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

Lane Shackleton (00:00:00):
Moments that stretch you or moments that you feel uncomfortable in or you find yourself saying, "Oh shit. I shouldn't be here," or, "I'm under qualified to be here," those are the moments you should be seeking out. Those are the moments that stretch you and give you a new foundation. So oftentimes you'll hear a career question like, "Hey, do you feel like you're growing in your role?" And that's a very ambiguous, in my opinion, way to ask this question. A much sharper way is like, "Hey, how many, oh shit moments have you had in the last 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 stretched in some meaningful way or I've felt like I'm under qualified to be there," then it may be worth digging into.

Lenny (00:00:51):
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'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. 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, 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 tried to keep this to under an hour and a half. With that, I bring you Lane Shackleton after a short word from our sponsors.

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(00:04:04):
Lane, thank you so much for being here. Welcome to the podcast.

Lane Shackleton (00:04:07):
So glad to be here. Thanks for having me.

Lenny (00:04:09):
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. Any relation to a certain very famous Antarctic explorer?

Lane Shackleton (00:04:36):
Yeah. It's probably distant at best. I wish it was close. I wish I could claim it was my father or grandfather. But I definitely grew up with those stories and reading a lot about him 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. 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 lessons from that, but that's as close as I can come to the greatness of Ernest Shackleton.

Lenny (00:05:09):
Okay. So there's a connection. When I think of Shackleton, I also think of the ad that he ran for recruiting people to join his journey. Low chance of survival, incredibly hard, chance for glory if you succeed, something like that.

Lane Shackleton (00:05:23):
It's a wonderful ad. I think I had a mug of that when I was a kid. Yeah.

Lenny (00:05:28):
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 why did you decide not to pursue that and get into product management? Completely different life.

Lane Shackleton (00:05:42):
Yeah. Yeah. Very, very different. Very different time. Didn't have kids back then. I think I was convinced at the time I wanted a career outside. Just loved spending time in the mountains and climbing, things like that. To be honest, I wasn't the best guide. There were a lot of amazing 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 what is a dream trip for mountain guides, which is we were flown to a remote portion of southeast Alaska. It's an hour long flight. Mountain called Mount Fairweather. Beautiful 15,000 foot peak. And as a part of climbing on glaciers 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 someone falls in a crevasse, you want to be able to stop them or pull them out.

(00:06:48):
So I was roped to a very nice client that I was guiding and he fell pretty close to the top on our way down. And luckily we were able to self-arrest and arrest that fall. But I spent probably the next six hours walking down that mountain thinking the same thing over and over again, which is I really don't want to die roped to someone that I barely know and don't trust or love. So that was the last season that I guided. But tons of great memories and learnings and I think it impacted my life in a pretty significant way.

Lenny (00:07:29):
Damn. Software much lower stakes. I guess just while we're on this topic, is there any parallels or big lesson you learned from that experience that you bring to product?

Lane Shackleton (00:07:37):
One is just preparation. I think when you go climbing or when you guide climbing, you spend months and months preparing for usually a few days of climbing. So there's that kind of preparation. There's also just a million checklists. So 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 ensure 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 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 I was 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." Put him on his back and we basically took turns carrying him out for a couple miles I'll just never forget instances like that where the clarity of stay calm, assess the situation, prioritize, take action. There's a mini version of that when you're building software, I think. So experiences like that, I think, even though I only did it for a handful of summers, were pretty profound.

Lenny (00:09:06):
Yeah. What a very different life that life path would've been.

Lane Shackleton (00:09:11):
Pre kids. Yeah.

Lenny (00:09:12):
Oh, man. So you mentioned your writing, you mentioned that this is something you want to write about. Shifting to the core topic of our chat, 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 pulled you into spending so much time and effort trying to understand how the best teams and people operate?

Lane Shackleton (00:09:53):
Yeah. Yeah. I've been asking myself that question a little bit lately. There's a few reasons. One reason is I just found myself giving a similar set of advice in one on ones. And so I think anytime you find as a leader yourself repeating the same lessons, it should be a good flag to say like, oh, I should probably scale this in some way. And as 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. Writing something down and then putting it out there, you start to get feedback back of where you might've 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 been pretty frustrated with career ladders. Most companies have career ladders with 10 or 15 levels and as soon as they hit some scale levels, there's levels between levels and I feel like I looked at the one at Google and you needed a PhD to decipher it and interpret how to operate within it.

(00:11:11):
And so that's one piece of the construct. If you think more broadly though, they aren't consistent across companies, so now you're in a situation where you're in your version of the rat race. And so I found that I basically wanted to have a broader set of principles that transcended level. 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. That's one. I won't rant further on that but I think that's one piece of it.

(00:11:49):
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 like a prototyper 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 Britten, showed this talk to the company and 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 following that principle. And it was just 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 what are my principles as it pertains to building software and other things. So those are the three reasons that led me to start writing these things down.

Lenny (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, 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?

Lane Shackleton (00:13:06):
When we were doing career ladders, first of all, we put it off for quite a bit of time and that was based on the advice of a lot of other leaders that said as soon as you introduce this, then the incentives flip from being company focused to being individual focused. So I think we delayed it for a good bit of time. There came a time where we 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 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. 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 don't use titles that much.

Lenny (00:14:11):
You said that it's not specific to role. Do you mean the same leveling attributes are the same from design and product and engineering?

Lane Shackleton (00:14:19):
We basically have five levels and we call them role stages and they go from apprentice to principal. So apprentice is ... Rope analogy here is learns about rope. Practitioner is can tie basic knots, shown complex knots. 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 bar is really, really high for principal in these levels and I think that that's appropriate. 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 maybe a little bit of contrast with other companies. I think most other companies, especially large companies 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. 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. So those are some differences.

Lenny (00:15:52):
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 five and they're described similarly.

