Jan. 15, 2023

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

John Cutler writes the popular and beloved product newsletter The Beautiful Mess. For many years, he was a Product Evangelist at Amplitude, which led him to meeting and working with a large number of product teams around the world. Through this role, he gained unique insight into how the best product teams operate. In today’s episode, John reflects on leaving his role at Amplitude, and explains the attributes that the top 1% of product teams share. We also go deep into some of his favorite frameworks and discuss the best way to apply these frameworks to your work. We also unpack skills like product sense and product mindset, and what he’s planning in his new role at Toast.

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Where to find John Cutler:

• Twitter: https://twitter.com/johncutlefish

• LinkedIn: https://www.linkedin.com/in/johnpcutler/

• Newsletter: https://cutlefish.substack.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/


• Amplitude: https://amplitude.com/

• The North Star Playbook: https://info.amplitude.com/north-star-playbook

• Craig Daniel on LinkedIn: https://www.linkedin.com/in/craigmdaniel/

Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• AppFolio: https://www.appfolio.com/

• High Leverage Product Evangelism: https://cutlefish.substack.com/p/high-leverage-product-evangelism

• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/

The Culture Map: Breaking Through the Invisible Boundaries of Global Business: https://www.amazon.com/Culture-Map-Breaking-Invisible-Boundaries/dp/1610392507

• Innovation Labs: https://innovationlabs.com/

• BEES: https://mybeesapp.com/

• Marty Cagan on Lenny’s Podcast: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan#details

Sooner Safer Happier: Antipatterns and Patterns for Business Agility: https://www.amazon.com/Sooner-Safer-Happier-Patterns-Antipatterns/dp/1942788916

• Teresa Torres on LinkedIn: https://www.linkedin.com/in/teresatorres/

• Andrew Huberman on Instagram: https://www.instagram.com/hubermanlab/?hl=en

• TBM 49/52: Pyramid of Leadership Self/Other Awareness: https://cutlefish.substack.com/p/tbm-4952-pyramid-of-leadership-selfother

• ChatGPT: https://chat.openai.com/chat

How to Measure Anything: Finding the Value of Intangibles in Business: https://www.amazon.com/How-Measure-Anything-Intangibles-Business-ebook/dp/B00INUYS2U

Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339

User Story Mapping: Discover the Whole Story, Build the Right Product: https://www.amazon.com/User-Story-Mapping-Discover-Product/dp/B08TZGKKF2

Build with Maggie Crowley podcast: https://podcasts.apple.com/us/podcast/build-with-maggie-crowley/id1445050691

One Knight in Product podcast: https://www.oneknightinproduct.com/index.html#page-top

Sunny Bunnies on Netflix: https://www.netflix.com/title/81286920

Booba on Netflix: https://www.netflix.com/title/81011059

• Toast: https://pos.toasttab.com/

• Drift: https://www.drift.com/


John’s list of high-performing people worth following:

• Dr. Cat Hicks (@grimalkina) https://www.linkedin.com/in/drcathicks/ 

• Stephanie Leue https://www.linkedin.com/in/stephanie-leue/

• Amy Edmondson (@AmyCEdmondson) https://www.linkedin.com/in/amedmondson/

• Dominica DeGrandis (@dominicad) https://www.linkedin.com/in/dominicadeg/

• Courtney Kissler https://www.linkedin.com/in/courtney-kissler-0930681/

• Christina Wodtke (@cwodtke) https://www.linkedin.com/in/christinawodtke/

• Matthew Skelton https://www.linkedin.com/in/matthewskelton/

• Heidi Helfand (@heidihelfand): https://www.linkedin.com/in/heidihelfand/

In this episode, we cover:

(00:00) What is a product evangelist? John’s unique role at Amplitude

(05:50) John’s reflections and feelings on leaving Amplitude

(17:28) What John’s doing next

(18:52) John’s newsletter: The Beautiful Mess

(27:49) What do the top 1% of product teams have in common?

(40:08) Different ways companies are successful, and why anyone can improve

(45:55) Investing in people vs. investing in processes

(48:49) The importance of culture and values

(49:59) Global company cultures: the individualist vs. the collectivist  

(55:55) Why it’s hard to make changes in large companies

(58:49) How to view frameworks

(1:01:02) The spectrum of performance in big and small companies

(1:05:27) Examples of high-performing people who work outside of Silicon Valley

(1:09:02) The skill of product management

(1:11:35) The value of learning a bit about everything

(1:13:46) Why do people often underestimate the loops available at their company

(1:16:20) Chronic vs. acute issues at companies

(1:18:07) Unpacking the skills behind product sense and product mindset

(1:20:44) A place for people without the traditional meritocracy mindset

(1:22:38) John’s writing process and what he plans on writing about next

(1:27:52) How to use ChatGPT for learning and levity

(1:31:56) Lightning Round

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John Cutler (00:00:00):

Let's say you're a founder and you're trying to decide, should I invest more on processes, or should I invest more in 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 nudge yourself a little bit away from your happy plate, but you're not going to go super far. You're not going to go from like a process-driven meritocratic, X, Y, Z person all the way to like I'm going to start a collectivist company where everything is sort of a consensus decision to do that. You're not going to do that. But I think it starts with self-awareness and then that's how people form their authentic leadership vibe, and then they flex a little bit and then they embrace other perspectives.

Lenny (00:00:49):

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 John Cutler. John 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 John's writings over the years and share his stuff often, and so it was a real honor to chat in depth with John. 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 John 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 integration 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 integration 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.


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John Cutler, welcome to the podcast.

John Cutler (00:04:21):

Yeah, thanks for having me, Lenny.

Lenny (00:04:23):

I kind of know you as John Cutler. I feel weird to call you just John. Do you find that to be true, and also do people call you John Cuttlefish because of your Twitter handle?

John Cutler (00:04:32):

Yeah, John Cuttlefish. There is this, I learned yesterday, there's a DJ, a famous DJ called Jon Cutler without the H, so I don't know if are people into house music knew that. Yeah, I think usually it just, like most Johns, it forms into Cutler or JC or something like that, but just John is good, yeah, for now, or Cuttlefish, you could just call me Cuttlefish. That'd be fine.

Lenny (00:04:51):

You said that actually, we were talking before this, you said you do some music, so is that DJ actually you?

John Cutler (00:04:57):

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

Lenny (00:05:15):

Okay, this could be the next phase of your career which we'll talk a bit about. But let me just say that I'm 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, I hope you're ready for potentially a marathon of an episode.

John Cutler (00:05:40):

Sure, yeah, I'm ready. This is exciting. I'm on vacation now between jobs, so this is the highlight of my day. We can go all day if you want.

Lenny (00:05:47):

All right. Eight hours. Let's do it.

John Cutler (00:05:49):


Lenny (00:05:50):

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 give 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. So, 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?

John Cutler (00:06:16):

Yeah, absolutely. So, first off, I remember almost specifically the day that Sandhya from Amplitude reached out and was sort of floated this idea of this role to me, and I'm so grateful for Sandhya, and Justin, Matt Althauser, Spencer, the whole team, because it was really, it was really kind of a weird role from the beginning. They were starting to get more and more customers who were not traditional startups or kind of growth 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? I guess, kudos to them 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 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 uplevel our customers, sort of uplevel the broader product community. I call them current customers and future customers. That's how I woke up every day, I'm either talking to a current customer, I'm talking to a future customer. This product transformation's happening all around the world, just means it's a matter of time, 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. I wrote the North Star Playbook in partnership with Jason who was a co-writer with that. We did a lot of one-to-one coaching sessions. I had these things called product therapy sessions when I would just wake up in the morning and just kind of soak in whatever problem people were having for the day. I did meet with hundreds and hundreds of people and did workshops for thousands and thousands of people and talks for more than that, tens of thousands, really, in terms of the talks. So, it was just a, yeah, crazy experience doing that. So, the technical details is I 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 going, ultimately we moved that over to customer success, and I went back to marketing. So, that's the technical side of it, I reported into marketing.


But I do remember the day I arrived and probably a couple weeks later, we had our all hands 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 an evangelist is there to help uplevel 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. It kind of is a crazy role, for sure.

