader, and then I was still on a team in Amplitude so I might go to my own meeting where we're challen- you know, working through our own challenges, and then it's like 4:00 or 5:00 in the afternoon and you're like, "Oh my God, I'm done" (laughs) uh, to be able to do that. And then I think it also left me with like a couple, you know, key lessons we could probably go into later when we're doing it. You know, one, you're talking to a bunch of different companies ache- achieving the almost similar results in like very, very different ways, they behave in different ways, the context in the pandemic, or the economy. Like, you would see the pandemic kick in and then you would talk to 50 companies that were dealing with the ramifications of it. So it's kind of funny, I joke with someone at Amplitude, they're like, "We were going through our own shit," and I'm like, "Yeah, and I've, I've seen how 50 other companies are going through their own shit" (laughs) where this is you're doing it. So the power of context, the regional differences were so fascinating, you know, you're, you're on with, I, I was on with a team that was based in India and th- just the passion and curiosity, there was not one jaded person in the room. Like, there was not one person, like, "Been there, done that," you know? "When's the performance review cycle ending?" Or anything like that. It was just like all-out passion and hunger for information, so those days were amazing, so yeah. Could talk a lot about it but it definitely, um, it feels like a relief in some ways because the amount of tension to do it.

3. 17:28 – 18:52

   What John’s doing next

   1. JCJohn Cutler17:28

      And so for my next plan, actually what I'm doing is I'm gonna work at Toast, um, in a couple weeks, and I've been in touch with, uh, a leader there, Craig Daniel, for a long time, kind of really liked what he did at Drift, but I think that what I realized over the course of these four years is that I wanted to pivot back to like help- put most of my energy into helping my own company. They're, they're growing super fast so the numbers are, you know, in the hundreds of everything, (laughs) or in the thousands of everything, and they're not just a POS business, they've got these different businesses like guest services and back office stuff and things, so I kind of wanted, like, uh, Amplitude was a super horizontal, if you think about it, it's almost like a diagonal, (laughs) and so it made your head spin and I kind of wanted to go back to vertical SaaS. There's a company here in, uh, Santa Bar- called AppFolio that I liked working at and I really, like had a soft spot for vertical SaaS, but I'm thinking...... put my energy into an internal team for a little bit to pivot, uh, to pivot back into that. And so I'll be helping like enable product teams and sort of doing what I was doing but within a company as well. So, it's gonna be an interesting shift.

   2. LRLenny Rachitsky18:29

      You touched on so many topics that I wanna dig further into, and you also talked about where you're heading next, which I was gonna ask, so that's great. (laughs) Thank you for covering all that. By the way, I was just gonna also say, uh, lucky Toast, wow, to, to get Jon Cutler. Go them.

   3. JCJohn Cutler18:42

      Oh, lucky me. I mean, geez, like Toast is this like gem, like... (laughs) I just was joking with Craig the other day, I was like, "I did not know all that stuff was going on at Toast."

4. 18:52 – 27:49

   John’s newsletter: The Beautiful Mess

   1. JCJohn Cutler18:52

      (laughs)

   2. LRLenny Rachitsky18:52

      Awesome. Okay. So, before we dig into some of the stuff that you brought up, like cultural differences between companies, what the best teams are doing differently, things like that, I actually... And you noticed, I asked on Twitter what I should ask you.

   3. JCJohn Cutler19:05

      Okay.

   4. LRLenny Rachitsky19:05

      You have a lot of fans on Twitter, and there's a ton of questions, and one actually got pretty spicy and I wanna touch, touch on it briefly. This guy, Jason Cohen, pointed out that a lot of the stuff you share online, in your newsletter and tweets and things like that, is, it often doesn't have a clear recommendation of, "Here's what you should do," or concrete piece of advice you could take away. It's kind of like messy, which is appropriate 'cause your newsletter is called The Beautiful Mess.

   5. JCJohn Cutler19:32

      (laughs)

   6. LRLenny Rachitsky19:32

      And so my question to you is, why have you found that you like to embrace the mess in your writing and your thinking and your advice?

   7. JCJohn Cutler19:38

      I was reflecting that like the newsletter, it's almost like an emo band. Um, like The Beautiful Mess is like so angsty, it couldn't have been-

   8. LRLenny Rachitsky19:45

      (laughs)

   9. JCJohn Cutler19:45

      ... like more... Like if I had a band, if I... I, I did not have an emo band when I was 16, but if I did, I would've called it The Beautiful Mess. Um, so it's probably pretty (laughs) consistent with personality to do those things. I mean, I actually really appreciated Jason pointing that out. And in fact, like at the end of this year, I put this post out to people saying, "Hey, here are things I'm grappling with, like the actionability of the content that I put out there, diversity of product advice that's important to me, and then what it's like to just be a weirdo." Like, you know, like we all have our, like weird freak things, (laughs) you know, to do these things. And so I, you know, sort of have, what does it mean to embrace those things? So it was really timely, I thought, that Jason put that out there. And so maybe I'll give like a little background about, you know, the newsletter and, and what I was looking for, for that. And so I think that the f- the first thing that I did was, you know, four years ago I kind of scanned the product advice landscape, and I noticed, you know, three things. First, there's sort of three perspectives that pervaded. And again, I just wanna make a huge caveat, this is not a judgment on any of these particular perspectives. It's more like I noticed a lot of it. And the first was that, you know, to be successful, number one, maybe success is tools, skills, mindset. So, that's kind of one group of particular things. The second that in terms of worldviews, we mentioned like international worldviews too, but there was like a, a high percentage of product advice that was kind of grounded where you think it would be grounded. So, it was grounded in this idea of a meritocracy, you know, like success is primarily about merit, very highly individualistic. And we don't realize that in the US until you do meetings with other teams, just how individualistic we can be (laughs) when it comes to how we think about teams should be set up and stuff. And then I think the third thing I realized was that it was very, uh, often very context-free. And I mean that actually in the nicest way. Like, it was optimized to make sure that someone... it could be actionable, that someone could take that away. And that's what I really like about like the content that you put out there, and I like about a lot of the guests on the podcast, like they kind of lay it out in those particular things. And so to kind of go through those, like, yeah, tools, skills, mindset, that makes sense, right? (laughs) Who does not want tools to be better? In fact, you know, a lot of the podcasts I like, we get into that later, like, "We're gonna give you the tools and tactics that the best people do." So, I really like that kind of stuff as well. The second part of that is like this idea of success being mostly about individual skills and chops. So, you know, this idea of like great leaders, high performing teams, 10X people, you know, kind of go on and on. And then the product mindset stuff, which is a little bit like you have it or you don't, or you develop or you don't. It's like very mysterious. (laughs) So again, I'm gonna go through these things and then think about how they inspire me. Part of me was like, "Okay, there's a lot of that stuff, but maybe not as much stuff kind of unraveling the dynamics, um, that, that happened behind those things." So, the meritocracy stuff and the individualism stuff, you know, it's like basically the people rise to the top, they try the hardest, they work the hardest, the best in companies employ them. There's top tier companies, there's second tier companies. So, there's this very like hierarchal view, and as I started to also dig in more into the stuff in Amplitude, I was like, "Wait, there's something right and wrong about this at the same time. There's something true but not true at the same time." So, that's something that I wanted to be able to explore in doing it. And then the context-free advice was obviously like, I noticed more and more that people trying to put tools in play out of context sometimes had worse effects than them just not doing it at all, to do that. So anyway, I kind of thought about it as a product, like, "Okay, what's my opportunity here?" There's a lot of this great advice, it's very actionable. I don't know, in the US we're pretty individualistic, so the advice probably lands with people really, really well. (laughs) And then also it's really actionable, and so I thought, "Okay, well, what would be my particular angle?" So, I thought about the angle about wanted to explore three things. I think the first one is this idea we do work in these complex adaptive systems, and so I really went deep in that particular area. So, we work in environments, there's lots of things that are interdependent on each other. We don't work in closed systems. I mean, like if you're in the Bay Area, you're in this broader system called the Bay Area, that's in this broader system called California, that's in this broader system called the (laughs) United States. You know, your team is like in a team of many, many teams in your company. The systems are nonlinear, so things... You know, the, the bird flapping its wings in Brazil, you know, creates the tornado type of stuff. And so I wanted to make sure that we got like dug into that particular stuff in The Beautiful Mess stuff.The next thing is that I'm a sucker for, like, weird counterintuitive dynamics in companies. I don't know what it is. Like, I absolutely love that. And so like, maybe I give, like, two examples. Like, one, I'm obsessed with this idea of high work and progress, like from a human level and a team level. Like, how even though we know that if you try to do less at once, you'll be more effective, teams routinely just load themself up with work. (laughs) And so, like in the, the newsletter, I wanted to explore stuff like that. Like, why, when a bunch of people know rationally that you should not load yourself up with work, why do really, really smart, capable, intelligent, passionate people in their personal lives and on their teams just, like, load themself with, up with work? (laughs) What are they optimizing about? You know, so that'd be like one example of counterintuitive stuff. The other stuff is, like, strategy stuff, you know. Every company has these three pillars, and it seems really smart for the CEO to have this, like, really clear three pillars, but then everyone walks away from the meeting being like, "I don't know if we're doing this." That's, like, another example of a counterintuitive thing. So, you know, that was the second thing, the counterintuitive stuff. I love the complex stuff. And then frankly, I think the other thing is I just wanted to help people who are weird like me do those things. So, like, I, I would say, like, I'm really, really triggered. People will say, "Oh, probably triggered by Jason." He said, "Why? What?" Bring solutions, not just problems. You know, like, that's my, like, Kryptonite, right? (laughs)

