What sets great teams apart | Lane Shackleton (CPO of Coda)

1. 0:00 – 4:03

   Lane’s background

   1. LSLane Shackleton0:00

      ... 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? Like those are the moments that stretch you and give you sort of like a new, uh, foundation. So oftentimes, you know, you'll hear like a career question like, "All right. 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 felt like I- I'm underqualified to be there," then it may be worth kind of like digging into.

   2. LRLenny Rachitsky0:49

      (instrumental music) Welcome to Lenny's Podcast, where I 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 Coda, where he is 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. Lane is an incredibly deep thinker, very first-principles oriented, and has built an incredible product team and culture at Coda. In part, he's done that by studying the principles and rituals of great product leaders and great product teams. In our conversation, Lane shares what he's learned and 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 in your career, plus so much more. I could talk to Lane for hours, but we try to keep this to under an hour and a half. With that, I bring you Lane Shackleton after a short word from our sponsors. This episode is brought to you by Eppo. Eppo is a next-generation A/B testing platform built by Airbnb alums from modern growth teams. Companies like DraftKings, Zapier, ClickUp, Twitch, and Cameo rely on Eppo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth team stack. This leads to wasted time building internal tools or trying to run your own experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved most about working there was our experimentation platform, where I was able to slice and dice data by device types, country, user stage. Eppo does all that and more, delivering results quickly, avoiding annoying prolonged analytic cycles and helping you easily get to the root cause of any issue you discover. Eppo lets you go beyond basic click-through metrics and instead use your North Star metrics like activation, retention, subscription, and payments. Eppo supports tests on the front end, on the back end, email marketing, even machine learning claims. Check out Eppo at geteppo.com. That's geteppo.com and 10X your 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, Calm, Quora, 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 and privacy frameworks such as SOC 2, ISO 27001, 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. Over 5,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC 2 and these other frameworks. For a limited time, Lenny's Podcast listeners get $1,000 off Vanta. Go to vanta.com/lenny. That's V-A-N-T-a.com/lenny to learn more and to claim your discounts. Get started today. (instrumental music)

2. 4:03 – 7:32

   Working as a guide in Alaska

   1. LRLenny Rachitsky4:04

      Lane, thank you so much for being here. Welcome to the podcast.

   2. LSLane Shackleton4:07

      So glad to be here. Thanks for having me.

   3. LRLenny Rachitsky4:09

      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 the years. My first question is completely unrelated. I have to ask, your last name's Shackleton. Uh, any relation to a certain very famous Antarctic explorer?

   4. LSLane Shackleton4:36

      Yeah. It's- it's- it's probably distant at best. I wish it was close. I wish I could claim it was- it was my father or grandfather. But I definitely grew up with those stories, um, reading a lot about him as a kid. In high school we read Endurance, uh, 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 have taken a lot of, you know, lessons, uh, from that. But that's- that's as close as I can- I can come to the- the greatness of Ernest Shackleton.

   5. LRLenny Rachitsky5:09

      Okay, so there's a connection. When I think of Shackleton, I also think of the ad that he ran for people, recruiting people to join his journey. Like, low chance of survival, incredibly hard, (laughs) some slight chance for glory if you succeed, something like that.

   6. LSLane Shackleton5:23

      (laughs) Oh, yeah. It's a- it's a wonderful ad. I've- I think I had a mug of that when I was a kid, yeah.

   7. LRLenny Rachitsky5:28

      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, how did- why did you decide not to pursue that and get into product management? Completely different life.

   8. LSLane Shackleton5:42

      Yeah. Yeah, very, very different. Uh, very different time. Didn't have kids back then. I was- I think I was convinced at the time I wanted a career outside. Uh, just like loved spending time in the mountains and climbing, things like that. To be honest, like I wasn't the best guide. There were- there were a lot of amazing, you know, uh, t-... uh, 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, uh, the quick story on why I stopped, uh, 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, uh, about an hour ... It's an hour-long flight. Mountain called Mount Fairweather. Beautiful 15,000-foot peak. Um, and as a part of climbing on glaciers, one of the things that you do, for context, is you ... 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, like, stop them or pull them out. Um, so anyway, I was roped to a very nice client that, uh, I was guiding. Um, and he fell, uh, pretty close to the top on our way down and luckily, like, we were able to self-arrest, um, 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, "I really don't want to die, you know, roped to someone that I barely know (laughs) and, like, don't trust or love."

   9. LRLenny Rachitsky7:17

      Nice.

   10. LSLane Shackleton7:18

       Uh, so that was, that was sort of the last season that I, I guided. But tons of great memories and learnings and, you know, I think it impacted my life in a, a pretty significant way.

   11. LRLenny Rachitsky7:29

       Damn. Software much lower stakes.

3. 7:32 – 9:12

   Parallels between guiding and building software

   1. LRLenny Rachitsky7:32

      I guess just while we're on this topic, is there any parallels or le- big lesson, I don't know, that you learned from that experience that you bring to product?

   2. LSLane Shackleton7:37

      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 checklists. So you ... Before you go on an expedition, you may check a checklist of all your equipment, stuff like that, a dozen times or more so you kind of, like, ensure redundancy, uh, across all your systems. That, 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, uh, I had a client pull a, a big chunk of rock off and break both of their feet, um, and that was ... You know, I, I was, like, the junior guide on that particular incidence 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 him on his back and we basically took turns ferrying him out for a couple of miles. And I'll just never forget, like, instances like that where the, the clarity of, you know, stay calm, assess the situation, prioritize, take action. You know, it's like th- 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, were ... You know, onl- even though I only did it for a handful of summers, uh, were pretty profound.

   3. LRLenny Rachitsky9:06

      Damn. What a very different life, uh, that life path would have been.

   4. LSLane Shackleton9:11

      Pre-kids,

4. 9:12 – 12:49

   Why Lane started studying and writing about product teams

   1. LSLane Shackleton9:12

      yeah.

   2. LRLenny Rachitsky9:12

      Oh, man. So you mentioned writing, you mentioned that there's 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. 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 and people operate?