Lane Shackleton (00:16:08):
That's right. They're described similarly at a high level, but then the specifics if you get into it are a little bit different.

Lenny (00:16:15):
Okay. I'm going to ask about what the principles are, or a few of them that you can share. But one other very tactical question. At what size of product teams, say just PMs, did you start to develop this framework?

Lane Shackleton (00:16:26):
We were probably at 20-ish PMs and designers when we did that.

Lenny (00:16:31):
Awesome. Okay. So let me just ask, what are some of these principles you've narrowed it on as principles of great product managers?

Lane Shackleton (00:16:38):
Maybe it's helpful to start with a little higher level context on the 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, everything is ambiguous all the time. It's like what's my role on this team? What problem are we solving? Who's the target customer? What prototype is going to solve this particular problem? So it's literally everything. And so if you're going to do the job well, you really need to get good at spotting ambiguity and turning it into clarity. And so the obvious question that follows from that is okay, great, that sounds like a great Hallmark card, but how do you actually do that? And so I think the principles that I've been writing down are very personal. They're my take on how to do this.

(00:17:41):
So the first one that I wrote about was systems not goals. And one of the ways that I started this post ... 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, he's done Seinfeld the show and he's got all this material from the last 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." And this is unheard of in comedy for someone to just throw away all their old material and start fresh. And so the question is 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.

(00:18:34):
But the goal isn't that important. What's important here is the system. So the system that he uses is he writes for an hour every morning, doesn't write for more if he doesn't want to, and then he goes and performs at night. 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 I take a lot of inspiration from that and I think product people can generally, which is instead of being obsessed with the goal, be obsessed with the system that gets you there. And so the phrase I sometimes use is goals with good intentions don't work. I really need to give a common example. A really common example is teams that are trying to learn about customers or do research. And 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 OKR. And then if you watch closely, the next quarter, they may not have a goal of talking to customers anymore. And so their learning is going up and down.

(00:19:49):
And to draw a contrast, that's just really different than a team that has some default on system for talking to customers. Every few times a week they're talking to customers for whatever reason. And the impact of that is really hard to see until you understand that the latter team tends to have really good product instincts or really good customer instincts. It's because they've just had this default on mindset 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, 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 sometimes we'd be scrambling the three hours before to 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. And so the way that we developed good customer instincts was not the goal, it was really just the system behind it. So that's one that I'm passionate about and I think it also translates into a lot of the rituals that we talk a lot about.

Lenny (00:21:06):
There's so many directions I can go with this. 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 a community person find someone in San Francisco that's a host. And there's no agenda, it's just let's have lunch and meet the team. Curious what you're wondering.

Lane Shackleton (00:21:22):
Exactly.

Lenny (00:21:22):
And Airbnb hosts are always so nice and has such a pleasant experience. Also makes me think about this book, The Score Takes Care of Itself.

Lane Shackleton (00:21:30):
Yep.

Lenny (00:21:31):
Have you read that?

Lane Shackleton (00:21:31):
Yeah.

Lenny (00:21:31):
Where it's just do the fundamentals and you'll win?

Lane Shackleton (00:21:34):
Totally.

Lenny (00:21:34):
The other thing it reminds me of is I have this quote hanging in my office here. 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."

Lane Shackleton (00:21:48):
I love it.

Lenny (00:21:49):
I feel like you just changed art-

Lane Shackleton (00:21:51):
Yeah. Rick Rubin's amazing.

Lenny (00:21:52):
Oh my god, it's so good. Just every section is this quotable thing I want ... I need to hold onto this thing.

Lane Shackleton (00:21:58):
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-

Lenny (00:22:10):
Yeah. What is that lesson?

Lane Shackleton (00:22:11):
The way he talks about it is essentially you want to listen and absorb 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. It's quite hard to do. Because your default mode is always the next step of the conversation. But I think if you can really challenge yourself, like he says, to pause and really try to internalize holistically what that person's saying, it's pretty powerful.

Lenny (00:22:55):
I was actually just reading that chapter and the next chapter is about this idea of the beginner's mind. I don't know if you remember that. I feel like people get sniped by Rick Rubin stuff. But anyway, I'm going to go down this thread. He talks about how AlphaZero or AlphaGo, the first AI thing that beat humans at Go and how there was this move it made, move 37 in the game that was just like ... The person the AI was playing walked out of the room. He's like, "I don't even know what just happened. This is out of anything I've ever imagined." And it won. And the lesson there 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 of coming from a beginner's mind and not being influenced by what's already been done.

Lane Shackleton (00:23:41):
Yeah. We have a walkthrough ritual that we do.

Lenny (00:23:45):
Tell me more.

Lane Shackleton (00:23:46):
The prompt is essentially put yourself in the shoes of someone who knows nothing about this topic whatsoever and have beginner's mind and then walk through with five or 10 people watching you and let's fix all the problems that we see.

Lenny (00:24:05):
Okay. 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 that want to check it out?

Lane Shackleton (00:24:21):
Just lane.substack.com.

Lenny (00:24:24):
Sweet. We'll definitely link into it. Yeah. Any other principles?

Lane Shackleton (00:24:28):
I think the other one is cathedrals, not bricks, and then the other one is proactive, not reactive. Cathedrals, not bricks I think is a classic one. I think I had a moment of realization and talking to Shishir in a one-on-one when I was at YouTube bemoaning the fact that my team wasn't performing to the potential that I thought they had. And he had a very pointed and unexpected question, which is like, "Do they know their cathedral? Do they have a cathedral?" And I'm sitting there like, "Man, what are you talking about? We're talking about performing as a team and you're asking me about cathedrals." And then he explained the cathedral story, which I can talk about. In that-

Lenny (00:25:11):
What's the cathedral story?

Lane Shackleton (00:25:11):
It was quite clarifying.