   10. LRLenny Rachitsky25:45

       Right.

   11. JCJohn Cutler25:45

       I like the systems thinking stuff. I like all that. So, anyway, long story short there, like, wanted to help people like me. I like the complexity stuff. I like all these weird counterintuitive dynamics, and then I thought that, like, there's a lot of representation for the very deterministic advice that people have.

   12. LRLenny Rachitsky26:02

       That's a really good explanation. (laughs) There's like a piece of, like, what does the market want and let me deliver it. And then, there's a piece of, like, how is my brain working. Yeah.

   13. JCJohn Cutler26:10

       I love the fact that people scan the market and say, "People wanna know about prioritization, and so I'm gonna tell the world about prioritization." Like, I really like that. In fact, I admire... I'm jealous of people who can produce that kind of content realistically. And interestingly enough, like, I probably in my doodling and posts, I've probably given frameworks to do that. I just don't think too much about it. I just kinda go on these things. So, yeah, there's always this balance. And one way that I think about is to get anything done, we need to reduce the world a little bit. You know, that's the difference. And, and, and back to this thing of complex problems, I think it's the difference between oversimplification and focusing. You can have, like, a really complex problem, and you can oversimplify it, and that's not great. But you can have a complex problem and be like, "You know what? I need to hold some things constant. Not gonna make any progress unless we hold some things constant to do that." So, that's, like, to me, the balance I'm playing all the time between, like, how many variables to hold constant to make sure that people can get some value out of it. Um, I don't know about you, but, like, that's the tension I have. But you, you write really actionable stuff, and, y- you know, the... So, I really admire that, too. I'm jealous.

   14. LRLenny Rachitsky27:15

       (laughs) I try. But then, I'm jealous of always having to kind of nail it down to something very concrete and simple. This last post actually was a little bit of a balancing act, where I wrote about how reality is mostly a myth, and I added the word "mostly" to it at the end. And it kind of, like... I was like, "Should I just go for it and be like, 'Reality is fully a myth'?" But I went-

   15. JCJohn Cutler27:33

       Oh.

   16. LRLenny Rachitsky27:33

       ... "No, it's not actually." So, I can't really go that far.

   17. JCJohn Cutler27:35

       See, it's kinda messy. You know?

   18. LRLenny Rachitsky27:37

       It's kinda messy. Yeah.

   19. JCJohn Cutler27:38

       It's like that... I love that. So, in, in the spectrum of advice, like, every post of mine will say, "mostly," "maybe," "it depends."

   20. LRLenny Rachitsky27:44

       (laughs)

   21. JCJohn Cutler27:44

       And then, like... So, we all have some opportunity to, like, flex into the other direction. (laughs)

   22. LRLenny Rachitsky27:48

       Okay.

5. 27:49 – 40:08

   What do the top 1% of product teams have in common?

   1. LRLenny Rachitsky27:49

      So, shifting a little bit. Coming back to just the bigger picture of Jon Cutler. You've had more exposure, I think, to product teams and product managers, more than... Like, E- you're definitely in the top 1% of people that I've talked to and met with and seen what happens within product teams. And so, there's a lotta stuff I wanna dig into there, and the first is around what you've found differentiates the highest performing teams. So, let me just ask you, kinda this very succinct question, and see where it goes. If you had to-

   2. JCJohn Cutler28:19

      (laughs)

   3. LRLenny Rachitsky28:19

      ... just like, boil it down, what have you seen most differentiates the highest performing product teams?

   4. JCJohn Cutler28:26

      First of all, they're, they're top 1%. They're super, super productive. They can levitate. Like, they can do, um...

   5. LRLenny Rachitsky28:32

      Mm-hmm.

   6. JCJohn Cutler28:33

      Yeah. They have no emotion. No, I'm just kidding.