Lenny (00:09:16):

That is wild. You're basically like a free product coach for product team. You just come in, help them uplevel the way they build product, and then Amplitude becomes... You 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.

John Cutler (00:09:30):

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 companies put money in and that sort of creates skin in the game. 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 from that team that maybe we should have monetized all these workshops. I know Gibb and other people, they're charging 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. In the middle of the pandemic at one point we were like, "What are we going to do? We can't travel for workshops." And I would put in my newsletter, "Hey, anyone want a workshop?" And then suddenly, our sales team, we had to grapple with what are we going to do with these 120 leads, how are we going to work with them. It was funny having to deal with it.


But yeah, in general, this is a unique role. I would definitely consider a SaaS company's 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, Ibrahim, Justin, and Abbie, and when Sandhya was at the company, and just, 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 that does it. So, yeah, recommended. It's a little tricky, but yeah, it was a cool move to do.

Lenny (00:11:19):

That sounds like a future post, how to do this in a different way where they don't have a John Cutler in place. You said you worked with hundreds of teams. Maybe just give us some numbers roughly of how many companies have you worked with, how many product managers do you think you've spoken to in this career.

John Cutler (00:11:32):

Oh geez.

Lenny (00:11:33):

This phase of your career.

John Cutler (00:11:34):

So, I think I did it... There might have been over the four years, maybe 800 one-on-ones, individual leader one-on-ones. I'm thinking it was at the peak, it was in one year's 150 workshops and then overlapped in the next year, then between 200, but mostly the average maybe let's say three or 400 workshops, a hundred a year. It's heavy. And then there was these just general conference talks and other things that we're doing. I tried to total, I exported all my Google Calendar invites, I tried to categorize all them at some point, 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.


We started to have our, I think it was Sandhya 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 how your North Star 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 Sandhya'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, people are like, "We used," and I made a whole point of saying we did not invent this thing, 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 are our retention playbooks and engagement playbooks. 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 did they pull it together?" I did some research and our CS team developed 110-page bulk of research from working directly with customers around retention engagement, then we had a PM and a great content writer, Archana, zero in and kind of make it palatable, then we did ARC for it. So, it didn't just magically appear. People think that these artifacts that Amplitude has just magically appeared, but they were just... It's a company filled with passionate experts of these things, 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 cornerstone pieces of content for your company. You don't just snap your fingers one day. So, anyway, I wanted to point that out. Huge group effort for all these things.

Lenny (00:14:22):

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

John Cutler (00:14:26):

Oh geez. Well, the immense amount of gratitude, definitely, mention that, wonderful people, wonderful customers. Just imagine like if you're a product nerd, one day you're with Amazon, 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 Figma. So, really, once in a lifetime experience to be able to do that. In fact, if I had been a paid consultant, I never would've been able to do that. Another thing too is that there's this sort of selection bias. 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. This person thinks in a very different way 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 absorbing just attention from teams. You're meeting leaders who are about to leave. Five days later, you're meeting people who are trying to save their team from the pandemic, imploding everything they're doing. Yeah, I'm joke about the product therapy thing, but I would finish the day at 2:00 or 3:00 and then have to do another one. Wake up at 5:00 to do an EMEA workshop, 5:00 to 7:00, be two in workshop, then take a break, then do another two-hour workshop, and then talk to a leader about how everything was going to 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 working through our own challenges, and then it's 4:00 or 5:00 in the afternoon. I'm done. Oh, to be able to do that.


And then I think it also left me with a couple key lessons we could probably go into later when we're doing it. One, you are talking to a bunch of different companies, achieving the almost similar results in very, very different ways. They behave in different ways, the context in the pandemic or the economy. 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 joked with someone at Amplitude, they're like, "We were going through our own shit," and I'm like, "Yeah, and I've seen how 50 other companies are going through their own shit," where this is you're doing it. So, the power of context.


The regional differences were so fascinating. I was on with a teen that was based in India and just the passion and curiosity. There was not one jaded person in the room. There was not one person like, "Been there, done that. When's the performance review cycle ending?" or anything like that. It was just all-out passion and hunger for information. So, those days were amazing. So, yeah, you talk a lot about it, but it definitely, it feels like a relief in some ways because the amount of tension to do it. And so, for my next plan actually what I'm doing is I'm going to work at Toast in a couple weeks, and I've been in touch with 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 help put most of my energy into helping my own company. They're growing super fast, so the numbers are in the hundreds of everything or in the thousands of everything, and they're not just the POS business. They've got these different businesses, like guest services and back office stuff and things. Amplitude is a super horizontal, if you think about it, it's almost like a diagonal, and so it made your head spin, and I kind of wanted to go back to a vertical SaaS. There's a company here in Santa Barbara called AppFolio that I like working at, and I really had a soft spot for vertical SaaS, but I'm thinking put my energy into an internal team for a little bit to pivot back into that. And so, I'll be helping enable product teams and sort of doing what I was doing, but within a company as well. So, it's going to be an interesting shift.

Lenny (00:18:29):

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

John Cutler (00:18:42):

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

Lenny (00:18:52):

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. You have a lot of fans on Twitter and there's a ton of questions, and one actually got pretty spicy and I want to 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, 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 messy which is appropriate because your newsletter is called A Beautiful Mess. 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?

John Cutler (00:19:38):

I was reflecting that the newsletter, it's almost like an emo band, The Beautiful Mess, it's so angsty. It couldn't have been more... If I had a band, I did not have an emo band when I was 16, but if I did, I would've called it The Beautiful Mess. So, it's probably pretty consistent with personality to do those things. I mean, I actually really appreciated Jason pointing that out, and in fact, 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, it's important to me," and then what it's like to just be a weirdo. We all have our weird freak things to do these things. And so, 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 a little background about the newsletter and what I was looking for that.


And so, I think that the first thing that I did was four years ago, I kind of scanned the product advice landscape and I noticed three things. First, there's sort of three perspectives that pervaded, and again, I just want to 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 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 international worldviews too, but there was 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 meritocracy. 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 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 often very context free, and I mean that actually in the nicest way. It was optimized to make sure that it could be actionable, that someone could take that away. That's what I really like about the content that you put out there, and I like about a lot of the guests on the podcast. They kind of lay it out in those particular things. And so, to kind of go through, yeah, those tools, skills, mindset, that makes sense, right? Who does not want tools to be better? In fact, a lot of the podcasts I like, we can get into that later, are like, "We're going to 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 this idea of success be mostly about individual skills in jobs. So, this idea of great leaders, high performing teams, 10 x people, 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 very mysterious. So, again, I'm going to 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 that happen behind those things."


So, the meritocracy stuff and the individualism stuff, it's 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 hierarchical 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 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 were pretty individualistic, so the advice probably lands with people really, really well, and then also it's really actionable," and said, "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, 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 United States. Your team is in a team of many, many teams in your company. The systems are non-linear. The bird flapping its wings in Brazil creates the tornado type of stuff. And so, I wanted to make sure that we got dug into that particular stuff in The Beautiful Mess stuff.


The next thing is that I'm a sucker for weird counterintuitive dynamics in companies. I don't know what it is. I absolutely love that. And so, maybe I'll give two examples. One, I'm obsessed with this idea of high work in progress, from a human level and a team level. 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? And so, in the newsletter, I wanted to explore stuff like that, like why, when a bunch of people know irrationally 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 load themself up with work? What are they optimizing about? So, that'd be like one example of counterintuitive stuff.


The other stuff is strategy stuff. Every company has these three pillars, and it seems really smart for the CEO to have this really clear three pillars, but then everyone walks away from the meeting and be like, "I don't know what we're with doing." That's another example of a counterintuitive thing. So, 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, I would say I'm really, really triggered. People will say, "But it's probably triggered by Jason." He said, "Why? Bring solutions not just problems." That's my krypton, right? I like the systems thinking stuff. I like all that. So, anyway, long story short, wanted to help people like me. I like the complexity stuff. I like all these weird counterintuitive dynamics. And then I thought that there's a lot of representation for the very deterministic advice that people have.

