A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

0:00 I often use this analogy of like if you're doing a home renovation, you can have like the most beautiful rendering of the new bedroom and we're gonna have these lamps on the side of the bed that are coming out from the wall. But if you haven't checked if there's electricity in that wall there or not, it's gonna drastically change the cost and the time and everything. What we need to do in a in a shaping session is we come out with Some kind of diagram where engineers, product, and design they're saying we understand that. So the first thing is we are not going to start something unless we can see the end from the beginning. We're not going to Take a big concept and then say, what's the estimate for this thing? We're gonna go the other way around and we're gonna say, what is the maximum amount of time we're willing to go? Before we actually finish something, how do we come up with a idea that's going to work in the amount of time that the business is interested in spending? Today my guest is Ryan Singer. Ryan was one of the first few hires at 37 Signals.

0:59 and through his experience of building basecamp and his 17 years of building products at thirty seven signals. He wrote a book called Shape Up. Which shares a very different approach to building software. Appetites instead of deadlines. A big focus on bringing design engine product together into a room to shape the plan, versus writing long PRDs or trying to finalize designs before you start building.

1:22 I've noticed more and more teams adopt the shapeup method, and especially with AI starting to change how we work and build product, there's a shift coming in how product teams will operate. And so I thought this was the perfect time to do a deep dive into the shape up method. This episode is basically gonna give you everything you need to give ShapeUp a shot on your team or at your company to see if it fixes the problems that you're having shipping great products. A big thank you to Desk Trainer, Bob Mesta, and Chris Speck. For suggesting questions and topics for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube.

1:57 Also, if you become a paid subscriber of my newsletter, you get an entire year free. Uh Perplexity Pro Notion, superhuman. Linear and granola. Check it out at Lenny's Newsletter.com.

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4:39 Ryan, thank you so much for being here and welcome to the podcast. I'm really happy to be here. Thanks a lot. I think this is gonna be a legendary episode. There's a lot of interest these days in different ways of working.

4:55 Uh, especially ways that aren't agile and safe and scrum and all these ways that people kind of hear about working. Especially in this world of AI where everything's just changing. feels like there's just an increased interest in exploring different ways of working and specifically it feels like there's been a rise in interest and shape up the stuff that you talk about. So I am really excited to basically help people understand what is this way of working.

5:18 Uh. Is it right for them? What are ways to start implementing it? What are maybe some pitfalls you may run into? And as much as possible get into a lot of real talk about how things are actually going on product teams that

5:29 People often don't like to hear. So first of all, just you Have you also seen this? Increased interest in Shape Up. Yeah, you know, I think it's interesting that we're talking now.

5:41 You know, I mean the book came out in twenty nineteen. And uh it's just I've been hearing more and more like, Oh w we s we know somebody who's trying it or we're hearing it when we go talk to other companies, you know, like So I I think it's a wave that's slowly building and It's funny, you know, like

6:00 When it came out I even tried to have like an online forum. to get everyone to who's interested to talk together. And what I started to learn pretty early on is that People don't like to talk about Their struggles.

6:12 Shipping. Especially, you know, CPOs and uh CTOs don't like to go in a public forum and say our company isn't shipping or our engineering team is stuck or our team is always lost in the weeds, you know? That's not a uh it's not an easy uh community uh topic on the on an online forum, you know? So I think there's also some reasons why it's been Word of mouth kind of slowly gathering steam. That's something I struggle with on this podcast. You know, it's as you said It's a product and product teams don't want to be sharing that things aren't going great. That's why I introduced failure corner on the podcast where it's like, Okay, but tell me at time things didn't go well.

6:45 Oh yeah, that's great. Yeah,'cause it's so hard to get to that, right? And it's not all just this golden path rosy where we're all, you know, shipping beautiful, meaningful things all day, you know? It's a It's a hard business and There's no like perfect school either that kind of produces expert product managers and and CPOs and CTOs and stuff like that. So we're all like trying to figure this out. And we don't have a lot of sources, you know, so it's it there is a lot of struggle.

7:12 And there aren't like many options for how to build product. Like all people really read about is Scrum slash agile slash safe as they scale, and then there's like waterfall, which no never do waterfall. And then there's uh like the start up way of just like ship and maybe one or two week cycles. And then their shape up. So it feels like it's one of the rare Other options.

7:32 That exists. And so That's one of the things I've been hearing. It's like I hear like Oh, we thought there was only Scrum or Kanban and then we heard there was this shape up thing? Like what's that? And I I think it's always been connected to Basecamp. We're gonna talk about that just like it's Like it works.

7:47 for companies that are nothing like base count. Maybe sh maybe just t touch on that briefly. Well I mean that Came as a surprise to me, you know. I mean, when I wrote the book I had been in base camp at that time, I think fifteen years. And uh uh I actually didn't even know the outside world.

8:07 You know, I mean it was Jason's idea to even write the book'cause he said, Look, like a a lot of people are gonna wanna know about this. A lot of people are struggling and I'm kinda like, Well, okay, I I knew our inside story. of we had some growing pains and we had to be able to formalize the way that we were working and shipping so that as we brought new people in that they could participate in that and we could stay fast, you know? So I knew our like internal struggles But I honestly didn't know anything about the outside world. And it was only after the book came out

8:35 that it gave me this kind of excuse to start talking to people from all kinds of different companies. And It's been really interesting. There are some really amazing cases of companies of very different characteristics from base camp like VC funded.

8:50 you know, significantly bigger. Like very different pressures, different team structure, different skills who are doing it. And at the same time there is Also, a lot of questions that are coming my way because honestly, there are so few teams that are structured just like Basecamp. that there are a lot of gaps in the book of like, well, what about this and what about that? And how do we do that in our situation? So

9:12 Like a lot of my focus today is actually kind of closing those gaps. and helping people figure out how can I make this work for me or for our team. And you specifically told me you now call it instead of shape up, it's shape up in real life or shape up for real life. Yeah, well, you know, um my wife heard me saying the same thing over and over again on every phone call. And she's she's overhearing me and she's like, You got you have to make a course. You have to do something, because you're just you're you always are saying the same thing. So then this this led to this uh course that we made, which is called Shaping in Real Life. And well, yeah, the idea is the real life part, right? How do I make this work?

9:45 If my designers don't code If you know, if I have actually uh it's very contentious to get engineering time, you know what I mean, like When there's all these different pressures that Basecamp didn't have. We're gonna get into the nitty-gritty of how this actually works and the key elements, but You just give like a very short over overarching summary of how shape up is different from how other

10:05 Product approaches are. I think the way it's different starts with The way we were working was a little bit different. Um

10:14 So I started working with Jason and David on the first version of Basecamp, you know, the which was like the flagship product of thirty seven signals back in two thousand three. And we were a team of three. And uh we were I mean I think it's

10:28 For any really small team when you're just starting out, you don't need a process, you don't need a way of working. It just kinda happens organically'cause you're together, you don't have to explain it to other people, you know, it just kind of happens on its own, right? But there was always this Really intense urgency. From both Jason and David like

10:46 We've got to get to something we can ship. We have to finish this and move on. We we have to get to something that's done. There was just no tolerance for kind of big things that got fuzzy and started to drag. We there was always this like sharpening to get to what is this thing really and when are we gonna get to the end soon.

11:05 When we were building V one David wasn't actually full time as the as our only technical person. He was programming ten hours a week. So we had this really intense pressure of like how can we really use David's time well, you know? We don't wanna ever kind of

11:22 give something that this is the thing we want to build, and then it turns out not to be what we want and we have to throw it away and then come back again. Or you know what I mean? Like th those kind of uh And cycles of waste. Let me actually ask about this, because this is really interesting. So this is DH H Uh he was working part time when Ten hours a week. Yeah. Was he working on like Ruby, basically and

11:44 No thing. Well, Rails came out of of of the first so he so he told he told Jason I wanna try building this in Ruby. And uh 'Cause before they had done some collaboration and David had done things in PHP before that.

12:00 And he had this new idea he wanted to try Ruby, this language he fell in love with. And then, you know, h the framework Ruby on Rails, th he he ended up releasing that after Base camp was standing. 'Cause it was kind of extracted from uh the things that were necessary to get V one of Basecamp to stand up.

12:16 So that's what he was doing the rest of his time instead of I don't know what I don't know what he was doing the rest of his time, you know. Probably something great. But he's always I mean he's always been like that, you know, he's always doing something interesting. Like he's either racing or who knows what. You know what I mean? Like uh so but all I knew was that we got ten hours of the of that time. I love that that was like a constraint to design a way of working that uses engineering time most efficiently. Yeah, I mean put that put that together. So David's constraint of ten hours a a week And then Jason has this, I mean, I think many really successful founders and especially CEOs have this thing. It's like all they want to see is movement. You know what I mean? Like

12:54 Forward, forward, forward. So like When do we get to see it? When do we get to try it? When do I get to put it into somebody's hands? So that combination, there was just so much urgency. Even though There was no outside pressure.

13:06 You know what I mean? It was completely just like let's say cultural energy of like how do we kind of keep getting somewhere and getting to something that we can celebrate and get excited about. Mm. I love that. That's in That that's like an attribute I think of a lot of successful founders. So that makes sense to hear that. Totally. Totally. And that's where where I come back to like this is the part of the story where

13:26 I think so many companies would say, Yeah, I know that experience, right? Because they think that's probably the seedling of a lot, as you said, of successful companies is that That combination of urgency and also that those guys were so talented and that they They had a clear of what they wanted to do and all of that. is this amazing time actually these early days.

13:44 Is there anything more to the backstory that's important to share? Super interesting. Yeah, I mean the other big piece of it was So Jason and I were like this kind of product. what do you call it, like the two thirds, you know? And then there were so I was doing UX at the time.