Lenny (00:25:13):
Yeah. Do share.

Lane Shackleton (00:25:14):
Yeah. The cathedral story is basically you walk up to three people, they're laying bricks. You ask the first person, "What are you doing?" They say, "Well, I take the bricks from over here and I put them on that sack 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?" And they say, "Well, we're building a cathedral." And the 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 be one task after the other, really execution oriented and maybe not take the time to 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 we've learned many times that one unexpected bit of this is that everybody needs to see a different facet of the cathedral.

(00:26:22):
So very often ... And I've made this mistake before plenty of times. Very often people will do a great writeup 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 this broader cathedral is. And so one of the things that we have tried to do when we go through big planning cycles is show all the different sides of this. So instead of just having a writeup, we may have a writeup, we may couple that with a metric, we may couple that with directional mocks and what the billboard might look like or how our homepage may change. And really what we're trying to do is take the mystery out of the set of broader constraints or where we're headed. I think great product teams and great PM leaders tend to always orient their teams towards a broader cathedral as opposed to laying bricks.

Lenny (00:27:26):
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."

Lane Shackleton (00:27:39):
Classic. Classic. It's Antoine.

Lenny (00:27:42):
That is right. Antoine de St. Exupery. 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 products, is there anything you found to be useful in helping 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?

Lane Shackleton (00:28:06):
Probably two things. One is reading really broadly. So I think not just reading PM style literature. Like I said, I tend to get a lot of inspiration from outside of tech. I think that's one thing. I think the other thing is insofar as you get the opportunity to mentor other people, think about what you're saying to these people. 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 this is a more deeply held belief. So I think noticing those instances was helpful for me.

Lenny (00:28:46):
Are there any books or topics or areas that you found most inspirational when you talk about reading and studying other non-product tech?

Lane Shackleton (00:28:53):
I mean definitely sports. I would say sports is really interesting to me. Team sports. I've always been a huge fan of everything team sports. Storytelling. 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 really like.

Lenny (00:29:15):
I was just going to mention that. That book is so good. Somebody mentioned this on the podcast and I read it. It's the most useful practical book for how to tell stories.

Lane Shackleton (00:29:23):
It's so good. The insight is amazing. Just in case your listeners are interested, the insight is basically the nugget of a great story is five seconds of transformation. So if you just orient everything else around that moment of transformation, then you end up usually telling a reasonably good story. I had a conversation with the author right after I read that book because I was just totally enamored with it. And then we ended up bringing him into Coda and he gave a great talk. So yeah, big plug for Matthew Dicks.

Lenny (00:29:58):
The other thing that stuck with me also from that same ... We're just going on 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 now, I'm like, "Okay, she's very shy right now. She's going to be very extroverted by the end of this movie." Or, "They love each other. Oh, they're going to have a lot of problems." That's so interesting. Oh, that's such a good idea. Okay, I'm going to get this guy on hopefully. And he's a Moth champion basically.

Lane Shackleton (00:30:30):
Yeah. I would say as maybe a principal version of this, the way that you learn or the way that everyone including me learns new things is you go seek out the best at that given craft. So in this case, you go to the Moth StorySLAM you see some really good stories. If you ever watch these on YouTube. And then you just unpack what they're doing and how they're doing it. And then obviously I think the other way to learn quickly is to throw yourself in the deep end. So insofar as you can put yourself in situations that are uncomfortable or 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 early in your career.

Lenny (00:31:18):
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.

Lane Shackleton (00:31:24):
And the world is much better for it. This podcast is an amazing resource.

Lenny (00:31:29):
Thanks man.

Lane Shackleton (00:31:29):
You've done something very special.

Lenny (00:31:31):
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 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. Can you talk about that?

Lane Shackleton (00:31:49):
Sure. Yeah. I think I picked this up originally from Seth Godin, the author, and it just totally stuck with me. The basic thesis is that moments that stretch you or moments that you feel uncomfortable in or you find yourself saying, "Oh shit, I shouldn't be here," or, "I'm under qualified to be here," those are the moments you should be seeking out. Those are the moments that stretch you and give you a new foundation. And so I have found that they turn out to be a pretty good way to calibrate whether someone is growing in their career. So oftentimes you'll hear a career question like, "Hey, do you feel like you're growing in your role?" And that's a very ambiguous in my opinion way to ask this question. And a much sharper way is like, "Hey, how many, oh shit moments have you had in the last 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 stretched in some meaningful way or I've felt like I'm under qualified to be there," then it may be worth digging into.

Lenny (00:33:04):
That is so good. Making me think about this podcast where I never wanted to do podcasts. I'm like I'm not a podcast person. 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."

Lane Shackleton (00:33:26):
Nice. That reminds me of ... Have you read the book The Obstacle is the Way?

Lenny (00:33:31):
No. Say More.

Lane Shackleton (00:33:33):
It's a great book by Ryan Holiday. And the core thesis is ... It's a bit about stoicism. But the core idea is essentially instead of running away from obstacles, you should be running toward them and that's where you experience either the most growth or the most profound moments of your life. He gives a lot of examples in that book of people throughout history who made that choice. And I think he's also given that talk to hundreds of sports teams. It's a good book. Worth reading.

Lenny (00:34:08):
It's so hard. It's so hard to do hard things, man. 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 of great teams and also just how do you actually go about learning about these rituals? I know you have this really interesting process.

Lane Shackleton (00:34:31):
Yeah. In general, I'm a big believer in good design and good product starts with noticing. Tony Fadell 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 see something happening with a customer, ask a few questions, get introduced to their team, hear about something interesting from a non-customer, ask for an intro, end up just probing and asking a lot of questions. And then in many cases nowadays with Coda, we're building new rituals alongside people. So someone has a creative idea about how to implement something and we're like partners or collaborators with them on that, which is honestly incredibly fun to just see people's creativity expressed in a tool and then by extension the social construct that they exist in. So that's a little bit about how we got started in that whole process. And then of course Shishir is writing a book called Rituals of Great Teams so we've been cataloging those. We've been hosting a bunch of rituals dinners where we basically get people together for a dinner and we usually have three or four presenters at those dinners. It's just a great chance to learn and think about how the engine runs in a lot of these companies.