   3. LSLane Shackleton9:53

      Yeah. Yeah, I've been asking myself that question a little bit lately.

   4. LRLenny Rachitsky9:56

      (laughs) Agreed.

   5. LSLane Shackleton9:58

      I, um ... You know, there's, there's a few reasons. One, one reason is I just found myself giving a similar set of advice in one-on-ones, you know, and, and so I think any time 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 could ... I should probably scale this in some way." And as you know, you know, as, 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 putting ... Writing something down and then putting it out there, uh, 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, a good learning experience there as well. I think the second reason is I've always been pretty frustrated with, uh, career ladders. You know, most companies have career ladders of, like, 10 or 15 levels and, you know, as soon as they hit some scale that the levels ... There's, like, levels between levels and I feel like ... I looked at the one at Google, uh, and, you know, you kind of, like, needed a PhD to decipher it and interpret, like, 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, the rat race. And so I found, I found that I basically wanted to have a broader set of principles 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, 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, the last reason I'll mention is I was pretty inspired by a, a talk that is by this guy named Bret Victor who's kind of like a prototyper, thinker. Um, you may have heard of his work. He has this talk called Inventing on Principle.

   6. LRLenny Rachitsky12:03

      Mm-hmm.

   7. LSLane Shackleton12:04

      And in the early days of Coda, uh, one of our first designers, this guy Jeremy Britton, showed this talk to the company- ... and like, my mind was blown. You know, and, 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 im- 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, what are my principles as it pertains to like building software and other things. So those are kind of like the three reasons that, you know, uh, led me to start writing these things down.

5. 12:49 – 14:10

   How Lane came up with the career ladder and guiding principles

   1. LSLane Shackleton12:49

   2. LRLenny Rachitsky12:49

      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, but I also want to understand how you actually ended up doing ladders and performance review stuff at Coda. Would it be better to talk about that later after we go through some of these things, or is there something you want to share first of just how you think about it at Coda?

   3. LSLane Shackleton13:06

      When we were doing c- career ladders, first of all, we, you know, we put it off for, uh, quite a bit of time and that was based on the advice of a lot of other leaders that said like, "As soon as you introduce this, then the incentives sort of like flip from being company-focused to being individual-focused." And so I, I think we, 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 like what it means to grow and what it means to be great. And so at about the same time 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, 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, uh, company dis- discussion. In fact, we, we kind of don't use titles

6. 14:10 – 16:30

   The five levels Coda’s career ladder

   1. LSLane Shackleton14:10

      that much.

   2. LRLenny Rachitsky14:11

      You said that it's not specific to role. Do you mean like the same leveling attributes are the same for design and product and engineering?

   3. LSLane Shackleton14:19

      We basically have five levels and, uh, 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. So the, the bar is like really, really high for principal in this, 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, our role stages. I find it, 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 has, 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, uh, role stages are not visible across the whole company. Like, you know, we're, we're not showing levels of any individual PM or designer, and that's partially because we just don't want to put a, a big focus on it. And then, uh, probably the biggest difference is, uh, we have a centralized compensation committee and that's who decides compensation. And so it's not the manager that drives, uh, your compensation. So those are some differences.

   4. LRLenny Rachitsky15:52

      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 right, these five stages are roughly the same across role. So designers have the same kind of five and they're described similarly.

   5. LSLane Shackleton16:08

      That's right. They're, they're described similarly at a high level, but then the specifics, like if you get into it, uh, are a little bit different.

   6. LRLenny Rachitsky16:15

      Okay. I'm going to ask about what the principles are or a few of them that you can share. But, uh, one other very tactical question. At what size of product team, say just PMs, did you start to develop this framework?

   7. LSLane Shackleton16:26

      Uh, we were probably at 20-ish PMs and designers

7. 16:30 – 21:06

   Principles of great product managers

   1. LSLane Shackleton16:30

      when we did that.

   2. LRLenny Rachitsky16:31

      Awesome. Okay. So let me just ask, what are some of these principles you've kind of narrowed in on as principles of great product managers?

   3. LSLane Shackleton16:38

      Maybe it's helpful to start with a little higher level context on the kind of unifying thesis. 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 a product manager, kind of like everything is ambiguous all the time, (laughs) you know? It's like, uh, "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?" 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, 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.

   4. LRLenny Rachitsky17:41

      (laughs)

   5. LSLane Shackleton17:41

      So the first one, uh, that I wrote about was, uh, systems, not goals. And one of the ways that I started this post, I'm a big fan of getting, uh, inspiration from outside of tech. And so, uh, one of the stories that I tell is basically the story of Jerry Seinfeld. Uh, 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 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? Uh, and the thing that he does is he sets a, a goal which is basically to build up to an hour of material again. But the goal isn't that important. The ... What's important here is, like, the system. 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, uh, that's how he builds up from five minutes to 15 minutes to 30 minutes, uh, 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 as ob- obsessed with the goal, you know, be obsessed with the system that gets you there. And so, uh, the phrase I sometimes use is, you know, goals with good intentions don't work. And I think that, uh, uh, really, you need to give a common example. A, a really common example is teams that are trying to, like, learn about customers or do research or ... 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, you know, 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, uh, until you understand that the latter team, you know, tends to have, like, really good product instincts or really good customer instincts is because they've just had this, like, sort of default on mindset of, of talking to customers. And in the early days of Coda, 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've had something that we've been baking for a while. But the point is that it was default on, right? And so, like, the way that we developed good customer instincts, uh, was not the goal. It was really just the sort of system behind it. So that's, that's one that I'm kind of passionate about and, uh, I think it's also translates into a lot of the rituals that we, we, we talk a lot about.

8. 21:06 – 24:05

   The beginner’s-mind ritual at Coda

   1. LSLane Shackleton21:06

   2. LRLenny Rachitsky21:06

      There's so many directions I can go with this. I re- I really like this one. It reminds me of something I did at Airbnb where we had a lunch with a host every Friday with the team and we had-

   3. LSLane Shackleton21:15

      Nice.