14:00 And I was doing hands on coding as well. So we're very, very integrated. Everybody kinda does a little bit of everything. All of us were Coding.

14:09 Like Jason was in the actual app templates as well. doing HTML and CSS to do the views. He's doing hands on design. We're all like very much connected with like why are we building this? What is this? You know, David's doing the David's doing the bulk of the programming. And Jason and I were having these

14:26 Little sessions. These little sessions where we would Really figure out what the idea was. And there would be this moment where you would have a few strokes of the Sharpie pen. On a big pad of paper.

14:40 And all of a sudden you'd be like, Oh yeah. Like that's the idea. That's the thing we want to go try to build. And For me, like those Those sessions with Jason, they were these short

14:51 Very, very intense. Sessions where you're trying to crack the nut together. Like Where's the idea? What's the concept? Like, how can we go? What's this thing that we're gonna go and like ten hours later?

15:04 Right, David's gonna come back and we're gonna be like, This is awesome, this thing works and it does something we're excited about. Right. That was really kind of the seedling I mean actually that continued over years and years and years, those sessions. And

15:17 That's the seedling of Um This word in the book shaping. What does it mean to do shaping? It wasn't uh sitting alone.

15:27 um writing a document, it wasn't making a bunch of requirements, it wasn't Making a beautiful Figma file to represent a concept that could maybe be a feature. You know? It was this like super intense.

15:41 Really? exciting collaborative, like what about this? What about that? Oh maybe this, you know? Uh so that was a a really big part of of how we worked also. very intensely collaborative sessions to figure out what the idea is. And

15:56 Getting it sharp enough and and crispy enough. Yeah, we could very confidently get a yes from David and that he would know exactly what it is and what it means and come back. And it would be what we pictured and it would work. The way that we hoped.

16:09 So that we would kind of keep going and we wouldn't have to reverse or or go back to the drawing board. What it sounds like is essentially our kind of Trying to maintain these startup way of working as the company grows. Like everything you're describing is how s it feels to be at a startup. And this is a method to keep that.

16:26 Does that sound Right. That's exactly What what kind of became shape up was how do we hold on to that as much as possible. I mean one big ingredient we had an advantage also, which was that

16:39 Jason and David. hired so deliberately slowly. And this is kind of um Like a fortunate Side effect of the fact that they didn't take

16:49 Investment money. So there was kind of there wasn't that there was never that moment. Of like now's the moment when we grow. It was always like one person. And then kind of the organism adapts.

17:00 One more person, you know? And so this Just natural way of working. It was It was organically spreading They

17:10 There were I think maybe ten years. Before We had the first kind of like Wait a minute, what just happened? Like that's not

17:19 Like that project didn't go well. That's not how things normally run. You know, I mean we really it was it was I mean there of course there were always like Ups and downs. But there was

17:29 It was it was about ten years later when we had the first project. I I mean I remember the project. I remember being at the end. Of It it was at that time already kind of it was maybe it had been like maybe six weeks or seven weeks. We hadn't yet completely locked the six week thing that went into shape up.

17:47 And I remember we had a review session. And there was a fairly new uh new person who was leading the the uh who's doing half of the work on that team. We had the review session and it was like instead of Oh look, this is about ready to ship. It was like

18:05 There are a lot of open questions here. And Not only are there a lot of open questions here We're not getting quick answers. When we have when you know, as we as we're asking.

18:17 And what we're starting to realize is like Oh, this is not only is this not gonna ship But we can't even see the end of this. You know? And uh and that was like one of those moments where you're like, Oh

18:30 This isn't going to automatically, organically Just keep it. Spreading as we hire forever. You know what I mean? We did reach a point where it's like oh this We're gonna have to figure out When this goes well.

18:43 Why does it go well? And what do we do differently? And how do we Kind of formalize that so it's It's reproducible as we keep onboarding more people. And that's That's actually when Shape up.

18:55 as a as a framework started. That's when I really kind of started to lean in and I sort of took over that responsibility of okay. How do I systematize this? That's a great segue to let's actually talk about how the shape up method works. What are maybe just at a high level, what are like the core ingredients to the shape up method? There's basically um Kind of like three uh maybe big things.

19:15 The so the first thing is This notion of We are not going to start something unless we can see the end from the beginning. So We're not going to

19:28 Take a big A big concept and then say what's the estimate for this thing. We're not gonna say, Oh, we need to be to build a calendar and then do a whole bunch of Figma files or write a whole bunch of requirements and then ask for an estimate. We're gonna go the other way around and we're gonna say What is our appetite for this?

19:44 What is the maximum amount of time we're willing to go? before we actually finish something and we have that startup moment. that we talked about that moment of like, ah, you know what I mean? It works. We got somewhere. We this at least this If not the whole project. This meaningful piece

20:00 We can literally walk away from So um Then what we found was that there was a lot of experimentation. We found that six weeks It's kinda the maximum. That we can see into the future.

20:13 where we could actually say, like, how do we work backward and figure out something we could build in that six weeks and really land it? You know? So that's kind of the first piece is Working backward from our the amount of time we actually want to spend on something. And say

20:29 What can we do? What could we shape? So that after that amount of time, we've gotten to somewhere we wanna be. You know it's kinda like If you're gonna buy a car, or you're gonna You're gonna you're gonna buy a house or you're gonna rent a new flat or whatever.

20:43 You have to have like a budget in mind, right? And the the the budget then Is how you choose between all kinds of alternatives and make a lot of hard choices and trade offs. to figure out like well, you know. I I I I want the faster engine, you know, but I can't afford you know, but I have to give this up or you know, I

21:01 I want it to be fun to drive, but we also need space for longer road trips and you know, you're making all these trade offs, right? So this is kind of This uh this second piece is is this work that we call shaping. And the shaping work is How do we actually

21:17 Take this Fixed amount of time that we've given ourselves. And vary the scope. How do we come up with A idea Some version of this

21:29 That's going to work in the amount of time that the business is interested in spending. So um this is that those creative sessions that I was talking about where we're jumping all over the all over the room in front of the whiteboard and uh and and getting to an idea. And there the really key thing is that We're getting to an idea where we can see the idea.

21:49 You know, we understand like why we're doing this. We're wrestling with the problem and we're wrestling with the solution until we have an idea that we can actually say Uh, this is what we want to go build. So it's not just Calendar or Dashboard.

22:04 Or you know uh newsletter builder, but it's like this idea of how we're gonna tackle This problem. about the calendar request, right? So that's the shaping. And then the third piece is

22:17 When we've Actually Carved out. A fixed amount of time. When we've shaped a solution.

22:25 That is F Experience standpoint. From a functionality standpoint, from a technical standpoint. doable and desirable something that we can make happen.

22:37 In that amount of time? Then we can give it to a team. And we don't have to do the Sometimes call scrum the the paper shredder. You know, that's where you take an idea.

22:48 And then you split it into a hundred tickets. Right. And you hope that it all glues together still after you've done that step, you know? We don't want to do that. Instead We want to have a whole idea. Give it to a team.

23:01 So they see the whole, they really understand it, right? And then they can come up with their tasks and they can figure out how to track that and break it into pieces. So they can actually take more responsibility. And so what we see is way more engagement, you know, especially from the technical team.

23:18 Right. Because instead of like here's your ticket, right? Or here's your user story. It's like Here's the thing you understand. Bad.

23:26 Make sense? And now you're gonna have freedom to figure out how to actually make this a reality. There's gonna be A million things to solve in the implementation detail. And now you have a bunch of fun problems and you don't have to keep asking questions to other people to understand what this is or how do I make a trade off or that kind of a thing.

23:44 One of the core elements of this, the and I wanna confirm is that you can pick and choose these things into your team. You don't need to do this wholesale. Right. Uh you don't need to do Uh yeah, any of it. So

23:59 So this is where we kind of it helps to It helps to look at like what's going wrong and what are we trying to fix? Yeah. And then you know, what do I want to bring into this, right? And usually what I notice is that people They like to start sometimes with, Oh, I wanna give the team

24:14 Let's say six weeks. And I and I wanna give the team more latitude or let's say more creative freedom that they're gonna be responsible in the six weeks to figure out how to make it happen, right? And usually a lot of the drive for that is I'm getting tired of having so many meetings and rituals and

24:33 things that are not actually working on the problem and doing the work, you know? I mean, especially Scrum teams, they they often complain about that. So would they sometimes see in this is like oh I love this idea that The team is just gonna be cooking for six weeks and they're not gonna, you know, we're gonna meet as needed and we're gonna work shop things, but we're not gonna be busy with all these rituals all the time. Right. Uh

24:54 Now the thing that's tricky. І за if you want That reality. Of the team happily. buzzing and humming like a you know, like some happy bee colony, you know, for this uh six weeks.

25:06 A lot more clarity. Around What's the thing that we're solving? Right.

25:12 And so when we start working backward from that, then what we see is that oh well if we don't Shape better. then the team isn't gonna have the clarity that they need to take over that responsibility. You know?

25:24 So they can make choices and make decisions and make trade offs. So that they can get to the end of this thing. And worse at the worst is that I sometimes see cases where people are like, Okay We're doing shape up.

25:35 So you guys are gonna build, you know. The newsletter builder. Okay. But you only get six weeks to do it. So Use your fixed time, vary your scope, and and and and enjoy your responsibility. You know what I mean? Which is just cruel, right?

25:50 Because Yeah. I think uh quote uh Bob Nesta, who's been on your show a couple of times. You can't put uh ten pounds of crap in a five pound bag. So uh high academic statement, you know? And uh we can't just take any project, no matter how giant it is, and then throw it at a team and say, figure it out and and ship ship something meaningful in six weeks by cutting away scope, right? So it starts it starts

26:15 It starts to it starts to raise questions. About How do we actually Decide together. what this project is, do we actually have clarity around what the idea is and what we're gonna build?