Lenny (00:36:03):
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?

Lane Shackleton (00:36:10):
There are so many. It's hard to choose. Maybe I'll choose two that are top of mind. One is Dharmesh Shah has this ritual from HubSpot called flash tags. Have you heard of this?

Lenny (00:36:24):
No.

Lane Shackleton (00:36:27):
We've all probably been in the situation where someone gives you feedback and you either under interpret it or over interpret it. And as an organization, I think the 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. He presented this in one of our dinners. And I absolutely love the phrasing of these as someone who's given a lot of feedback on product stuff in their career. So it ranges from ... I think it's FYI, suggestion, recommendation, plea. So FYI is basically like I had a thought, take it or leave it kind of thing. Suggestion is ... And he uses this hill dying metaphor. So is this a hill I'm going to die on? And FYI is there's no hill in sight. Suggestion is there's a hill. I'm not going to die on it but this is what I would do if I were you. You can take it or leave it. Recommendation is I'm climbing the hill. I'm not going to die here, but I've thought about this a lot, so don't ignore this.

(00:37:41):
And then the fourth one, plea, is hopefully rarely used in the organization. It's like, I don't like dying on hills. That's not what we do here. But this is a pretty good candidate for it. You should really trust me. And so we have ended up using that. 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, hey, we got 100 pieces of feedback and there's one plea. Okay, let's spend our time on that. Or there's a whole bunch of FYIs. I think we're fine. Let's keep going. No worries.

Lenny (00:38:20):
That's amazing. It's interesting none of them are just do it this way. I imagine that's very intentional.

Lane Shackleton (00:38:25):
Yeah. Honestly it's a sign of ... In Dharmesh's case, I don't know him super well, but it's a sign of a really experienced leader to know that scale. But every time I look at the scale and I'm weighing where I am between suggestion or recommendation, I have to giggle to myself.

Lenny (00:38:45):
And how do you actually use it? In the feedback you put a hashtag plea kind of thing?

Lane Shackleton (00:38:51):
The way gets used in code docs and the way I think other companies have made it a ritual is you'll have a feedback table and you'll write your feedback and then there'll just be a little select list and you can select between those four. And usually what people do is they include the description so you can as you're choosing it, think do I really feel that strongly about this? And honestly, it's good hygiene. Otherwise, every bit of feedback is taken the same. Which just fundamentally the impact of that is it slows everything down because now you're looking at a list of 100 pieces of feedback and you're going like, "Oh man, we got to address all this feedback." Whereas as soon as you distinguish between what's most important, it's much easier to sort through that.

Lenny (00:39:46):
What about if it's in person? Do you say this is a plea or this is a FYI?

Lane Shackleton (00:39:50):
Oh, I've definitely heard that in many meetings. Are you making a recommendation or are you making a plea?

Lenny (00:39:57):
Amazing.

Lane Shackleton (00:39:58):
And making the person think through that choice I think is just a very helpful shared language.

Lenny (00:40:04):
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 going to be taken really seriously and the team's going to rush back and be like, "Oh, Lane told us to change this thing." I imagine it helps you just make it clear. No, you don't need to actually change this. It's just my thoughts.

Lane Shackleton (00:40:21):
Yeah. Exactly. Yeah.

Lenny (00:40:22):
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(00:42:15):
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 a genius?

Lane Shackleton (00:42:21):
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, the review forum is just a really important part of the product development process. And the core insight for most review forums or product reviews or decision forums is that they generally suffer from two problems that are hard to spot unless you've sat through hundreds of them. The first is they have standing attendees, and the second is they're normally single-threaded, meaning they're normally 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 with a standing set of attendees, you either have the situation where you have too many people in the meeting or you have not enough people in the meeting, and both of those can cause problems.

(00:43:25):
So 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? They're not a part of the standing set of attendees?" You either have to reschedule the meeting or worse, you just do the discussion without the person who's most knowledgeable, which seems crazy in retrospect. The second problem is single-threaded. So one topic at a time. So if you think about if a product development process is somewhat of a chaotic assembly line for a second, your review or your decision forum ends up being a big time bottleneck in many cases. And obviously you want to be in a situation where product people have a lot of autonomy and they can make most of the decisions themselves. And I'm a big believer in decentralized leadership and all of that, but there are things that cut across the company that need to get reviewed by a broader set of stakeholders.

(00:44:29):
And so what happens when those things are single threaded is either the meeting is really long, so it's a three-hour review meeting once a week, and by the end everyone is about to fall asleep, or it's really short and it's really hard to get on the calendar. You're like, "Oh, can we get on the calendar in two weeks?" And the downside of the not being able to get on the calendar is that now you've just slowed down the whole velocity of the company because the 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, braintrust, and interested. It's a very transparent system.

(00:45:28):
So 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 the person who's actually going to drive the meeting, drive the decision, drive the outcome, things like that. And basically, this is all centralized in 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 three topics going all at the same time because they don't have overlapping attendees. And the impact of this, I think if you really watch it in progress is huge. You basically have many topics running all at the same time, so the throughput is much better 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 of weeks ago, we spent a while remaking the template for that one.

Lenny (00:46:45):
I love that ritual. You actually wrote even in more depth in the post that we worked together on how Coda 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. 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? How much 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?