   4. LRLenny Rachitsky21:15

      ... our community person find someone in San Francisco that's a host and there's no agendas, just let's have lunch, meet the team, curious what you're wondering.

   5. LSLane Shackleton21:22

      Exactly.

   6. LRLenny Rachitsky21:22

      And, and everybody we host are always so nice and it's such a pleasant experience, (laughs) always. Also makes me think about this book, uh, The Score Takes Care of Itself.

   7. LSLane Shackleton21:30

      Yep.

   8. LRLenny Rachitsky21:30

      Have you read that?

   9. LSLane Shackleton21:31

      Yeah, 100%.

   10. LRLenny Rachitsky21:31

       Where it's just like do the fundamentals and you'll win.

   11. LSLane Shackleton21:34

       Totally.

   12. LRLenny Rachitsky21:34

       The other thing it reminds me of is I have this, uh, quote hanging in my office here from, I believe it's from the Rick Rubin book, and the quote is, "The object isn't to make art. It's to be in that wonderful state which makes art inevitable."

   13. LSLane Shackleton21:48

       I love it.

   14. LRLenny Rachitsky21:49

       I feel like we just changed arts to-

   15. LSLane Shackleton21:51

       Yeah, Rick Rubin's book is amazing.

   16. LRLenny Rachitsky21:52

       Oh, my God. It's so good. (laughs) There's just like every, every section is, like, this quotable thing I want to, like, I need to hold onto this thing. Yeah.

   17. LSLane Shackleton21:58

       He's got a great thing on, uh, listening. I think I, I really admire what he says about listening, uh, and I think that a lot of PMs could take, uh, take that lesson, which is...

   18. LRLenny Rachitsky22:10

       Yeah. What is that lesson?

   19. LSLane Shackleton22:10

       The way he talks about it is essentially you want to listen and absorb sort of every fragment of what that person is saying, including, you know, their body language and everything else and try to turn off the side which is crafting your response or, you know, talk- 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 of the conversation. But I think if you can really challenge yourself, uh, like he says, to pause and really in- try to internalize sort of holistically what that person's saying, it's pretty powerful.

   20. LRLenny Rachitsky22:55

       I was actually just reading that chapter and the next chapter is about this, the idea of the beginner's mind.

   21. LSLane Shackleton23:00

       Yeah.

   22. LRLenny Rachitsky23:00

       I don't know if you remember that. We're going... I feel like we get s- people get sniped by Rick Rubin stuff. But anyway, I'm gonna (laughs) go down this thread. He talks about how, uh, AlphaZero or AlphaGo, the first-

   23. LSLane Shackleton23:09

       Yeah.

   24. LRLenny Rachitsky23:10

       ... AI thing that beat humans at Go and how there was this move it made, Move 37, in a game that was just, like ... Like, the person, the AI was playing walked out of the room. He's like, "I can't ... I don't even know what, 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 comprehended. And so it's a really good example of the power from, of coming from beginner's mind and not being influenced-

   25. LSLane Shackleton23:39

       100%.

   26. LRLenny Rachitsky23:39

       ... by what's already been done.

   27. LSLane Shackleton23:41

       Yeah, we do ... We have, like, a walkthrough ritual that we do.

   28. LRLenny Rachitsky23:45

       Hm. Tell me more.

   29. LSLane Shackleton23:46

       Uh, where we ... The, 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, uh, five or 10 people watching you and let's, you know, let's, let's sort of fix all the problems that we see.

9. 24:05 – 27:46

   Two rituals: “cathedrals not bricks” and “proactive not reactive”

   1. LSLane Shackleton24:05

   2. LRLenny Rachitsky24:05

      Okay. So I want to talk about rituals. We're getting ahead of ourselves a little bit. Is there any other 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, 'cause I want to check it out.

   3. LSLane Shackleton24:20

      Uh, just lane@ sub- or lane.substack.com.

   4. LRLenny Rachitsky24:24

      Okay. Sweet, we'll definitely link to it. Uh, yeah, any other principles?

   5. LSLane Shackleton24:28

      I think the, the other one, uh, is cathedrals not bricks, and then, uh, the other one is proactive not reactive. Uh, cathedrals not bricks I think is a kind of classic one. I think I had a moment of realization in, in talking to Shishir in a one-on-one when I was at YouTube, sort of bemoaning the 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 was 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, like, performing and, uh, as a team and, you know, you're asking me about cathedrals." And then he sort of explained the cathedral story, uh, which I can, which I can talk about. And that-

   6. LRLenny Rachitsky25:11

      What is the cathedral story?

   7. LSLane Shackleton25:11

      ... I think was quite clarifying.

   8. LRLenny Rachitsky25:13

      Yeah. Do share.

   9. LSLane Shackleton25:14

      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, you know, 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, what are you doing?" And they say, "W- well, we're building a cathedral." Uh, 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 and maybe not take the time to sort of help the team take a broader frame, open the aperture a little bit, uh, and have a, uh, 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, and I've made this mistake before, uh, plenty of times, very often people will, you know, do a great write-up on vision or strategy or whatever it is and the result is people can't quite see their, their version of what this, like, broader arc is or this broader cathedral is. And so one of the things that we have tried to do, uh, when we go through big planning cycles is kind of show all the different sides of this. So instead of just having, like, a, a write-up, we may have a write-up, we may 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, may change. And really what we're trying to do is kind of take the mystery out of the set of, like, broader constraints or where we're headed. And so I think that that is a, uh, you know, I think great product teams and great PM leaders tend to always orient their teams towards a broader cathedral as op- as opposed to laying bricks.

   10. LRLenny Rachitsky27:27

       Such a beautiful metaphor. Reminds me of this other quote I just looked up while you were 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."

   11. LSLane Shackleton27:39

       Classic.

   12. LRLenny Rachitsky27:39

       Classic.

   13. LSLane Shackleton27:40

       Saint Antoine. Yeah, classic.

   14. LRLenny Rachitsky27:42

       That is right, Antoine de Saint-Exupery, Exupery.