   7. LRLenny Rachitsky28:34

      (laughs)

   8. JCJohn Cutler28:34

      I don't like to do this. No. Okay. This is my tack for answering the question. So, first of all, I, I have this friend, Josh Arnold, and he had this great principle that held true in my experience talking with teams, and he calls it the Reverse Anna Karenina Principle. And so, in, in Anna Karenina, Tolstoy is basically like, "The dysfunctional families are all different, and the happy families are the same." And what he said is, it's the reverse of that with product teams, that actually the dysfunctional companies are all the same, and then the happy companies, (laughs) or like, the higher performing companies can be very, very different. And so, that's something that stuck with me, because either you have easy to identify anti-patterns, and I'm gonna admit, like, earlier in my career, maybe five or six years ago, I made like, my content was about identifying things that people would be like, "How did you know that was working in my company?" And I would just be like, "Well, I just know." E- even Spencer and I had this thing. I put something on Twitter, and Spencer writes me. He's like, "Jon, is this about Amplitude?" I'm like, "No, man. It's like that Carly Simon song, Spencer. You probably think the song is about you, but it's not." (laughs) Like, it's just, it's just is, you know? It's just like those things. So, either you have the very easy to identify anti-patterns, or you have the high level principles. You know, like, "You must trust each other," or you must do something like that. But the way that companies achieve those particular high performing things can be, like, vastly, vastly, vastly different. So, let's just start with that as a basic thing, which is one reason why it kinda makes me hard, um, to answer the question. So, you know, great example here is great product leadership. Like, we need great product leaders. But you meet enough product leaders, and you see that, like, some people are, like, these humble, curious, certain product leaders. They're not really talking a lot, and they're just growing the system that way. And you know what? There's other companies with really successful people that are just badass, strong, dominant, you know-They like to spar. (laughs) You know, I need people who can spar with me. So that's just, like, one potential example there of, like, okay, y- you meet enough teams and you see that there's, uh, many ways to achieve great leadership, even an example. Another example would be... And then I'm gonna start listing these things off and then hopefully this makes more sense as it gets to it.

   9. LRLenny Rachitsky30:46

      Yeah. That's great.

   10. JCJohn Cutler30:47

       Like you meet lots of great teams, and the better teams make high, better decisions faster. Now, that's like that high level thing that you... I say that to you, and you're probably like, "Well no shit." (laughs) That's what I would assume to do that. But if you think about, like, good decisions and stuff, like, what do you need for good decisions, right? You need information, it pays to have diverse perspectives, you need to be able to analyze the data. You probably need chops, some kind of chops in the domain to be able to do it. You usually need a goal in mind, like what are you optimizing for? It's very hard to make a decision just to make a decision to be able to do that. Okay, so those are, like, the, the basics, but still none of that's all that interesting, right? You're like, "Oh, you're saying you need information to make decisions," and it's kind of not very satisfying (laughs) to think that, right? But then if you think about three companies, let's say think three... We could even play the game together. We c- you know, I'll give you two, you could give me the third one. But, like, let's say company A buys into the whole idea of an extremely rigorous decision-making process. It's, it's very process-driven. It's like you do this, you do that. We red team our decisions, we bring in people to, like, push back, we've got this particular thing. So maybe that's how they achieve it. Company B, maybe they're just all about this kind of mushy, diverse perspectives thing. There's not really... They're not very process driven, but they achieve really good decisions by making sure that there's these, like, serendipitous connections between people at the right time with the right set of ??????. There are highly successful companies that achieve both of those particular things. I don't know, what am I missing? So Lenny, you think about it. It's like, what are... You know, so there's the rigorous process-driven approach, then there's the company that's all about, like, the ad hoc work together, collaborative approach. What's another way that some companies make really good decisions all the time?

   11. LRLenny Rachitsky32:28

       What comes to mind is a very top-down, CEO-driven, "Here's what we're doing, here's the roadmap."

   12. JCJohn Cutler32:32

       Yeah. Absolutely. And so this is the thing, I'm sitting there and the, the very idealistic product managers are like, "You gotta have empowered teams and you gotta push decision-making down to the bottom," and I'm like, "Huh. Well, that company's doing pretty well and the CEO just tells everyone what to do. And in fact, they attracted people who just don't mind that and like their vision (laughs) and do it," right? And you find people who really like the process-driven approach, and you find people who do those things. So, like, that's like one principle done a different way. But then I'll just take, like, a couple principles. So I just wanted to get that out of the way, that, like, every one of these I mention could be achieved in a couple different ways. So the first thing you notice is that companies that are very high performing have coherence between the structure of their company and their current strategy. And this is, like, a structural thing. I think when they're startups things are very fluid and the strategy's in flux, and so they have a f- a fluid structure, but then as companies grow, there's sort of a physics to the problem that starts to catch up to them, p- particular things. So their funding approach, their incentives, the org structure, the architecture, even their technical architecture supports their strategy back and forth. And the reason why I mention this one is you can have brilliant teams, you meet these brilliant teams where they've just hired in, like, the quote unquote "best of the best," and they're just struggling with the strategy structure mismatch and no amount of, "Let's empower people," or no amount of doing whatever is gonna, like, knock them out of that. And so what do you need? You need a strategy, then you need to line the structure around it. So this is different than saying you're asking me, like, what do I observe when they're doing really well? Now, the tactics to achieve this might be different (laughs) depending on the company, but you could get that. I think the second thing, if I admit it, is, like, the strong opinions loosely held, which is there is this balance of believing in certain things. Believing maybe in the power of products or the power of connecting with customers or maybe key strategic things that they need to do, or, or even believing that this is a done deal and you just need to move faster than every, everyone else in the space. Or even the belief that you need to just go straight to commodity pricing like Amazon with whatever you're doing. Like, there is just a stubborn, strongly held belief that is then balanced with their ability to have the loosely held thing. So I would just observe this in meeting after meeting with these, like, teams that seem to be having a bout of being more high performing. You know, they would be stubborn about some things that they were doing, even when it didn't make sense in the short term. (laughs) Right? And then they would do that. So I think that that's, like, another thing. I think related to that when it comes to the product world is just, like, a core belief in the power of products. The, you know, the Jeff Bezos thing that, like, the success of today was set in motion three years ago, that, like, product is a layer cake and that you are layering on decisions. Like, the success you're having now is like a layer cake of decisions from the last bunch of years that you're doing it. You could rationalize that all you want, but at the end of the day it's often because either the founders or other people involved have seen how that can work because there is a leap of faith. And there's a leap of faith that no amount of data or no amount of A/B testing or no amount of rationalizing or no amount of spreadsheet math to figure out the ROI of what you're doing will ever help you. It's just not. And I just noticed that pattern over and over, that there was just a slightly irrational belief in the power of what it would take to have, like, you know, a, a, a n- a nine craft level product versus a seven craft level product (laughs) or a six craft level product. So I think that that's, like, another component. I have a couple more in depth like that. Like, definitely the leadership is coherent. So that's like, you know, walking the walk, talking the talk. And I think this is one of the most fascinating ones because it's very much about being who you are and not being embarrassed about that thing. So there are companies, probably all know that, like, outspoken, domineering...... believe that the company is just ... should be run a certain way, and they set this vibe. It's kind of this coherent that they, their actions and words match together. And so when you think about it that way, it makes more sense. Like, the company that's like, "Oh, well, we want to empower our teams and do whatever, and, and we believe in our customers," and their actions don't match those particular things, like, that's not very, very coherent, (laughs) to do these particular things. So, you know, I think that that's one, like, the coherent things, and so ... Okay, so you've got those high-level ones. I think you can definitely add skills and experience. I mean, those definitely matter. I think one thing that happens a lot is how the company views its skills. So here's like a challenge we had in Amplitude, just sharing this is like, you could view Amplitude as just another B2B SaaS company, or maybe just an analytics company, but one of the challenges we had when it was like, how to build our team is to think about where do you draw the line between someone who's just done B2B SaaS for the last 10 years, is a pro at what they're doing, and then how someone could embrace this kind of weird problem, sort of bottom-up motion, top-down motion. It's in product, it's a messy space. You need to be more strategic to do that. So the skills need to be, like, mediated, obviously, between, like, the environments to do those things. And then, like, all the other, you know, they know how to build software, things don't break, they can experiment without risks, they don't ... I don't know, they have positive habits. I could go on and on. Hopefully this is a helpful, just hearing my thought process to go through these things, but like, I think that the, the, you know, the TLDR of this whole thing is, those top ones I mentioned seem like common sense and it's, like, how do you put it in motion in your company? I was just reading that, like, um, Working Backwards book about Amazon, and they're in this chapter about basically their bar raisers thing, and I share it with my partner who's the head of HR at a company. She's like, "Yeah, this is sort of like common sense hiring."