Lane Shackleton (00:47:15):
Yeah. I think it depends a lot on what your role in the company is. Maybe to say the extremes for a second, if you're a brand new PM to an organization, you probably shouldn't go try to remake the whole product review cycle that the head of product is really passionate about and has crafted. But you can probably take a decision template or some interesting ritual that has facilitated a team in the past and use it with your team. Another one of my favorites there is a hundred dollar voting. We use that a lot in the context of planning, and I find that creative rituals like that are easy to pick up for teams because oftentimes it's like, okay ... And maybe I'll describe the ritual real quick.

Lenny (00:48:01):
Yeah. I was going to ask.

Lane Shackleton (00:48:02):
The ritual is essentially you can take any set of problems or solutions or themes or whatever you want to get people's input on, and you put those 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, "Oh, 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 especially in planning processes, little rituals like this are great at getting the elephant in the room out. So it's like, "Oh wow, we have a huge spread on this one particular problem. You think it's a huge problem. I don't think it's a problem at all. Let's talk about it." Going back to the thesis of turning ambiguity into clarity, a lot of this is like we're trying to get the ambiguous stuff out there so that we can make it more clear.

(00:49:03):
And so I use that as an example because you can be a brand new PM, run a brainstorm, run a planning session like that, and you're probably going to get great feedback. People are probably going to go, "This is cool. I've never done this before." Now to go to the other side of the spectrum, we help a lot of companies that want to remake a whole process. They want to remake a review system like Catalyst or they want to remake their decision rituals. And so in that sense, we're usually talking to a head of product or director of product or VP of product and someone who tends to have a lot more agency over the way that the team works.

Lenny (00:49:48):
Coda is interesting in that it feels like you have pretty stable processes for planning and reviews. I find most companies just every six months rethink a lot of these things. 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 changing the way you operate versus working in similar ways? How do you think about that percentage wise?

Lane Shackleton (00:50:11):
People are always coming up with new creative ways to make their teams run better, make decisions go smoother. And we're continuously adopting those, but there's definitely a backbone of the system. The backbone of the system is Catalyst and tag-ups and the concept called Bullpen. And then 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 individual topics got added. That took us launching 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, we did it very manually. So I think there's still a lot of creativity that I see every day.

(00:51:06):
So I'll give one quick example. One of our PM leads on core product, this guy Nathan, he basically saw that a lot of decisions 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 who to involve in these decisions? Because every one of these with core product feels like they impact everybody. And so a very simple thing that he did 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, "Oh, 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 heavily involved in this decision."

(00:52:10):
And it was such a pro move. It was 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, the majority of those, Shishir or I or Oliver, the head of engineering will say, "I may have some opinions, but keep going." That's often the default. And then there are plenty where we say, "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, "Hey, you don't really need to involve as wide a group as you think, so just keep going and check in later." So I think those types of little iterations are usually based on a really good insight.

Lenny (00:53:02):
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 handbook you're working on, which is going to I think, cover a lot of these things.

Lane Shackleton (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 it's really an anti-pattern. 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 where you'll have a conversation with your manager in a one-on-one, they'll go back and translate to their engineering and design lead, and of course the fidelity of the game of telephone, something is lost in all of those transmissions. And so the core idea is have a group one-on-one with the key stakeholders. And so we have this concept of braintrust that's modeled off after Pixar's braintrust.

(00:54:11):
And so we'll have a tag-up with a small set of people from a given team, or sometimes we have larger groups, and then they meet with their braintrust and it's once a week. It's the same mindset of a one-on-one. It's their time. So anything that they need to unblock a decision or to make progress, they should use that time for. And they often start by reviewing OKRs and metrics and things like that. But then we generally get into a table of topics. Anyone can add a topic. Those topics are up voted, so people will react and then the table will sort itself. And then we'll say, "Okay, this is clearly the topic on people's mind." And that's a version of what we call Dory, which I can talk about. But essentially the principle is you should discuss that project work with the whole group there. With the whole triad there. And oftentimes with the sales person there and with the marketer there and with everybody else. So I found that that is just a really good practice to try to move a lot of that work out of one-on-ones and into a small group setting.

Lenny (00:55:26):
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?

Lane Shackleton (00:55:36):
One of the realizations I had the other day, probably a month or two ago when we started working on this thing, was I was talking to someone about Catalyst and a couple other concepts, and they were like, "I get it. I'm sold. I want to implement some of these things. Where do I look?" And so I found myself sending them a bunch of links to individual templates. So that cued us into the fact that we needed to have a better 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 hopefully by the time this recording is done. And in it, we'll talk about everything from rituals like Catalyst to decision rituals to a lot of 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 how to implement these things. I think that's what has been lacking sometimes.

Lenny (00:56:50):
Amazing. We'll definitely link to that. Hopefully it's live by the time goes out. We'll make it happen. I know also you said Shishir's working on a book that's related and basically rituals of great teams and Shishir was on the podcast and 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.

Lane Shackleton (00:57:09):
Yeah. I remember that.

Lenny (00:57:11):
Okay. Cool. 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?

Lane Shackleton (00:57:11):
Yes.

Lenny (00:57:24):
Okay. Awesome. So in that post, which we'll link to, you share this story of how you and the YouTube team came up with skippable ads, which I didn't realize it was such a controversial ... But in thinking about it, obviously 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?

Lane Shackleton (00:57:46):
Yeah. So I moved over to YouTube shortly after the acquisition. It was an amazing tight-knit team. It definitely felt like the Wild West. 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 a site of cat videos and dogs on skateboards and things like that. And then I guess the other context, the sales team was very nascent and all they wanted to sell was the homepage and for good reason. That was where you made your money as a salesperson. And so I had just been sponsored by Salar and Shishir to become a PM. It's a longer story that I'll leave out for now and we can go into. But on day one of being a PM, Shishir's like, "Great. You're the new guy. You get the project that nobody else wants and that's called skippable ads. 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 per views." And the latter part we hadn't quite cemented yet, but it was part of the core idea.