Lenny (00:26:02):

That's a really good explanation. There-

PART 1 OF 4 ENDS [00:26:04]

John Cutler (00:26:00):

... advice that people have.

Lenny (00:26:02):

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

John Cutler (00:26:10):

I love the fact that people scan the market and say, "People want to know about prioritization and so I'm going to tell the world about prioritization." I really like that. In fact, I admire, I'm jealous of people who can produce that kind of content realistically. Interestingly enough, probably in my doodling in post I've probably given frameworks to do that. I just don't think too much about it. I just kind of go in these things. 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. That's the difference.


Back to this thing of complex problems, I think it's the difference between oversimplification and focusing. You can have 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 going to make any progress unless we hold some things constant to do that. That's, to me, the balance I'm playing all the time between how many variables to hold constant to make sure that people can get some value out of it. I don't know about you, but that's the tension I have. But you write really actionable stuff and so I really admire that too. I'm jealous.

Lenny (00:27:15):

I try, but then I'm jealous of always having to nail it down to something very concrete and simple. This last post actually was a little bit of an balancing act where I wrote about how virality is mostly a myth, and I added the word mostly to it at the end. Then I was like, "Should I just go for it and be like virality is fully a myth?" But no, it's not actually, so I can't really go that far.

John Cutler (00:27:35):

See, it's kind of messy.

Lenny (00:27:36):

It's kind of messy.

John Cutler (00:27:38):

I love that. In the spectrum of advice, every post of mine will say mostly, maybe, it depends, so we all have some opportunity to flex into the other direction.

Lenny (00:27:49):

Shifting a little bit, coming back to just the bigger picture of John Cutler, you've had more exposure I think to product teams and product managers, you're definitely in the top 1% of people that have talked to and met with and seen what happens within product teams. There's a lot of stuff I want to dig into there and the first is around what you've found differentiates the highest performing teams. Let me just ask you this very succinct question and see where it goes. If you had to just boil it down, what have you seen most differentiates the highest performing product teams?

John Cutler (00:28:26):

First of all, they're top 1%, they're super, super productive, they can levitate, they can do ... they have no emotion. No, I'm just kidding. No. Okay, this is my tack for answering the question. First of all, 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. In Anna Karenina, Tolstoy is basically the 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 or the higher performing companies can be very, very different.


That's something that stuck with me because either you have easy to identify anti patterns, and I'm going to admit earlier in my career, maybe five or six years ago, 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." Even Spencer and I had this thing. I put something on Twitter and Spencer writes me, he's like, "John, is this about amplitude?" and I'm like, "No man. It's like that Carly Simon song, Spencer. You probably think this song is about you, but it's not." It just is. It's just like those things. Either you have the very easy to identify anti patterns or you have the high level principles, 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 vastly, vastly, vastly different. Let's just start with that as a basic thing, which is one reason why it makes me hard to answer the question. A great example here is great product leadership. We need great product leaders. But you meet [inaudible 00:30:11] product leaders and you see that some people are these humble, curious servant product leaders. They're not really talking a lot and they're just growing the system that way. You know what? There's other companies with really successful people that are just badass, strong, dominant, they like to spar. I need people who can spar with me. That's just one potential example there of okay, you meet enough teams and you see that there's many ways to achieve great leadership [inaudible 00:30:41] example.


Another example would be, and then I'm going to start listing these things off and then hopefully this makes more sense.

Lenny (00:30:46):

Yeah, it feels great.

John Cutler (00:30:48):

You meet lots of great teams and the better teams make high, better decisions faster. Now, that's like that high level thing that I say that to you and you're probably like, "Well, no shit. That's what I would assume to do that." But if you think about good decisions and stuff, like what do you need for good decisions? You need information, 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.


Those are 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 to do that." But then if you think about three companies. We could even play the game together. I'll give you two, you could give me the third one. But let's say company A buys into the whole idea of an extremely rigorous decision-making process. It's very process driven. It's like you do this, you do that, we red team our decisions, we bring in people to push back, we've got this particular thing. Maybe that's how they achieve it. Company B, maybe they're just all about this kind of mushy, diverse perspectives thing. They're not very process driven, but they achieve really good decisions by making sure that there's these serendipitous connections between people at the right time with the right set of [inaudible 00:32:08].


There are highly successful companies that achieve both of those particular things. I don't know, what am I missing? Lenny, you think about it. There's the rigorous process driven approach, then there's the company that's all about the ad hoc work together collaborative approach. What's another way that some companies make really good decisions all the time?

Lenny (00:32:28):

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

John Cutler (00:32:32):

Absolutely. So this is the thing, I'm sitting there and the very idealistic product managers are like, "You got to have empowered teams and you got to 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 and they do it." You find people who really like the process driven approach and you find people who do those things. That's one principle done a different way. But then I'll just take a couple principles. I just wanted to get that out of the way, that every one of these I mentioned could be achieved in a couple different ways.


The first thing you notice is the companies that are very high performing have coherence between the structure of their company and their current strategy. This is a structural thing, I think when there's startups, things are very fluid and the strategy's in flux, and so they have a fluid structure, but then as companies grow, there's sort of a physics to the problem that starts to catch up to the particular things. Their funding approach, their incentives, the org structure, the architecture, even their technical architecture supports their strategy back and forth. The reason why I mentioned this one is you can have brilliant teams. You meet these brilliant teams where they've just hired in the best of the best and they're just struggling with a strategy structure mismatch and no amount of let's empower people or no amount of doing whatever is going to knock them out of that.


So what do you need? You need a strategy, then you need to line the structure around it. This is different than saying ... you're asking me what do I observe when they're doing really well? Now, the tactics to achieve this might be different depending on the company, but you could get that. I think the second thing, if I admit it, is 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 even believing that this is a done deal and you just need to move faster than 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.


There is just a stubborn, strongly held belief that is then balanced with their ability to have the loosely held thing. I would just observed this in meeting after meeting with these teams that seem to be having a bout of being more high performing. They would be stubborn about some things that they were doing even when it didn't make sense in the short term and then they would do that. I think that that's another thing. I think related to that when it comes to the product world is just a core belief in the power of products. The Jeff Bezos thing, that the success of today was set in motion three years ago, that product is a layer cake and that you are layering on decisions, the success you're having now is 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 AB 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. 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 a nine craft level product versus a seven craft level product or six craft level product. I think that that's another component. I have a couple more in depth like that.


Definitely the leadership is coherent, so that's 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. There are companies probably all know that outspoken, domineering believe that the company just should be run a certain way and they set this vibe, this coherent ... that their actions and words match together. When you think about it that way, it makes more sense. The company that's like, "Oh, well we want to empower our teams and do whatever and we believe in our customers," and their actions don't match those particular things, that's not very, very coherent to do these particular things. I think that that's one, the coherent things.


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. Here's a challenge we had in Amplitude, just sharing this, is 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 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 mediated obviously between the environment to do those things.


Then like all the other, they know how to build software, things don't break, they can experiment without risks. I don't know. They have positive habits. I could go on and on. Hopefully this is helpful just hearing my thought process to go through these things. But I think that 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 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 common sense hiring. They're just talking about de-biasing the hiring and having standards and having those linked into the jobs and just not rushing it."


It's like these things that seem so common sense are actually hard with what they're doing. 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 to put in motion.

Lenny (00:38:53):

Yeah, and there's also a lot of power to just making it a very important value to the company. Just calling it bar raisers-

John Cutler (00:39:02):

[inaudible 00:39:02]. I'll use the example of a company. I mentioned this company AppFolio here in Santa Barbara, but Klaus and Jon who founded that company, it's just a gem of a company, it's an amazing vertical B2B SaaS company. But I think in the story that they tell us when they started AppFolio, they're like, "We want to find a place where the money flows and we want to be really close to customers and we just want to ..." Well, they were engineers who had seen the light around customer development, just getting close to customers, just being in service to the customers, not just gold plating every technical decision you did. They bought in early to the ideas of test-driven development, pair programming because they believe that the quality ... you should never be worried about the quality. They just believe that quality wasn't something you sacrifice as the norm. It's just got to work.


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 how much customer contact is it not?" These two founders basically are like, "That's it. We don't sacrifice on those things." They've done really well with that.