   13. LRLenny Rachitsky38:32

       (laughs)

   14. JCJohn Cutler38:32

       They're just talking about de-biasing the hiring and having standards and having those linked into the jobs and just not rushing it, and isn't that kind of ... Like, it's, it's like these things that seem so common sense are actually hard (laughs) with what they're doing. So, I don't know if you've noticed that, but it's, like, a lot of the advice is common sense. That doesn't mean it's easy-

   15. LRLenny Rachitsky38:52

       Yeah.

   16. JCJohn Cutler38:52

       ... to put in motion.

   17. LRLenny Rachitsky38:53

       And there's also a lot of power to just making it, like, a very important value to the company. Like, just calling it bar raisers-

   18. JCJohn Cutler39:00

       Yeah, that's the coherence thing. Yeah, that stubbornness.

   19. LRLenny Rachitsky39:01

       Right.

   20. JCJohn Cutler39:01

       You know, I'll use the example of a company, the, I mentioned this company AppFolio here in Santa Barbara, but Klaus and Jon founded that company. It's just a gem of a company. It's an amazing vertical B2B SaaS company, but I think, you know, and the story that they tell is, like, when they started AppFolio, they're like, "We wanna find a place where the money flows, and we wanna be really close to customers, and we just wanna" ... where they believed in custom- ... they were engineers who had, had seen the light around customer development, just getting close to customers, just being in service to the customers, not just like gold plating every technical decision you did. They bought in early to the ideas of, like, test-driven development, pair programming, 'cause they believe that the quality, you know ... You should never be worried about the quality. They just believed that quality wasn't something you sacrifice as the norm. It's ju- it's just gotta work, and they believed that was possible. And when you think about it, those things are always debated, like, "Oh, should we get technical debt or not?" Or like, "How much customer contact is or not?" And, like, these two founders basically are like, "That's it. We don't sacrifice on those things." (laughs) And y- y- like, they've done really well with that.

6. 40:08 – 45:55

   Different ways companies are successful, and why anyone can improve

   1. JCJohn Cutler40:08

   2. LRLenny Rachitsky40:08

      That's a thread I wanna actually follow up on, is just the power of culture and values and things like that. But before we do that, let me just summarize maybe the top five attributes and kind of traits you've just shared, and then I have a, a two-part question around this. So, I wrote these down. So the things you've ... Basically the things you've found are true for the companies that seem to be best at building product and software and-

   3. JCJohn Cutler40:29

      Yeah.

   4. LRLenny Rachitsky40:29

      ... running product teams. One is coherence between what they're doing and what their strategy is. Two is strong opinions loosely held. Three is belief in the power of product. Four is the leadership is coherent, that their advice matches their words and their actions. And then five is just, like, the necessary skills and experience in building ..........................

   5. JCJohn Cutler40:50

      Yeah. Contextual skills, too. Like, um, yeah. Exactly.

   6. LRLenny Rachitsky40:54

      So, kind of a two-part question. One is, if there's, like, a pie chart of what contributes-

   7. JCJohn Cutler40:59

      (laughs)

   8. LRLenny Rachitsky40:59

      ... to this working out, what percentage would you say is just the people that they hire that contributes-

   9. JCJohn Cutler41:04

      Yeah.

   10. LRLenny Rachitsky41:04

       ... to them succeeding here? And then, related question, just like, can you change a team to be high performing? Like, does that happen? Or is it often just like, this is just the way they are and their culture and their founders are this way, and it's really hard?

   11. JCJohn Cutler41:18

       The pie chart, that's the problem.

   12. LRLenny Rachitsky41:20

       Mm-hmm.

   13. JCJohn Cutler41:20

       I mean, that is the, like, the trillion-dollar question, so I don't really have an answer. (laughs) .......................... I, I have a couple thoughts on it. Um, what do we know? Right? We know that you can have a bunch of geniuses in the room, and if there's not coherent leadership and there's not coherent structure in what you're doing, they'll fail. Okay, so we know there's a limit on one side of this particular problem, right? (laughs) And we know on the other side of the problem is, like, if no one's done this before, who knows? Because how many startups were started by people who hadn't done it before, you know, who had passion for doing something? This is ... Now they made a lot of mistakes. Now, granted people would say like, "All right, now after three failures, I'm gonna tell you what we need to do to succeed," so maybe they have to, like, fail (laughs) a couple times to do that. So, with the right things in motion, you can do that. I would also ... Let's ... Another data point. At a lot of companies that are known to be higher performing, they're one of two categories. Either everyone in the company is this extremely vetted, like, genius at what they're doing, or they have a culture where people stay for three, four, five, six years, they build their career, or seven, eight, nine years, there is a concentration of people who are very skilled, but they have a knack for bringing people up. Like, they have a knack for taking someone who has some of the raw materials to be able to do it, and making them really good at their job.... to be able to do it. So, I don't... I'm not gonna throw out a percentage point into it. I'm just gonna note that like, I think that the biggest challenge is that we all need to challenge our biases. I do too. So four or five years ago, I would have said, "Well, personal skill is nothing. It's all the environment." There's people on Twitter who do this all the time, they're like, "Bad management kills everything. You know, skills aren't important. You should just be able to do anything with anyone," and I used to be one of those particular people. And I also have this sort of like humanist bent to what I'm doing and so I very much want to believe like... I'm always the person that's like, "Oh, we should give them the seventh chance." Like (laughs) I'm-

   14. LRLenny Rachitsky43:12

       (laughs)

   15. JCJohn Cutler43:13

       ... like, I know myself, right? To do that. And I would suggest that there's people on the other end of the spectrum who could benefit from shifting a little bit to embrace some other ideas too, you know? So they are the people who are like, "Well, it's... it's 100% their skill. We will hire complete A+ players all a particular time. Everything will work out as expected." And/or they trace everything back to leadership anyway. So when anything's wrong, they're like, "Well this happened under this person's watch, therefore they are a failure," you know? But how many SaaS comp- uh, huh, you know, how many companies in general will hire a string of highly qualified people into a particular department and then fail each particular time? Right? So I don't know. I don't have the answer for you on that one, (laughs) but I think that everyone can benefit from like challenging their, uh, their, maybe their, their happy place, me included-

   16. LRLenny Rachitsky43:57

       I like that.

   17. JCJohn Cutler43:57

       ... uh, to be able to do those things.

   18. LRLenny Rachitsky43:57

       It's like, it's an optimistic perspective basically. Any, anyone can change, anyone can improve. Don't assume that it's just not possible.

