Lenny's Podcast: Product | Career | Growth - What sets great teams apart | Lane Shackleton (CPO of Coda)

Starting point is 00:00:00 moments that stretch you or moments that you feel uncomfortable in or you find yourself saying, like, oh, shit, you know, I shouldn't be here. I'm underqualified to be here. Those are the moments you should be seeking out, right? Those are the moments that stretch you and give you sort of like a new foundation. So oftentimes, you know, you'll hear like a career question like, hey, do you feel like you're growing in your role? And that's like a very ambiguous, in my opinion, way to ask this question. A much sharper way is like, hey, how many like, oh, shit moments have you had in the last like six months, year, two years? And what are they? I think if you ask yourself that question and the answer is it's been a really long time since I've been like stretched in some meaningful way or I've

Starting point is 00:00:43 felt like I'm underqualified to be there, then it may be worth kind of like digging into. Welcome to Lenny's podcast where interview world class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today, my guest is Lane Shackleton. Lane is Chief Product Officer at Cota, where he's held the role for over eight years. Before that, he was group product manager at YouTube, a product specialist at Google, and as you'll hear, he started his career as an Alaskan Mountain Guide, and then as a manual reviewer of Google AdWords ads.

Starting point is 00:01:16 Lane is an incredibly deep thinker, very first principles-oriented, and has built an incredible product team and culture at Cota. In part, he's done that by studying the principles and rituals of great product leaders and great product teams. In your conversation, Lane shares what he's learned, what he's found, great PMs, and great teams do differently. He shares a bunch of his favorite rituals and principles, how you can implement them on your own team, plus a really clever and unique way of understanding if you're making progress

Starting point is 00:01:44 in your career, plus so much more, I could talk to Lane for hours, but we tried to keep this to under an hour and a half. With that, I bring you Lane Shackleton, after a short word from our first. sponsors. This episode is brought to you by Epo. Epo is a next generation A-B testing platform built by Airbnb Alums for Modern Growth Teams. Companies like Draft Kings, Zapier, ClickUp, Twitch, and Cameo, rely on Epo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth team stack. This leads to waste of time building internal tools or trying to run

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Starting point is 00:02:53 learning clients. Check at Epo at getepPO.com. That's getepo.com and 10x year experiment velocity. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate your growth. Thousands of fast-growing companies like Gusto, Com, Cora, and modern treasury trust Vanta to help build, scale, manage, and demonstrate their security and compliance programs and get ready for audits in weeks, not months. By offering the most in-demand security, security and privacy frameworks such as SOC2, ISO-271, GDPR, HIPAA, and many more, VANTA helps companies obtain the reports they need to accelerate growth, build efficient compliance processes, mitigate risks to their businesses, and build trust with external stakeholders.

Starting point is 00:03:40 Over 5,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC2 and these other frameworks. For a limited time, Lenny's podcast listeners get $1,000 off Vanta. Go to Vanta.com slash Lenny. that's V-A-N-T-A-com slash Lenny to learn more and to claim your discounts. Get started today. Lane, thank you so much for being here. Welcome to the podcast.

Starting point is 00:04:07 So glad to be here. Thanks for having me. It's absolutely my pleasure. I've always really admired the way that you write about product, the way you think about product. And it feels like Coda has one of the strongest and also the most thoughtful product teams out there. And so I am really excited to have you on here and learn from what you've learned over

Starting point is 00:04:24 the years. My first question is completely unrelated. I have to ask, your last name is Shackleton. Any relation to a certain very famous Antarctic explorer? Yeah, it's probably distant at best. I wish it was close. I wish I could claim as my father or grandfather. But I definitely grew up with those stories.

Starting point is 00:04:45 And reading a lot about them as a kid. In high school, we read Endurance, which is a great book. If you haven't read it, it's an amazing story, basically, you know, very inspiring. how he put people first and brought back all of his men from this journey to the South Pole. So I have taken a lot of, you know, lessons from that. But that's, that's as close as I can come to the greatness of Ernest Shackleton. Okay, so there's a connection. When I think of Shackleton, I also think of the ad that he ran for people,

Starting point is 00:05:13 recruiting people to join his journey, like low chance of survival, incredibly hard, some chance for glory if you succeed, something like that. It's a wonderful ad. I think I had a mug of that when I was a kid. Amazing. Okay. So on that same topic, I noticed maybe your first job was a mountain guide in Alaska. Was that inspired by this legacy? And also, why did you decide not to pursue that and get into product management, completely different life? Yeah. Yeah, very, very different. Very different time. Didn't have kids back then. I was, I think I was convinced at the time I wanted a career outside. just like love spending time in the mountains and climbing things like that. To be honest, like I wasn't the best guide.

Starting point is 00:05:58 There were a lot of amazing, you know, guides out there that just had, they were almost invincible in terms of their ability to climb for 20, 30 hours. But I learned a lot from the experience and maybe the quick story on why I stopped guiding. I was on sort of a what is like a dream trip for mountain guides, which is we were flown to a remote portion of southeast Alaska, about an hour, it's an hour-long flight, mountain called Mount Fairweather, beautiful 15,000-foot peak. And as a part of climbing on glaciers,

Starting point is 00:06:36 one of the things that you do for context is you're roped to another person. And the reason that you do that is because if you fall, if someone falls in a crevasse, you want to be able to stop them or pull them out. So any of those ropes to a very nice climb, that I was guiding and he fell pretty close to the top on our way down. And luckily, like, we were able to self-arrest and arrest that fall. But, you know, I spent probably the next like six hours walking down that mountain thinking the same thing over and over again, which is like,

Starting point is 00:07:11 I really don't want to die, you know, rope to someone that I barely know and like don't trust or love. So that was that was sort of the last season that I guided, but tons of great memories and learnings. And, you know, I think it impacted my life in a pretty significant way. Damn. Software, much lower stakes. I guess just while we're on this topic, is there any parallels or a big lesson? I don't know if you learn from that experience that you bring to product. One is just preparation. I think when you, when you go climbing or when you guide, you know, climbing, you spend like months and months preparing for usually like a few days of climbing. So, you know, there's that kind of preparation. There's also like just a million check. So before you go on an expedition, you may check a checklist

Starting point is 00:07:57 of all your equipment, stuff like that, a dozen times or more. So you kind of like insure redundancy across all your systems. So that was definitely a parallel. The other thing I think about a lot is just how to stay calm in like challenging or scary scenarios. We had another instance where I had a client pull a big chunk of rock off and break their feet. And that was, you know, I was like the junior guide on that particular instance. And the more senior guide looked at me, looked at the situation and was like, okay, we're getting this guy out of here right now. You know, put them on his back and we basically took turns varying out for a couple miles. And I'll just never forget like instances like that where the clarity of, you know, stay calm, assess the

Starting point is 00:08:50 situation, prioritize, take action. You know, it's like that's sort of like a, there's a mini version of that when you're building software, I think. So experiences like that, I think we're, you know, even though I only did it for a handful of summers, uh, were pretty profound. Damn. What a very different life that life path would have been. Free kids, yeah. Oh, man. So you mentioned your writing. You mentioned that this something you want to write about. Shifting to kind of the core topic of our chat is it's very clear that you spent a lot of time studying how great product managers operate and how great product teams operate. You've been doing a bunch of writing on the principles of great product management and also the rituals of great teams.

Starting point is 00:09:32 And so I want to spend a bunch of time trying to extract as much as I can from your learning. so that listeners can learn essentially what are principles of great product managers, what are rituals of great teams, and generally how do the best teams operate? And my first question is just why is this something that you started doing? What kind of pulled you into spending so much time and effort trying to understand how the best teams that people operate? Yeah, yeah, I've been asking myself that question a little bit lately. I, you know, there's a few reasons.

Starting point is 00:10:01 One reason is I just found myself giving a similar to have advice and one-on-we. ones, you know, and so I think anytime you find as a leader yourself kind of like repeating the same lessons, it's a good, it should be a good flag to say like, oh, I should probably scale this in some way. And as you know, you know, as soon as you write something down, you have to clarify your own thinking. And so it becomes very useful for that. And I don't think I quite expected how useful it would be in that sense, like writing something down and then putting it out there, you know, you start to get feedback back of like where you might have been right or where you might not be right. And so for me, it's been a good learning experience there as well. I think the second reason is I've always

Starting point is 00:10:47 been pretty frustrated with career ladders. You know, most companies have career ladders with like 10 or 15 levels. And, you know, as soon as they hit some scale, that levels, there's like levels between levels. And I feel like I looked at the one at Google and you kind of like need. You kind of like needed a PhD to decipher it and interpret how to operate within it. And so that's sort of like one piece of the construct. If you think more broadly, though, they aren't consistent across companies, right? So like now you're in a situation where you're like in your version of the rat race. And so I found I found that I basically wanted to have a broader set of principles

Starting point is 00:11:28 that transcended level. Right. So things that could be true when you are an ICPM starting your career and things that can also be true when you're the head of product or running a product team or things like that. And so like that's sort of one, I won't rant further on that, but that's, I think that's one sort of piece of it. And then I think the last reason I'll mention is I was pretty inspired by a talk that is by this guy named Brett Victor, who's kind of like a prototype or thinker. may have heard of his work. He has this talk called Inventing on Principle. And in the early days of Coda, one of our first designers, this guy, Jeremy Britton, showed this talk to the company.