Lenny (00:40:08):

That's a thread I want to 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 just shared and then I have a two part question around this. I wrote these down. Basically the things you've found are true for the companies that seem to be best at building product and software and 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. Then five is just the necessary skills and experience in building stuff they're building.

John Cutler (00:40:51):

Contextual skills too. Yeah, exactly.

Lenny (00:40:54):

Kind of a two part question. One is if there's a pie chart of what contributes to this working out, what percentage would you say is just the people that they hire that contributes to them succeeding here? Then related question is just like can you change a team to be high performing? 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?

John Cutler (00:41:18):

The pie chart, that's the problem. I mean, that is the trillion dollar question so I don't really have an answer. I have a couple thoughts on it. What do we know? 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 and we know on the other side of the problem is if no one's done this before, who knows? Because how many startups were started by people who hadn't done it before, who had passion for doing something? Now, they made a lot of mistakes. Now, granted people would say, "All right, now after three failures, I'm going to tell you what we need to do to succeed," so maybe they have to fail a couple times to do that.


With the right things in motion, you can do that. Also, 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 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. 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. I'm not going to throw out a percentage point into it. I'm just going to note that I think that the biggest challenge is that we all need to challenge our biases.


I do too. Four or five years ago, I would've said, well, personal skill's nothing. It's all the environment. There's people on Twitter who do this all the time. They're like, "Bad management kills everything. Skills aren't important. You should just be able to do anything with anyone." I used to be one of those particular people and I also have this sort of humanist bent to what I'm doing, and so I very much want to believe ... I'm always the person that's like, "Oh, we should give them the seventh chance." 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. They're the people who are like, "Well, it's 100% their skill. We will hire complete A plus players all a particular time. Everything will work out as expected." 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."


But how many companies in general will hire a string of highly qualified people into a particular department and then fail each particular time? I don't know. I don't have the answer for you on that one, but I think that everyone can benefit from challenging maybe their happy place, me included [inaudible 00:43:57].

Lenny (00:43:57):

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

John Cutler (00:44:05):

And give it a shot and then can you create a coherent environment where maybe that could happen. Frankly, we're maybe getting into this later, there's a lot of companies that were flying high and are not flying high anymore. High performance is not this 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 and we feel those lows. That's kind of how I think about that particular thing.

Lenny (00:44:37):

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Coming back to the first question about people, and maybe you just answered this, but do you find that it's all about the people and who you hire and may be at the top that lead to the result at the company? Or you're saying it's sometimes the right amazing people? Sometimes it's the process, sometimes it's the market, [inaudible 00:46:12]

John Cutler (00:46:12):

It's the latter and I think that's why I called the damn thing the beautiful mess. Because I think we all have confirmation bias. We'll point to that company and say ... I mean, let me just use an example. Satya Nadella and Microsoft. You could argue you 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 did? He got rid of some bad people and created the air cover and set in motion the couple of strategic imperatives that we're going to 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 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.


Even that situation, you can idolize that particular leader for doing it, but there's many things that could happen to be able to do that. There's this idea of great man theory, and this is something I talk about a lot where in great man theory success is the result of these highly influential, highly effective men, in a lot of cases, and that you can explain history through these heroic men. That's sort of a thing. A lot of people base history on doing that. I think that this, again, just the other perspective here is that things are a lot messier and you can't just trace everything to these sort of single heroes men in many cases that make it happen. I'm just presenting both sides of it as we kind of dig into it. I think, though, 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? Not just what do I believe in that you think the whole rest of the world ... 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? You know what? You can nudge yourself a little bit away from your happy place, but you're not going to go super far. You're not going to go from a process-driven, meritocratic, X, Y, Z person all the way to I'm going to start a collectivist company where everything is sort of the consensus decision to do that. You're not going to do that. But I think it starts with self-awareness and then that's how people form their authentic leadership vibe and then they flex a little bit and then they embrace other perspectives. That's just my perspective on it.

Lenny (00:48:49):

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 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, it's not necessarily the person. Could just be other factors that make it feel like everything's going great.

John Cutler (00:49:16):

And people are great. There are people that have an outsized effect in particular companies. A great example there is 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. So well, there's that great man leaders, 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. If you talk to any CEO, they'll be like, "You think [inaudible 00:49:47]. I've got people bossing me around too." It's always a mix. That's the way I see it.

Lenny (00:49:54):

Which is why if things don't go well, their ass is on the line.

John Cutler (00:49:58):

Yeah, exactly.

Lenny (00:49:59):

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 the power and importance of, I don't know, strong value, strong culture. Have you found that that's just not essential? What are your thoughts on-

John Cutler (00:50:13):

No, I think it's kind of the fabric that creates those other things. It's the fabric that creates coherence. 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, maybe I just almost take it for granted that that's sitting underneath those particular things. But here's an example where sometimes nuances matter. I'll just use Amplitude. We had some values and we had HOG, humility, and it's this idea of ownership and a growth mindset to do these things.


Ownership defined in an individualistic culture is going to look very, very different than ownership defined in a collectivist culture. What I find with companies is that ... 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 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 ... what we would do successfully and Spencer and other people do successfully is talk about the behaviors that represented that level of ownership, then that tells you something about what the culture is. Maybe when I was answering that, I kind of took that for granted. But there's a set of beliefs and values that sit underneath all those things, I bet.

Lenny (00:51:38):

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

John Cutler (00:51:52):

I will mention some companies, but I'm not going to mention what people think in doing this. I'm just going to mention moments where I was like, "This thing is really clicking," and not because it wasn't easy-

PART 2 OF 4 ENDS [00:52:04]

John Cutler (00:52:00):

I was like, this thing is really clicking.

Lenny (00:52:01):


John Cutler (00:52:02):

And not because it wasn't easy, or 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. This is really hard. This business is transforming. They've got one of the biggest, most iconic brands in the whole world at their hands. And I'm sitting and I'm just going to single out her. Yeah, there's this situation here. It's not easy, it's not great. It's not high performing by any, you take a tiny Silicon Valley company. Yeah, it's hard to be 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 what I got to say to this question. I think of it more of these moments where I'm like, "Wow, this shits hard. 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.


Some of these larger companies might take a decade to really work themselves through. And so I don't know, when you asked that question, I thought more about 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...

Lenny (00:53:21):


John Cutler (00:53:22):

Yeah, I'm not going to give a lot of names.

Lenny (00:53:22):

No, it's great.

John Cutler (00:53:23):

But just shout out Angela. She's doing an awesome job.

Lenny (00:53:25):

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

John Cutler (00:53:46):

Yeah. And again, I'm not an expert in this and I think Erin Meyer wrote that or Meyer, I'm not sure how to pronounce her name, wrote that book, The Culture Map. And so you should just find what those people wrote because they're much smarter than I am about this. But here's the individual things that I noticed is definitely the individualist and what I would call almost like communitarian vibe.


The idea of 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'll find this situation where you've got this one engineering manager and they are brokering the projects with every single engineer on their team and everyone wants the promotion.


And there's this whole, instead of the PM 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. There's no pair programming. There's nothing like that. That's a whole other debate, but. And so that's 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 18 months or 24 months or... 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 much more consensus driven. The team perceives itself as a team having a team goal.


They have a team objective. And certainly even in the Bay Area, there's companies that are more the collectivist vibe and the more. So to say that it's just about the world is not really just right. So I think that yeah, the collectivist individualistic thing is important. I do think that certain cultures are much more sort of hierarchically oriented.


There's much more deference to the hierarchy in the particular where people are sitting and the information flows in a certain way. And 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, you do this. So it's not like rules are flowing from the top down. It's more just 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.

Lenny (00:55:55):

This 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.

John Cutler (00:56:06):


Lenny (00:56:06):

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

John Cutler (00:56:11):


Lenny (00:56:11):

They're 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 advice doesn't actually work for them. What have you found along those lines of just companies going through this and things you've learned there?

John Cutler (00:56:24):

So putting myself in the shoes of those particular companies, like I said, I think some of my most rewarding interactions have been with these 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 thing to keep in mind is that those, let's just take these bigger companies for a second, big enterprise companies. Part of the thing is just realizing how much inertia they're up against when you're chatting them. So I do believe that there's some structural things that probably they could avoid, but then there's also just structural things that are just part of the game to do that.