   19. JCJohn Cutler44:04

       Yeah, and then... And give it a shot, and then can you create a coherent environment where may- maybe that could happen? And frankly, uh, we may be getting to this later, there's a lot of companies that were flying high and are not flying high anymore. So, high performance is not this like state you achieve, it's actually a continuum that you're always... We have this in our personal lives too. We're flying high and we think we do everything and then we get to that point and then we go back down into feeling we don't know anything again. (laughs) And, you know, we feel those lows. So that's kind of how I think about that particular thing.

   20. LRLenny Rachitsky44:37

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7. 45:55 – 49:59

   Investing in people vs. investing in processes

   1. LRLenny Rachitsky45:55

      Coming back to the first question about people-

   2. JCJohn Cutler45:57

      Yeah.

   3. LRLenny Rachitsky45:57

      ... and maybe you just answered this, but do you find that, like, it all about the people and who you hire at the, maybe at the top, that lead to the result at the company? Or you're saying, like, it's sometimes the right, amazing people, sometimes it's the process, sometimes it's the market, it's other things?

   4. JCJohn Cutler46:12

      It's the latter. And I think that's, that's why I called the damn thing The Beautiful Mess (laughs) because I think that everyone, we all have confirmation bias, you know? We'll point to that company and say... L- I mean, let's... Let me just use an example.

   5. LRLenny Rachitsky46:23

      Yeah.

   6. JCJohn Cutler46:23

      Like, Satya Nadella and Microsoft, you could argue, you know, it's... You've obviously have someone who's this very humble, very capable leader in that particular thing. But I imagine that at some point in the future there'll be books written about that and they'll say like, "Hey, it was kind of that, but you know what he, he did? He's basically like, he got rid of some bad people and created the air cover and, and set the... In motion the couple of strategic imperatives that were gonna let the things going." Now, imagine Microsoft didn't have all the wealth of talent that it had or all the wealth of structures or their... Or like, the good parts of the tradition. Or let's say the bad parts served them well for a long time but maybe they started to become a little bit outdated and then they were putting them in a competitively bad situation. It's... Even that situation, you can like idolize that particular leader for doing it, but there's many things that could happen to be able to do that. And so there's this idea of like Great Man Theory, and, and this is something I talk about a lot, where in Great Man Theory, you know, success is the result of these like highly influential, highly effective men in a lot of cases (laughs) and that... Like, you can explain history through these heroic men. And that's sort of a thing, you know? Like, a lot of people base history on doing that. And I think that this, again, just the ah- the other perspective here is that things are a lot messier (laughs) and you can't just trace everything to these sort of like, you know, single heroes, men in many cases, that make it happen. So, I'm just presenting both sides of it as, as we kind of dig into it. So-

   7. LRLenny Rachitsky47:51

      Yeah.

   8. JCJohn Cutler47:52

      ... I think that, let's say you're a founder and you're trying to decide, should I invest more on processes or should I invest more in people? The first thing is introspection. What do you believe in, really? And not just what do I believe in that you think the whole rest of the world def- Like, not like, "I think the rules of the world are that blank happens." It's like, what do you believe in and what do the people around you believe in, and how can you be a coherent leader? And you know what? You can't... You can nudge yourself a little bit away from your happy place but you're not gonna go super far. You're not gonna go from like a process-driven meritocratic X, Y, Z person all the way to like a, "I'm gonna start a collectivist company where everything is sort of a consensus decision to do that." You're not gonna do that. But like, I think it starts with self-awareness and then that's like, that's how people form their authentic leadership, uh-... vibe, and then they flex a little bit and then they embrace other perspectives. That's just my perspective on it.

   9. LRLenny Rachitsky48:49

      That really resonates. It makes me think about companies, especially in the past couple years, that did really well because the market was pulling them and everything was just killing it. They're just growing like crazy, and you would assume it's the founder, the CEO, that's the result of that. But then when the market tanks, things stop working. And that's a really good, I think, example of just, like, it's not necessarily the person. It could just be other factors that make it feel like everything's going great.

   10. JCJohn Cutler49:16

       And people are great. There are people that have an outsized effect in particular companies. A great example there is, like, people forget that, for example, leaders or CEOs also have a lot of formal structural power at their disposal to be able to change things. And so, you know, like, well there's that great man leader who's a genius. They do have more knobs to move and even then, they're not the boss. You know what? There's a board. There's investors. Like if you talk to any CEO, they'll be like, "You think I am the boss." (laughs) "I've got people bossing me around too." So it's kind of... Yeah, it's always a mix. That's the way I see it.

   11. LRLenny Rachitsky49:53

       Yeah, which is why they're... You know, if things don't go well, their, their, their ass is on the line.

   12. JCJohn Cutler49:58

       Yeah, exactly.

8. 49:59 – 55:55

   Global company cultures: the individualist vs. the collectivist

   1. JCJohn Cutler49:59

      (laughs)

   2. LRLenny Rachitsky49:59

      Coming back to a thought I had as you were talking earlier about values and culture. It's interesting that wasn't on your list of just, like, the, the power and importance of, I don't know, strong values, strong culture. Have you found that that's just not essential and what are your thoughts on...

   3. JCJohn Cutler50:13

      No, I think it's kind of the, the fabric that creates those other things.

   4. LRLenny Rachitsky50:18

      Mm-hmm.

   5. JCJohn Cutler50:18

      You know, it's the fabric that creates coherence. Like coherent around what? If culture is what we're doing is what we're acting, and the way we act is sort of a function of some of the belief systems and the culture and the value systems that we have, I sort of ma- maybe I just almost take it for granted that that's, like, sitting underneath those particular things. But here's an example where sometimes, you know, nuances matter. I'll just use Ampli- Amplitude. We had some values and we had HOG, you know, humility, and there's like this idea of, like, ownership and a growth mindset to things. Ownership defined in an individualistic culture is gonna look very, very different than ownership defined in a collectivist culture. So what I find with companies is that like... And certainly we struggled to communicate this too, and I think we were pretty good at communicating where we sat on this particular thing, but like, a lot of times people write up these cultural documents and they're just like, "Well, this is our culture. We're into ownership." It's not saying much, saying that you believe in ownership without the addition of, like... Which what we would do successfully, and Spencer and other people did successfully, is talk about the behaviors that represented that level of ownership. Then that tells you something about what the culture is. So maybe when I was answering that, I kind of took that for granted. But yeah, there's a set of beliefs and values that sit underneath all those things, I bet.

   6. LRLenny Rachitsky51:38

      When you think of the companies you worked with over the years, and you don't have to answer this if you don't want, but when you think of, like, the companies with the best culture or the best way, or some of the best companies in terms of how they built product, who, who comes to mind?

   7. JCJohn Cutler51:51

      I mean, I, I will g- no, I will mention some companies. Like...

   8. LRLenny Rachitsky51:55

      Oh.

   9. JCJohn Cutler51:55

      Um, but I'm not gonna mention what people think, like, in doing these. I'm just gonna mention moments where I was like, "This thing is really clicking."

   10. LRLenny Rachitsky52:01

       Yeah.