Starting point is 00:12:11 And like, my mind was blown. And I think it was one of those examples of someone developing a clear view of what principles they should operate with and then like following that principle. Right. And it was just sort of a meta example of how important it is and how impactful it can be when you decide on a principle and then follow it. And so ever since then, I've been thinking, like, you know, what are my principles? Is it pertains to like building software and other things? So those are kind of like the three reasons that, you know, led me to start writing these things now.

Starting point is 00:12:49 Amazing. We're going to find that talk and link to it in the show notes. I want to ask about what principles you've come to. you, but I also want to understand how you actually ended up doing ladders and performance review stuff at Cota. Would it be better to talk about that later after we go through some of these things, or is there some you want to share first of just how you think about it, Dakota? When we were doing career ladders, first of all, we put it off for quite a bit of time,

Starting point is 00:13:14 and that was based on the advice of a lot of other leaders that said, as soon as you introduce this, then the incentives sort of like flip from being company-focused to being individual focused. And so I think we delayed it for a good bit of time. There came a time where we kind of decided, hey, look, we really do need to provide better guidance here about what it means to grow and what it means to be great. And so about the same time,

Starting point is 00:13:42 we were doing the levels thing. I started writing down some of the principles that I've been publishing. One of the things that I think about a lot when talking about levels is just how to keep everyone oriented toward their team and their company, right? And I think that we've done a really good job of that over the years. So levels aren't by any means at the forefront of any company discussion. In fact, we kind of don't use titles that much. You said that it's not specific to role.

Starting point is 00:14:12 Do you mean like the same leveling attributes or the same for design and product and engineering? We basically have five levels. And we call them role stages, and they go from apprentice to principal. So apprentice is kind of rope analogy here is learns about rope. Practitioner is can tie basic knots, shown complex knots, you know, sort of given a problem, they can do it. Career is you can calculate rope strength. You know a lot about knots. Principal is basically invented nylon.

Starting point is 00:14:48 So the bar is like really, really high. for principal in these levels. And I think that that is, you know, that's appropriate. Like it should be aspirational that the bar is exceptionally high at the highest level of our role stages. I find it's a pretty good process to draw a contrast, maybe a little bit of contrast with other companies. I think most other companies, especially large companies,

Starting point is 00:15:13 have 10 to 15 levels. I think we've made a really conscious choice to have only five. I think the other bit of contrast I would draw is basically role stages are not visible across the whole company. Like, you know, we're not showing levels of any individual PM or designer. And that's partially because we just don't want to put a big focus on it. And then probably the biggest difference is we have a centralized compensation committee, and that's who decides compensation. and so it's not the manager that drives your compensation.

Starting point is 00:15:50 So those are some differences. Super cool. I've never seen it done this way before. I think it's an awesome example of first principles thinking, which I see a lot come out from your product team. And then just to make sure I heard you write, these five stages are roughly the same across role. So designers have the same kind of five,

Starting point is 00:16:05 and they're described similarly. That's right. They're described similarly at a high level, but then the specifics, like if you get into it, are a little bit different. Okay. I'm going to ask about what the principles. or a few of them that you can share.

Starting point is 00:16:18 But one other very tactical question at what size of product team, say just PMs, did you start to develop this framework? We were probably at 20-ish PMs and designers when we did that. Awesome. Okay. So let me just ask, what are some of these principles you've kind of narrowed it on as principles of great product managers? Maybe it's helpful to start with a little higher level context on the kind of unifying thesis.

Starting point is 00:16:45 I think the unifying thesis. is the core job of a product person in general is to turn ambiguity into clarity. And if you think about the job of a product leader or product manager, kind of like everything is ambiguous all the time. You know, it's like, what's my role on this team? What problem are we solving? Who's the target customer? You know, what prototype is going to solve this particular problem?

Starting point is 00:17:11 So it's like literally everything. And so if you're going to do the job well, You really need to get good at spotting ambiguity and kind of turning it into clarity, right? And so the obvious question that follows from that is like, okay, great, that sounds like a, you know, great hallmark card, but, you know, how do you actually do that? And so I think the principles that I've been writing down are very personal. They're like my take on how to do this. So the first one that I wrote about was systems, not goals. And one of the ways that I started this post,

Starting point is 00:17:47 I'm a big fan of getting inspiration from outside of tech. And so one of the stories that I tell is basically the story of Jerry Seinfeld. If you haven't seen the documentary comedian, it's amazing. It's definitely worth watching. But the story goes, you know, he's done Seinfeld the show, and he's got all this material from the last like 15 years. And he comes in one day and he says, look, I'm going to throw away all my material.

Starting point is 00:18:15 and I'm going to start fresh, right? And this is like unheard of in comedy for someone to just like throw away all their old material and start fresh. And, you know, so the question is like, what does he do next? And the thing that he does is he sets a goal, which is basically to build up to an hour of material again. But the goal isn't that important. What's important here is like the system.

Starting point is 00:18:38 So the system that he uses is he writes for an hour every morning, you know, doesn't write for more if he doesn't want to. And then he goes and performs at night, right? And so when you rinse and repeat that system, do it hundreds of times, that's how he builds up from five minutes to 15 minutes to 30 minutes of material. And so I think that, you know, I take a lot of inspiration from that. And I think product people can generally, which is instead of being obsessed with the goal, you know, be obsessed with the system that gets you there. And so the phrase I sometimes use is, you goals with good intentions don't work. And I think that a really, to give a common example, a really common example is teams that are trying to like learn about customers or do research or,

Starting point is 00:19:26 and, you know, one thing I've observed is a team may have a goal like an OKR of talking to 10 customers this quarter. And they may or may not hit that, you know, that OKR. And then if you watch closely, you know, the next quarter, they may not have a goal of talking to customers. anymore. And so they're sort of like learning is going up and down. And to draw a contrast, that's just really different than a team that has some default on system for talking to customers. You know, every few times a week, they're talking to customers for whatever reason. And the impact of that is like really hard to see until you understand that the latter team, you know, tends to have like really good product instincts or really good customer instincts. It's

Starting point is 00:20:14 because they've just had this sort of default on mindset of talking to customers. And in the early days of Koda, we actually did something similar. We had a time allotted on Fridays. And it was basically like it was on the calendar, a customer or a potential customer was coming in. And so you knew that it was going to happen. And you had to have something to show. And so like sometimes we'd be scrambling, you know, the three hours before to, you know, have a prototype ready for a customer. sometimes we would have had something that we've been baking for a while.

Starting point is 00:20:47 But the point is that it was default on, right? And so, like, the way that we developed good customer instincts was not the goal. It was really just the sort of system behind it. So that's one that I'm kind of passionate about. And I think it's also translates into a lot of the rituals that we talk a lot about. There's so many directions I can go with this. I really like this one. It reminds me something I did at Airbnb where we had a lunch.

Starting point is 00:21:12 with a host every Friday with the team. And we had our community person find someone in San Francisco that's a host. And there's no agenda. It's just let's have lunch. Meet the team. Curious what you were wondering. Exactly. And an Airbnb host are always so nice and it's such a pleasant experience.

Starting point is 00:21:26 Always also makes me think about this book. The score takes care of itself. Yep. You read that? Yeah. Where it's just like, do the fundamentals and you'll win. The other thing reminds me of is I have this quote hanging in my office here from, I believe it's from the Rick Rubin book.

Starting point is 00:21:41 And the quote is, the object isn't to make art, it's to be in that wonderful state which makes art inevitable. I love it. I feel like you just change arts. Oh my God, it's so good. There's just like every section is like this quotable thing I want to.