26:29 You know? Let me follow up on a couple of the elements. So appetites I think for any product manager. engineer, designer, anyone that is like Experienced

26:38 Okay, we're gonna we estimate this l this landing page is gonna take a couple of weeks. Great, let's work on it and then ends up being six weeks. Uh can understand why this makes sense. It's just like this landing page is not that important to us. Let us just say we will commit two weeks to it. We'll do as much as we can in two weeks. And then we move on.

26:55 And scope is not allowed to go beyond that. Makes total sense. Like this just makes so much sense. as you listen to this, uh, especially for people that have just fallen to the The problems of Estimates not being accurate.

27:08 Mm-hmm. Then there's a six week element. And the key there is your s you're And this is uh kind of counter to maybe two week sprints like Scrum, is that kind of the Where does this come from?

27:19 You know, actually it turns out that the six week is only a maximum. Mm. And that's really where this number does some work for us. If we think of six weeks as a maximum that's gonna force us to ask some really good questions to ourselves about Where do we actually what

27:36 What piece of this do we really think we can land? Because if you try to say, you know, in six months We're gonna ship this thing. You can't get your arms around all of the problems that have to get solved for an entire six month Chunk of work.

27:51 to actually happen. There are so many unknowns. There are so many ticking time bombs of things that we didn't understand or couldn't foresee. You know, but If we if we set a ceiling at six weeks We have a much better chance of I think that's the size of something where we can actually shape it.

28:09 And reveal that complexity before we're in the middle of it, right? it doesn't mean that we can't use this technique to do a two week project, you know, especially if you're on a growth team. You don't want to wait six weeks, or you know what I mean? There you're gonna have to artificially bundle things together to do six weeks. It's like look I've got I've got something I wanna

28:28 I want to ship in the next week. And then I've got a thing that might take two weeks after that and then a week after that, right? So uh it's it's it's more a question of what we're trying to take on, you know, it's really that upper limit. Okay. So it could be a two week cycle. And that's it.

28:43 Cool. So it's like we're gonna build this new landing page. We're gonna give it two weeks and then do a shaping session on that. Now the the other thing, the other side of that is When it comes to feature development or you know, building something that's gonna be me enough to sell.

28:57 You know? Then There's very few things that are gonna be uh substantial value add to a product that you can do in two weeks. Right.

29:07 So then you get into a point where Well now we're just kind of sprinting and we're just kind of taking one bite after the other. And then that's where we can land in that situation where we feel like, ah, I can never see the end of this. I just keep going back and saying one more sprint, one more sprint, one more sprint, right? But six weeks is a long enough chunk. Or sometimes four weeks.

29:28 What's big enough that we can actually get somewhere with this amount of time, right? And there's an implied element to this that I think is worth Highlighting. The whole idea is you commit to the appetite and if you

29:40 are not on track to hit That Instead of extending the date you cut. In order to still hit it. This is

29:49 Uh tricky one. Yeah. So you're right that it's implied. But the thing is. In real life.

29:57 If you make a commitment and you get alignment that we're gonna spend six weeks of engineering time. Building this thing? You know? If you get to that end of that six weeks.

30:08 And Something is going wrong. You know? It wasn't shaped. We can't see the end of it. It's more complicated than we thought.

30:15 All these different things. And by the way, we can also talk about kind of why those things happen, you know? But When we get in that situation, if we're at the end of the six weeks and it's not looking good. I mean

30:26 We can't just cut off What we agreed to That made this thing valuable. You know? We can't just like cut the scope and say, Oh, well now we manage to ship inside of six weeks.

30:37 That's gonna kill everybody's morale. Everyone's gonna feel disappointed. We're gonna feel like This wasn't really worthwhile and now We go into the next cycle with this kind of like Debt feeling.

30:48 You know? that we didn't actually finish the thing we were kind of supposed to finish, so now we're like over time, you know? None of that is good. And if we also go the other extreme And just say, um

30:58 Well, like it we actually we say in the book, you know, we had this principle at at Basecamp, which was this notion of the circuit breaker. Like If a project is not on track to actually finish after the six weeks, we're just gonna cancel it. and rethink. You know?

31:13 Almost no teams have the stomach for that. But Mm. The the version of that that's more stomachable? Is look, we can't just

31:22 Uh we can't just cancel the project and then say, Let's see what comes next, right? But what we can do. is say we're not gonna keep reinvesting in something that we don't understand. You know, so let's take this out of build mode. And bring this back into shaping mode.

31:40 Which might mean Different people. A different conversation, asking different questions. You know, doing a different kind of work. To

31:48 sus out like what is it that's fuzzy here? What is it that we couldn't see? Like what do we not understand that's Right. How do we get to the clarity that we need? So that we can actually say like this thing is going to happen if we give it another whack. I love just how real this approach is, not this like theoretical okay, cool. After six weeks you s just decope and it's all that's cool. Yeah, you just cut the scope, you know? Yeah, no problem. Ship put your gut. I've seen some shape up adoptions that look like that, by the way. And that's it's uh

32:17 You know, it's it's that's that's not the way. Uh we the the shaping step is crucial. And you know what what you mentioned with your landing page example, by the way. It's so Seductive. Because we can imagine, you know, oh I th you know Parkinson's law, right? If you give me six weeks to do the landing page, I'll find a way to use it.

32:36 But if you give me two weeks, you know, then I'll stop after two weeks. But When it comes to Real Product work.

32:43 You know, where there's some functionality that we have to figure out how to make it exist. We can't just Cut the scope. If we run out of time. So what it means is that the shaping work

32:58 Is Really? Working hard together to figure out what are the main moving pieces of this thing. Right. How do we narrow down our understanding of the problem?

33:10 And how do we identify what the moving parts are of the solution? Like what actually connects together for this feature to work. You know? And when we really get to the level where we can say, Oh, we need to do this, this, this, this And then the engine is gonna turn, you know?

33:26 That's that's the place where we can say, Oh, this is well shaped. You know? And and that's a that's a It's a different kind of work. We in in shaping in real life we call it Yeah, we actually teach it as doing live shaping sessions. And uh this was how

33:40 I did it for years and with Jason, we'd get into the room, you know. And I had both the technical and the UX side. So the Both sides were kind of represented there in one person in that case. But for a lot of teams today we actually teach them how to bring Uh.

33:54 The Kind of the the s the senior engineering person. Who isn't just senior in title, but you know, like the one who actually knows where the bodies are buried, you know? Like how the old stuff works and what's truly possible and what's hard and what's easy in our infrastructure, like the person that really knows, right? You bring that person together.

34:13 with the product person who deeply understands the backstory of why this is an opportunity and what we're trying to solve with this. You know? And then a designer in the room and they're like whiteboarding and wrestling with each other to get to

34:26 What's a version of this thing that we believe in that's real that we can actually finish in that time? This is great. Let's g let's go one level deeper on this shaping session. So a few tactical questions. How long are these sessions? It sounds like the people that join are the a designer and an engineer and an MPM. So add anything else there. And when do they happen is at the end of

34:46 Uh a cy Do you call a cycle, by the way, or sprint as the six ish period? What I actually like is time box. Actually. Because the thing is that um Mm-hmm. S some teams need regular cycles because they have m parallel teams and they need that cadence in order to kind of reduce management overhead.

35:06 You know? But if you're small and you only have like one or two teams, you might not need to be on a fixed cadence or a cycle plan. You might be able to just set one time box after another. Right. So the key thing is actually that that time is pushing back at you. And that you're being intentional about

35:21 kind of what's my time budget that I need to shape into. Let me take a quick tangent because if you're that's so interesting that the Time boxes. Can be very different lengths. Imagine at a larger company this gets complicated when other teams are trying to there's dependencies and timelines launch and go to market dates and all these things.

35:39 What's like the largest company this Sh this approach has worked out. Like like what's the ideal company stage? For shape, but It can function in very large companies. Uh we have, for example, uh I have uh some friends at a uh at a uh they're a uh uh what is what is it called? They're doing uh clinical trials, so they're in the pharmaceutical industry. And I mean the companies, you know, thousands of people.

36:04 And It's not that every team is doing this. But they have a few teams. That are working in important areas, you know? And they're doing this.

36:13 And uh It's completely possible in that context. If you have someone who's Yeah, at a senior level on f on the engineering side. who is able to

36:23 uh make the right architectural choices and also do some S some negotiating and kind of be the backstop to make sure that someone isn't going to get pulled away onto something else. You know, you can kind of carve out Oh, this system can be worked on independently of that system. This was actually what David at at Basecamp has always been

36:44 Amazing at? Is This dependency hell, it's actually not It's not a So many people are used to it and they think that it's just how it is.

36:53 But it's actually not. It is possible for engineering leadership, good engineering leadership. Untangles things. So we can work on this system without having to be thinking about this other system somewhere else, you know? So when you have some untangling

37:08 With your infrastructure and with your architecture from an engineering standpoint. Then you have some freedom. And then if you can also figure out the capacity management side of I'm gonna protect this team from that other work for this number of weeks, you know, you can really get a lot done.

37:23 This insight that you can operate this way at a larger company and the whole company doesn't have to operate this way, I think is really freeing to a lot of people. What's kinda like the adapter. I'm and I wanna come back to the actual shaping process, but I I can't help but ask this. Say the company's operating like a quarterly cadence or six month cadence, and then there's like a team operating on a two week, sometimes six weeks, sometimes four week. Cadence. Advice on how to like what's the adapter that connects those two cadences.

37:49 So uh there's there's kinda two different things. So like I've seen cases where They've decided on a uh like a a four week plus two week or like so th so they'll do like a like five week and then one week of cool down in between and then They they they time it so that it adds up to a quarter. You know, I've seen that.