So 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. Certainly in a lot of 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 crazy annual budgeting cycles and planning cycles, or maybe there's a big IT industrial complex that they're sort of trying to transform into doing these things. So anyway, my point is, is that they, so many of these companies just have structural things that make it very difficult 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 larger kind of transforming companies. And I think that the couple things that I sort of remark on is that one, 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, a team can get in the reps that they're trying to be able to do.


So it's sort of a little miniature version of that. And 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.

Lenny (00:58:41):

And reps meaning shipping, shipping product.

John Cutler (00:58:43):

Shipping and learning, going through the full loop. Can they go through the full loop of what they're doing? And I think that the other thing that comes up with that is that most of those companies need to think of frameworks appropriately.


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. They kind of look there. And sometimes maybe even you write a post, it's like, "Well, how does Figma work?" And they're like, "We use these frameworks."

Lenny (00:58:57):


John Cutler (00:59:15):

And so this company's like, "Well, we've got to use these framework." 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 that's another thing maybe some of those companies could benefit from doing, where we're getting kind of more into the kind of digital transformation or the big company space. But I think 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. The only disruption has come from scale, not from being a legacy, a huge global brand or huge global business, and then being disrupted by new things. The only problems, not the only because it's really hard, but 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 rideshare and food delivery conglomerates are figuring out. They're like, " Oh, this is a lot harder than we thought." When you're dealing with moving people around and logistics and things, 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 adapt this advice on the small instead of thinking they're just going to install all the frameworks or install everything they're doing.

Lenny (01:01:02):

Yeah, this is really, really good advice. I imagine folks are listening that may be working at a company like that. It feels like there's two sides to it. One is there should just be an awareness of this may not work at us, we're not going to be Figma.

John Cutler (01:01:02):


Lenny (01:01:15):

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

John Cutler (01:01:29):

But maybe it can. And I talk about this a lot, 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 they can do that actually overestimate the kind of 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. 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. I'm a genius 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. We paint some of these large enterprises on one end of the spectrum and then these other company, these modern product companies. But I brought up that plumbing company in Australia. You meet these companies, you know what? Their revenue is literally 50 startups. 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 a liquor distribution app. And it's literally one of the biggest B2B companies in the world. And you know what? Anheuser-Busch, it's like what? We're going to distribute beer because the pandemic. And so we're going to have, and I think actually they started to become more even used for logistics.


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, there's the big smoke companies and then there's the fast nimble companies, but there's everything in between. Another example is a lot of tech companies started 2000 to 2008, kind of are on their third or fourth act at the moment, second or third or fourth act, bought a lot of companies, they're trying to absorb them.


They might be trying a product-led growth motion by spanning all the different acquisitions they had. You know what? They are on top of their game. This is not a slouch company, but it's really hard for them to do that. Or we at Amplitude, we'd have a lot of, not old FinTech, but not newest companies. They're printing money and they're just embracing this particular thing. And then compare that to, I did a big Northstar session or more of a coaching session at NewBank in Brazil when there was just 15 people in a room and now they're massive.


So I think that we tend to paint things as a form of modern product adoption. There's 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 Angela and her team or 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. And Carrie, who's the leader there, that company is one of the best leaders I know.


And Jesse, who's one of the founders is Harvard PhD student who understands AI doing these things. And I actually would encourage a lot of PMs to think about, look, especially in this economy, what are these unsexy businesses that are kicking butt and small here, it's in sunny Santa Barbara? So I don't know. I think that there's a lot more diversity than just the high performing, low performing spectrum. There's just a whole universe of fun companies out there.

Lenny (01:05:26):

Well, as you were talking, I was thinking about there's a small group of people like you and Marty Kagan 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. Marty Kagan is who comes to mind first, but I don't know if you have anyone else. And if not, that's all good.

John Cutler (01:05:52):

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

Lenny (01:06:00):


John Cutler (01:06:01):

List a couple of these.

Lenny (01:06:01):

We'll put it in the show notes.

John Cutler (01:06:02):

And I'll give you an example of 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 what, he led this transformation. And then 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 the thing book, the book is really interesting. And the thing that I noticed when talking to John is the order of magnitude of complexity of problems that has unraveled and what he had to put in motion to take an old school bank and at least try to get some part of some kind of transformation working in that particular company, I think there's a whole realm of people like that. And I'm going to list a, maybe I'll follow up with a couple more lists of people.

Lenny (01:06:57):


John Cutler (01:06:58):

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. You can teach an element of product thinking with her techniques or this opportunity solution tree or this continuous discovery thing that everyone can find accessible no matter where your company is at. And I have a lot of respect for those types of techniques because they're more universal versus some very arcane niche activity.

Lenny (01:07:36):

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

John Cutler (01:07:41):


Lenny (01:07:42):

So I've been asking a lot of very specific questions. I want to give us a chance to kind of zoom out a little bit.

John Cutler (01:07:46):


Lenny (01:07:47):

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

John Cutler (01:08:04):

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

Lenny (01:08:04):


John Cutler (01:08:19):

Get these podcasts going. You can listen to anything you want.

Lenny (01:08:22):


John Cutler (01:08:23):

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

Lenny (01:08:38):

Right. Cold plunge.

John Cutler (01:08:39):

Can I be healthier.

Lenny (01:08:40):

Sunlight. Yeah.

John Cutler (01:08:41):

Yeah. I got my sunlight. I went from my sunlight before screens to prepare for our talk today.

Lenny (01:08:47):

Wait, actually?

John Cutler (01:08:47):


Lenny (01:08:48):

That's great.

John Cutler (01:08:49):

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

Lenny (01:08:59):

Yeah. Optimizing.

John Cutler (01:09:02):

But I think that you need to keep in mind that 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 the particular things. And so I think that I learned about that a lot working with learning experience designers in Amplitude that 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 in Amplitude, we have this data informed product loop that we would teach, and it's basically, you need a strategy, you need to develop qualitative models, you need to add measurement to those models. So Northstar 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 learned 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 them. We could do all that right, but you don't design any bets and can't ship anything. Oh, that's kind of a problem. But you could do all that right and you don't know the impact of anything you ship.


But you could even do all that right and not circulate the learning back in your company and then you're still not going to succeed in these things. So that's an example of when I mean by 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, 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 are you putting, because I worry that people are loaded up with knowledge and feel almost... 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 they feel like their company's never good enough, like they can't empower their team, they just can't follow anyone's advice. And so I think people are beating themselves up when I think that you shift for some people to focus to 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 probably a pretty safe bet. So I would think that that's one thing that comes to mind.

Lenny (01:11:31):

Partly being responsible for some of that is what I...

John Cutler (01:11:34):

Yeah, me too.

Lenny (01:11:35):

My advice to people is don't feel like you need to read everything coming across your plate.

John Cutler (01:11:40):


Lenny (01:11:40):

It's instead wait for the moment when you need that thing. I'm working on SEO right now. Cool.

John Cutler (01:11:40):


Lenny (01:11:45):

I saved that thing about SEO, I'm going to go do it. Just like a just in time learning because you learn it so much better and like, "Oh, shit. I have to load all the stuff in my head in case it becomes useful."

John Cutler (01:11:53):

Absolutely. And I think one thing you think of is think about the podcast you listen to and think about that content is almost like you don't know what you don't know often. So I think that the challenge is, is that if you've been doing PM for a while, product management for a while, you don't really, I don't fit everything in my head.


I just, for example, pricing. I know pricing is a thing. I know that there's some people are amazing at pricing. I know that if someone told me like, "Well, you should just price it like this," my spidey sense would say, "You don't know what you're talking about because I know that there's more to it than just what you just said." You develop your spidey sense for things and you know that there's people. You have to dip your toes in understanding. That's the beauty of podcasts, your mind can get blown and then it puts in the back of your brain. You're like, there are some people who know a lot about that versus the founder who believes that they're going to figure everything out for themselves and is just like, no, it's actually a thing.