Starting point is 00:21:56 I need to hold on to this thing. Yeah. He's got a great thing on listening. I really admire what he says about listening. And I think that a lot of PMs could take that lesson, which is. Yeah, what is that lesson? The way he talks about it is essentially,

Starting point is 00:22:12 you want to listen and absorb sort of every fragment of what that person is saying, including their body language and everything else, and try to turn off the side, which is crafting your response or figuring out what you're going to say next or what the problem with their argument is or whatever. You know, it's really, it's quite hard to do, right? Because like your default mode is always sort of the, next step at the conversation, but I think if you can really challenge yourself, like he says,

Starting point is 00:22:48 to pause and really try to internalize sort of holistically what that person's saying. It's pretty powerful. I was actually just reading that chapter, and the next chapter is about this idea of the beginner's mind. I know if you remember that. I feel like people get snipe by Rick Rubin stuff, but anyway, I'm going to go down this thread. He talks about how Alpha Zero or AlphaGo, the first AI thing that beat humans and Go and how there was this move it made, move 37 in a game that was just like

Starting point is 00:23:16 the person the AI was playing walked out of the room, he's like, I can't, I don't even know what just happened. This is out of anything I've ever imagined. And it won and it was and the lesson there is it was trained not on what we've learned, but it trained itself and figured things out from first principles and then came up with this thing we've never even

Starting point is 00:23:33 comprehended. And so it's a really good example of the power of coming from a bigger mind and not being influenced. it's already been done. Yeah, we do, we have like a walk through ritual that we do. Tell me more. The prompt is essentially like sort of put yourself in the shoes of someone who knows nothing about this topic whatsoever and like kind of have beginner's mind and then, you know, walk through with a five or ten people watching you and let's, you know, let's sort of fix all the problems that we see. Okay, so I want to talk about rituals. We're getting ahead of ourselves a little bit. Is there any of their

Starting point is 00:24:08 principles that you can share either just on a high level or in depth that you've come across. And I know people can go to your substack and read this. And by the way, what's your substack? URL for people because I want to check it out. Just lane at sub or lane dot substack. Okay. Sweet. We'll definitely link to it. Yeah. Any other principles? I think the other one is cathedral is not bricks. And then the other one is proactive, not reactive. Cathedral is not bricks, I think, is a kind of classic one. I think I had a moment of realization in talking to Shishir and a one-on-one when I was at YouTube, sort of bemoaning the

Starting point is 00:24:46 fact that my team wasn't performing to the potential that I thought, you know, they had. And he had a very sort of pointed and unexpected question, which is like, do they, do they know their cathedral? Do they have a cathedral? And I'm sitting there like, man, what are you talking about? Like, we're talking about performing as a team and you know, you're asking me about cathedrals. And then he sort of explained the cathedral story, which I can, which I can talk about. And that I think it was quite clarifying. Yeah. Do you share?

Starting point is 00:25:14 Yeah, the cathedral story is basically, you know, you walk up to three people. They're laying bricks. You ask the first person, you know, what are you doing? They say, well, I take the bricks from over here and I put them, you know, on that stack over there. You ask the second person, what are you doing? they say, well, I take this little cement and I put it on top of the brick that that person lays. You ask the third person, what are you doing?

Starting point is 00:25:36 And they say, well, we're building a cathedral. And the sort of core insight here is that you want your teams to feel like they're building a cathedral and not laying bricks. And I think it's really, really easy to do when PMs are really busy on a day to day to just like be one task after the other, really execution oriented,

Starting point is 00:25:57 and maybe not take the time. to sort of help the team take a broader frame, open the aperture a little bit, and have a view of what the cathedral is. And I think, you know, we've learned many times that one kind of unexpected bit of this is that everybody needs to see a different facet of the cathedral, right? So very often, and I've made this mistake before, plenty of times, very often people will do a great write-up on vision or strategy or whatever it is. And the result is people can't quite see their version of what this broader arc is or

Starting point is 00:26:42 this broader cathedral is. And so one of the things that we have tried to do when we go through big planning cycles is kind of show all the different sides of this. So instead of just having like a write-up, we may have a write-up. couple that with a metric. We may couple that with directional mocks and, you know, what the billboard might look like or how our homepage may change. And really what we're trying to do is kind of take a mystery out of the set of like broader constraints or where we're headed. And so I think that that is a, you know, I think great product teams and great PM leaders tend to

Starting point is 00:27:20 always orient their teams toward a broader cathedral as opposed to laying bricks. Such a beautiful metaphor. Reminds me of this other quote I just looked up while you're chatting. If you want to build a ship, don't drum up the men to gather wood, divide the work and give orders. Instead, teach them to yearn for the vast and endless sea. Classic. Classic. Same, Antoine.

Starting point is 00:27:41 That is right. Antoine de Saint-Expuri. Okay. Something I was curious about as you're chatting also is for folks that want to develop their own principles and define how they want to think about product. Is there anything you found to be useful? in helping kind of emerge these into principles that you can come to? Is it just sitting around thinking? Is there anything else you've done that has helped you define these things?

Starting point is 00:28:05 Probably two things. One is reading really broadly. So I think not just reading kind of like PM-style literature, like I said, I think tend to get a lot of inspiration from outside of tech. I think that's one thing. I think the other thing is, you know, insofar as you get the opportunity to mentor other people, think about what you're saying to these people.

Starting point is 00:28:29 You know, like, think about, okay, this person came to me with this challenge. What was my response? Why was that my response? Am I giving that response a lot of times? Okay, maybe like this is a more deeply held belief. And so I think noticing those instances was helpful for me. Are there any books or topics or areas that you found most inspiration of? They talk about reading and studying other non-product tech.

Starting point is 00:28:53 I mean, definitely like sports. I would say like sports is really interesting to me. Team sports have always been a huge fan of everything. Team sports. Storytelling, you know, go go look at some of the best storytellers in the world. And they're actually out there on a stage telling stories. There's a book called Storyworthy that I was just going to mention that. That book is so good.

Starting point is 00:29:17 Somebody mentioned this on the podcast and as I read it, it's like the most useful practical book for how to tell their stories. The insight is amazing. the insight, just in case your listeners are interested, the insight is basically the nugget of a great story is like five seconds of transformation. So if you just orientes like everything else around that like moment of transformation, then you end up usually telling you a reasonably good story. And so we actually had, I had a conversation with the author right after I read that book because I was just like totally enamored with it. And then we ended up bringing him in Dakota and he gave a great talk.

Starting point is 00:29:55 So, yeah, big plug for Matthew Day. The other thing that stuck with me also from that same, we're just going all kinds of tangents from that same insight is, and I watch movies completely differently now, where basically the characters you meet at the beginning of the story, they're going to be completely opposite at the end of the story because of this transformation that takes place. So I'm watching movies with my wife and I'm like,

Starting point is 00:30:14 okay, she's very shy right now. She's going to be very extroverted by the end of the movie, where they love each other or they're going to have a lot of problems. Yeah. It's so interesting. Oh, that's such a good idea. Okay, I'm going to get this guy on hopefully. And he, and he's like the moth. He's like a moth champion basically. Yeah, I mean, that's like what I would say is like, is like maybe a principal version of this. You know, the way that you learn or the way that everyone and including me learns new things is like you go seek out the best at that given craft. So in this case, you go to the moth story slam. You see some like really good stories. Like if you're watching these, on YouTube. And then you just kind of like unpack what they're doing and how they're doing it. And then obviously, I think the other way to learn quickly is to like throw yourself in the deep end. So insofar as you can put yourself in situations that are uncomfortable or having,

Starting point is 00:31:07 you know, force you to do things like tell a story or force you to come up with a clear strategy. You should always opt into those, especially, you know, early in your career. The first thing you said, that's basically the whole premise of this podcast, find the best at all these things and learn from them, extract and share. And the world is much better for it. Yeah, this podcast is an amazing resource. Thanks, man. You've done something very special.

Starting point is 00:31:31 Oh, I appreciate it. This podcast episode is already very special. The point you just made reminds me of something that I heard you talk about, which is kind of this, oh, shit, moment. I don't know if it's related to what you shared, of just giving people a sense of whether they're making progress in their career. Yeah. Can you talk about that?

Starting point is 00:31:49 Sure. Yeah. I think I picked this up originally from Seth Godin, the author, and it just like totally stuck with me. The basic kind of thesis is that moments that stretch you or moments that you feel uncomfortable in or you find yourself saying like, oh shit, you know, I shouldn't be here. I'm underqualified to be here. Those are the moments you should be seeking out, right? those are the moments that stretch you and give you sort of like a new foundation. And so I have found that they turn out to be a pretty good way to calibrate

Starting point is 00:32:24 whether someone is growing in their career. So oftentimes, you know, you'll hear like a career question like, do you feel like you're growing in your role? And that's like a very ambiguous, in my opinion, way to ask this question. And like a much sharper way is like, hey, how many like, oh shit moments have you had in the last like six months, year, two years. And what are they? And like, I think if you ask yourself that question and the answer is it's been a really long time since I've been like stretched in some meaningful way or I've felt, you know, like I'm

Starting point is 00:32:59 underqualified to be there, then it may be worth kind of like digging into. That is so good. Makes me think about this podcast where I never wanted to do podcasts. I'm like, I'm not a podcast person. I don't like, I just want to sit there and type out newsletters. How cool is that? And I'm like, no, I got to do it because it's hard. And I'm glad I did it. It also reminds me of this quote that I love that I always think back to, The Cave You Fear contains the treasure you seek.