38:09 Um the other thing I've seen is When the team is just continuously delivering meaningful things. It doesn't have to line up. Because

38:19 From the executive level If you are CPO or CTO. Or I mean in these bigger cases it's more like, you know, a VP in some area. But You're coming to the table where you're supposed to be reporting of what your group is doing.

38:32 And when you are consistently saying, We said we were gonna do this and nothing finished and now we're doing this and it's gonna finish. And the next time you say, We said we were gonna do that and it's finished, you know, without excuses and without well, maybe another few more months or you know, we're working at it like That I mean that's that's what That's what everyone wants to see is that movement. You know?

38:52 Yeah. If you're doing great, people will leave you alone. That makes sense. For sure. For sure. I love that. I love that point. Okay, coming back to shaping, one one maybe one way that would make it uh really easy for people to understand, what's the output of the shaping session? The output of the shaping session Is So and by the way, about shaping session, you know, let's maybe we can talk a little bit about what shaping is not, you know, because um we need the contrast sometimes.

39:17 So Very often when people try Shape Up, what I see is A product team. Kind of. Creating either a lot of figmaphiles.

39:28 Or Maybe uh a lot of documentation. You know, like a like a PRD with a bunch of requirements and a bunch of backstory and good reasons why we're doing this and stuff like that. And what you see is that um when you When you give that to a team.

39:44 As like this is what we shaped. What happens is like Yeah. It blows up. So

39:51 I mean you probably uh know about what happens when the the the Figmaphile makes first contact with the engineering team. There's a reality check that happens there, you know? And very often there's a kind of a back to the drawing board. So when there's a lot of solution All the way down to detail without engineering involved. Usually that's a painful recipe, you know. And then it's kinda like no, we can't do that. Actually it doesn't work like that.

40:16 And then On top of it, the other big challenge is that There's so much that you can't see on the surface. Of a UI. You know?

40:25 How do we flow from here to there? What are the different cases of of logic like In which case do we move from here to here to here in the flow, like what is happening behind the scenes? It's like The engineering team, they have to put on their X ray goggles.

40:40 And like study this thing to try and understand like what's happening underneath, you know? I often use this analogy of like uh if you're doing a home renovation, you know You can have like the most like uh Beautiful rendering. of here's the new here's the new bedroom and we're gonna have these lamps on the side of the bed, you know?

40:57 that are coming out from the wall. He's like, you know, and you can have have the perfect rendering and the perfect lamp and the perfect color. But if you haven't checked if there's electricity in that wall there or not. Right. It's gonna drastically change the cost and the time and everything if you're gonna have to rip open those walls to feed some lines up to those lamps, right? So What we need to do in a in a shaping session when it's going well

41:19 As we come out. With Some kind of Uh I

41:26 Where Engineers. product and design are all looking at that and they're saying we understand that. I know exactly what to go build. Right.

41:35 I'll use the example of the calendar from the book. So What is a calendar? You know? So first of all there was this

41:43 work that we had to do before we could even shape it. Which is like Can we actually narrow down this problem? In shaping in real life we call this framing. And uh in the book there's a chapter called Setting the Boundaries where we get into this and it's like

41:57 Look, we we we we We're not gonna just build calendar, which is like Google calendar, you know, where we who knows where it ends. We narrowed it down to We understand that for our specific customers who are requesting this again and again. It's more about I need to see empty spaces and in the existing agenda view, I can only see things that are already scheduled and I can't see free spaces where I could book something.

42:20 Okay. So we got to that point of like So the What we're trying to solve here Is the empty spaces. So that's a good frame.

42:29 Then What are we actually gonna build? We came to Here's a good rule of thumb. If it's shaped well.

42:37 You can usually describe it. In Less than ten moving pieces. Okay, if I can say It's gonna have this, this, this, this, this, and this, and that's how we're gonna let people see the empty spaces, you know?

42:51 That's a good indicator that it's clear enough that that that it's that it's shaped well. So in this case, we had a You know when you go to an airline and you and you want to book something, you see this like two month grid? Right. Mm. Two months side by side.

43:05 But um They're just gonna have dots in them to indicate if there's if there's a free day or not. Or I mean if there's something in that day or not. Kind of like, you know, the uh iPhone calendar, I think still has this where it's just dots on the month view. And then if you tap a day with a dot in it. Or without a dot in it. There's going to be an agenda view that slides underneath.

43:24 Which is gonna show you what's scheduled in that day. Right. And then there's going to be navigation to go forward and back in the months. There's going to be a create button to create an event.

43:35 Right. And That's more or less that's more or less it. So w what you can see here is it's not a Like what is a calendar? You know, it's not a calendar.

43:44 It's a it's a it's a Two months. Dot grid. With scrolling agenda view underneath. Right.

43:51 And uh and the ability to to hit new when you're looking at an empty space to create something in what you're viewing. Right. So that's the kind of thing where That's shaped. And we can talk about what that means and what it entails and we can have a really

44:05 Practical realistic conversation about Is that a thing we can do in six weeks? You know? That's that's gonna be a real conversation and not looking at a whole bunch of mock-ups and

44:16 And trying to x ray to figure out what's actually the intent here and what's really real and what's not and what's possible and what's not. That was a great example. This is really helpful. So if I were to try to describe this. Essentially what you're coming out of it. With a shaping session with is uh

44:31 kind of like the user the the user experience with just like wireframes slash sketches. of the screens and the key buttons and flows. So it's kinda like the architecture. With key components. Not like a

44:46 Dock of spec. And not Final design. And also not just like a user story. As a user I need to be able to see

44:54 Empty spaces. Exactly. So'cause that's the thing where it goes wrong, you know, if If we're going to commit engineering time. You know, and it's like We believe there's some way to see empty spaces, but you know, uh the way is a question mark.

45:09 It's a really risky way to spend that time. Because you're committing, right? It's like I'm going to be able to do it. Yeah, you're we're committing and that time is really valuable. Right? That's six weeks of engineering's time, you know? And that time wasn't easy to get in the first place, right? Because of course there's all these other forces in the company that want to be doing something with the engineers, right? You know, so if we want that team To be really using that time well.

45:32 where they are moving, they understand what they're solving and they're creatively engaged because they know what it's supposed to be doing, right? You know, they need to have that clarity. Both on the problem side of this is about the empty spaces. And on the solution side of It's a dot grid with two months and a scrolling agenda view and a button. There's still a million

45:53 interesting creative tasks there. in the actual high fidelity design, in the code, you know? There's so many things to solve there. But that is something that they can all hold in their heads and understand and and work on. This episode is brought to you by Airtable Product Central, the unified system that brings your entire product org together in one place.

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46:40 And because it's built on Airtable's no code platform, you can customize every workflow to match exactly how your team works. No limitations, no compromises. Ready to see it in action? Head to airtable.com slash Lenny to book a demo. That's airtable dot com slash Lenny. You mentioned and I think a lot of PM listening to this are gonna be like oh I'm scared of doing this is if you get too detailed.

47:05 Uh the engineers and designers on the team are just like, What the hell? You're just telling me what to build, that sucks. I don't wanna I don't want that kind of work. So what's like Is is the solution to that the engineering lead was super involved in detail and the design lead was super involved.

47:20 And so you can trust that it's That you're not just the code monkey building the thing they told you to build. That's really interesting. I gotta tell you. The dominant failure case that I see in the real world.

47:32 It's Always, again and again. Not enough detail. Mm. And it's also the most common failure mode where

47:42 Engineers. Run back to the To the product folks and say I'm not getting enough from you. It's it's it's it's really like that.

47:51 But I can understand why the um The hair stands up on the back of the neck a little bit, you know, thinking about it. Because um Of course, if you if you give a senior engineer like, here's how I want you to go implement the schema for this database change for this model, they're gonna be like what do you like like Duke.

48:10 Who are you? But well what's really interesting. Is It's not a universal thing. The amount of detail that the team is gonna feel

48:21 Helps them. Is a dial that we can turn that depends on Who's on the team? So if you have a more junior person Who's on the build team.

48:32 And then you have a more senior engineer who's involved in the shaping. they can make that junior engineer much more successful with additional detail. Right. So like we're gonna do this and I would suggest approaching it like this, this, this, and this.

48:47 Right. That junior person is when they don't know how to do it. They're not gonna ask. 'Cause they don't want to show that they don't know. And they're gonna hide the fact that they're lost.

48:57 And it's gonna blow up later in the project. And and on the other hand, if they are given more guidance, they're going to be able to be successful. They're going to learn about, you know, this is how this person who knows well kind of approached it. And then in the next round or a few, you know, a few projects later, you can dial it back and say, Well, let's let's give less deal detail and see how they handle it, right? So you can really give people bigger shoes to grow into. and and and help them to be successful.

49:25 And then of course you can also do it the other way around. Where Uh. If if you've got some really stellar talent on the team And you have a long history and you have a lot of trust that they are gonna be able to understand and solve it, then of course you can leave things out, right?

49:40 But The the the thing that I often see is If there's someone on the build team Who really feels that they should be involved in the fundamental Decisions about the approach.

49:52 Then a better solution would be to actually bring them into the shaping. And have them play that technical role. In the shaping session. You know, if they're re if they have the right skills and the right perspective and the right knowledge to play that role well, then just bring them into the shaping, right? So it's all about

50:09 How do we Bring people into a moment. Where we are using their strengths. You know? And then we're giving them an input so that whatever their kind of work step is, that they're able to apply the maximum creativity.

50:23 But also have the maximum clarity so that they can really use that time well and also like feel good about what they're doing. Feels like the core of this is uh the risk, the biggest risks. and uh address the biggest unknowns as much as possible. Like there's probably this eighty percent of here are the risks, let's just uh understand them deeply before we come into this.

50:41 Appetite. That is exactly right. Um there are these uh uh you know, we can call them rabbit holes, we can call them time bombs. There are these things where we say, Oh, you know, it'll be fine. You know, like one example, like simple example, I worked with a team and They they had a step of onboarding in a fintech product.