   11. JCJohn Cutler52:02

       And not because it wasn't easy or like... There, there is a leader at Lego and her name is Angela, and when I'm talking to her, I'm just like, "This person just has it dialed in." You know, like this is really hard. This business is, like, transforming. They've got one of the biggest, most iconic brands in the whole world at their hands, you know, and I'm like sitting and, and I'm just gonna single out her. Like yeah, there's this situation here. It's not easy, it's not great, it's not like high performing by any... You know, like, uh, you know, you take a tiny Silicon Valley company. Like yeah, it's hard to be at Lego with thousands of people trying to build this and trying to take an iconic brand and turn it into something having to do with digital stuff. But I just want to give a shout-out to her. That's (laughs) what I'm gonna say to this question. Like I- I think a bit more of these moments where I'm like, "Wow, this shit's hard, um, it's not ideal," and that people are coming to work every day and there's a group of people in this room who are extremely well-meaning. And you know what? The impact of their work might not even be seen in their tenure at that company. Thi- th- ... Some of these larger companies might take a decade to really, like, work themselves through. And so I don't know. Uh, when you asked that question, I thought more about, like, individual moments where I spent time with teams or like that team I mentioned to you in India where it's like everyone's super humble and whatever. So...

   12. LRLenny Rachitsky53:21

       Awesome.

   13. JCJohn Cutler53:21

       Yeah, not gonna give a lot of names, but just shout-out-

   14. LRLenny Rachitsky53:23

       No, that's great.

   15. JCJohn Cutler53:23

       ... Angela. She's doing an awesome job. (laughs)

   16. LRLenny Rachitsky53:25

       Go Angela. That reminds me of something I wanted to ask around the cultural differences between product teams in different countries. Talked about India.

   17. JCJohn Cutler53:33

       Yeah.

   18. LRLenny Rachitsky53:33

       Talked about Lego. What have you found to be the main differences in how product teams operate and companies operate across different countries, like say California versus Paris versus Australia?

   19. JCJohn Cutler53:45

       Yeah. And again, I'm not an expert in this and I think Erin Meyer wrote that, or Mayer, I'm not sure how to pronounce her name, wrote that book, The Culture Map.

   20. LRLenny Rachitsky53:51

       Mm-hmm.

   21. JCJohn Cutler53:51

       And so you should just, like, find what those people wrote 'cause th- they're much smarter than I am about this. But here's, like, the individual things that I noticed. It's definitely, like, the individualist and what I would call almost, like, communitarian vibe. You know, the idea of like, individualism versus the idea of the team being sort of a community of people together. So that's one, and you pick up about that a lot when you go to different places. I mean, in the United States, you know, you'll find this situation where you've got this one engineering manager and they are like brokering the projects with every single engineer on their team and everyone wants the promotion and there's this whole, um... You know, instead of the PM like working with the team, it's like the PM brokering stuff with an engineering manager to give everyone their premier project. No one's really working together.

   22. LRLenny Rachitsky54:38

       Mm-hmm.

   23. JCJohn Cutler54:38

       There's no pair programming, there's nothing like that. That's a whole other debate, but like-And so that's, like, highly individualistic, and it might work in that particular environment. In fact, it might be optimized for environments where you're burning through people every, like, 18 months or 24 months, because you just want to put another cog into the particular machine so that you can grow and so you can do stuff. And that's an extreme example, but then you compare that to other parts of the world, it's, like, much more consensus-driven. The team perceives itself as a team, having a team goal. They have, like, a team objective. And certainly, even in, like, the Bay Area, there's companies that are more, like, the collectivist vibe and more... So, so to say that it's just about the world is not really just right. So I think that the, yeah, the collectivist, individualistic thing is, is important. I do think that certain cultures are much more sort of hierarchically oriented. There's much more deference to the hierarchy and the particular, you know, where people are sitting, and the information flows in a certain way. And you know, some companies tend to that being more bureaucratic, and then some countries tend to that being, like, it's still a tall company, but it's very much like, "You, manager, you own this." Like, "You do this." You know, so it's not like rules are flowing from the top down. It's more just, like, a pretty big org chart. So those are some of the things that come to mind, yeah, as we're going through it, so yeah.

9. 55:55 – 58:49

   Why it’s hard to make changes in large companies

   1. JCJohn Cutler55:55

      (laughs)

   2. LRLenny Rachitsky55:55

      This, this, uh, relates a lot to something else you often talk about, that much of the advice on the internet and books, newsletters like ours, is geared towards Silicon Valley-type tech startups.

   3. JCJohn Cutler56:06

      Yeah.

   4. LRLenny Rachitsky56:06

      And in reality, most PMs don't work at companies like that. A lot of them are going through transformations-

   5. JCJohn Cutler56:11

      Yeah.

   6. LRLenny Rachitsky56:11

      ... or trying to transform the way their culture works, and I imagine a lot of companies you work with are trying to get to that point, and that just a lot of the advice doesn't actually work for them. What have you found along those lines, of just companies going through this and, and things you've learned there?

   7. JCJohn Cutler56:24

      So putting myself in the shoes of those particular companies, like I said, I think some of my most, like, rewarding interactions have been with these, like, uh, non-Silicon Valley companies. I certainly learn a lot when I talk to companies in the Bay Area and in the United States to do those particular things. I think that the first, the first thing to keep in mind is that those... Well, let's just take these, like, bigger companies for a second, you know, like big enterprise companies. Part of the thing is just realizing how much inertia they're up against when you're chatting them. So you know, I do believe that, like, there's some structural things that probably they could avoid, but then there's also just structural things that are just part of the, part of the game (laughs) to do that. So you know, like, they, they'll be in situations where maybe none of the executives have shipped product before. They also assume that there's only one way to do things. Like, certainly in a lot of, like, high-performing companies, I have friends who will go and work at those companies, they're like, "Oh, no, no one changes the rules here. We just do it this way at Amazon," or, "We just do it," whatever. So this similar thing happens in these particular companies, like, there's only one way to do things. They've got these, like, crazy annual budgeting cycles and planning cycles, or maybe there's, like, a big IT industrial complex that they're sort of trying to transform into doing these things. So anyway, my, my point is, is that they... So many of these companies just have structural things that make it very difficult, you know, to just immediately convert that particular advice as they're doing that. So I think the first thing that comes to mind with that is how to adapt that advice, maybe, for some of those, like, larger kind of transforming companies. And I think that a couple things that I sort of remark on is that, one, like, reps matter in those particular situations. So in many of those companies, they should focus on creating these sort of areas or pods where a company can g- a, a team can get in the reps that they're trying to be able to do. So it's sort of like a little miniature version of that. And, and you know, there's a whole problem with innovation labs. There's a whole problem with that kind of idea. But the idea that you can create these little bastions where a team can get in the reps is important.

   8. LRLenny Rachitsky58:41

      And reps meaning shipping, shipping product.

   9. JCJohn Cutler58:43

      Shipping and learning.

   10. LRLenny Rachitsky58:44

       Mm-hmm, mm-hmm.

   11. JCJohn Cutler58:44

       Like, going through the full loop, you know?

   12. LRLenny Rachitsky58:46

       Mm-hmm.