Starting point is 00:33:26 Nice. That reminds me of, have you read the book, The Obstacle is the Way? No. Say more. It's a great book by Ryan Holiday. And the kind of core thesis is, it's a book a bit about Stoist. But the core idea is essentially, you know, instead of running away from obstacles, you should be running toward them. And that's, you know, where you experience, like, either the most growth or the

Starting point is 00:33:52 most sort of profound moments of your life. And he gives a lot of examples in that book of people throughout history who sort of made that choice. And I think he's also given that talk to, like, hundreds of sports teams. So it's a good book worth reading. It's so hard. It's so hard to do hard things, man. God damn. So we've been talking about principles of great product managers. You also spent a lot of time looking at the rituals of great product teams. And I know you're working on this handbook that I'm excited to learn more about.

Starting point is 00:34:21 Can you just talk about, I guess, one, where this idea came from of studying rituals at great teams? And also just how do you actually go about learning about these rituals? I know you have this really interesting process. Yeah, I mean, in general, I'm a big believer in, you know, good design and good product starts with noticing, and I think Tony Fidel has a great talk on this. So I think a bunch of us that are really obsessed with rituals, we just honestly try to be great at noticing. So, you know, see something happening with a customer, ask a few questions, get introduced to their team,

Starting point is 00:34:58 hear about something interesting from a non-customer, ask for an intro, you know, end up kind of like just probing and asking a lot of questions. And then in many cases, you know, nowadays with Kota, we're building new rituals alongside people. So someone has a creative idea about how to implement something. And we're, you know, we're like partners or collaborators with them on that, which is honestly incredibly fun to just like see people's creativity expressed in a tool. And then, you know, by extension, kind of the social construct that they exist in. So that's, that's a little bit about how we, we got started in that whole process. And then, of course, Shashir's writing a book called Rituals of Great Teams.

Starting point is 00:35:42 So we've been kind of cataloging those. We've been hosting a bunch of rituals dinners where we basically get people together for a dinner. And we usually have, you know, three or four presenters at those dinners. And, you know, it's just a great chance to learn and think about, you know, how the, how the, how the engine runs in a lot of these companies. What are some rituals that you've learned from these dinners and these, and this research you've done, have really stuck with you. There are so many. It's like it's hard to choose.

Starting point is 00:36:14 Maybe I'll choose two that are top of mind. One is Darmesh Shaw has this ritual from HubSpot called Flash Tags. Have you heard of this? No. So, yeah, we've all probably been in the situation where, you know, someone gives you feedback and you're either like underinterpret it or overinterpret it. And as an organization, you know, I think the kind of core principle here is like, you want to be calibrated on how much to pay attention to a bit of feedback. And so he outlines four flash tags.

Starting point is 00:36:52 He presented this in a dinner, one of our dinners. And I absolutely love the phrasing of these as like someone who's given a lot of feedback on product stuff in their career. So there ranges from, I think it's FY, suggestion, recommendation. plea. So FYI is basically like, I had a thought, you know, take it or leave it kind of thing. Suggestion is, and he uses this like hill dying metaphor, so is this a hill I'm going to die on? And FYI is like, you know, there's no hill in sight. Suggestion is like, there's a hill. I'm not going to die on it. Like, you know, this is what I would do. If I were you, like, you can take it or leave it. Recommendation is like, I'm climbing the hill. I'm not going to die here.

Starting point is 00:37:37 but like I've thought about this a lot. So like don't ignore this, you know. And then the fourth one plea is, you know, hopefully rarely used in the organization. It's like, I don't like dying on hills. That's not what we do here. You know, but this is a pretty good candidate for it. Like you should really trust me. And so we have ended up using that.

Starting point is 00:37:58 I was actually just at an offsite and someone gave a lightning talk to our team on how valuable this has been just to calibrate, you know, hey, we got 100 pieces of feedback and there's like one plea. Okay, let's spend our time on that, you know, or, you know, there's a whole bunch of FYIs. I think we're fine. Let's keep going. No worries.

Starting point is 00:38:20 That's amazing. It's interesting. None of them are just do it this way. I imagine that's very intentional. Yeah, I think it's, I mean, it's honestly, it's a sign of a, in Darmathe's case. I don't know him super well, but like it's a sign of a really experienced leader, you know, to know.

Starting point is 00:38:36 that scale. But every time I look at the scale and I'm sort of weighing where I am between suggestion or recommendation, I have to kind of like giggle to myself. And how do you, how do you actually use it? In the feedback, you like put a hashtag plea kind of thing? The way it's used in code docs and the way I think other companies have made it a ritual is like you'll have a feedback table and you know, you'll write your feedback and then they'll just be like a little select list and you can selects between those four. And usually people, what people do is they include the description. So you can kind of like, as you're choosing it, think, you know, am I really, do I really feel that strongly about this? And honestly, it's just, it's good hygiene, you know, otherwise every bit of feedback has taken

Starting point is 00:39:26 the same, which is just fundamentally like the impact of that as it slows everything down. because now you're looking at like a list of 100 pieces of feedback and you're going like, oh man, we got to address all this feedback. Whereas, you know, as soon as you distinguish between what's most important,

Starting point is 00:39:44 it's much easier to sort through that. What about if it's in person? Do you say this is a plea or this is a FYA? Oh, I've definitely heard that in many meetings. Like, are you making a recommendation or are you making a plea? Amazing.

Starting point is 00:39:57 And making the person think through that choice, I think is, is just a very helpful shared language. Imagine one of the other benefits of this is, I think, most leaders that rise up the ranks eventually realize anything they say in a meeting is going to be taken really seriously and the team's going to rush back and be like, oh, we told us to change this thing. I imagine it helps you just make it clear.

Starting point is 00:40:17 No, you don't need to actually change this. It's just my thoughts. Yeah, exactly. Yeah. Awesome. This episode is brought to you by Azra, the leading full-body cancer screening company. I actually used Ezra earlier this year.

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Starting point is 00:42:11 That's eZRA.com slash Lenny. Any other rituals that stand out as really interesting, either more recently you've learned or something here's just like, oh, wow, that was genius? I guess one that I get asked about a lot on our team is called Catalyst. And I guess maybe to set some context on this one, in most product teams,

Starting point is 00:42:31 the review forum is just like a really important part of the product development process. And the kind of like core insight for, you know, most review forums or, you know, product reviews or decision forums is that they generally suffer from two problems that are like kind of hard to spot

Starting point is 00:42:51 unless you've sat through, you know, hundreds of them. The first is they have standing attendees, and the second is they're normally single-threaded, meaning they're normally like one topic at a time. So maybe I'll talk about both of those because I think they're not exactly intuitive. So when you think about what happens in a standing with a standing set of attendees, you either have the situation where you have like too many people in the meeting or you have like not enough people in the meeting.

Starting point is 00:43:21 and both of those can cause problems, right? So, like, if you've ever been in a meeting, I certainly have where it's like, hey, do we have the salesperson who knows most about this, or do we have the engineer who's actually implementing this here? Oh, great, they're not here.

Starting point is 00:43:35 They're not, like, a part of the standing set of attendees. You either, like, have to reschedule the meeting or worse, you just, like, do the discussion without the person who's, like, most knowledgeable, which seems, you know, crazy in retrospect. The second problem is single-threaded, so like one topic at a time. So if you think about, you know, if a product development process is like, you know, somewhat of a chaotic assembly line for a second, you know, your review or your decision forum ends up being a big time bottleneck in many cases. And like obviously, you know, you want to be in a situation where product people have a lot of autonomy and they can make, you know, most of the decisions themselves and a big,

Starting point is 00:44:19 believer in kind of like decentralized leadership and all of that. But there are things that cut across the company that like need to get reviewed by a broader set of stakeholders. And so what happens when those things are single threaded is, you know, either the meeting is like really long. So it's like a three hour review meeting once a week. And by the end, everyone is like, you know, about to fall asleep or it's really short. And it's like really hard to get on the calendar. You're like, oh, can we get on the calendar in two weeks? And the the downside of both the downside of the, you know, not being able to get on the calendar is that now you've like just slowed down the whole velocity of the company because the like

Starting point is 00:44:59 throughput of your review meeting is really slow. So we built catalyst to really solve those two problems. And so the way it works is it's essentially three one hour blocks throughout the week. And the assumption is that the whole company is free. So you can get anyone in the company for those three hours. And each topic has essentially four roles, driver, maker, brain trust, and interested. It's a very transparent system. So like a salesperson can say, oh, I'm interested in this product development review. I'm just going to mark myself as interested. And then the driver is like the person who's actually going to like drive the meeting, drive the decision, drive the outcome, things like that. And basically, this is all centralized in like one doc. And what happens

Starting point is 00:45:47 is the day before that hold that's on calendar gets removed, and then you have specific topics that get added. So there may be like three topics going all at the same time because they don't have overlapping attendees. And, you know, the impact of this, I think if you really watch it in progress, is huge. Like it's you basically have many topics running all at the same time. So the throughput is much better.