10. 27:46 – 31:17

    How to develop your own guiding principles

    1. LRLenny Rachitsky27:46

       Okay. Something I was curious about as you were 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've found to be useful to, 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 to define these things?

    2. LSLane Shackleton28:06

       Probably two things. One is, is reading really broadly, so I think, uh, not just reading kind of, like, PM style literature. Like I said, I, 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, is, you know, in so far as you get the opportunity to mentor other people, think about, like, what you're saying to these people, 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, uh, so I think noticing those instances was helpful for me.

    3. LRLenny Rachitsky28:46

       Are there any books or topics or areas that you found most inspiration of? You talk about reading and studying other non-product tech.

    4. LSLane Shackleton28:53

       I mean, definitely, like, sports.

    5. LRLenny Rachitsky28:55

       Oh, wow.

    6. LSLane Shackleton28:56

       I, I would say, like, sports is, is really interesting-

    7. LRLenny Rachitsky28:58

       Interesting.

    8. LSLane Shackleton28:58

       ... to me. Team sports, have always been a huge fan of everything team sports. Storytelling. You know, go, go look at, uh, some of the best storytellers in the world and they're, they're, they're actually up there on a stage telling stories. Uh, there's a book called Storyworthy that I really like.

    9. LRLenny Rachitsky29:15

       I was just gonna mention that. That book is so good. Somebody mentioned this on the podcast, and I was ... I read it. It's, like, the most useful practical book for how to tell better stories.

    10. LSLane Shackleton29:23

        It's so good. It's so-

    11. LRLenny Rachitsky29:23

        So good.

    12. LSLane Shackleton29:23

        The insight is amazing. The, 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 orient, like, everything else around that, like, moment of trans- you know, transformation, then, uh, you, you end up usually telling a, a reasonably good story. And so, uh, we actually had ... I, I had a conversation with the author right after I read that book 'cause I was just, like, totally enamored with it. And then we, we ended up bringing him into Coda, uh, and he gave a great talk. So yeah, big, big plug for Matthew Day. Great.

    13. LRLenny Rachitsky29:58

        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 gonna be completely opposite at the end of the story because of this-

    14. LSLane Shackleton30:11

        Yeah.

    15. LRLenny Rachitsky30:11

        ... transformation that takes place. So-

    16. LSLane Shackleton30:13

        Yeah.

    17. LRLenny Rachitsky30:13

        ... I'm watching movies with my wife now. I'm like, "Okay, she's very shy right now. She's gonna be very, like, extroverted by the end of this movie."

    18. LSLane Shackleton30:18

        (laughs)

    19. LRLenny Rachitsky30:18

        Where they love each other-

    20. LSLane Shackleton30:19

        Right, yeah.

    21. LRLenny Rachitsky30:19

        ... or they're gonna have a lot of problems.... yeah. (laughs) 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. So you Yeah. I mean that, that's like what, what I would say is like as a maybe a, a principle version of this, you know, the way, the way that you learn or the way that everyone and in- including me learns new things is like you go seek out the best, uh, at that given craft. So in this case, you go to The Moth, StorySLAM, you see some like really good stories like if you ever watch these on YouTube. Uh, 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 ... In so far as you can put yourself in situations that are uncomfortable or having, you know, force you to, to do things like tell a story or force you to come up with a clear strategy. Uh, you should always opt into those, especially, you know, early

11. 31:17 – 36:03

    Learning from your “oh shit” moments

    1. LRLenny Rachitsky31:17

       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.

    2. LSLane Shackleton31:24

       And the world is much better for it. Yeah, this podcast is an amazing resource you've done.

    3. LRLenny Rachitsky31:29

       Aw, thanks man.

    4. LSLane Shackleton31:29

       You've done something very special.

    5. LRLenny Rachitsky31:31

       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 us, people a sense of whether they're making progress in their career.

    6. LSLane Shackleton31:47

       Yeah.

    7. LRLenny Rachitsky31:48

       Can you talk about that?

    8. LSLane Shackleton31:49

       Sure, yeah. I think I picked this up originally from Seth Godin, the author, and it just like totally stuck with me. Uh, 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 under-qualified to be here," those are the moments you should be seeking out, right? Like, those are the moments that stretch you and give you sort of like a new, uh, foundation. And so I have found that they turn out to be a pretty good way to calibrate whether someone is growing, uh, in their career. 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. 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, 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, I'm under-qualified to be there, then it may be worth kind of like digging into.

    9. LRLenny Rachitsky33:04

       That is so good. (clears throat) Makes me think about this podcast where I never wanted to do a podcast. 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, uh, I'm like, "No, I got to do it 'cause it's hard." And, uh, and I'm glad I did it. It also reminds me of this quote that I love, that I always think a- back to. "The cave you fear contains the treasure you seek."

    10. LSLane Shackleton33:26

        Nice. That reminds me of, uh, have you read the book The Obstacle is the Way?

    11. LRLenny Rachitsky33:31

        No. Say more.

    12. LSLane Shackleton33:33

        Uh, it's a, it's a great book by Ryan Holiday and the kind of core thesis is i- it's, it's a book a bit about Stoicism. But, um, the, 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 most sort of profound, uh, moments of your life. And, uh, he has a lot of examples in that book of people throughout history who sort of made that choice. And I think, uh, he's also given that talk to like hundreds of sports teams. Um, so, uh, it's a, it's a good book worth reading.

    13. LRLenny Rachitsky34:08

        It's so hard. It's so hard to do hard things, man.

    14. LSLane Shackleton34:10

        Mm-hmm.

    15. LRLenny Rachitsky34:10

        God dammit. 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. 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, how do you actually go about learning about these rituals? I know you have this really interesting process.

    16. LSLane Shackleton34:31

        Yeah, I mean, in general, um, I'm a big believer in, you know, good design an- and good product starts with noticing. And I, I think, er, Tony Fa- del has a great talk on this. So I think a bunch of us that are really obsessed with, with rituals, uh, we just honestly try to be great at noticing. So, you know, see something happen with a customer, ask a few questions, get introduced to their team, 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 Coda we're, 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, uh, 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, Shishir's writing a book called Rituals of Great Teams, uh, 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, 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.