   13. JCJohn Cutler58:46

       Can they go through the full loop of what they're doing?

   14. LRLenny Rachitsky58:48

       Mm-hmm.

10. 58:49 – 1:01:02

    How to view frameworks

    1. LRLenny Rachitsky58:49

    2. JCJohn Cutler58:49

       And I think that the other thing that comes up with that is that most of those companies need to think of frameworks appropriately. Like, they'll read about these particular frameworks or what particular companies do or don't do, and I think that for a lot of those companies, they see adopting the frameworks as the end goal. You know, they kind of look there, you know, and sometimes, like, maybe even you write a post that's like, "Well, how does Figma work?" And they're like, "We use these frameworks."

    3. LRLenny Rachitsky59:14

       Yeah.

    4. JCJohn Cutler59:14

       And so this company's like, "Well, we've got to use these frameworks." And I think that the way that I tend to think about frameworks is that they're more like a job aid. They're more like a learning tool that the team kind of uses to keep themself on track. But part of the thing is that those companies will reinvent the things they're using when things aren't working out. So I think that, like, that's another thing maybe some of those companies could benefit from doing. But we're getting kind of more into the kind of digital transformation or the big company space, but I think, like, back to that particular question, I think you need to view a lot of advice coming from Silicon Valley just contextually. It's startup. There's a tradition of how these companies work. Many of them are just optimized very much for that first big arc of growth. They've never really been disrupted. Like, the only disruption has come from scale, not from being, like, a legac- you know, a huge global b-brand or huge global business and then being disrupted by new things. Like, the, the only problems, not the only, 'cause it's really hard, but, like, the problems have been primarily scaling, so they're kind of optimized for wrapping their head around that. And then many of them are just pure digital product companies. And so I think this is a thing that a lot of the big ride-share and food delivery conglomerates are figuring out. They're like, "Oh, this is a lot harder than we thought." (laughs) Like, when you're dealing with moving people around and logistics and things, like, it's an order of magnitude more complex to do that. So I don't know if that helps kind of explain my perspective on that, but I think that it's like you have to adapt...... the advice, and you also need to acknowledge that for some of these companies, there are these sort of just structural areas of inertia that they're trying to work through. And that a lot of them maybe need to, like, adapt this advice on the small, instead of thinking they're just gonna, like, install all the frameworks or install everything

11. 1:01:02 – 1:05:27

    The spectrum of performance

    1. JCJohn Cutler1:01:02

       they're doing.

    2. LRLenny Rachitsky1:01:02

       Yeah. This is really, really good advice. I imagine folks who are listening that may be working at a company like that, s- it feels like there's two sides to it. One is there should just be an awareness of, "This might not work at us. We're not gonna be Figma."

    3. JCJohn Cutler1:01:15

       Yeah.

    4. LRLenny Rachitsky1:01:15

       "And let's just get used to that." And then two, this good, like, reflection for me that I'm probably causing some damage with people reading a post on, like, "Here's how Figma builds product," and then not adding a little bit of like, "Maybe this won't work at your company." You know?

    5. JCJohn Cutler1:01:29

       But maybe it can.

    6. LRLenny Rachitsky1:01:31

       Hmm.

    7. JCJohn Cutler1:01:31

       And I talk about this a lot, this- this sort of, I do believe there's sort of this fundamental attribution bias at play, where people in these high-performings don't acknowledge the amount that luck and inertia has been a part of what they're doing. And that the people in the big companies, or these not, these companies that believe that it's not the way that- that they can do that, actually overestimate the kind of, like, systemic drag in their organization, and underestimate what can be possible. And you think about that, we do that a lot in just our lives in general. You know, we see someone being really successful and we'll say, "Well, but my situation is this." And when things are working for us, we're like, "I'm a genius." You know? Like, "I'm a genius-"

    8. LRLenny Rachitsky1:02:11

       (laughs)

    9. JCJohn Cutler1:02:11

       "... for doing this particular thing." When things work, we're competent. When things don't, it's like the system and everyone else's incompetence to be able to do it. So I do think that there's opportunities. I think there's another thing, too, that there's a vast spectrum of companies. Like, we paint some of these, like, large enterprises on one end of the spectrum, and then these other company, you know, these modern product companies. But I brought up that, like, that plumbing company in Australia, like, you meet these companies. You know what? Their revenue is literally, like, 50 startups.

    10. LRLenny Rachitsky1:02:41

        (laughs)

    11. JCJohn Cutler1:02:41

        They are not doing bad. They are not doing bad. And you know what? They're actually doing interesting things. One of Amplitude's customers, Anheuser-Busch, has this thing called Bees. And Bees is basically like a liquor distribution app, and it's literally one of the biggest B2B companies in the world. And you know what? Anheuser-Busch is like, "What? We're gonna distribute beer, because the pandemic, and so we're gonna have..." And I think, uh, actually they started to become more even used for logistics. Like, you could... You're a bodega in one of those countries, you can order beer for doing it. So, I think that we tend to kind of paint this world of, like, there's the big smoke companies and then there's, like, the fast, nimble companies, but there's everything in between. You know, another example is, like, a lot of tech companies started 2000 to 2008, kind of around their third or fourth act at the moment, like second, or third, or fourth act. Bought a lot of companies, they're trying to absorb them. They might be trying, like, a product-led growth motion by spanning all the different acquisitions they had. You know what? They are on top of their game. This- this is not, like, a slouch company, but it's really hard for them to do that. Or, you know, we at Amplitude, we'd have a lot of, like, not old fintech, but not newest fintech companies. They're printing money, you know? And they're just, like, embracing this particular thing. Then compare that to, like, I did a big North Star session, or more of a coaching session at Nubank in Brazil when there was just, you know, 15 people in a room. And now, like, they're massive. So there's... I think that we tend to paint... There's like the... We tend to paint things as a, as a form of, like, modern product adoption. There's, like, the high-performing companies and the low-performing companies. When in fact there's just a whole plethora and diversity of different companies riding different waves, adopting different things at different times. And many of them doing really wholesome, humble, good work just dealing with their circumstances at the particular time. So I think everyone should absolutely know how Figma works, for example. And then we need to try to boost the stories of like Angela and her team or, you know, some of these, like, some of these companies that you'd never even expect. There's a company here in Santa Barbara that's, like, they do refrigeration, use AI to refrigerate industrial facilities.

    12. LRLenny Rachitsky1:04:52

        Wow.

    13. JCJohn Cutler1:04:52

        And Carrie, who's the leader there, that company is, like, one of the best leaders I know. And Jessie, who's, like, one of the founders is, you know, Harvard PhD student who understands AI and doing these things. And I actually would encourage a lot of PMs to think about, like, look, especially in this economy, what are these unsexy businesses that are, like, kicking butt and small? Here it's in sunny Santa Barbara.

    14. LRLenny Rachitsky1:05:18

        (laughs)

    15. JCJohn Cutler1:05:18

        You know? So I don't know. I think that there's a lot more diversity than just the, like, high-performing, low-performing spectrum. There's just a whole universe of fun companies out there.