(00:59:04):
And so the thing I write about in this post is as a new PM, this feels like a really consequential decision. It's like we've got this new product idea. Nobody really wants it. Advertisers don't want it. The sales team doesn't want it. And it's a very unproven thesis. And so the thing I write about is these are the types of things that you can debate for months or years. 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 trying to figure out what to do and how to handle all the different dynamics. And he just stops and he's like, "You know what? Just test the extremes. Start the experiment tomorrow. We'll figure it out." Essentially.

(00:59:49):
And I think his point was like, look, we can debate this forever. So I would rather us see the upper and lower bounds of how good this could be or how bad this is going to be immediately. And so we launched a set of experiments. This guy Jamie Kerns who's still there. Tiny little skip button 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 based on some very directional data that we were onto something. And so the lesson that I took, this is many years ago and I've seen this proven out hundreds of times since, is stop talking about it and go make something. Go run an experiment. Go make a prototype, go write a doc, go make a mock. Just don't talk about it.

(01:00:49):
And I found that also as a leader, people really follow that concept. And I also found that it transcends level. I am not talking just to ICPMs. I'm talking to heads of product and CPOs and CEOs to some degree. You should always be out there trying to learn by expressing your ideas and putting them out there. And that's much more valuable in many cases than pontificating about it or having endless circular discussions on it.

Lenny (01:01:23):
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 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.

Lane Shackleton (01:01:39):
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.

Lenny (01:01:46):
You mentioned in your early career ... We talked about your Alaska guide phase. Something else I saw is that you were on the AdWords approval team. You basically were reviewing ads people submitted to run on AdWords and that's 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?

Lane Shackleton (01:02:13):
That was a really memorable time. There's an amazing cohort of people that started in tech. I think there was 200 or 300 of us at that time and then eventually thousands that 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 before that was 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 mark it family safe, non-family safe, porn. And then based on that, it would either run or it wouldn't. And actually, funny enough, some of my most successful friends were terrible at the approval event. They failed the rote task of approving ads. They just couldn't handle it and they went on to be really, really successful.

(01:03:08):
So after working on ad approvals, at that time, I moved to chat support. It was basically 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 rollercoaster ride. It was basically one minute you would pick up the phone and it would be someone from a Fortune 100 company trying to spend millions of dollars on AdWords and then the next minute you would be on the phone with a psychic or a taxi driver that was warring with their compatriots over some really specific keyword. I think there were 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 you have to get customer facing from the very beginning because you're going to end up serving a customer your whole career. Even when you're the CEO of a company, you're going to be serving a customer. So you better get really good at being in any customer scenario and being able to handle it. And so I think that that turned out to be insanely good advice. And if I think about a piece of advice that I give out to people who are early in their career, I've definitely recycled that advice.

(01:04:29):
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 AdWord's case, people did not care about AdWords. You were the expert on it and you're trying to tell them about ad groups and how this ad format works and blah, blah. And most of the time people are like, "Dude, I'm a small business owner. I'm trying to get people to come to my auto mechanic store." Or, "I'm trying to get people to come to my taxi service," or whatever it was. I don't care. Basically the product had to get out of the way and really just drive impact for the customer. It was like they just want more phone calls or they want more people in the store. So those are I think two pieces that I think about from those days still.

(01:05:21):
And then I worked in a variety of other roles. I worked in a role called product specialist, which is an awesome role back when there were 15 product specialists at Google. For me, that was an amazing time because I was getting to sit on seven or eight different core product teams. And in my observation, these days, most PMs don't get to sit on other people's core teams. And so I had these three or four years of just ... I call it a masterclass in PMing because I was getting to watch what was working for some PMs and what wasn't working for other PMs and just taking notes behind the scenes. So that was a really influential role. And then went on to various PM roles at Google and YouTube.

Lenny (01:06:09):
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. 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, from I guess being at a tech company to getting your first PM role? Just to give people a sense.

Lane Shackleton (01:06:33):
Let's see. I probably worked for at least four, five years before being able to move to PM and I think that was a slightly harrowing journey because at the time, you had to have a computer science degree.

Lenny (01:06:46):
At 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 a PM immediately."

Lane Shackleton (01:06:55):
Totally.

Lenny (01:06:56):
I think that's a good example of 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 as being customer facing. And in this case being in retail as customer facing, is your advice get in a tech company and work on something customers use or is even working at Starbucks or Abercrombie, does that count?

Lane Shackleton (01:07:24):
Yeah. I think maybe to relate it to what you just said, if I were to give advice to someone who really aspires to be a PM or trying to get into PM, I think in many cases if you're in a customer facing role, you are the expert on the customer and that is really, really valuable in tech organizations. And oftentimes it's undervalued. And so I think people who want to move into PM roles who are not currently in PM roles 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 where you are in the organization, you're always serving a customer. You can't just talk to one big enterprise customer and you can't just talk to the smallest customer. You 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 customer's headed and what they want and stuff like that. And so the stakes I think are pretty high. The good news is it's easier than ever with all these tools to really get into the mindset of a customer.

Lenny (01:08:47):
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, here's what I've heard again and again and again, people will just like, "Oh Lane, tell us more." And they bring you into conversation because providing value, you're not just there sharing opinions. Everyone's got opinions.

Lane Shackleton (01:09:15):
That's basically how both me and ... I had a friend named Bill Ferrell who transitioned into PM at the same time and that's essentially how we got the try at being a PM inside of Google was we knew the customer really, really well and we were often in conversations bridging the gap from here's what I think they're really saying, or here's what I think we should build based on what they said.

Lenny (01:09:41):
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 Connolly, who was a hotelier. He created the Joie de Vivre hotel chain and just 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, you're telling hosts, 'Hey, the product's going to be updated. We're going to launch all these features.', they think their 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 on Airbnb and staying in their home." So I think it's a really good reminder of 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.