Starting point is 00:46:18 And you have the right attendees every single time. And you have a clear set of drivers and roles in these meetings. So that means that we can review work much, much faster with the right people. And ideally, that results in more value to our customers, more things getting shipped, just a higher velocity organization. So that's one that we get asked about a lot. And actually a couple weeks ago, we spent a while kind of remaking the template for that one. I love that ritual.

Starting point is 00:46:46 You actually wrote even in more depth in the post that we work together on on how code it builds product, which we'll link to. If folks want to try this out and you link to actual templates, people can actually use it their companies. Yeah. When someone's listening to this and they're like, oh, wow, this is extremely cool. How easy is it do you find for people to take a ritual from a company and implement it? Like how much of that is cultural and it's hard to transplant?

Starting point is 00:47:10 Or do you find people can take this catalyst idea and plug-in play at a lot of companies? Yeah, I think it depends a lot on what your role in the company is. Like, you know, if you're maybe to say the extremes for a second, if you're like a brand new PM to an organization, you probably shouldn't go try to remake the whole review product review cycle that like the head of product is really passionate about and is like crafted. But, you know, you can probably take a, you know, a decision template or some interesting ritual that has facilitated a team, you know,

Starting point is 00:47:43 in the past and use it with your team. Another one of my favorites there is $100 voting. We use that a lot in the context of planning. And I find that like creative rituals like that are easy to pick up for teams because oftentimes it's like, okay, maybe I'll describe the ritual real quick. Yeah, I was going to ask. The ritual is essentially you can take any set of, you know, problems or solutions or themes or, you know, whatever you want to get people's input on.

Starting point is 00:48:11 and you put those in into a table, and then people can basically vote with their dollars, and usually you allocate $100, and so people will go through and say, like, I want to allocate $10 to this and $20 to this and $50 to this, because I think it's really important. And I have found that,

Starting point is 00:48:32 especially in planning processes, little rituals like this are great at kind of like getting the elephant in the room out. So it's like, oh, wow, we have like a huge spread on this one particular, you know, problem. You think it's a huge problem. I don't think it's a problem at all. Let's talk about it, you know. And so I think a lot of, you know, going back to the thesis of turning ambiguity and the clarity,

Starting point is 00:48:57 you know, a lot of this is like we're trying to get the ambiguous stuff out there so that we can make it more clear. And so I use that as an example because you can be, you know, a brand new PM, run a brain or run a planning session like that, and you're probably going to get great feedback, right? Like, people are probably going to go, this is kind of cool. I've never done this before. Now, to go to the other side of the spectrum, you know, we help a lot of companies that want to remake a whole process. They want to remake like a review system like Catalyst or they want to remake, you know, their decision kind of like rituals. And so in that, in that sense, we're usually talking to like a head of product or director of product or VP of product.

Starting point is 00:49:41 and someone who tends to have a lot more agency over, you know, the way that the team works. Code is interesting in that it feels like you have pretty stable processes for planning and reviews. I find most companies just like every six months rethink a lot of these things. I guess there's probably a sign that you found something that's really good and works and you don't have to redo it. How much are you radically changing the way you operate versus working in similar ways? Is there like a, how do you think about that percentage-wise? People are always coming up with new creative ways and to kind of like make their teams run better, make decisions go smoother.

Starting point is 00:50:21 And we're kind of continuously adopting those, but there's definitely a backbone of the system. Like the backbone of the system is catalyst and tagups and the concept called bullpen. And then, you know, there'll be a lot of iteration on top of that. And even those systems went through a lot of iteration. I talked about how the calendar hold got removed, and then like individual topics got added. I mean, that took, that took us launching like automations and the ability to add things to calendar

Starting point is 00:50:51 in order for that whole process to really work. So in the years prior to us launching that, you know, we kind of did it with very manually. So I think there's still a lot of creativity that I see every day. So I'll give one quick example, one of our PM leads on core products. This guy, Nathan, you know, he basically saw that a lot of decisions

Starting point is 00:51:19 had a lot of different stakeholders because he's in the core product. And now he's leading the core product team. So he's trying to figure out what guidance do I give to each of these PMs on like who to involve in these decisions? Because like every one of these with core product feels like they impact everybody. And so like a very simple thing that he did,

Starting point is 00:51:38 probably in the last six months was he had a table of all the upcoming decisions and then at a tag up, which I can explain if you want. But basically with a small set of stakeholders, he had all the upcoming decisions and then he let people hit a little reaction and say,

Starting point is 00:51:58 oh, I want, you know, I don't need to be involved, just notify me of the decision after or, hey, I have some opinions, but you can keep going. Or, no, I really want to be like, heavily involved in this decision. And it was like such a pro move.

Starting point is 00:52:12 You know, it was like such a, I've been through a million of these. I don't want to treat every one of them the same because if I do, it's going to slow down the velocity of this whole organization. And so instead, you know, the majority of those

Starting point is 00:52:27 Shashir or I or Oliver, the head of engineering will say, I may have some opinions but keep going. Like that's kind of like often the default. And then there are plenty where we say like, just notify us of the decision after. And in doing that, Nathan can now give better guidance to the PMs on his team and say, like, hey, you don't really need to involve, like, as wide a group as you think.

Starting point is 00:52:49 So just, like, keep going and, you know, check in later. So I think those are those types of little iterations are usually based on a really good insight. It sounds like a dream come true for a platform team to reduce how many people have to be involved in all your planning and decision making. And that process in ritual, you call it TagUp, maybe just briefly explain it. And then I want to talk about this handbook you're working on, which is going to, I think, cover a lot of these things.

Starting point is 00:53:17 Tag Up is based on this insight that a lot of work and project work tends to get discussed in one-on-ones. And actually, that's like, it's really an anti-patter. It's a pattern you should try to avoid. So if you're talking to your manager about product work, what's not happening in that moment? is your Eng lead and your design lead, they're not hearing that. And so you end up with this big game of telephone,

Starting point is 00:53:44 where you'll have a conversation with your manager and one-on-one, they'll go back and translate to their engineering and design lead. Of course, like the fidelity of the game of telephone, something is lost in all of those transmissions. And so the core idea is kind of have a group one-on-one with the key stakeholders. And so we have this concept of brain trust that's kind of modeled after Pixar's brain trust. And so we'll have a tag up with a small set of people from a given team or sometimes we have kind of larger groups.

Starting point is 00:54:20 And then they meet with their brain trust. And it's once a week. And it's really the, it's sort of the same mindset of a one-on-one. It's like their time. So anything that they need to unblock a decision or to like make progress, they should. use that time for and they often start by like reviewing okay rs and metrics and things like that. But then we generally get into a table of topics. Anyone can add a topic. You know, those topics are upvoted. So people will react and then the table will sort itself. And then we'll say, okay,

Starting point is 00:54:53 this is clearly the topic on people's mind. And that's like a version of what we call Dori, which I can talk about. But essentially the kind of principle is you should discuss that project work with the whole group there, right? Like with the whole triad there. And oftentimes with the salesperson there and with the marketer there and like with everybody else. So I found that that is just a really good practice to try to sort of move a lot of that work out of one-on-ones

Starting point is 00:55:23 and into a small group setting. Awesome. Okay. So you're working on a handbook that's collecting a lot of these rituals. Talk about that. And then when can people maybe, look for it. One of the realizations I had the other

Starting point is 00:55:39 day, probably like a month or two ago when we started working on this thing was someone, I was talking to someone about catalyst and a couple other concepts and they're like, I get it. I'm sold. Like, let me, like, I want to implement some of these things. Where do I look? And

Starting point is 00:55:54 so I found myself sending them a bunch of links to individual templates. So that was kind of like that queued us into the fact that we needed to have like a better kind of core handbook for teams that wanted to adopt some of these rituals and also learn from all the rituals that we have learned from and feel very fortunate to have partnered with so many customers on. And so what we did was started writing this handbook. And it's going to come out

Starting point is 00:56:22 hopefully by the time this recording is done. And in it, you know, we'll talk about, you know, everything from rituals like catalyst to decision rituals to a lot of like planned. and strategy and roadmaps, that kind of stuff, and trying to pull out the most interesting patterns and also give people a pretty practical view of how to implement these things. I think that's what has been lacking sometimes. Amazing. We'll definitely link to that.

Starting point is 00:56:51 Hopefully it's live by the time this goes up. We'll make it happen. I know also you said Shashir's working on a book that's related and basically rituals of great teams. And Shishir was on the podcast and talked to some of these other. He talked about Dory, so we don't have to get into that If people want to learn about Dory, they can watch that episode. It's one of the earliest episodes, actually, one of the most popular.

Starting point is 00:57:09 Yeah, I remember that. Okay, cool. So I have a bunch of random questions now. I'm just going to go in a few different directions. One is you wrote this post that you call Learn By Making, Not Talking. Is that another principle, by the way? Is that amongst your many principles? Okay, awesome.