50:59 Okay. And There was this step of onboarding. And they would lose a lot of people in the funnel at that step because you had to fill out a whole bunch of information. And they they figured out that

51:11 they could actually pipe that data in from one of the partners that they had because they were partnered with banks. And they're like, Oh, we don't even need to be asking people this. Right. So we're gonna in we're gonna fix conversion. We're gonna eliminate a step from our user experience, it's gonna be great.

51:24 Right. You know? The thing that they didn't look at Was If you go into the code on that step two.

51:32 It's not actually one step. It was like three different branches of that stuff depending on which bank the customer is is integrated on.

51:42 You know? And so that's the kind of thing where it all sounds so great and simple, and then you get into the weeds and you realize like, Oh, wait a minute. You know what I mean? So now we have decisions to make. Now if you're in the middle of a project and it's already been resourced. Right. And people are already on the hook that we're supposed to be doing this.

51:59 And you already got the alignment that the engineering time is happening for this. And you're finding that out in week four. You know what I mean? Uh you did all these beautiful drawings by the way, and now you're finding this out in week four.

52:11 Like That's a bad place to be. But if we're in the shaping room And we didn't kick this thing off yet. Right. We didn't even green light the project yet.

52:21 And we have an engineer there. Not just the product people, not just the designer. But we have that engineer who really insists on Sometimes I like to think of it, you know, like the grumpy old plumber who's seen everything. And he insists on opening up the walls and looking at the pipes before he'll give you a quote.

52:37 Right. So it's like when you've got that person in the room They're saying Yeah, that all sounds great. Let's take a quick look at the code and figure out what screen you're actually talking about. Just let's just take a quick look. And it only takes a moment to open up the code.

52:52 Find this thing that we're talking about. And really look at it and say, Oh You know? It's more complicated than we thought. And now

53:00 It's not like okay, now we're screwed and the project is gonna be bigger. Oh now we can have a really cool conversation about trade offs. So Let's say we've got three different integrations here. Three different segments integrated into different banks.

53:14 How big are they relative to each other? Right. In terms of the deals we made or the percentage of customers who flow through those three different conditions, right? If we just did this on one of those branches, would it be a win?

53:27 You know? And like if we did it on all three. How much more time would we have to negotiate for? And would it feel worth it? You see, like we're getting into this horse trading. Of like

53:37 What is important, what's worth it, what do we need to get out of it. And that's really productive. That's and when you're doing that before the project starts off. that feels like, oh, we're talking about the important things. We're not failing right now. we're engaged in the hard questions that are gonna enable us to really ship something that's successful later. Well let's go one level deeper uh on the shaping session because clearly that is so core to this working. And I know you have a whole book about like how to actually do this. So we're not gonna answer all the questions and there's a lot of detail and new ones.

54:06 But l a few questions. How long do these usually take is like sounds like a whole day kind of experience. And then sounds like you invite as few people as possible, but not too few people. What's your guidance on who should join? So we um we run uh in this uh shaping in real life course we've been doing workshops where we try to help people to learn

54:25 what it's like in a shaping session. And one of the things that's always interesting to me Is how So like Kathy and I will be running the session. And

54:36 We have to Like People aren't used to working so fast. You know, to like Like what are we actually doing right now? What's the decision? Like what's an idea?

54:46 Like right now. We're not gonna go away. And and and and draw something and then and then all comment on a document and then come back and get together tomorrow. Like What ideas do we actually have right now?

54:59 Like starting from zero. So like imagine like Uh we We We've narrowed down the calendar problem to it's about empty spaces.

55:11 Right. We are willing from a business standpoint. To spend six weeks on a whack at this where it's solved. We believe there's a way that's possible. So what can we come up with?

55:23 And that's how you that's the input to the framing session. Or sorry, the shaping session. Exactly. So that's so the the having a narrowed down problem from the framing work. And this is a whole other topic of you know very often the PMs are sometimes just taking something at face value and not negotiating down to really narrow down what is this really, you know, and where is the value in this, but let's suppose that that's happened, right? that we've narrowed down the problem. So now we've got a narrow problem.

55:52 So now what we need to do is Try out. Different ideas. And

55:57 And this is the real thing. We have to try to break them. So I wanna draw an idea. And then I want the technical person to find like, oh, this isn't gonna you know I mean this isn't gonna work because of this reason.

56:11 Or the product person is going to be looking in and saying, I don't think like I get that that's really an easy way to do it technically, but I don't think that we're actually delivering the value if I play through the customer scenario here. You know what I mean? So there's these different angles. Where the idea can fail. And uh one of the things that we also coach people to do in a session is

56:32 Not just to go down one path. And then be sort of stuck in one idea, and now you're kind of going in circles around little details of one idea for three hours. But to really Step back and say, here's an approach. You know, what if we had the scrolling agenda view?

56:48 Okay. And that's idea A. Like Then What's what's a very different way of doing this?

56:55 You know what I mean? Like if we didn't want to have the agenda view there, like is there a way to do this where it's just the month view? Let's like see if we can draw that. You know? So that's that's the kind of thing that's happening. You asked about the time And I started with like

57:09 People aren't used to Just Going all the way into actually trying ideas, you know? So f there is a a little bit of uh a learning how to just face that blank page and start Trying things together, you know?

57:26 What we find is that A three hour session. can be very, very productive to help you figure out kind of What? What do we already have that are possible approaches to this?

57:38 What are some Major missing Things. You know? Like.

57:42 Okay. I've got the I've got the calendar dot dot grid. I've got the agenda idea. But like what about what about multi day events? Do you know what I mean? Like So there can be these things these like what about?

57:55 So then Maybe we break. And We think for a little bit and somebody sketches some ideas on that and does a spike or two on something. And we come back again.

58:04 You know, for another three hours. We come back the next day. Right. If If

58:11 The project that you're trying to do. Із дубо. With Let's say your existing technology.

58:19 Right. You're not inventing a new algorithm. You're not inventing some new database or you know what I mean? You're not doing um a new new AI model. It's more about like how do I use The APIs and the frameworks and the tech stack that we have. How do I put that together to build something, you know?

58:36 Then You know, If if if the if the problem is clear and the time is now, like you will be able to f come to a conclusion. About what's possible to build. In you know, three sessions.

58:47 Something like that. You know. The key thing. is leaning into those sessions. And really wrestling with each other.

58:54 You know? Uh if you have just the product and the designer there. Uh and And and then it's kind of like well, we'll show this to the technical person later. Then it

59:04 it can all blow up and then you find out it's more complicated than you thought. You have to go back to the drawing board. We need to have the right All the right the necessary information In the same room for these sessions to go fast. There's so much genius built into this approach.

59:19 And it Like sits on top of human. Nature. Uh one is just you you need to actually Spend like go into the deep

59:28 edge cases and nuances and not just like Let me let yeah, that's fine. Let's go. More concreten. Very concrete, very like in in depth. And The appetite I there's just like so many elements of this that just connect with the way humans work versus

59:43 A theory of just like yeah, well how long this will take, it'll be go great. And we'll figure it out as we're building. We don't need to really figure this out. Yeah, we don't have time for that. And we're solving a puzzle together. You know, if it needs to be doable in this amount of time, but it also has to hit these points in terms of the problem we're solving.

1:00:02 You know what I mean? It kinda has to do these things, but in this time and You know, one other thing that I would mention is that um We can't be drawing Figma files. It by the way, I'm I'm I'm I'm being very uh uh g mean to to to Figma, you know, so far in this conversation. There is a time, right? When

1:00:20 When It's the right time for the Figma file, right? What we wanna do is have that clarity. Around You know, the let's say we already know

1:00:30 Where the sink is going in the kitchen. And now we can make final calls about the tile. And and the the the the exact fixture and stuff like that. Right, grout color. We don't wanna have to throw it all away every time something changes, you know? So there's a time and a place where Figma is amazing and feels good. And it's like, oh now it's beautiful. You know, now it's amazing, right?

1:00:52 But In a shaping session. You can't collaborate. on on something so high fidelity, right? And so we need also some ways to collaborate, and this is where you see these techniques in the book like breadboarding.

1:01:05 And fat marker sketching. These are tools to help us express an idea. very very clearly in detail you know we're gonna hit this button and from this button go to here This calculation runs Then we get this answer and then we have this choice to go here or here, right?

1:01:22 Like that's the kind of thing that we need to be seeing. And that's that's kind of the sort of the level of detail. where we can move fast together, but still see something real as more this kind of breadboarding level. fat marker session is like very evocative of what what this whole session is about. It's like very High level sketches.

1:01:39 Uh that's a great term. The danger there that I often see is that um what we don't want is to say, Oh, Figma isn't the right thing at this level. So instead we're gonna do fat marker sketches. And what you get is the equivalent of a blurry figma.

1:01:54 Do you know what I mean? Just less detail. What we need from a from a fat marker sketch for it to be Valuable to us as As builders. is it has to really communicate the idea.

1:02:08 Yeah. So when I look at that, I'm like, oh, now I get it. Right. And if it's kind of more this sort of general wireframe of like, you know Dashboard goes here. And there's gonna be four reports.

1:02:19 And it's like I still don't know what to build. Right. So if it's not telling me what to build, so maybe this is a way to come back to your question about what's the output of the shaping session. It's like It's shaped.

1:02:32 If we can give this to a technical person and they say, Yeah, I know what to go build now. I'm very happy with our overview of the process. I think we've done a really good job giving people The just And obviously if they want to actually implement it, they can get the book.

1:02:45 and dive in or work with you, which will point people to Say someone's like This is awesome. I wanna do this. What would you say is a good first step for a team that's currently Let's say like they're in startup land and they're just like shipping every two weeks, maybe every week.