Lane Shackleton (01:10:30):
I think most people can be way more concise with their communication. Even internally, people don't care. You should assume that people don't care. Or if you're talking to customers, writing a blog post for customers, 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 style.

Lenny (01:10:53):
And one final question before we get to our very exciting lightning round. I heard a story that at Coda there's this moment called Tim Ferriss Day that drove a lot of traffic. Can you share that story? Does that ring a bell?

Lane Shackleton (01:11:08):
Yeah. There's lots of memorable days at Coda. One of them was Tim Ferris Day. So I guess maybe for context, we had built this very nascent publisher motion where we were going out and helping people publish their rituals. And this is what you see in the Coda Gallery and 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 the people around Tim Ferriss and basically finally got an in to him and figured out a really neat way to implement one of his rituals and wrote a doc. And so none of us really knew this, but this was all happening. And anyway, we wake up one morning and traffic is just spiking through the roof, signups are spiking, no one knows what's going on.

(01:11:59):
I'm convinced this is all spam. I'm like, "Something's wrong with our data or something's going haywire." At the time, we were also in the China Basin office and the fire alarm went off. And so now we're outside on our laptops. We were 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 we eventually figured out that we had been featured in Tim Ferriss' email newsletter and I think early on you hear this lesson or this adage of first time founder, build a great product, second time founder, build a great distribution. I think that was 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, what's next?" And we definitely spent a few months trying to reach that high watermark that was set that day in traffic and sign-ups. So it was a fun memorable day and people for the subsequent one or two years would refer to it as Tim Ferriss Day.

Lenny (01:13:15):
So funny. I bet Tim Ferriss had no idea what he did.

Lane Shackleton (01:13:18):
No idea.

Lenny (01:13:19):
Hoping you have a Lenny's podcast day once this comes out. Everyone's going to be freaking out. What is going on here? Is there anything else you wanted to share before we get to our very exciting lightning round?

Lane Shackleton (01:13:30):
Maybe we're talking really briefly about two-way writeups.

Lenny (01:13:33):
Yeah, let's do it. I had that in my notes, but I skipped it, so I'm glad you mentioned it.

Lane Shackleton (01:13:37):
Cool. Yeah, 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 how work gets discussed and decided upon and broke it down into three phases. And so the first phase was 1980s we had PowerPoint. It was this amazing tool. You could manipulate shapes on a screen and we were all using fancy clip art and it was really fun, but we've all had the experience of being in a really long PowerPoint presentation and someone's droning on in their slides and stuff like that. Second phase is in the early 2000s, two things converged. 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 online collaborative editing.

(01:14:35):
And the other thing was Jeff Bezos sent this very famous memo, which basically said no more PowerPoint at Amazon. And what that did was started in earnest their six pager ritual. You can read all about this in the book Working Backwards. It's a really good book. Colin Breyer's book. And so that started I think what I'll call the one-way writeup phase, which is you're writing down your ideas, you're expressing them clearly. It's in prose so you have to be really clear. That was a big step up I think from always presenting work and deciding on work via presentations. And then the thesis is that we're in the midst of a new phase, which is essentially two-way writeups and that's where it's more conversational and feedback and discussion is actually part of the content itself. So that's the broader historical arc. But if you think about it, PMs and product people are always at the brunt.

(01:15:31):
They feel this the most because they're the ones that are driving decisions and really the ones that are driving discussions oftentimes in companies. And so I think the problem with one-way writeups 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 who's read your write-up. So I have many memories of sending a write-up out at 11:30 PM and then waiting patiently for the avatar of the SVP in my area to show up in there. And that was a sign that they had read it, which is 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 this is a space that's really built for grammar and spell checking and things like that. And you're having these really meaningful discussions in this a hundred pixel right margin.

(01:16:30):
And part of that I think is there are all these questions that are being raised, and so you have really no idea what the most important question is. And so if you're facilitating those discussions in one way writeups, you're often going through the comments in the 20 minutes before that session trying to figure out 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 in one way writeups that you see a lot is there'll be just a mega comment thread on the title of the doc. And people are like, "I don't think we should do this," or you'll get into this 30 comment thread on the title because that's the best place to put your overall thoughts. And I saw this pattern all the time. So if you live that life, I think the world of two-way writeups and the way that I think a lot of our customers are doing it, and you can do this on other tools besides Coda too, I think is quite a bit better.

(01:17:26):
I guess the alternative to go down that list is you have a done reading button at the end of a writeup. So now you can say, oh, these are all the people that have read this. And I think even you see a pattern in some of our customers where if it's a particularly long writeup, you'll have three done reading buttons so you can see 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 upload those. And that's what we call Dory. And then I think probably the most valuable is sentiment or pulse, which is, well, how do you feel overall about this particular proposal?

(01:18:13):
And if you think about the contrast between 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 is just wildly different. 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 it 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, "One smiley face. We shouldn't do this." And I was like, oh man. This particular person's not really vocal in meetings. And so I would not have heard that feedback. It was very unlikely I would've heard that feedback unless they had had a sentiment table, a place to add that. And so I think the punchline on all of this is I really authentically believe that this is where we're headed and hope that a lot of PMs and product teams adopt this in general.

Lenny (01:19:23):
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. Yeah.

Lane Shackleton (01:19:31):
Great. Yeah.

Lenny (01:19:32):
Awesome. Is there anything else that you think that we should touch on that we haven't touched on?

Lane Shackleton (01:19:37):
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 of insights there. I think there's 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 OKRs are not actually strategy. So I think the way that we plan and the way that our customers plan, the key point is it's critical to disconnect strategy discussions from OKR discussions. And it sounds really obvious, but it's I think a very common mistake. And I think a really simple question to ask yourself is do we have a separate strategy process or strategy ritual that is distinct from OKR setting and metric setting and goal setting? And I have found you can pick whatever strategy framework works for you, but I do think it's quite important to pull those two things apart.