Starting point is 00:57:25 So in that post, which we'll link to, you show the story of how you and the YouTube team came up with skippable, skipable ads, which was, I didn't realize it was such a controversial, but thinking about it, obviously, like letting people skip ads. I could see why people were not excited about that? Could you just tell that story? And basically, it's like the story of how skippable ads on YouTube came about. Yeah. So I moved over to YouTube shortly after the acquisition.

Starting point is 00:57:51 It was amazing, like, tight-knit team. It definitely felt like the Wild West. It was, you know, we were getting sued by Viacom for a billion dollars when that was a lot of money. no advertiser wanted to talk to us. It was essentially viewed as like a site of cat videos and dogs on skateboards and things like that. And then the say, I guess the other context, the sales team was like very nascent and all they wanted to sell was the homepage. And for good reason. Like that was where you made your money as a salesperson.

Starting point is 00:58:22 And, and so, you know, I had just been sponsored by Salar and Shashir to become a PM. that's a longer story that I'll leave out for now, and we can go into. But on day one of being a PM, she shares like, great, you're the new guy, you get the project that nobody else wants. And that's called skippable ads.

Starting point is 00:58:44 And we've got this crazy idea that we can align the incentives of advertisers and viewers and creatives in this really clever way by putting a skip button on the ad and then charging people for views. And the latter part, We hadn't quite cemented yet, but it was sort of a, it was like part of the core idea.

Starting point is 00:59:04 And so the thing I write about in this post is like as a new PM, this feels like a really consequential decision, right? It's like we've got this like new product idea. Nobody really wants it. Like advertisers don't want it. The sales team doesn't want it. And it's like a very unproven thesis. And so the thing I write about is like these are the types of things that you can debate for like

Starting point is 00:59:24 months or years, you know? And I was sitting in a one-on-one. with this guy named Phil Farhe, who's an amazing product leader and was my boss at the time. And we're trying to figure out what to do and how to handle all the different dynamics. And he just kind of like stops.

Starting point is 00:59:40 And he's like, you know what? Like just test the extremes. Start the experiment tomorrow. Like then we'll figure it out, essentially. And I think his point was like, look, we can debate this forever. So, like, I would rather us see the upper and lower bounds of like how good this could be

Starting point is 00:59:58 or how bad this is going to be, like immediately. And so, you know, we launched a set of experiments. This guy Jamie Kearns, who's still there, a tiny little skip button, you know, on one experiment, giant skip button that covered the entire player on the other side of the experiment. And within a few weeks, I think we had developed some conviction, you know, based on some very directional data that we were on to something.

Starting point is 01:00:26 And so the lesson that I took, you know, this is many years ago, and I've seen this proven out hundreds of times since, is, you know, stop talking about it and like go make something. Go, go, like, run an experiment, go make a prototype, you know, go write a doc, go make a mock. Just don't talk about it. And I found that people, you know, also as a leader, people really follow that concept. And I also found that it's like, it transcends level, you know, like I'm not talking just to ICPMs. I'm talking to like heads of product and CPO's and CEOs to some degree. Like, you know, you should always be out there trying to learn by expressing, expressing your ideas and putting them out there.

Starting point is 01:01:15 And that's much more valuable in many cases than, you know, pontificating about it or having endless, you know, circular discussions on it. It makes me think a little bit about Twitter, where they spent years just thinking about the edit button or all these different changes. They're so scared. They did so much research. And then now it's just like they're changing things left and right. Everything's fine. Everyone's still using it. It shows you that you don't have to be so delicate.

Starting point is 01:01:38 Yes. It's almost never as bad as you think it's going to be. So, yeah, it's just a question of how much better it can be oftentimes. You mentioned in your early career, we talked about your Alaska guide phase. Something else I saw is. that you are on the AdWords approval team. You're basically reviewing ads, people submitted to run on AdWords. And that's kind of how you started in tech.

Starting point is 01:02:03 So I guess, first of all, is that true? And then second of all, how did you graduate from that phase and become this chief product officer of one of the fastest growing most interesting companies in the world? That was a really memorable time. It was, there's an amazing cohort of people that started in tech. I think there was like two or three hundred of us at that time. And then eventually thousands that started in Cheryl Sandberg's organization, I guess maybe some quick context.

Starting point is 01:02:32 Before running ads on Google.com at that time, you had to have them manually approved by a human before that was like handled by machine learning and outsourced to other countries. And so there was this process where basically an ad would show up on your screen. You would market family safe, non-family safe porn. and then you would, based on that, it would either run or it wouldn't.

Starting point is 01:02:54 And actually, funny enough, some of my most successful friends were terrible at the approval event. Like, they failed the rote task of approving ads. They just, like,

Starting point is 01:03:04 couldn't handle it. And they went on to be, like, really, really successful. So after working on ad approvals, at that time, I moved to chat support.

Starting point is 01:03:14 It was basically, like, when AdWords was launching chat support. I remember very fondly having two chats, chatting with two advertisers at once, moved on to phone support. That was eight hours a day of talking to AdWords customers, really a total roller coaster

Starting point is 01:03:30 ride. It was basically like one minute you would pick up the phone and it would be someone from a Fortune 100 company trying to spend like millions of dollars on AdWords. And then like the next minute you would be on the phone with like a psychic or a taxi driver. It was like warring with their compatriots over some really specific keyword. I think there were kind of like two lessons that I would draw from this. One is I had a mentor at the time and his advice when I was starting my career was basically like you have to get customer facing from the very beginning because you're going to end up

Starting point is 01:04:05 serving a customer your whole career. Like even when you're the CEO of a company, you're going to be serving a customer. So you better get like really good at being in any customer scenario and being able to handle it, you know. And so I think that that turned out to be. insanely good advice. And if I think about, you know, something that, a piece of advice that I give out to people who are earlier in their career, I've definitely recycled that advice. I think the other thing that I took away from that experience was it's just a great lesson in when people don't

Starting point is 01:04:36 actually care about your product. So in AdWords case, people did not care about AdWords. Like, you were like the expert on it and they were trying to tell them about ad groups and like how this ad format works and blah. And like most of the time, people are like, dude, I'm a small business owner. I'm trying to like get people to come to my auto mechanic store. I'm trying to get people to come to like my taxi service or whatever it was. I don't care, you know? And so like you're basically the product had to kind of get out of the way and really just drive impact for the customer. You know, it was like they just want more phone calls or they want more people in the store. So those are I think two kind of like pieces that I think about from those days still.

Starting point is 01:05:21 And then I worked in a variety of other roles. I worked in a role called product specialists, which is an awesome role back when they're like 15 product specialists at Google. And that was, for me, that was an amazing time because I had, I was getting to sit on like seven or eight different core teams, core product teams. And in my observation, most people these days, most PMs don't get to sit. on other people's core teams. And so I kind of had these like three or four years of just, you know, I kind of call it like a master class in PMing because I was getting to watch like what was working for some PMs and what wasn't working for other PMs

Starting point is 01:05:58 and just kind of like taking notes behind the scenes. So that was a, that was a really influential role. And then, yeah, went on to various PM roles at Google and YouTube. Coming back to noticing comes up again and again in our chat. This is so interesting because it feels like you basically came from the mail room of tech to the top of the product field. And so I think there's a lot of inspiration people can take from this journey. One quick question is, how long was that journey from not being a PM? Like, from, I guess, being at a tech company to getting a first PM role, just to give people

Starting point is 01:06:33 sense. Let's see. I probably worked for at least four, five years before being able to move to PM. And that was, I think that was like a slightly harrowing journey because at the time you had to have a computer science degree. I Google, right. Cool. So I think that's one takeaway, too, is give it time. It's not going to happen. There's a lot of people that are just like, I need to become up him immediately.

Starting point is 01:06:55 Totally. I think that's a good example of like, it's not going to happen overnight. Coming back to your two lessons, I think they're really interesting. And I'm curious if there's anything else that comes to mind of what you found was essential to you succeeding in this path. So the first lesson you shared is being customer facing. And in this case, like being in retail as customer facing is your advice. like get in a tech company and work on something customers use or is even like working at

Starting point is 01:07:19 Starbucks or you know, Abercrombie, does that count? Yeah, I mean, I think maybe to relate it to what you just said, if I were to give advice to someone who really, you know, is trying, aspires to be a PM or trying to get into PM. Like, I think in many cases, if you're in a customer facing role, you are the expert on the customer. And that is like really, really valuable in tech organizations. and oftentimes it's kind of undervalued. And so I think people who want to move into PM roles who are sort of not currently in PM roles

Starting point is 01:07:53 can often lever that experience and that knowledge of the customer in ways that are pretty profound for the organization and pretty insightful for the organization if they really are creative about it. And then I think the other thing is, regardless of like where you are in the organization, you're always serving a customer. You can't just talk to one big enterprise customer

Starting point is 01:08:17 and you can't just talk to the smallest customer. You kind of have to have a diverse and continuous stream of customer interactions in order to have good intuitions about what to do next. And your engineers aren't going to really trust you unless you have good intuitions about where the customers headed and what they want and stuff like that. And so the stakes, I think, are pretty high.