Pricing is a thing or you know what? Meeting design is a thing. There's people who obsess about it or service design is a thing or interaction design or strategy [inaudible 01:12:56]. So that's building on what you said, I think that there is a, especially if you're starting out, there is a definite value of almost seeing the 501 level courses or hearing that genius lecturer.


When you're in college as a freshman, I remember, I dropped out, but you would see the genius professor and you wouldn't understand any of it, but you'd know it's a thing and then it helped you guide the way you're doing. So I think that you should kind of balance out those things. But to your point, at the end of the day, you got to just put this stuff in motion somehow.

Lenny (01:13:25):


John Cutler (01:13:26):

How to do it.

Lenny (01:13:26):

And then just know that it's there when you need it. Find some way to store it.

John Cutler (01:13:30):


Lenny (01:13:30):

Save it. Maybe even just assume Google will find it for you.

John Cutler (01:13:33):


Lenny (01:13:33):

One more question along that same thread is you talked about the importance of going through these loops. At some companies, you just can't really, the company moves slowly, it's super waterfall, they plan really long. Do you have any advice for someone that's like, "Oh, I want to go through loops more often? This is really good advice."

John Cutler (01:13:47):

Point number one is you often underestimate what loops are available to you in that company. They throw up their hands. I've tried to mentor people like this and I think we've done a decent job, but the first thing I'm like, "Just don't throw up your hands and say it's all going to shit." Just at least document what was the.


So even if someone from on high says, "Build X," you can at least say, "You know what? Selected option is X. What would the one-pager look like if X was one of five options?" Write the one-pager. Go and talk to that executive and say, "Look, I know you've told me to do this, but what would we observe if this was working versus not working? I'm here to help you with that."


Great. You've got some metrics along [inaudible 01:14:29] is what you're doing. Just nudge it. Just one little thing. Hey, nothing's stopping you from writing down all the potential assumptions and risks that you have. Even if someone's like, "Forget all that, you're just going to build the thing." You've gone through the motions for doing it.


And I think people underestimate that because the environments are kind of feel like stellifying, I guess is one word, or stilted. And so they just sort of throw up their hands. But I would say that work with what you've got, because the last thing you want is to have a job opportunity two or three years from then and all you can do is shrug your shoulders and say, "I worked at a fucked up. I worked at a messed up company."

Lenny (01:15:09):

You can curse. It's all good.

John Cutler (01:15:10):

Yeah. Well, yeah. So you, "I worked at a messed up company. It was all shit." You're not really honoring yourself for doing that. So I'd say that that's my point about the fundamental attribution bias. Is it hard? Yes. Is it easier in those Silicon Valley companies? Well, maybe not. Maybe those are a shit show too. I've talked to plenty of them that are shit shows.


But do you have an opportunity to kind of nudge things forward in your space? Probably. And bring to the systems thing, is it true that some people don't have the privilege of leaving their company for whatever reason? That is true also. So many things can be true, but that doesn't mean that you can't try, I think to kind of almost write your portfolio as you go. Because if you wait two years, you're going to think it was just all a blur and messed up. Whereas the opportunities might be there in your day-to-day as you're working through.

Lenny (01:15:55):

I love how much your advice is optimistic and empowering and not just, "That's the way it is." And...

John Cutler (01:16:00):


Lenny (01:16:02):

And your point about how top tier companies can also be messed up and everything could be going to shit is very true. Especially a hyper-growth company where you're just...

John Cutler (01:16:11):


Lenny (01:16:11):

Constantly changing. It's also very chaotic and things are just breaking all the time.

John Cutler (01:16:16):

And there's people too who just assume it just has to be that way. I would say that one model that I use is the sort of the chronic and acute challenges of the companies. And especially in the last year, you meet a bunch of companies dealing with the same economic conditions. And I will tell you, no, not all companies are equally dysfunctional.


And no, not all high performing companies are equally beautiful in all roses. Legitimately some companies work down the chronic issues, which allows them to face the acute stressors, and other companies are just mired in acute issues to do those things. So it's kind of, again, both things can be true. It's like, yeah, there's nothing perfect in product. However, it is true that some companies are healthier than others.


An example of that is the companies that leaned in to responding to the pandemic instead of counting the days until it was over. Massive difference. I've seen this over and over, probably with 15 to 20 companies. The companies that were intentional in designing their response to the pandemic versus being like, "Just let managers deal with it, whatever, we're just going to sort it out," have had an order of magnitude better.


Now maybe the share price hasn't necessarily reflected it, but the happiness of the people there, they're going to come out of this stronger than the companies that were just like, "It's going to go back to normal and we're going to delay all these org design decisions until some future date." So I don't know if that tells you about high performing, but it's like the high performing companies saw the threat of what existed and then took deliberate steps, coherent steps to frame what their response would be. So that's just an example of that.

Lenny (01:17:54):

Awesome. I took us off track a little bit. I think you were going to go onto a second piece of advice.

John Cutler (01:18:00):

Yeah, I think that there's, well, okay, so one, definitely slightly annoy.

PART 3 OF 4 ENDS [01:18:04]

John Cutler (01:18:00):

Yeah, I think that there's, well, okay, so one definitely slightly annoying to me recently... I'll just get into the stuff that annoys me is that-

Lenny (01:18:06):

Let's do it.

John Cutler (01:18:07):

I personally don't think, I used to use words a lot, like product sense and product mindset and product things like that. I'm personally trying to do a better job this year about trying to unpack those things as legitimate skills and competencies. So if you think about product sense, what is it? Might be the ability to model problems, systems thinking, decision-making under conditions of uncertainty, facilitation tools that you have the ability to look at a competitive ecosystem and maybe see a thing and yeah, maybe there's a little bit of sense to it. It's like, "I want to help customers," or whatever. But I think that I'm trying to make a concerted effort to unpack those things into things that could be taught.


And that's going to certainly be part of my role at toast. The last thing I want to do is be like you have a product mindset or you don't. A great example, I was even talking with Craig just the other day and we were talking about how in some environments there's this should/can divide, which I really like, which is some people are just locked into the can. They're uber pragmatic people, so it's like, "Can we do this? Is it possible, given the debt, whatever constraints that you have?" And then there's people who for some reason go in and say, "Should we do it? What should we do here? If those things were not an issue, what should we do?" So it's very easy to... I joked with Craig, it's like it's so easy to go down the path of being like, "Well there's can people and should people, there's high agency people and low agency people, there's this person and that person."


It's much more interesting to go and be like, "Yeah, there might be a little bit of a personality component to it, but what skills is the should person bringing to bear on that particular situation?" Maybe it's a level of systems thinking, maybe it's a level of looking at the environment and being able to decouple the current tactics from maybe the optimal tactics for doing it. So that's one thing that I'm excited about, to do that. And yeah, there's a bunch of other things. The diverse perspectives, diverse mental models, maybe working with someone like you to try to raise up some of this more diverse... I really want someone to be like who's working at some company X, to be able to go and say, " Now that leader I can relate to, they're dealing with certain challenges that we are having to deal with at our company," and I'd love them to be able to have role models like that.

Lenny (01:20:41):

Like highlight people that aren't on Twitter that are doing the work.

John Cutler (01:20:46):

And not like meeting here. Not any of these particular people where they can say, "Well that leader..." I was speaking to someone recently, I wrote about this in my newsletter and she was just sort of forlorn. She was like, "I follow these people in this space and I know what my beliefs are and I know that that person has beliefs that I'm not sure vibing with completely. But the message to me is, the only way to get ahead in tech is to have those beliefs. And John, is that right? Do you need to believe this?" In this case, it was this very individualistic, very meritocratic kind of get ahead, push ahead type of vibe, which I respect that thought leader for putting out there, but this person didn't buy into it, which would've all been okay except she said, "Is there a place for me in this environment. Will I need to sacrifice my beliefs to get ahead?"


And I told her about some companies that I know. I told her about Carrie, who I just mentioned, who's been working on building the diversity, even in a small company. I told her about different leaders in different companies that, "Hey, there's some companies where it is a real team vibe and there's some companies that that", and she was like, "That's really good to know. So I think that that's one thing I want to work on in the next year, to make sure that people have role models and not the people talking like me, but actual... Maybe I could be a role model to people in my new role, but ideally there's role model leaders who they can relate to. That would be great.