12. 36:03 – 42:15

    Rituals from great product teams: HubSpot’s FlashTags

    1. LSLane Shackleton36:03

    2. LRLenny Rachitsky36:04

       What are some rituals that you've learned from these dinners and these ... and this research you've done that have really stuck with you?

    3. LSLane Shackleton36:10

       There are so many. (laughs) It's like it's hard to choose. Um, maybe I'll choose two that are, that are top of mind. One is, uh, Dharmesh Shaw has this, this ritual from HubSpot called flash tags. Have you heard of this?

    4. LRLenny Rachitsky36:24

       No.

    5. LSLane Shackleton36:25

       Um, so yeah. We- we've all probably been in the situation where ...... uh, you know, someone gives you feedback and you're, you either like under interpret it or over interpret it and as an organization, you know, the, 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. Um, and so he outlines, uh, four flash tags. Uh, he, he presented this in a dinner, one of our dinners. And I, I absolutely love the phrasing of these, as like someone who's given a lot of (laughs) feedback on product stuff in their career. Um, so the, it ranges from I think it's FYI, suggestion, recommendation, uh, plea. So FY- FYI is basically like I had a thought, you know, take it or leave it kind of thing. Suggestion is ... And, and he uses this, like, hill dying metaphor. So is this a hill I'm gonna die on? And FYI is like, uh, you know, there's no hill in sight. Suggestion is like there's a hill. I'm not gonna die on it, (laughs) but 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 gonna die here, but like I've thought about this a lot, so, like, don't ignore this. You know? Uh, 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, (laughs) um, 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. We ... I was actually just at a offsite and, uh, someone gave a lightning talk, uh, 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.

    6. LRLenny Rachitsky38:20

       That's amazing. It's interesting none of them are just, just do the, do it this way. I imagine that's very intentional.

    7. LSLane Shackleton38:25

       Yeah. I think it's ... I mean, it's honestly it's a sign of a, a ... In Dharmesh's case, I, I don't know him super well, but, like, it's a sign of a, a really experienced leader, you know, to, to know, uh, that, that scale. But, uh, every time I look at the scale and I'm sort of weighing where I am between, you know, suggestion and recommendation, I have to kind of like giggle to myself.

    8. LRLenny Rachitsky38:45

       And how do you, how do you actually use it? Do you ... In the feedback you, like, put a hashtag plea kind of thing?

    9. LSLane Shackleton38:51

       The way it gets used in Codedocs 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 feedbacks and then there'll be, just be a, like, a little select list and you can select, um, between those four. And usually people, what people do is they include, uh, the descriptions 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 i- honestly, it's just, it's good hygiene, you know? Otherwise every bit of feedback is taken the same, which is ju- just fundamentally, like, the impact of that is it slows everything down, 'cause n- now you're looking at, like, a list of a h- pieces 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, it's much easier to sort through them.

    10. LRLenny Rachitsky39:46

        What about if it's in person? Do you say, "This is a plea," or, "This is a FYI?"

    11. LSLane Shackleton39:50

        Oh, I, I definitely heard that in many meetings. Like, is ... "Are you making a recommendation or are you making a plea?" (laughs) You know?

    12. LRLenny Rachitsky39:57

        Mm. Amazing.

    13. LSLane Shackleton39:58

        And making the person think through that choice I think is, is just a very helpful shared language.

    14. LRLenny Rachitsky40:04

        I 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 gonna be, like, taken really seriously and the team's gonna rush back and be like, "Oh."

    15. LSLane Shackleton40:14

        Exactly.

    16. LRLenny Rachitsky40:14

        "... when you told us to change this thing." I imagine it helps-

    17. LSLane Shackleton40:16

        Yeah.

    18. LRLenny Rachitsky40:16

        ... to just make it clear, "No. You don't need to actually change this. Just my thoughts."

    19. LSLane Shackleton40:21

        Yeah. Exactly. Yeah.

    20. LRLenny Rachitsky40:22

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13. 42:15 – 47:01

    Rituals from great product teams: Coda’s Catalyst

    1. LRLenny Rachitsky42:15

       Any other rituals that stand out as really interesting, either more recently you've learned or something you're just like, "Oh, wow. That was genius"?

    2. LSLane Shackleton42:21

       I guess one that I get asked about a lot on our team is, uh, called catalyst. And I guess maybe to set some context on this one, in most product teams their review forum is just, like, a really important part of the product development process.... and the, the kind of like core insight, uh, for, you know, most review forums or, you know, product reviews or decision forums is that they, they generally suffer from two problems that are like kind of hard to spot unless you've sat through, you know, hundreds of them. The first is, uh, 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, 'cause I think they're not exactly intuitive. Um, so when you think about, uh, what happens in a standing, uh, with a sa- 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. 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 like knows most about this?" Or "Do we have the engineer who's actually implementing this here? Oh, great. They're not here?" 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, uh, in retrospect. The second problem is a single threaded, so like one topic at a time. So if you think about, you know, if, if a product development process is like, you know, somewhat of a chaotic assembly line for a second, you know, your, your review or your decision forum ends up being a big time bottleneck in, 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 I'm a big believer in kind of like decentralized leadership and all of that. But there are things that cr- cut across the company that like need to get reviewed, um, by a broader set of stakeholders. And so what happens when those things are single threaded is, uh, 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, like 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 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, you know, review. I'm just gonna mark myself as interested." And then the driver is like the person who's actually gonna like drive the meeting, drive the decision, drive the outcome, things like that. And basically this is all centralized in, in like one doc. And what happens 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, 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, is much better, and you have the right attendees every single time. And you have like a clear set of, of like drivers and roles in these meetings. So that means that like we can review work much, much faster with the right people. And ideally, that results in, you know, more value to our customers, more things getting shipped, just a higher velocity organization. So that's, 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.