Starting point is 01:08:39 And it's, you know, the good news is it's like easier than ever with all these tools to really get into the mindset of a customer. My lesson touches on something a previous guest talked about Paige Costello, where she was often the youngest person in the room and built a lot of respect and people really trusted her over time. And her lesson was, know thy customer. If you know the most about what they need and you can show like, here's what I've heard this again and again.

Starting point is 01:09:06 People just like, oh, Lane, tell us more. And they bring you into conversation because you're providing value. you're not just there sharing opinions. Everyone's got opinions. I mean, that's basically how both me and I had a friend named Bill Farrell who transitioned into PM at the same time. And that's essentially how we got, you know, the try at being a PM inside of Google is like,

Starting point is 01:09:27 we needed the customer really, really well. And we were often in conversations, you know, sort of bridging the gap from, here's what the customer thinks that, you know, here's what I think they're really saying or here's what I think we should build based on you know what they said. The other thing I wanted to mention, you talked about the product

Starting point is 01:09:43 and how a lot of customers don't care about the product. They just care about just any of this thing done. Reminds me at Airbnb, we hired this guy, Chip Connolly, who was a hotelier. He created the Zawada V Hotel chain and just like is steeped in hospitality. And he came to Airbnb and started doing this worldwide tour, talking to hosts.

Starting point is 01:10:03 And he's just like, guys, when you talk about product, like you're like telling hosts, hey, the product's going to be updated, we're going to launch all these features. Like they don't, like, they think they're, home is the product of Airbnb. They don't understand what you're talking about when you're talking about the online experience and the website. That's the last thing they think about. It's the experience of someone traveling at Airbnb and staying in their own. So I think it's a really

Starting point is 01:10:23 good reminder of like most people don't care about the product. They just have this problem. And you just happen to be this website that'll help them solve it. You know, I think most people can be like way more concise of their communication. Like even internally, people don't care. You know, like you should assume you should assume that people don't care. Or, you know, If you're talking to customers, writing a blog post for customers, like you should assume that they don't care. When you start with that assumption, you really force yourself to be a little bit sharper in your communication.

Starting point is 01:10:53 And one final question before we get to a very exciting lightning round. I heard a story that at Cota, there's this moment called Tim Ferriss Day that drove a lot of traffic. Can you share that story? Does that ring a bell? Sure. Yeah, there's lots of memorable days. Dakota. One of them was Tim Ferriss Day. So I guess me for context, we had built this kind of like publisher, very nascent publisher motion where we were going out and helping people, you know, publish their rituals. And this is what you see in the gallery, the CODA gallery, and, you know, a lot of what we talked about today. But we had this one person on that team, this guy Al Chen, Tim Ferriss fan. And also I think had been really tenacious with like the people around Tim Ferriss and, uh,

Starting point is 01:11:40 and basically finally got an end to him and like figured out a really neat way to implement one of his rituals and protodoc. And so none of us really knew this, but like this is all happening. And anyway, we wake up one morning and traffic is like just like spiking through the roof. Signups are spiking. No one knows what's going on. Like I'm convinced this is all spam. I'm like something's wrong with our data or like, you know, something's going haywire.

Starting point is 01:12:05 At the time, we were also in the China Basin office and the fire alarm went off. And so, like, now we're, like, outside on our laptops. We were, like, in a war room trying to figure out what was happening. And now we're outside trying to figure out what's going on. So anyway, make a long story short, data scientists, investigate. And, you know, we eventually figure out that we had been featured in Tim Ferriss's email newsletter. And, you know, I think early on, you hear this lesson or this adage of, like, first-time founder, build a great product, second-time founder,

Starting point is 01:12:41 filled a great distribution. I think that was like one of those early big cues to think about the importance of content distribution and the importance of these publishing flywheels. And it definitely made us double down. We're like, okay, if we can do this with Tim Ferriss, like what, you know, what's next? And we definitely spent a few months

Starting point is 01:13:02 trying to reach that, you know, that high watermark that was set that day in traffic and sign up. So it was a fun memorable day and people for like the subsequent one or two years, you know, would refer to it as Tim Ferriss Day. So funny. I bet Tim Ferriss had no idea what he did. No idea. And I'm hoping you have a Lenny's podcast day, once this comes out. Everyone's going to be freaking out.

Starting point is 01:13:23 What is going on here? Is there anything else you wanted to share before we get to a very exciting lightning round? Maybe we're talking really briefly about two-way write-ups. Yeah, let's do it. I have that in my notes, but I skipped it, so I'm glad you mentioned it. Cool. Yeah, I think, I mean, this is a concept that I wrote a bunch about and I often now get asked about. And I guess maybe the historical view of this, I got really obsessed with the history of like how work gets discussed and decided upon and kind of broke it down into like three phases.

Starting point is 01:13:55 And so the first phase was 1980s. We had PowerPoint, you know, it was like this amazing tool. You could like manipulate shapes on a screen and we were all like using fancy clip. part, it was really fun, but we've all had the experience of being in a really long PowerPoint presentation and kind of like someone's droning on in their slides and stuff like that. Second phase is in the early 2000s, kind of like two things converge. One was Google bought this company called Rightly. That became Google Docs. So instead of having Word on your desktop and sending files around, you now had kind of like online collaborative editing. And the other thing

Starting point is 01:14:34 was Jeff Bezos sent this very famous memo, which basically said, no more PowerPoint at Amazon. And what that did was kind of started in earnest their six-bager ritual. It says you can read all about this in the book, Working Backwards. It's really good book, Colin Breyer's book. And so that started, I think, what was kind of like what I'll call the one-way write-up phase, which is like, you're writing down your ideas, you're expressing them clearly. It's in prose, so you have to be really clear. That was like a big step up, I think, from from presenting, always presenting work and deciding on work via presentations. And then kind of the thesis is that we're like in the midst of a new phase, which is essentially two-way write-ups. And that's where it's more conversational.

Starting point is 01:15:18 And feedback and discussion is like actually part of the content itself. So that's kind of like the broader historical arc. But if you think about it, PMs and like product people are always at the like brunt, you know, they sort of feel that. the most because they're the ones that are like driving decisions and really the ones that are driving discussions oftentimes in companies. And so, you know, I think the problem with one-way write-ups, I felt very deeply at Google and YouTube. And just to name them, the first one is you would always be trying to figure out like who's read your write-up. So, you know, I have many memories of sending a write-up out at 1130 p.m. and then like waiting patiently for the

Starting point is 01:16:00 avatar of like the SVP in my area to show up in there. And that was like a sign that they had like read it, which is like, you know, just totally insane if you think about that behavior. The second one is you end up having a lot of the discussion in the comments itself. So, you know, this is a space that's really built for like grammar and spell checking and things like that. And you're having like these really meaningful discussions in this kind of like 100 pixel right margin. And part of that, I think, is, like, there are all these questions that are being raised. And so you have really no idea, like, what the most important question is. And so if you're facilitating those discussions in one-way write-ups, you're often, like, going through the comments

Starting point is 01:16:41 and the 20 minutes before that session, trying to figure out, like, which one of these do I want to address? And then the other behavior, and I don't know if you've ever seen this in a doc, but, like, in one-way write-ups that you see a lot is, like, there'll be just a mega comment thread on, like the title of the doc. And it's like, people are like, I don't think we should do this or like, you know, you'll get into this 30, you know, 30 comment thread on the title because that's like the best place to put your like overall thoughts. And I saw this like pattern all the time. So if you, if you live that life, I think the world of two way writeups and like the way that I think a lot of our customers are doing it. And you can do this on other tools besides Cota too. I think it's

Starting point is 01:17:22 quite a bit better. You end up, you know, I guess the alternative to go down that list is you have a done reading button at the end of a write-up. So now you can say like, oh, you know, these are all the people that have read this. And like, I think even you see a pattern in some of our customers where if it's like a particularly long write-up, you'll have three done reading buttons. So you can kind of see like where everyone has gotten to. And then the second thing is making sure that you're actually addressing the most important question. So instead of pulling questions out of the comments and trying to figure out which one to address, just putting those in a table and then letting people up with those.

Starting point is 01:18:01 And that's what we call Dory. And then I think probably the most valuable is sentiment or pulse, which is, you know, how do you feel overall about this particular proposal? And if you think about, you know, the contrast between like a comment thread on the title and seeing a list of all the sentiment, how everybody feels about this proposal, and really being inclusive to the entire audience, it's just wildly different.