Lenny (01:22:16):

Awesome. I love that. I feel like you just talking about that makes an impact there. Something I'm definitely trying to do with this podcast is not just have all the same people that we see on Twitter all day and have a lot of people people have never heard of, but if you have suggestions, let's definitely talk offline. I'd love to do more and more of this.

John Cutler (01:22:31):


Lenny (01:22:33):

So those are clearly some of the things on your mind as you're kind of in this period of reflection. I'm curious if you are going to keep writing and keep your newsletter up, maybe publish more books and then just broadly, how do you make time, while you have a day job, to write? Because a lot of people always wonder that. I'm curious if you have any pieces of advice.

John Cutler (01:22:54):

I'm obsessed with the writing, obviously, and I think a bit of background about me is I was pretty involved in music and song writing and it was similar kind of thing, I just liked writing lots of songs. I like that there's a certain buzz you get when you're creating. And in the case of music, it'd be like you record the demo and you get it out there. I think what people have correctly picked up on is because I have a full-time job, sometimes it'll be Thursday night and my kid's finally asleep and it's one in the morning and I'm just like, "I've got to write this post." And so sometimes it comes off as being a little bit rough or even accentuating the fact that I don't give them an answer because it's like two o'clock in the morning now and I don't want to give them an answer. I want to go to sleep to do these things.


So I think one of the things I'm going to hope to do is maybe be more deliberate about trying to provide at least maybe some mental models for dealing with the mess. I mean there's things like that out there. There's this thing [inaudible 01:23:57], which is a way to understand the systems and decision-making problems have, are you dealing with a clear system, a complicated system, a complex system, or a chaotic system? And I like things like that because that helps do two things I like. One, I want to give people something actionable to be able to address what they're doing, but it doesn't remove the complexity in the particular situation. So I have role models in that. This guy, Simon Wardly does this kind of mapping, which I think is great. There's these other techniques that I want to try to lean into and maybe develop some of my own that sort of help people have something actionable and embrace the mess, if that makes sense.


So for example, I recently wrote about something called the leadership, the Pyramid of Leadership, self awareness. And it's a simple model, but it goes deep how I want it to go deep. So the idea is that at first we know nothing about ourself and then the next level is that we start to become self-aware, but believe the whole world is wired just like we're wired. And then you go up to the next level and you believe that the world thinks different things, but you still think your way is the best way to be able to do that. So an example is, I remember talking to an executive and they're like, "People only stay because of their managers and because of their money. That's it." And I said, "Everyone?" They said, "Yes." "Do you believe that?" "Yes, because everyone believes it. It's a physical law of light." And here I am like, "Oh my God, I joined a company because the mission of the company or whatever."


So they're kind of stuck down on that second level where they believe that, "Yeah, the world thinks different things, but I'm absolutely right." And then as you get up to the top, you become a little bit more aware that there's other valid views and then at the top you're sort of like, "No, you don't dishonor yourself and throw away who you are, but you realize that this is a huge asset in the world, that there's diverse views that you can bring together to do really, really amazing things." So that's an example of some writing I've even done recently where I'm kind of like, it's a complex topic, but I try to make it more actionable to do that. So that's one whole thing. The other thing too is leveraging all the crap that I have. I think it's like 700, 800 posts, maybe 900.

Lenny (01:25:23):


John Cutler (01:26:07):

I had this whole blog beforehand that I did it. And then I have these hundreds of images with these frameworks and then it's like 50, 70 talks that I've done floating on YouTube and then there's all the mural boards I made at Amplitude. It's a different model. So I kind of feel like I could pull some of that together to make it more actionable for people, give people almost like a meta guide to Cutler content so that they're not just dropped into me writing something at 1:00 AM and being like, "Oh, just another one of those." Like, "Damn it, you didn't give me an alternative to NPS. This newsletter sucks." I mean, frankly, I would say the same thing too if I just stumbled into the newsletter to do it. So those are a couple things that I'm thinking about for the content, definitely not going to stop doing those, sharing those things and doing that. So yeah, excited about this next year.


Also, the question about writing, I mean, one thing with a full-time job where most of my work is internal, obviously I need to respect my team. Again, I go back to that funny thing with Spencer, he is like, "You're writing about Amplitude." I'm like, "No, dude, I'm not writing about Amplitude. It's like every company has that problem." But if I'm working alongside people, I obviously can't be like, "No," I can't say, "Oh, your manager sucks." It's like Craig's going to read that to do that particular thing, but I can, what I'm really excited about is that part of my job will be involving doing a lot of writing and a lot of teaching, is hopefully work it out with the company so that I can share things that are not too specific about the company, but much more. They've got five different businesses at Toast, they've got all these people, so it's going to be a education every day. So I'm hoping to maybe get that inspiring my work in different ways.

Lenny (01:27:40):

Amazing. I imagine you might rename your newsletter The Beautiful Mess, slightly less messy.

John Cutler (01:27:46):

Yeah. Jam and Toast. The Jam and Toast decision. The addition.

Lenny (01:27:50):


John Cutler (01:27:51):

Yeah, there we go. 2023.

Lenny (01:27:52):

Also, as you were talking, I imagined a chat GBT three type chat bot powered by John Cutler content could be something to try.

John Cutler (01:28:01):

Oh, it could be a funny, yeah, I mean I'm sort of obsessed. I like the ChatGPT thing because I like having things, having a developer inspired by Hemmingway debate, a developer inspired by Tolstoy discussing how to resolve a GIT issue. So that's what I've been obsessed by lately is when you know how ChatGPT works, you can actually make it do really funny things. And back to the worldview things, it's actually really effective. This is a very actionable tip, if you feel you're heavily grounded in let's say the, I don't know, maybe you're like a hardcore objectivist or you believe in individualism, you can just type into ChatGPT and say, "Take this situation and interpret it by five different worldviews." And it'll be like, you'll get the humanist view and you'll get the communitarian view and you'll get the collectivist view. You'll do that. So anyway, it's a fun tool for that. It's really cool.

Lenny (01:28:52):

It is awesome. We checked the checkbox talking about AI, very, very hot these days.

John Cutler (01:28:57):

Yep. Score.

Lenny (01:28:57):

Score. One final question before we get to our exciting lightning round, I'm going to come back to the questions that folks asked you on Twitter. And there's a question that I saved up and the question, it was by Jeff Fedor and his question to you, he was, "What have you always wanted to say but couldn't now that you're between gigs?"

John Cutler (01:29:18):

Oh, that's good. So one thing is I didn't really need to filter myself very much when I was at Amplitude, which is kind of the beauty of the gig. I wrote this blog post, probably six years ago called How to Know You're Working in a Feature Factory. And I've always, this has all been my jam. The outcome, outcome and impact focus thing. So it's not like I've really had to hide anything. And so one thing I could say is the power of qualitative data, but even Spencer says that too. He's talking about early on in Amplitude you can rely a lot on qualitative data. So that wouldn't be all that controversial. That's a funny thing. There's not that much, I pretty much say what I say partially under the guise that I'm talking to so many teams. So therefore it's never about Amplitude. Absolutely not.


I think the one thing that I would change, I don't think that many people in the company would disagree with me, but one anti pattern I see a lot on the part of implementing analytics is that people go in and undertake this huge implementation. They want to implement all their events, they want to get, they want to treat it like this big project. And again, I don't think it's too controversial internally, but I think I might have been much more adamant to people that's just like use our free plan and get 20 events going and you might wipe them out later, but you don't even know what you don't know yet. You would see these companies that are really qualified companies and it would be a couple months of back and forth of them trying to document every question they have and every metric they need and everything that you had.


And I would watch them and I understood why they were doing that, but I really just wanted to shake them, which again, I wouldn't have done this because then I would've been talking about the companies I was talking about every day. I just wanted to shake them and just, "Sit me down with the developers at your company for three hours and let's like Hello world, a couple events here, this is, you could be getting value this whole time." And again, I don't think that people at Amplitude would disagree, but I think that that's, I wasn't going to talk about that all day because that would be sort of belittling customers who do want this big implementation thing. So pretty kind of inside baseball for analytics, but that's one thing that I was thinking about for Jeff.