(01:20:43):
The other rule that we live by on the planning side is what we call a 10% planning rule, which is essentially 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. I mean, this is a hard fought rule because we've made that mistake before. But you end up getting bogged down in planning or saying, 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 just planning way too much and oftentimes you really don't know what's ahead until you've launched or learned something. And so I think that's a pretty good rule to follow.

Lenny (01:21:32):
I love that rule. I found the same heuristic. 10%. If you're planning for a week, plan 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 round. Are you ready?

Lane Shackleton (01:21:46):
I'm ready.

Lenny (01:21:47):
What are two or three books that you've recommended most to other people?

Lane Shackleton (01:21:51):
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. Very simple framework that I've reused a bunch. Maybe outside of tech, Waking Up is 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.

Lenny (01:22:27):
Amazing. On Good Strategy/Bad Strategy, I'm working on getting Richard Rumelt on the podcast. I'm in talks with his agent and they seem to be excited. So we'll hope that actually happens. And then you inspired me to try to get the Storyworthy guy on. So what a cast of characters we're going to get on here.

(01:22:43):
Next question. What is a favorite recent movie or TV show that you really enjoyed?

Lane Shackleton (01:22:48):
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 love any sports documentary. All those.

Lenny (01:22:59):
Have you seen Underrated, Steph Curry's new documentary?

Lane Shackleton (01:23:01):
No, I haven't. I got to watch that.

Lenny (01:23:03):
Ooh. It's really good.

Lane Shackleton (01:23:05):
I've been rewatching Arrested Development. That's also just a timeless classic.

Lenny (01:23:11):
Classic. I love that Michael Cera is in the Barbie movie, not to give any spoilers. That was a funny surprise.

(01:23:18):
Next question. What is a favorite interview question that you like to ask candidates?

Lane Shackleton (01:23:22):
There's two I really like. One is teach me something that I don't already know. I think it's just an awesome way of seeing if someone's going to lean in and really figure out what you don't know and then how passionate they are about pitching what they do know I think is really fun. And then Shishir 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.

Lenny (01:23:49):
Shishir 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 our most viewed clip, I think on TikTok. Or just like, what would your 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.

Lane Shackleton (01:24:10):
Yeah. We-

Lenny (01:24:11):
Don't know if we screwed you.

Lane Shackleton (01:24:13):
I also recently wrote a post about my favorite ref check question, which I think I would love to learn other people's favorite ref check questions.

Lenny (01:24:20):
References check. Oh man. That's its own. Oh man, I'd love to do a podcast just on that. That is such an 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 where Maya, the Head of Product for Spotify podcasts, asks what would your podcast be if you were to start a podcast?

Lane Shackleton (01:24:40):
I like that.

Lenny (01:24:42):
So feel free to steal it.

Lane Shackleton (01:24:45):
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, "Okay, now you have to explain that to your grandparent." And then now you just told me about sewing or some hobby of yours. Now sell it in its most technical form to someone who knows everything about this particular topic. And so it's kind of fun to also see the range that people can operate.

Lenny (01:25:13):
Awesome. What is a favorite product that you've recently discovered that you really love? Either digital or physical, anything that comes to mind?

Lane Shackleton (01:25:21):
A few. I'm becoming a real sleep nerd, so those eye masks that cup around your eyes, I love. Obviously in the tech world, ChatGPT. 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 different ... All of your forehands or all the longest rallies or all that and 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.

Lenny (01:25:57):
We live not so far from each other, so we got to play some tennis and I could check out this very cool product.

Lane Shackleton (01:26:01):
Yeah, let's do it.

Lenny (01:26:03):
You're on. That'll be our sequel. Just our game. Next question. What is a favorite life motto that you either repeat to yourself often, like to share with people around you, share with your kids maybe?

Lane Shackleton (01:26:16):
I don't know if it's as motto as much as it's just a way of being. It's essentially the present moment is all that we have. 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 said a version of make things happen, and so I really try to apply that to anything that I do. If that's work or life or sports, I try to be the person who creates momentum and positive change and progress. And so I think that that's generally a good motto to live by.

Lenny (01:26:58):
Beautiful. What is the most valuable lesson that your mom or your dad taught?

Lane Shackleton (01:27:03):
My mom's a psychologist and a professional counselor so certainly active listening. Maybe the tech version of that or the modern version of that is steal manning someone's argument, being able to 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.

Lenny (01:27:28):
Final question. You were a guide in Alaska helping people climb. If someone were to pursue climbing, 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?

Lane Shackleton (01:27:43):
There's a saying, which is the safest climber is the one who knows when to come down essentially. And I think that there are many times that you have to put your ego in check and come off a mountain or come out of a climb because it's not quite as safe as you thought it was. So I think that's maybe one. I think the other is it's probably not a one-way door. 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 always come back from them. So it's maybe not as big of a choice as some people think it is.

Lenny (01:28:24):
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 trickles down from. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out and ask you any other questions? And how can listeners be useful to you?

Lane Shackleton (01:28:42):
I'm on LinkedIn and Twitter and I have a Substack. We'll be releasing that handbook for product teams that I will probably post on Substack. And in terms of useful to me, yeah, give Coda a try. Give us feedback. I love hearing from product people all over. It's one of the bright spots in my day to hear all the creative rituals that come from this community. You've created just a legendary community of people and so they always give very thoughtful feedback so I'm very open to all of that. And yeah, thanks for having me.

Lenny (01:29:22):
Awesome. Lane, thank you again so much for being here.

Lane Shackleton (01:29:25):
Thanks.

Lenny (01:29:26):
Bye everyone.

(01:29:29):
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. 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 lennyspodcast.com. See you in the next episode.