    3. LRLenny Rachitsky46:45

       I love that ritual. You actually wrote a, even in more depth in the post that we worked together on, on how Coda builds product, which we'll link to if folks want to try this out.

    4. LSLane Shackleton46:54

       Yeah.

    5. LRLenny Rachitsky46:54

       And you link to actual templates, people can actually use at their companies.

    6. LSLane Shackleton46:57

       Yeah.

    7. LRLenny Rachitsky46:58

       When someone's listening to this and they're like, "Oh, wow. This is extremely cool."

14. 47:01 – 49:48

    Implementing rituals from other companies

    1. LRLenny Rachitsky47:01

       How easy is it do you find for people to take a ritual from a company and implement it? Like how much of the, is cultural and it's hard to transplant? Or do you find people can take this Catalyst idea, plug and play at a lot of companies?

    2. LSLane Shackleton47:15

       Yeah. I think it, it depends a lot on what your role in the company is. Like, you know, if you're ... Maybe to, 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 like remake the whole review, (laughs) product review cycle that like the head of product is really passionate about and has like crafted. But, you know, you can probably take a, a, you know, decision template or some interesting ritual that has facilitated a team, you know, in the past and use it with, with your team. Another one of my favorites there is $100 voting. Uh, 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. So-

    3. LRLenny Rachitsky48:01

       Yeah, I was gonna ask.

    4. LSLane Shackleton48:02

       ... 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. And you put those in, into a table, and then people can basically vote with their, their dollars and usually you allocate $100. And so people will go through and say like, "Oh, I want to allocate $10 to this and $20 to this and $50 to this, 'cause I think it's really important." And I have found that, especially in, in planning processes, little rituals like this, uh, are great at, 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. We, 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, if going back to the thesis of turning ambiguity into clarity, 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, uh, and so I use that as an example because you can be, uh, you know, a brand new PM, run a, a brainstorm, run a planning session like that, and you're probably gonna get great feedback, right? Like pe- people are probably gonna go, "Oh, 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 and, and someone who tends to have a lot more agency over, you know, the way that the team works.

15. 49:48 – 53:02

    How to navigate changing vs. sticking with current rituals

    1. LSLane Shackleton49:48

    2. LRLenny Rachitsky49:48

       Coda's 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.

    3. LSLane Shackleton49:56

       Mm-hmm.

    4. LRLenny Rachitsky49:57

       I guess that'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, uh, changing the way you operate versus working in similar ways? Is there like a, how do you think about that percentage wise?

    5. LSLane Shackleton50:11

       People are always coming up with new creative ways and to, to kind of like make their teams run better, make decisions go smoother. And we're, we're kind of continuously adopting those. But there's definitely a backbone of the system. Like the, the backbone of the system is Catalyst and tag-ups and the concept called bullpen. And then, you know, uh, there'll be a lot of iteration on top of that. And even those systems, uh, went through a lot of iteration. Like 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 in order for that whole process to really work. So in the years prior to us launching that, you know, we, we kind of, uh, did it with, uh, very manually. So I think there's still a lot of creativity that's, that I see every day. So I, I would give one quick example. One of our PM leads on core product, uh, this guy Nathan, you know, he, he basically saw that a lot of decisions had a lot of different stakeholders because like 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 the, every one of these with core product feels like they impact everybody. And so like a very simple thing that he did, uh, re- you know, probably in the last six months was he had a table of all the upcoming decisions and then add 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, "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, you know? It was like such a, I've been through a million of these, I don't want to treat every one of 'em the same because if I do, it's going to slow down the velocity of, of this whole organization. And so instead, you know, the majority of those, Shishir 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, 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, so just like keep, keep going and, and, you know, check in later." So I think those are, those types of little iterations are usually based on a really good insight.

16. 53:02 – 55:27

    “Tag up” and why one-on-one meetings are harmful

    1. LSLane Shackleton53:02

    2. LRLenny Rachitsky53:02

       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 which you call it tag-up, maybe just briefly explain it. And then I want to talk about this, uh, handbook you're working on, which is gonna I think cover a lot of these things.

    3. LSLane Shackleton53:17

       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 an, it's really an anti-pattern or it's a pattern you should try to avoid. So if you're talking to your manager about product work, uh, 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 like big game of telephone where, you know, you'll have a conversation with your manager in one-on-one. They'll go back and translate it to their engineering and, and design lead. And of course like the fidelity of, you know, the game of telephone, something is lost in, in all of those, uh, 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 off 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 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, make progress, they should use that time for. And they often start by like reviewing OKRs 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 they, the table will sort itself. And then we'll say, "Okay. This is clearly the topic on people's mind." And that's like a, a version of, uh, what we call Dory, uh, which I can talk about. But essentially the, 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, uh, to try to sort of move a lot of that work out of one-on-ones and into, uh, a small group setting.

    4. LRLenny Rachitsky55:26

       Awesome.

17. 55:27 – 57:10

    Lane’s handbook on strategy and rituals

    1. LRLenny Rachitsky55:27

       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?

    2. LSLane Shackleton55:36

       One of the realizations I had the other day, probably like a m- a month or two ago when we started working on this thing was someone ... I was talking to someone about catalysts and a couple other concepts, and they're like, "I get it. I'm sold. Like, let me (laughs) ... Like, I want to implement some of these things. Uh, where do I look?" And, and so I found myself sending them a bunch of links to individual templates. So that was kind of like that cued, cued 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, this handbook, um, and it's going to come out hopefully by the time this recording is done. And in it, you know, we'll talk about, you know, everything from rituals like catalysts, to decision rituals, to a lot of like planning 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 like how to implement these things. Uh, I think that's, uh, that's what has been lacking sometimes.

    3. LRLenny Rachitsky56:50

       Amazing. We'll definitely link to that. Hopefully it's live by the time this goes up. We'll make it happen. I know also you said Shishir's working on a book that's related and basically the rituals of great teams. And Shishir was on the podcast and talked a lot of ... 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 was one of the earliest episodes actually, one of the most popular.

    4. LSLane Shackleton57:09

       Yeah.