Lenny (01:31:41):

Awesome. Great answer. Also actionable advice. How about that?

John Cutler (01:31:44):

Yeah, can do. You just need to find it. You just send me a message and say, "Do you have the actionable advice for it?" I probably do somewhere. I just maybe didn't have the time to organize it.

Lenny (01:31:53):

Good tip. You're going to get a lot of DMs. With that, we've reached our very exciting lightning round. I've got five questions for you. I'm just going to go through and whatever comes to mind fire away. Are you ready?

John Cutler (01:32:06):

Yeah, yeah, absolutely.

Lenny (01:32:07):

What are two or three books that you've recommended most to other people?

John Cutler (01:32:11):

Yeah, this one's pretty easy because they are fairly similar lately. So I really like the book How to Measure Anything, finding Intangibles or Finding the Value of Intangibles in Business. So that's by Douglas Hubbard. And the reason why I like that is again, at Amplitude the number of people who would come in like, "What are all our competitors measuring? We want to know exactly which metric to measure." And again, I'm laughing with you because I know you have these posts. Here's exactly the metrics that you should track. I really respect those posts and that's the power that you have. That's all really good. But what Hubbard reminds you is why the hell are you measuring things to begin with? It's to reduce uncertainty for critical decisions or to achieve certain objectives that you have. The reason why it's important to read that book is A, you figure out someone who's again, actionable, has thought this through. So he gives you kind of a framework to thinking about it.


But B, he really challenges this idea of when making decisions in conditions of uncertainty, you only need to reduce the uncertainty to an acceptable amount to be able to make the next decision that you need to make. And we never have, people are like, "Product is science." It's really an art, like a game that's being played out. You never have complete information to do it. So I think that's a good book to remind people about what... To be more creative and thinking about measurement instead of thinking about measurement and metrics is just about adopting the exact metrics that everyone has and doing that.


The second one I think would probably be Accelerate. So Nicole Forsgren, Gene Kim, Jez Humble, that's just one of the best books in the world about the factors contributing to performance. And it's built on many... It's six, I don't know, it's been out for a while now, 10 years? They did the Dora report, which was their yearly report where they did big surveys, like 10, 20, 30, 40,000 people responding to it. And Nicole Forsgren is an amazing scientist. So they structure their thing correctly. They would have a hypothesis about what is equal to performance and how all these individual practices contribute to it.


And then they've updated it over time. And I think that Google bought Dora, I don't know exactly how all the parts came into place, but that book is amazing, just sort of teaching you how to think about the idea of performance because they'll include things like the Western topology, which is your company operating a bureaucracy or... These certain culture elements to it, but then also the practices and things that you're doing. So that's a great book when you're trying to think about, "How do I model performance?" And then it's also an amazing book because you can just literally put the stuff into motion about improving your development practices and things you're doing.


And then I think probably the last one, man, I just love this book, this Jeff Patton book about user story mapping. I love what Jeff Patton did. He took this extremely simple idea, which is that you can lay out a customer journey and then organize, take a slice across that journey and develop it. And he gives this pretty basic straightforward method to do it. But I tell you, I'll go into companies like a year after they had Jeff in and learned this and they're still like buzzing about, "Hey, user story map." And it's just, he's a super humble guy and he would never outstate the value of this. He'd be like, "Yeah, it's just a journey map with a couple sticky notes on it." But I always, when someone's new at product management, I'm like, "Hey, this is a deceptively simple book. You'll learn this very basic idea, but it'll teach you a lot about product when I do that." So those are three that come to mind.

Lenny (01:35:50):

Killer suggestions, I love answers of books I've never heard of that seem really amazing. So you check the checkbox there. Thank you. Next question. Favorite other podcast other than the one you're currently on?

John Cutler (01:36:02):

I'm in a... I got a four-year-old. I don't really spend a lot of time... I'm the sort of, I'm such a lightweight, it's like I'll do knowledge project because Shane sent me, you know what I mean? I'll just listen to some, I'll binge things, but I do really like, I've actually been going through old episodes of Maggie Crowley's podcast that she did when she was at Drift. Lots of good guests and I really like Maggie's perspective and I like the guests that she had on there. So sometimes I'll go back to an old podcast. He does these really great memes and stuff, but Jason Knight actually has a fun podcast that I listen to and some of those things. So I think that, but realistically I'm not a huge podcast listener. I'd like to go back to a podcast that hasn't been out for a while, like Maggie's and just sort of catch up on all the guests because I thought that was really good.

Lenny (01:36:52):

Awesome. Jason, we love hearing that. Next question. Favorite recent movie or TV show that you really enjoyed?

John Cutler (01:36:57):

Oh man, again, I have a kid. It's nothing. There's this thing called, there's a show called Sunny Bunnies. It's these fluffy bunnies. That's really good. And then there's this animated series called Booba and he's this funny guy. I like Booba [inaudible 01:37:13].

Lenny (01:37:13):

Great. I'm sure these will be useful to families.

John Cutler (01:37:17):

Hardcore product, movies. Really, those are going to up your game a lot.

Lenny (01:37:22):

Yeah, I'm sure there's something to learn. Two more questions. Favorite interview question that you like to ask folks?

John Cutler (01:37:30):

Oh, so one that I like to do is, I do the behavioral questions like, "Tell me about stuff," but then I'll ask them like, "Imagine I'm interviewing a person you worked with. Now answer in there, tell me about of the same situation." So you'll be like, "Oh, Lenny, tell me about a time that you were faced with adversity and you did this and then you worked with the team to do it. And you would go through it and then you'd answer it.


And then maybe in the process of doing that, you mentioned someone you work with and I'll be like, "Now imagine that you're Mary, who you just spoke about, and things, and how would she answer the tell me about thing as it relates to you?" And so I think it can show some really interesting self awareness. Often people answer that question like they are the hero of the story and the other people are the accomplices in it, but then if you challenge them, "What was that story from the perspective of one of the people you worked with?" I think it's really interesting.

Lenny (01:38:21):

Awesome. [inaudible 01:38:23].

John Cutler (01:38:23):

So it is a behavioral question. I do think that's the right way and if you dig enough you can really get the depth of the story, but I do think it's fun to challenge people to see how flexible their thinking could be about that situation. I don't know if that's right from an HR perspective, but I like it.

Lenny (01:38:39):

I like it too. Final question, you mentioned you have kids. What's the best lesson someone taught you about raising kids?

John Cutler (01:38:45):

It's a challenge every day. I just think they operate better when they are fed. The kid as a product is like if you feed the product, then they were just, everything's better. And when you don't, like everything falls apart. So just have snacks with you. That's basically the advice that I have for people.

Lenny (01:39:04):

Very practical. Look at you, actionable advice left and right.

John Cutler (01:39:07):

Yeah. You got it.

Lenny (01:39:09):

John, and I feel comfortable calling you John now, I feel like I just got to know you. You're just like, "I'm John now." We hit our goal of, I think it's going to be the longest episode I've done. This was amazing. John, we've reached the end. Two final questions. Where can folks find you online if they want to learn more, reach out, ask questions if you want them to? And then two, how can listeners be useful to you?

John Cutler (01:39:32):

I still am using Twitter a fair amount I think, but LinkedIn could be good. John Cuttlefish on Twitter and then just John Cutler at LinkedIn. Yeah, I think what I would love to hear from people is just send recommendations of people we should hear more from. I think that would be really helpful. Even in the role that I have, I want to start like a guest speaker series to bring people in to talk to our team. And so I think that that would be something that I can work on.

Lenny (01:40:02):

Amazing. John, thank you so much for doing this. I'm really excited for this new adventure that you're on, and I'm excited to maybe follow up maybe in a couple years of just what you've learned from this next phase of life.

John Cutler (01:40:14):

I really enjoyed the show and thank you for having me.

Lenny (01:40:17):

Awesome. Thanks, John.


Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenny'spodcast.com. See you in the next episode.

PART 4 OF 4 ENDS [01:40:43]