1:02:59 So maybe for that bucket of folks. And then also for a larger company that's, you know, I don't know, agile scrum safe, and they're just like, Oh, let's try something different. Sometimes uh dev teams Uh They like the idea of not having the scrum ritual.

1:03:13 So they wanna take in the six weeks. But Uh Unless B.

1:03:18 Engineering and product come together to figure out how to collaboratively shape. Like we talked about before, you know? That time box isn't gonna go well. So they think they're gonna not have to do stand ups, but now it's like a day of of hard Thinking.

1:03:33 It well, it kinda turns into Um Even more meetings'cause we don't know what to do. And the more meetings is just that shaping session specifically. No, what I mean is that if we didn't if we didn't if we only adopted the if we only adopted the six week cycle and said, uh we're gonna figure it out and we didn't adopt the shaping. Then we just don't know what to do. And then we reach the end and we're basically scrambling to shape it as we go. And then we run out of time. And then we feel like this wasn't, you know, it was nice to get a break from the from the scrum rituals. But we can't say that we are

1:04:06 Um You know what I mean? Uh knocking the champagne bottle on the boat because we're celebrating the launch, you know, or whatever, you know, again and again. Right. This is a good actually time to maybe talk about there's obviously the sprint kickoff in Scrum. Uh what's like the main difference for people'cause they may be thinking, Oh, that's just like a sprint kickoff. That's a good one. That's a good one.

1:04:25 So what you often see in uh in a scrum team is that there's somebody who creates these um Tickets. I've like these are the things that are gonna happen inside of the sprint. You know?

1:04:37 And really in in in In my opinion, too many cases. It's not the person who's doing the building who's creating those tickets. Like a product owner. So there's a big, big gap there.

1:04:49 There's Uh we could talk a lot about that. Um but there's There's gaps in context. The person who's writing the ticket doesn't actually understand the work that's involved. You know what I mean? So there are so many unknowns and time bombs. waiting in those tickets that sound reasonable.

1:05:05 but they weren't really created by the person who understands the work. that needs to happen, you know? So the k difference Uh is two things. So in Scrum you have you have

1:05:16 A a person who's not the builders. um making tickets. And this is what in you know uh in the in the cruel picture is the paper shredder. In in the shape up world you have A single Idea.

1:05:31 That was shaped. This is the thing we shaped. Right. With the two months in the agenda view and da. Go make your own tasks. Because you're the professionals.

1:05:42 You know what I mean? So like The contractors, you know, like if you're building a house, like they have to know the plans. But you don't have to tell them, now take the hammer and go over here, you know? Uh that's their expertise.

1:05:53 Right. So in a shape up world a kickoff is uh Here's the well shaped idea, and now this time box starts. And um at in at Basecamp it was It was really, really loose.

1:06:06 Because I mean they are just stocked with senior people. I mean they have. So many very senior engineers. And all the designers are coding, they're very technical, really, really skilled people.

1:06:18 And um what I found is helpful when the team is a little bit more mixed. If they're not all super senior. is a simple exercise of at kick off Take whatever was shaped. And just draw a grid with nine boxes.

1:06:32 And Give me nine boxes of the nine major chunks that you think have to get implemented. From an implementation standpoint. So like Translate this. into nine major scopes of implementation that need to somehow happen over the time box.

1:06:46 It's a really, really useful exercise to uh to kick things off. And we have a lot of teams doing that now. You know, if you take six weeks That's like uh thirty business days. You divide that by nine, it's like Kinda like four days. Per box.

1:07:00 You know? So you're gonna get a lot of clarity. From a quick exercise. And again, this is done by the builders. This is a really also good exercise for them to Notice like oh

1:07:12 Wait a minute. We think there's too much scope here, even though it seemed reasonable. When we put it into nine boxes, it's like oi, you know? I don't think we can do this all. Or it's also a good moment where Somebody who's more junior might kind of describe their implementation approach.

1:07:27 And then someone who's senior can review that and say, Actually You know, we've done that before and we'll run into this trouble if we don't use this other thing. You know? So those kind of really nice kind of coaching moments can happen. Got so this is like if you were to try this approach and have a shaping session. This is a sign you're heading in a good direction is af if the output

1:07:46 The team that's building it can Nine. And is it like more like does it have to be nine? Is it like six school? Ten cool.

1:07:55 Uh what I found is um If If it's uh if it's more than ten then you just get into ticket land of here's a million things I have to do. You know what I mean?

1:08:05 If you have a hundred things, it's like that doesn't tell me anything. But if it has to be nine or less Okay. Uh I I actually think I I actually think I'm I'm s I'm speculating here, but you know, the UX designers in your audience will know about this rule of seven plus or minus two. It's this cognitive science principle that was found about how many things someone can hold in their head at once. Yeah.

1:08:27 And uh So this nine is the upper limit of seven plus or minus two. And it basically, you know, it's kind of like, do we actually have a picture of what it means to build this that we can also hold in our heads? Can we kind of see the whole castle? So what I'm hearing is like if you're on a say agile scrum team today, if you want to start trying this out. It's schedule a shaping session.

1:08:48 Assume it's six weeks to start. Try to get into uh come into it with a framing of like here's the problem we're trying to solve. Is that a good way to think about it? Like the problem we're trying to solve? Yeah, for sure. The question is what problem are we trying to solve, you know? Because the shaping work is more what are our options for the solution.

1:09:06 You know? And if the problem is too fuzzy and big, if the problem is just calendar, you know, then the shaping is gonna be this ever expanding, never ending thing, and we're not gonna be able to get anywhere. Yeah. Okay. So you you spend like three hours, maybe six hours Uh like in the first session, would you recommend like try to keep it to this many hours when you're first trying it out? Yeah.

1:09:26 No, I wouldn't do that. You know, um I think um The the the key thing Is actually If you get to the point where you're trying to hold a shaping session and you manage to get product and engineering into the same room to do it.

1:09:39 You are far along. You're doing great. If you're at that point, you know? Al so much of the challenge. Is getting to the point.

1:09:50 Uh kind of a lining between product and engineering. Yeah. We cannot keep We cannot have projects that are dragging and dragging and dragging.

1:09:59 We can't keep ending in a place where like we're this is the end of a sprint or the end of a cycle and we still can't see the end of it, you know? Or We have to make so many cuts and and and compromises at the last minute. that it's not the quality of or it's it's not really matching what it was supposed to be in the first place.

1:10:17 When those problems are happening or you know Also, by the way, this is surfacing at the exec level. Imagine, you know. You're the CPO, you're the CTO. And you're supposed to be

1:10:27 answering to uh how's that how's that work going, right? And it's like well Mm-hmm. Actually, you know, we're working on it. I mean oh. Like

1:10:37 I can I can I can just think of couple of times when I needed to go to Jason and and and And he expected me to be making progress on something and I had gotten nowhere on it, you know? And that feeling, you know, when you're with top leadership in the room and you don't have a good answer for where you are on something is like, oh, it's it's brutal, right? And then from the CEO's perspective, it's like Where's the movement? We're running a business here. Like really nothing is

1:11:00 Shipping still. You know? This is like this can't just keep happening, you know? So there's some recognition somewhere, either at the top higher levels or within the team, you know. of like

1:11:13 We don't wanna keep dragging, we don't wanna keep being lost in the weeds. And then This Can B the

1:11:19 you know, like the activation energy, like you gather the power to be like, okay, we actually want to try something different. And in that case what I would say is What usually works best is okay, we're gonna try a pilot project. And what we want to do is as you said kind of Choose a problem that's important enough to all of us that we think it's meaningful, it's gonna be worth

1:11:40 You know, trying to do well. And it doesn't have to be six weeks. It could be something that is a little bit smaller, maybe you feel comfortable taking on a three week thing for the first time. What's important is just matching matching these things together, right? Here's a problem that we actually care about.

1:11:58 It's timely. Something that we would like to be s shipped soon. It's not so small that we're not gonna actually learn this new muscle. You know? Uh, and it's big enough that it's gonna feel like we really achieved something.

1:12:10 Right. So maybe that's gonna be four weeks, maybe it's gonna be six, maybe it's three, I don't know. And then Kind of Getting to a place where we have Uh uh we we wrestle a bit with the problem to get the problem narrowed down, we get into our shaping session.

1:12:25 And then We do our best. Do you know what I mean? And usually what happens too is If we have an engineering team that's gonna become free To do this work.

1:12:35 For those X number of weeks. That's the upper limit on how long we can spend to shape. Right. And that's another kind of like real life thing is sometimes we talk about like, you know Uh you know. Like if

1:12:49 If On the one hand there's this universe of kind of never ending documents back and forth to get fight feedback and comments, you know? And then on the other hand, there's like the team is gonna be available. We're trying to actually do this, so Actually, we've got a week to shape'cause engineering needs to kick off next week.

1:13:07 You know what I mean? That's kind of a little bit more the real scenario when you're actually in this aligned world of like we want to We want to ship something now. Yeah, real life constraints. That's a really helpful way of telling you how much time you have to do this. For people that are just like

1:13:23 This is like like I don't know any friends that are using this. It's like weird. this way of working. Like it's not a thing I hear about all the time. Uh What can you say to them to help them be like, Okay, I should actually give this a try? Here's like How many people are using it, here's impact that you've seen, anything you can share there to help them get over that home.

1:13:40 I would say um Wait until it hurts more. You know? If if if if if the unfamiliarity is kind of the big problem with it, you know, then then maybe the things are fine.

1:13:56 I mean because it's not like this is the only way. Uh It's more like um I mean changing is really hard. You know?

1:14:04 And um If there's a good reason to do it. And It's like look, we've we've done it the old way. We've tried different experiments.

1:14:11 You know, we've even already churned through a new head of product or we've got a different CTO in, you know, and we're still having the same problems. Then there comes a point where it's like Like I know that this is uncomfortable and I Don't know somebody who's done it, but You know, like I think we need to try something different because we can't continue this way.