18. 57:10 – 1:01:46

    How skippable ads came about on YouTube

    1. LSLane Shackleton57:10

       I remember that.

    2. LRLenny Rachitsky57:11

       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?

    3. LSLane Shackleton57:22

       Yes.

    4. LRLenny Rachitsky57:22

       Is that amongst your many principles? Okay. Awesome. So in that post, which we'll link to, you show the story of how you and the YouTube team came up with skippable, skippable ads, which was ... I didn't realize it was such a controversial. Uh, but in re- 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.

    5. LSLane Shackleton57:46

       Yeah. So I moved over to YouTube, uh, shortly after the acquisition. Uh, it was an amazing like tight-knit team. It definitely felt like the Wild West. It was-

    6. LRLenny Rachitsky57:57

       (laughs)

    7. LSLane Shackleton57:57

       You know, we were getting sued by Viacom for a billion dollars when that was a lot of money. (laughs) No advertiser wanted to talk to us. Uh, it was essentially viewed as like a site of cat videos and dogs on skateboards and things like that. And then the sa- ... I guess the other context, the sales team was like very nascent and all they wanted to sell was the homepage and, and for good reason. Like, that was where you made your money as a salesperson. And, and so, you know, I had just been sponsored by Salar and Shishir to become a PM. That's a longer story that I, I'll leave out for now and we can go into. But, you know, on day one of, of being a PM, Shishir's like, "Great. You're the new guy. Uh, you get the project that nobody else wants."

    8. LRLenny Rachitsky58:42

       (laughs)

    9. LSLane Shackleton58:42

       And, uh, and that's, that's called skippable ads. And you know, we've got this crazy idea that we can align the incentives of advertisers and viewers and creatives in this like really clever way by putting a skip button on the ad and then charging people, uh, per views. And, and the latter part we hadn't quite cemented yet, but it was sort of a ... It was like part of the core idea. 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 (laughs) 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 months or years, you know? And I was sitting in a one-on-one with this guy named Phil Farhi who's an amazing product leader and was my boss at the time, and we're, you know, we're trying to figure out what to do and how to handle all the different dynamics. And he just kind of like stops and he's like, "You know what? Like, just test the extremes. Start the experiment tomorrow. Like, then we'll let ... We'll figure it out." Essentially. And I think his point was like, "Look, you ... We can debate this forever." So like, I would rather us see the upper and lower bounds of like how good this could be or how bad this is going to be like immediately. And so, you know, we launched, uh, a set of, uh, experiments. This guy Jamie Kerns who's still there. Um, little, tiny little skip button, you know, on one experiment. Giant skip button that covered the, the entire player, uh, 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 onto something. 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, 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 products and, and CPOs and, and CEOs, uh, 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. And that's much more valuable, uh, in many cases than, you know, pontificating about it or having endless, you know, circular discussions on it.

    10. LRLenny Rachitsky1:01:24

        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 just like they're changing things left and right. Everything's fine. Everyone's still using it. Shows you that you don't have to be so, uh, delicate.

    11. LSLane Shackleton1:01:39

        Yeah. It's, it's almost never as bad as you think it's going to be. So yeah. It's, it's just a question of how, how much better it can be oftentimes.

19. 1:01:46 – 1:07:02

    Lane’s path to CPO

    1. LSLane Shackleton1:01:46

    2. LRLenny Rachitsky1:01:46

       You mentioned in your early career ... We talked about your Alaska guide, uh, phase. Something else I saw is that you were on the AdWords re- approval team. You basically were reviewing ads people submitted to run on AdWords and that's kind of how you started in tech. 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?

    3. LSLane Shackleton1:02:13

       That was a, a really, uh, memorable time. (laughs) It was, uh ... There's an amazing cohort of people that started in tech there. I think there was like 200 or 300 of us at that time, and then eventually thousands that sha- started in Sheryl Sandberg's organization. I guess maybe some quick context. Before running ads on google.com at that time, you had to have them manually approved by a human. Um, before that was like handled by machine learning and, you know, outsourced to other countries. And so there was this process where basically an ad would show up on your screen, you would mark it family-safe, non-family-safe porn, and then you would, you know ... Based on that, it would either run or it wouldn't. And actually funny enough, some of my most successful friends, uh, were terrible at the approval bit. Like they failed the rote task of approving ads. (laughs) They just like couldn't handle it. And they went on to be like really, really successful. So, uh, after working on ad approvals, at that time I moved to chat support. It was basically like when AdWords was launching chat support. I remember very fondly having two chats, chatting with two advertisers at once. Uh, moved on to phone support. That was eight hours a day of, of talking to AdWords customers. Um, really a total rollercoaster ride. It was basically like one minute you would pick up the phone and it would be, uh, 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 that was like warring with their compatriots, uh, 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, uh, 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 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, uh ... A piece of advice that I give out to people who are early 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 actually care about your product. So in AdWords case, people did not care about AdWords. Like, you were like the expert on it and you're trying to tell them about ad groups and like how this ad format works and blah, 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," or, "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, 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, uh, that I think about from those days still. And then I worked in a variety of other roles. I worked in a role, uh, called product specialist, which is an, uh, an awesome role back when there were like 15 product specialists at, at Google. And that was, uh ... For me, that was a 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 and just kind of like taking notes behind the scenes. So that was a, that was a really im- influential role. And then yeah, went, went on to various PM roles at Google and YouTube.

    4. LRLenny Rachitsky1:06:09

       Coming back to noticing, it 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.

    5. LSLane Shackleton1:06:20

       Yeah.

    6. LRLenny Rachitsky1:06:20

       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 your first PM role, just to give people a sense.

    7. LSLane Shackleton1:06:33

       Let's see. I probably worked, uh, 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 'cause at the time you had to have a computer science degree-

    8. LRLenny Rachitsky1:06:46

       Mm-hmm. At Google. Right.

    9. LSLane Shackleton1:06:47

       ... uh, to be a-

    10. LRLenny Rachitsky1:06:48

        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 a PM immediately."

    11. LSLane Shackleton1:06:55

        Totally.