    16. LRLenny Rachitsky1:05:26

        W-

12. 1:05:27 – 1:09:02

    Examples of high-performing people who work outside of Silicon Valley

    1. LRLenny Rachitsky1:05:27

       as you were talking, I was thinking about, there's a small group of people like you and Marty Cagan and a few other folks that have worked with tons of different and diverse product teams and not just, say, Silicon Valley teams. And I'm curious if there's any other names of folks you think listeners should follow if they work at maybe a non-Silicon Valley type team. Like Marty Cagan is who comes to mind first, but I don't know if you have anyone else. And if not, that's all good.

    2. JCJohn Cutler1:05:51

       Well, yeah, there's a couple people, but I feel like I should go back and, like, just generate, like, this full list for people, maybe would be interesting. Maybe I'll take that as an action item to, like-

    3. LRLenny Rachitsky1:06:00

       Yeah.

    4. JCJohn Cutler1:06:00

       ... list a couple of these people.

    5. LRLenny Rachitsky1:06:01

       We'll put it in the show notes.

    6. JCJohn Cutler1:06:01

       But I'll give you an example of, like, one- one guy, and his name is John Smart, and he wrote this book called Better, Sooner, Safer, Happier. And he... I think he was at Barclays Bank, I think that's how you say it, in England. And you know what? He, like, led this transformation, and then he, I think he's gone on to... He has a consultancy now for doing things. And the guy is just awesome to talk to. He's really, really humble about what, you know, the thing, the bo- like, the book is really interesting. And the thing that I noticed when talking to John is, like, the order of magnitude of complexity of problems that he has unraveled, and what he had to put in motion to take, like, an old school bank and at least try to get some part of some kind of transformation working in that particular company. Like, I think there's a whole, like, realm of people...... I like that. And I'm gonna, like list a co- and maybe I'll follow up with a couple more lists of like people-

    7. LRLenny Rachitsky1:06:58

       Yeah.

    8. JCJohn Cutler1:06:59

       ... who, who can do that. And then I do think there's the people like Teresa Torres and others that have come up with a technique that is universal. Like you can ap- like you can teach an element of product thinking with her techniques, or this opportunity solution tree, or this continuous discovery thing that like everyone can find accessible no matter how, where your company is at. And I have a lot of respect for those types of, um, techniques because they're, they're more universal versus like some very like arcane niche activity.

    9. LRLenny Rachitsky1:07:36

       Awesome. Cool. And then we'll do our best to include, uh, whatever full list you come up with in the show notes.

    10. JCJohn Cutler1:07:41

        Yeah.

    11. LRLenny Rachitsky1:07:42

        So I've been asking you a lot of very specific questions. I wanna give us a chance to kinda zoom out a little bit-

    12. JCJohn Cutler1:07:47

        Yeah.

    13. LRLenny Rachitsky1:07:47

        ... and see what other advice you may have for product managers and, and the product community broadly. Like, it feels like you're in this kind of reflective phase after working with all these companies and you've taken time, you have more time to think. So I'm curious what comes to mind when you think of just like, "Here's, here's advice I have to share."

    14. JCJohn Cutler1:08:04

        Yeah. I think, um, kind of going back to the reps thing, I think that there's this fire hose of amazing information that's out there and like I contributed to it, and you contribute to it, and there's just... I mean, think like what a time to be alive.

    15. LRLenny Rachitsky1:08:18

        (laughs) Yeah.

    16. JCJohn Cutler1:08:18

        Like you can literally just get the podcast going, you can listen to anything (laughs) you want.

    17. LRLenny Rachitsky1:08:22

        Yeah.

    18. JCJohn Cutler1:08:22

        You know? Like that's, that's like pretty amazing. And, and I was thinking to myself, the joke as I saw you put this thing about Andrew Huberman who, about, who gives these sort of like life hacks things, like there is absolutely a place for this type of content. Like, I just want someone to summarize what the hell I should do when I wake up in the morning-

    19. LRLenny Rachitsky1:08:38

        Right, cold plunge.

    20. JCJohn Cutler1:08:39

        ... and like can I be healthier?

    21. LRLenny Rachitsky1:08:40

        Sunlight. Yeah.

    22. JCJohn Cutler1:08:41

        Yeah, I got my sunlight. I went for my s- my sunlight before screens-

    23. LRLenny Rachitsky1:08:45

        (laughs) Oh.

    24. JCJohn Cutler1:08:45

        ... to prepare for our talk today.

    25. LRLenny Rachitsky1:08:47

        Wait, actually?

    26. JCJohn Cutler1:08:48

        Yeah, I went.

    27. LRLenny Rachitsky1:08:48

        That's great.

    28. JCJohn Cutler1:08:49

        Yeah, I have it in my habit tracker, sunlight before screens like every day. Yeah. I got my, got my like watch that I got a couple d- I'm on vacation, I'm between jobs now, so it's about like all health, um-

    29. LRLenny Rachitsky1:08:59

        Yeah, optimizing.

    30. JCJohn Cutler1:09:00

        ... ... at some

13. 1:09:02 – 1:11:35

    The skill of product management

    1. JCJohn Cutler1:09:02

       point. Um, but I think that you need to keep in mind that this like, this is a skill, and skill is knowledge times practice mediated by your environment, the habits you form, and the motivation that you have, and your particular things. And so I think that I learned about that a lot like working with learning experience designers in Amplitude that like we tend to think that this is just a function of the knowledge that we pick up and the number of podcasts that we listen to, but really it's about going through this loop. So at an Amplitude we have this data informed product loop, uh, that we would teach and it's basically like you need a strategy, you need to develop qualitative models, you need to add measurement to those models, like North Star Framework would be an example of a qualitative model. You need to add measurement to those models, figure out how you're doing it. You need to prioritize where to focus. You need to design bets. You need to measure the impact of those bets, and then you need to circulate what you learn back into the strategy, back into your models, back into how you prioritize, et cetera. And it helps you figure out where you're kind of weak at the moment. So for example, you need a strategy. Without that, nothing is possible. But you could have an amazing strategy and you don't deploy it with the right models, no one can prioritize anything. Or you could do all that right, but you don't design any bets and can't ship anything. Oh, well that's kind of a problem. Or you could do all that right, and you don't know the impact of anything you've shipped, or you could even do all that right and not circulate the learning back in your company, and then you're still not gonna succeed, (laughs) anything. So that's an example of what I mean by like the loop. And so one thing you could think about for your career that I think people should focus on, and also in terms of sharing the content that they share, so we're sharing a lot of content around knowledge and job aids, like knowledge, and job aids, and maybe a little bit of motivation, like how did that person succeed and do that and... But if you think about your career, just think about how many times can you get around that loop, and what, what are you putting... 'Cause I, I worry that people are loaded up with knowledge and feel almost, um... I meet some of these leaders and they feel beaten up by the advice industry. They feel beaten up that they can never be good enough, they cannot be like whatever company or, you know, they feel like their, their company's never good enough, like th- they can't empower their team. You know, they just can't follow anyone's advice. And so I think people are beating themselves up when I think that you should, for some people to focus to like taking that knowledge and just getting that loop going for your teams, or getting that loop going for your career, or getting that loop going for your company is like probably like a pretty safe bet. So I would think that's uh, that's like one thing that comes to mind.

Episode duration: 1:40:43