1:14:30 That is a great answer. Following that same thread. Just what are signs that It's time to try something like what sort of pain do you often see that's like, okay, this is Well you shouldn't look into this, seriously.

1:14:43 Інодер пан. All along the journey. So I mean I think um the the the place where it's most obvious is at the end of the line. When We thought we were gonna be done and this thing is just dragging and dragging and dragging, right? Like the teams like we're not shipping things, we're running in place, we keep going in circles on this, like

1:15:05 We don't see the end. Of course, that's kind of like the culmination. You know? But there's also a lot of pain points along the way. So there's If we go all the way upstream. You know, there's

1:15:17 If we go to the source of a project, right? Sales talk to a customer. You know what I mean? Or sales talk to a lead and we and and want us uh they have this idea of this thing we need to build, right? Or The CEO had this idea in the shower the other day.

1:15:30 Or the product team did a whole bunch of research and they have a big case for why this is the thing that's important to build next. Whatever it is, there's there's a there's a source, right? For the From the business perspective of like this is the thing we should do next. If it's If if we just say dashboard and we don't negotiate what that means, if we just say calendar and we don't negotiate like What that actually is.

1:15:52 Then Uh what do we experience this kind of Fuzzy Faz thing where, you know, like it it's really hard to get to a conclusive answer about like

1:16:04 Yeah, that's what we need to go do. You know? It's kind of like the ever expanding Blob. You know?

1:16:10 So if we've if you've felt that before, that's already a a first pain. And then of course, where does it go from there? So we say calendar. So we don't know what it means, but we say calendar. So now we give it to product and We've either got A whole bunch of Figma files, or we have the PRD with a million requirements about what a great calendar is, you know? And

1:16:31 Of course, I you know, I don't want to be cruel to the people who are putting their hearts into that work'cause the figma file is beautiful. You know? It's just coming a little early. Right.

1:16:40 And the PRD is full of A lot of true things that are probably really important. for decision making in the project. But the way that it's packaged at that moment. Isn't something that gets absorbed.

1:16:53 You know, I mean you write this document and who I mean who actually I'm sorry, like who actually reads it. You know what I mean? Like and I know it's painful, but it's like that, you know? And then even when we Try to read it.

1:17:06 Because it wasn't shaped and we didn't get down to it's this, it's that, it's that, and that's how it works. It's hard to It's hard to walk away from reading that and kind of have anything that's in your head, you know? as like this is what we're gonna go build. It's kind of like a million puzzle pieces that you're gonna have to solve.

1:17:24 Right. So What we see is Either You know, there's the figma file and then there's the pushback from engineers, you know?

1:17:32 There's the There's the um the PRD, but then it's like okay, but we still don't actually know what to build. There's kind of all those things where instead of moving forward, there's like more and more questions, more and more pushback, more and more going back to the drawing board. So that's another kind of big indicator that something is going wrong.

1:17:50 And then uh and then when we're in the building And we thought we knew what we agreed to. We thought we all said, Yeah, this is what we want to go make. And it's just more and more questions coming out, you know, more and more unexpected complexity, things that we didn't anticipate. You know, and it's just it just doesn't feel like we're getting warmer and And coming closer, it just feels like it's getting harder and harder, you know? Those are all

1:18:14 Those are all the signs that like Whatever process you use, you know, that there's a lack of There's a lack of cleaping and there's a lack of clear framing because there's a lack of clarity, right, around what it is that we're doing. Before we started recording, you made this interesting point that there's all this talk of feature factories. And that uh rarely are they actually like efficient factories. Like they don't actually

1:18:35 Work. Yeah. Talk about that. Yeah, well I I understand what the feature factory critique is supposed to be. Uh it's actually to the framing point. Of um we're not negotiating the value and the outcome we're trying to get from something. We're just kind of taking it and building it, you know?

1:18:53 And then of course in the end uh according to the feature factory critique. We just built it because somebody said we should build it and then people didn't use it and didn't value it and the product is just getting bloated, right? The thing is that like I would say if you have a feature factory, meaning you're continually cranking out features.

1:19:10 You're probably quite healthy. All you need to do is feed a different input to the beginning of the factory. Right. U what most teams are struggling with is that they can't they can't they don't have predictable repeatable shipping of things, you know. I I mean at least from my experience

1:19:27 The bigger really widespread struggle is like stuff isn't moving. It's dragging, I can't see the end. I'm losing my Like I'm feeling burned out. You know what I mean? Like it's not exciting to work on this anymore, like all that kind of a thing. Maybe last question here is what's what's kinda like the sweet spot stage for a company to

1:19:45 I know you basically worked. in this way from the very beginning when it was just three people. What do you find? Is like should startups that are just starting out start working this way? Or do you find it's more useful later on? We didn't formalize it until we had to.

1:20:00 And there was a long time where there wasn't a fixed length for projects, there was just an understanding of the urgency. And kind of a feeling of what too long felt like. You know? And it didn't actually click into Oh, this is a cycle length and this is six weeks, and then we pause and this is how this is who comes together to make the decision of like what's the next project and here's

1:20:22 who is mainly doing the shape, you know what I mean? Like all that stuff didn't get solved. Until we had reached a certain size. Usually the main tipping point if we start from smaller to big Is You know, there's a phase when the founders are still involved in everything.

1:20:36 And so it doesn't matter what your process is, it's gonna be fine. But then you start to hire the first other people. And then for the first time you try to delegate some of those things and the founders try to be less involved. And that's often where a lot of these problems start to appear. And the founders start to ask themselves like

1:20:54 We used to be fast. And now we hired people. Because we needed to scale, but now we're slow. You know? So like

1:21:01 How will we be fast again? 'Cause we know what it's like. If we if we just got back in there as founders And you know, got our hands dirty, like we could make this go, but how do I get How do I get these like the people that we've brought in To make these

1:21:16 make these trade offs and make these decisions and how do I get the work to flow again, you know? So that's something that we definitely see there. So that's a really good moment. I'm onboarding new people. I don't know what to tell them how to work. I don't want to introduce a bunch of scrum rituals. Just winging it on Kanban isn't working because they don't have enough clarity around what to go after. So I have to babysit them all the time. You know what I mean? Like

1:21:39 These kinds of things. There is another extreme. Which is um Alright. We've already gone past that.

1:21:48 You know, we've been scrum or whatever for years. You know? Um The the company Has been growing.

1:21:57 Like revenue is coming in, like sales is doing their job, like things are running. But man, nothing is getting out the door. And we're years in. And we have an entrenched Development.

1:22:09 We have like an entrenched engineering team, which is a wall away from an entrenched kind of product team and everybody's apart and this thing is like we're like stuck. And and that is more where There's going to be some tensions that are starting to appear at the executive level. There's going to be some finger pointing. There's going to be some like, why isn't this moving? Why isn't this happening? How can we be spending so much money and all these engineers and we're not like don't have anything to show for it, you know?

1:22:34 And that's a point where uh There can be kind of a Mm. So hard some hard conversations need to start happening about How do we actually start to negotiate around how we spend time.

1:22:46 And we can't just have endless refactorings and infrastructure projects, but We need to be actually building things. They had. That we can sell again. What an idea. Yeah, you know, but it it can

1:22:58 You know, there are a lot of um Kind of uh. Engineering orgs that have been standing around for a while, you know, and it's all refactoring all day and tech debt and stuff like that. And There's reasons why all those things Got there.

1:23:11 But there comes a point where we have to figure out how to cut through it and make some hard choices so that we can carve out time to To build the stuff that's actually going to to be needle moving again and not just sustaining us where we are to like run in place. I imagine this ladder bucket is who you mostly work with, the kind of companies that bring you in. Actually it's been so far a lot of the

1:23:32 It's been a lot of the folks who still remember what it was like to be fast. And they're kind of newly Too big. And they don't like being slow. I've had a lot of that.

1:23:43 I actually think that there is I think that your intuition is right. that the the market for the last category is the biggest. But um It's hard it's hard to reach them. Uh it's it's not easy to talk about these things. These are sensitive topics. Do you know what I mean? Like

1:23:58 Our engineering team isn't shipping, you know? And like it's like the and it's happening at leadership level. There's a ton of complaints happening. Deeper in the org. But none of nobody down in the org can change anything. At at the end of the day, it's actually the interface at the executive level of being able to say

1:24:14 How are we using our time? Like we we have to change something. To make it even more concrete in that first bucket, what's like the size of org that you find is most in you to this is like how many engineers or is it like when they hire their first PM? Like what's kind of the I sometimes have the like, how the heck do I hire the first PM and what do they do conversation, you know? But um usually it's later than that. It's after they hired the first PM.

1:24:38 After they hired the second PM. And maybe even the third, you know. And they're kinda getting to like the product and engineering together are like thirty, fifty people, you know? And it's like we we thought we put everybody in the right roles. We kinda did what we were supposed to do and everything is just grinding and like why are we so slow? Perfect. So

1:24:58 Thirty to fifty ish people. Seems like a good time to that's probably like like basically you're finding that's when things start to really break down. That's when they show themselves, you know. And I think uh I mean if if someone kind of hears this and it all starts to make sense and they're earlier in that wave, then of course the earlier that you can anticipate it the better. Right. Yeah, that's a good point. I I I I mainly hear about it when it's too late. You know, that's why they're reaching out. Got it. So maybe closer to thirty. Okay. But I think uh I I really think it I honestly I think it starts the first project.

1:25:29 Where For example, the the founding engineers hands off and then the the new hire is is taking over responsibility or the the the the the person who was like sort of founder slash CEO

1:25:41 is like first giving it to a PM. To kind of Thinking they're gonna carry it through, you know? And then it's not exactly meeting their expectations of what they thought was going to happen. You know, I think that's when those disconnects actually start. It's it's the first. Step away from the work.