Starting point is 01:18:30 I think in my particular experience, I'll give you one example. I wrote this proposal. This is now a couple years ago. I thought it was going to sail through, no problem. I thought I was going to get four out of five and five out of five smiley faces from everybody. That's sort of how the sentiment table works. and one of the lead designers basically said like one smiley face we shouldn't do this

Starting point is 01:18:52 I was like oh man this particular person's like not really vocal in meetings and so I would not have heard that feedback it was like very unlikely I would have heard that feedback unless you know they had had a sentiment table a place to to add that and so I think the you know the kind of punchline on all of this is I really authentically believe that this is like a this is sort of where we're headed and hope that a lot of PMs and product teams adopt this in general. I'm so glad that we touched on it. And there's a template or an explanation of this that you wrote up that we'll link to. Great.

Starting point is 01:19:30 Yeah. Awesome. Is there anything else that you think that we should touch on that we haven't touched on? Yeah, I think one thing that we've discussed before is just about strategy and planning and stuff like that. So it may be useful to touch on a couple kind of like insights there. I think there's kind of like two insights in the strategy and planning thing, and this is, again, in the handbook that we're writing. But the first that I end up seeing a lot is just this idea that like OKRs are not actually strategy.

Starting point is 01:20:02 So, you know, I think the way that we plan and the way that our customers plan, the kind of key point is it's critical to disconnect like strategy discussions from OKR discussions. And it sounds really obvious, but it's like, I think, a very common mistake. And I think a really simple question to ask yourself is like, do we have a separate strategy process or strategy ritual that is like distinct from OKR setting and like metric setting and goal setting? And I have found, you know, you can pick whatever strategy framework works for you. But I do think it's quite important to pull those two things apart. the other kind of like rule that we live by on the planning side is what we call it 10% planning rule, which is essentially, you know, just ensure that you're not for a given time period planning for more than 10% of that execution period. And I think this is a really easy mistake to make.

Starting point is 01:21:01 I mean, this is a hard fought rule because we've made that mistake before. But you end up getting kind of like bogged down in planning or saying like planning felt rushed. And so we need to make it three weeks instead of one week or whatever. And the byproduct of that over the course of a lot of time is that you end up, you know, just planning way too much. And oftentimes, you know, you really don't know what's ahead until you've, you know, launched or learned something. And so I think that's a pretty good rule to follow.

Starting point is 01:21:31 I love that rule. I found the same he was a 10% like planning for a week, planned for half a day, planning for a month, maybe like three days. Yeah, I love it. With that, we've reached our very exciting lightning ground. Are you ready? I'm ready. What are two or three books that you've recommended most to other people?

Starting point is 01:21:49 One that comes to mind is turning the flywheel. It's a little manuscript book. Jim Collins wrote it. It's really, I think, a very succinct and very fast read about how flywheels work. We talked about storyworthy. I recommend that book a lot. Good strategy, bad strategy. Love that book.

Starting point is 01:22:07 Very simple framework that I've reused a bunch. maybe outside of tech, waking up as a book by Sam Harris on mindfulness that I really like. And then an old one that I really like is the inner game of tennis by Timothy Galway, which is a kind of classic.

Starting point is 01:22:25 Amazing. On good strategy, bad strategy, I'm working on getting Richard Ramalt on the podcast and talks with his agent and they seem to be excited. So we'll hope hopefully that actually happens. And then you inspired me to try to get the storyworthy guy on.

Starting point is 01:22:39 So what a, cast of characters we're going to get on here. Next question. What is a favorite recent movie or TV show that you really enjoyed? Yeah, it's a little bit hard with three kids and a job these days to watch a lot of TV. I would say I really enjoyed The Last Dance. I like love any sports documentary, all those. Have you seen underrated Steph Curry's new documentary? No, I haven't. I got to watch that. It's really good.

Starting point is 01:23:03 I've been, I've been rewatching a Rested Development. That's also just a timeless classic. classic. I love that Michael Sarah is in the Barbie movie, not to give any spoilers. That was a funny surprise. Next question. What is a favorite interview question they like to ask candidates? There's two. I really like one is teaching me something that I don't already know. I think it's like just an awesome way of seeing if someone's going to lean in and like really figure out what you don't know and then how passionate they are about sort of pitching what they do now. I think is, is really fun. And then Shashir and I have been asking a version of teleporter question and evolving it for many years now. So I like that question quite a bit. Shashir shared that question in his episode and we make TikTok clips out of some of these conversations and that clip just went crazy. People love it. It's the most of you clip I think on TikTok or just like what would you

Starting point is 01:24:01 answer to that question. So we'll try to link to it in the show notes if you want to watch just that one interview question. I think you maybe gave it away. So maybe that's why you're evolving it. I don't know if we screwed you. I also read a recently wrote a post about my favorite ref check question, which I think is I would love to learn other people's favorite ref check questions. References check. Oh, man.

Starting point is 01:24:19 That's its own. Oh, man. I'd love to do a podcast just on that. That is such a important skill. The first question you mentioned of asking people to teach you something, I heard the best version of that in a previous episode, or Maya, they had a product for Spotify podcasts, asks, what would your podcast be if you were to start a podcast?

Starting point is 01:24:38 I like that. Yeah. So feel free to steal it. Yeah, I do, I sometimes do a version of making them explain it two different ways after and making the candidate explain it two different ways and saying like, okay, now you have to explain that to, you know, your grandparent. And then like now, you know, you just told me about sewing or some hobby of yours. Like, I'll sell it in its like most technical form to, you know, someone who knows everything

Starting point is 01:25:05 about this particular topic. And so it's like kind of fun to also see the range that people can operate. Awesome. What is a favorite product that you've recently discovered that you really love, either digital or physical, anything that come to mind? A few, I'm like, become a real sleep nerd. So those eye masks that like sort of cup around your eyes, I love. Yes.

Starting point is 01:25:29 Obviously in the tech world, like Chad GPT, there's a product I got really obsessed with tennis during the pandemic. There's a product called Swing Vision that's really good. It basically cuts up your match into like different, you know, all your forehands or all the longest rallies or all that. He uses AI to do that. There's a corresponding meditation app to the book Waking Up that I really like. That one's a very good one.

Starting point is 01:25:55 We live not so far from each other. So we got us to play some tennis and I can check out this very cool product. Yeah. All right. You're on. That'll be our sequel. Just our game. Next question, what is a favorite life motto that you either repeat yourself often, like to share with people around you, share with your kids maybe?

Starting point is 01:26:15 I don't know if it's a motto as much as it's just a way of being. Essentially the present moment is all that we have. You know, realizing that our attention is very often on the past or the future. And in so many ways, the present is where it should be always. And so I think that that is something I think about a lot. I think maybe more broadly, I had a mentor who roughly set a version of like make things happen. And so I really try to apply that to anything that I do if that's like work or life or sports. You know, I try to be the person who creates like momentum and positive change in progress.

Starting point is 01:26:53 And so I think that that's like generally a good kind of model to live by. Beautiful. What is the most valuable lesson that your mom or your dad taught? My mom's a psychologist. and a professional counselor. So certainly active listening, you know, maybe the tech version of that or the modern version of that is like steel manning someone's argument,

Starting point is 01:27:15 being able to like repeat back to someone, what they said in a better form, more clear form. So yeah, she's an amazing woman. taught me a lot about listening. Final question. You were a guide in Alaska helping people climb. If someone were to pursue climbing,

Starting point is 01:27:33 is there a tip or a lesson or something that you think people should know to get better at this or to know before they go down this route? You know, there's kind of a saying, which is like the safest climber is the one who knows when to come down, you know, essentially. And I think that there are many times that you have to kind of like put your ego in check and come off a mountain or come out of a climb because it's not as safe as you thought it was. So I think that's maybe one. I think the other is, you know, it's probably not a one-way door.

Starting point is 01:28:08 So I think in many ways you can do climbing and you can do some of these outdoor pursuits on the side, or you can, you know, you can always come back from them. So it's maybe not as big of a choice as some people think it is. Lane, I said at the top of this episode, Coda has one of the most thoughtful product teams out there. And I think it'll be clear to people after listening to this, why that's the case and where it trickle. down from. Thank you so much for being here. Two final questions. Where can folks finding online if they want to reach out and ask you any other questions? And how can listeners be useful to you? I'm on LinkedIn and Twitter and I have a substack. We'll be releasing

Starting point is 01:28:47 that handbook for product teams that I will probably post on substack. And in terms of useful to me, yeah, give go to try, give us feedback. I love hearing from product people all over It's like one of the bright spots in my day to hear all the creative rituals that come from this community. You've, you know, created just an legendary community of people. And so, you know, they always give very thoughtful feedback. So I'm very open to all of that. And yeah, thanks for having me. Awesome. Lane, thank you again so much for being here. Thanks. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.

Starting point is 01:29:36 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 lenniespodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - What sets great teams apart | Lane Shackleton (CPO of Coda)

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