    12. LRLenny Rachitsky1:06:55

        And I think that's a good example of like that's not going to happen overnight. Uh, coming back to your two lessons, I think they're really interesting and I'm curious if there's

20. 1:07:02 – 1:10:53

    Advice for aspiring PMs

    1. LRLenny Rachitsky1:07:02

       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 is customer facing. Is your advice like get in a tech company and work on something customers use? Or is even like working at Starbucks or, you know, Abercrombie, does that count?

    2. LSLane Shackleton1:07:24

       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, 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, I think people who are, who want to move into PM roles who are sort of not currently in PM roles can often lever that experience and that knowledge of the customer in ways that are, you know, pretty profound for the organization and pretty insightful for the organization if they, if they really, uh, 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. (laughs) You can't just like talk to one big enterprise customer and you can't just talk to the smallest customer. You kind of have to like have a diverse and continuous stream of customer interactions in order to have good intuitions about what to do next. And, you know, your engineers aren't going to really trust you unless you have good intuitions about like where the customer's headed and what they want and stuff like that. And so the stakes, I think, are, are pretty high. And it's ... You know, the good news is it's like easier than ever with all these tools to, uh, to really get into, you know, the mindset of a customer.

    3. LRLenny Rachitsky1:08:47

       That lesson touches on something a previous guest talked about, Paige Costello, where she was like the, 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 and again, people will just like, "Oh, Lane, tell us more." And they bring you into conversation 'cause you're providing value. You're not just there sharing opinions. Everyone's got opinions.

    4. LSLane Shackleton1:09:14

       I mean, that's, that's basically how, uh, both me and I had a friend, uh, named Bill Ferrell who transitioned into PM at the same time, and that's essentially how we got, you know, the, the try at being a PM inside of Google is like we knew 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 to, 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.

    5. LRLenny Rachitsky1:09:41

       The other thing I wanted to mention, you talked about the product and how a lot of customers don't care about the product. They just care about just, "I need this thing done." It reminds me at Airbnb we hired this guy, Chip Conley, who was a hotelier. He created the Joie de Vivre hotel chain and just like is steeped in hospitality. And he came to Airbnb and started doing this worldwide tour talking to hosts 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 their home is the, 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 like that. That, that's the last thing they think about. It's the experience of someone traveling on Airbnb and staying in their home. So I think it's a really 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.

    6. LSLane Shackleton1:10:30

       You know, I think most people can be like way more concise with their communication. Like even internally, people don't care, (laughs) you know? Like you should assume, you should assume that people don't care or, you know, if you're, if you're, you know, 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, you know, your communication style.

21. 1:10:53 – 1:13:24

    Tim Ferriss Day at Coda

    1. LSLane Shackleton1:10:53

    2. LRLenny Rachitsky1:10:53

       I have one final question before we get to our very exciting lightning round. I heard a story that at Coda there's this, uh, moment called Tim Ferriss Day that, uh, drove a lot of traffic. Can you share that story? Does that ring a bell?

    3. LSLane Shackleton1:11:08

       Sure. Yeah. There's lots of memorable days at Coda. Um, one of them was, uh, Tim Ferriss Day. So I guess maybe 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, uh, 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, uh, had been really tenacious with like the people around Tim Ferriss and, uh, and, and basically finally gotten into him and like figured out a really neat way to implement one of his rituals in Coda doc. And so none of us really knew this, but like this is all happening. (laughs) And anyway, we, we wake up one morning, uh, 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." Um, at the time, we were also in the China basin office, uh, 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, 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, uh, 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, you hear this lesson or this, uh, adage of like first time founder build a great product, second time founder build a great distribution. I think that was like one of those early big cues to think about, you know, 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, uh, with Tim Ferriss, like what, you know, what's next?" And we definitely spent a few months trying to reach that, uh, you know, that high watermark that was set that day in, in traffics and sign-ups. So it was, it was a fun memorable day and people, uh, for like the subsequent one or two years, you know, would refer to it as Tim Ferriss Day.

    4. LRLenny Rachitsky1:13:15

       So funny. I bet Tim Ferriss had, had no idea what you did.

    5. LSLane Shackleton1:13:18

       No idea. Yeah.

    6. LRLenny Rachitsky1:13:19

       And I'm hoping you have a Lenny's podcast day once this comes out.

    7. LSLane Shackleton1:13:21

       (laughs)

    8. LRLenny Rachitsky1:13:21

       Everyone's going to be freaking out, "What is going on

22. 1:13:24 – 1:19:30

    Using two-way write-ups

    1. LRLenny Rachitsky1:13:24

       here?" Is there anything else you wanted to share before we get to our very exciting lightning round?

    2. LSLane Shackleton1:13:29

       Maybe we're talking really briefly about two-way write-ups.

    3. LRLenny Rachitsky1:13:32

       Yeah. Let's do it.

    4. LSLane Shackleton1:13:33

       Yeah?

    5. LRLenny Rachitsky1:13:33

       I had that in my notes, but I skipped it, so I'm glad you mentioned it.

    6. LSLane Shackleton1:13:36

       Cool. Um, yeah. I think, I mean this is a, a concept that I, I wrote a bunch about and I often now get asked about. And I guess the, maybe the historical view of this, I got really obsessed with the history of like how work gets discussed and decided upon and, um, and kind of broke it down into like three phases. And so the first phase was, uh, 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 art and it was really fun. Um, 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. Um, second phase is in the t- early 2000s kind of like two things converged. One was, uh, Google bought this company called Writely, 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 was, uh, 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-pager ritual. This is, you can read all about this in the book Working Backwards. It's really good, a really good book. Colin Bryar'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 by presentations. And then kind of the, the thesis is that we're like in the midst of a new phase which is, uh, essentially two-way write-ups and that's where it's more conversational 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 this the most because they're the ones that are like driving decisions and, and really the ones that are driving discussions oftentimes in, 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, who's read your write-up. So you know, I have many memories of sending a write-up out at 11:30 PM and then like waiting patiently for the 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-

Episode duration: 1:29:51