1:25:56 Where the seeds of all of these problems actually start. I wanna talk about Basecamp and how Maybe not every company can operate like Basecamp. Before we get there, is there anything else along the lines of shape of the

1:26:08 That you wanna add or share Yeah. Um which is um The role of the PM. I think what we see today out of necessity in a lot of teams is that the PMs spend a lot of time Um kind of chasing around inside of the build.

1:26:27 phase inside the time box to Try and make sure that, you know, people aren't stuck and and getting lost in the weeds and try and keep things moving, you know? And um Yeah. can sometimes be too close to project management rather than product management, you know?

1:26:43 And what we see in Really And shape up teams when they hit their stride. Is that the PM moves? Upstream.

1:26:52 So the PM is less busy. with how do I get this project to like Not be in a bad state when it's getting built. And they're way more in How do I understand the the the business context? How do I narrow down the problem?

1:27:06 How do I negotiate back and forth with maybe the CPO who kind of brought this to me to understand where the core of it is. That That really getting Deeper understanding.

1:27:18 of the business and the problem and the customer domain. And like what problem is worth solving, and what's even slice of that problem. is the valuable slice to to argue that we should spend a few weeks on, you know. that's the place where the PMs can really contribute a lot in in the shape up world. They're that's kind of what they do rather than shepherding the process or being a ritual master or something like that.

1:27:42 That sounds pretty wonderful. Uh, I've been doing some thinking about what a world an AI oriented world does to the role of PM and it feels like very similar to that actually. Where the building now is going to happen for you with AI tooling.

1:27:57 And that means The bigger question now is like what the hell should I build? And is the thing I've built. Right and correct and likely to work. And it feels like this is similar. It's like the PM spending a lot more time up front.

1:28:10 Thinking through what to build. And then the building is more a lot more hands off. So hands off it gets done in like five minutes when you're just like well, build this thing for me, but there it is. Yeah, let's see. Let's see. Yeah. I'm I'm I'm also very curious. Yeah. Oh man, what a wild time. Okay, let's talk about base camp.

1:28:28 Uh I think We talked about this ahead of the podcast. Yeah. You want people to know that it's Uh Basecamp is very unique and not everyone can work.

1:28:38 The way base camp works. Just talk about your insight there and advice there when people see all this advice coming out of base camp. I gotta tell you, I had no idea how unique we were until I was outside. And There are so many things, for example, it's a lot of the things that people asked me about.

1:28:54 That are kind of not in the book. that started to reveal those things to me. You know, that's so many things that I was just taking for granted. I mean Every designer. Codes. Imagine if every designer codes

1:29:07 And not and I don't just mean HTML. I mean like running the app locally. Going into the place where that view is rendered. to make that thing look the way that they want it to look or or whatever, right? I mean like really codes. Every designer.

1:29:22 So every designer codes. Where's the wall between design and engineering? Where is that? Where's the moment where you arrive with the Figma file and then all of your you like the disappointment and all of the your hopes get destroyed because the engineers tell you no, right? Like those moments don't even exist.

1:29:40 Right. In that world. And then also, uh I think also there was this Lack Oh.

1:29:47 Distance between sort of the business objective, the thing that we're trying to the reason we want to maybe do this project. And the blessing of the founders And the Like there wasn't this kind of

1:30:00 You know, executives far away. With some big targets. And then some layer of PM and then some building. I mean the founders were always there right there in the problem definition.

1:30:13 Still. I mean, I can't say today, but I mean up until twenty twenty one when I was still there. You know? So it meant that there was so much clarity. All the time.

1:30:23 around what we're solving and why and why we're making time for it. And then of course on the engineering side as well. I mean imagine you have no sales org. You have no marketing. Yeah.

1:30:35 All of sale sale selling and marketing is happening by the unicorn founders. So it means that there isn't contention for engineering time. that there isn't kind of like all these different uh sources of requests that you have to wrestle with, you know. And David did such an extraordinary job. Oh.

1:30:54 I mін the more I see the world world, the more I'm amazed. And how Every six weeks. There was Clear runway.

1:31:03 In engineering of like we have time. Or whatever the whatever we agree together is the most important thing. Just blank check, like six weeks at a time. Yeah, not a blank check, but you know what I mean? Like a blank six weeks. Yeah. Uh again and again and again. Years without end, you know? Keeping that

1:31:21 engineering capacity focused on readiness for product, you know, and and totally leaning into like what's exciting to do. to build for the product. and not getting lost in all this refactoring and new infrastructure and technical dad and stuff like that. I mean that's those are amazing. So

1:31:39 Those are some really big differences and um it doesn't mean that you have to be basecamp to do shape up. But what it does mean Is that when we say, Oh, just have a shaping session and if you have the the pressure of the time box, then you can make trade offs together. It's like well if if if we are used to having a big wall between

1:31:56 For example, engineering and design. Then we're gonna have to learn uh somebody who wants to start shaping is gonna have to learn like well oh I need to figure out kind of Who to bring together. And how to have that session.

1:32:09 And how do we interact with each other? So that we're combining all of that Knowledge that Maybe at base camp was all in the same head in a lot of cases. This is such an important point for people to hear because there's so many people that come on podcasts like this and share here's how here's how to do it.

1:32:25 Based on their experience. And there's so many just uh Assumptions about their resources, the people they hire, the way the founders operate. Like no sales team, I think. That's like I don't even think about that.

1:32:35 Yeah, imagine you never no such thing as a request from sales. Yeah. No such thing as pressure of like we need this thing in order to upsell. Right. Or to close this deal. Never.

1:32:46 It sounds like you're kind of in this like base camp. By the way, was it called thirty seven signals? Like it's interesting to call Basecamp, not thirty seven signals. Yeah. I mean, so uh it's just like uh the timing of when I left, you know? We were originally thirty seven signals and then base camp became so big that we renamed ourselves to base camp. I didn't know that. Yeah. And then so for example, like on the book You know, on the it's it says shape up and there's a base camp logo on the bottom, not a thirty seven singles logo, you know. But then they since uh went back. Uh uh so it's thirty seven singles again. So I sometimes struggle with I don't know what to call it, you know, but it's both. Whatever whatever people can recognize, it's the same, you know. It's the same powerhouse. Okay, cool. I'm glad I'm not the only one that's confused. But thirty seven signal is the current name. Great. Yeah.

1:33:30 So you said that it kinda felt like you left and it was like this bubble you got out of it. What was was there like a moment where you're like You wrote this book, everyone you're like, Hey, this is how you should work and then you're like, Oh wait, and this doesn't actually work in real life for a lot of people. Is there a moment there? It wasn't that this doesn't work.

1:33:46 I was just in it. It's like a foreign country. You know? It was like um We tried it.

1:33:53 And it didn't work? You know? One of the common things I would hear is um The projects kept running over. You know, we weren't finishing them at the end of the cycle, they kept running over and running over.

1:34:03 And then I would be like Huh. So can you show me your shaping work? And then they would show me a PRD. I feel like

1:34:12 Like, well that's not that doesn't look like what's in the book. And then uh and then I would they they and again, like can you show me your shaping work? And they'd show me like a bunch of Figmaphiles, you know? And then and then I what I started to understand was like Mm-hmm. We have some people in a role who were used to making a certain artifact at a certain step and they just kind of kept doing that, you know?

1:34:32 And um I didn't appreciate It took me a while to realize like there's no engineer in the picture here. And uh And it was when we started to actually do the course.

1:34:44 I well I I did actually a couple projects where I helped teams hands on. And I learned that they they it was the first actually consulting project I did where I helped a team who was stuck. And what we did was we we we chose the engineer who was best suited. Two

1:35:01 come over to product and be there in the shaping. And that was the moment when it was like ah Now I'm in the world I know again. When we when we had all of that mixed in the same room again. And so that was kind of like

1:35:15 That was really something I mean, it was a total learning curve for me. You know, and there's a lot of things like that, but that was, for example, a really big one. It's like, Oh, we have to get engineering in there. You're the type of guest I most love having on this podcast because you basically Work with many, many companies, study what's working, what's not. You're like in You're not like in the clouds pontificating about something and

1:35:36 You're like Working with teams to make things better. And then you take all of that learning, put it into a book. And share with us all. And so the ROI is just incredible for us all. Cause you've spent so much time doing this and you've actually done the work. You're not just In theory.

1:35:51 About it. So So this was amazing. Uh but we're not done yet. Uh one question I wanted to ask is Jason was tweeting that there's he's working on a neck a follow up

1:36:02 Shape up book, what's happening there? Are you involved in that? What's the story? So I also saw the tweet. And uh I have to admit I was a little surprised when I saw this tweet, you know? But I had had a conversation with Jason a year earlier.

1:36:16 And uh he reached out and he said, Hey, you know, we're thinking about doing a second edition of the book. And My first reaction I mean, I was imagined I was actually really in the middle of Learning.

1:36:28 You know, all these things. That Teams need to learn in order to kind of catch up to what was natural for Basecamp to do. And uh So

1:36:37 For me it was like Interesting. I have a lot of new things. I have a lot of new ideas. Maybe a sec collaborating on the second edition could make sense. But what I understood was that what he wanted to do was to kind of make an updated version of how of how they work. Because that's always been kind of a big thing of how

1:36:56 I have to should I use the right name, thirty seven signals. of how they how they market and also how they lead. Is They like to really show a clear example. Not like this is how you could do it, this is how some people do it, but like this is how we do it.

1:37:09 And I think it's their strength that they are very, very clear like this is how we do it and kind of take it or leave it. What I understood was that If I did another version of the book that was just kind of how Basecamp does it. I think it would leave so much opportunity on the table. Like there's so many people. Where what they need to learn is more like how can it come closer to where I am?

1:37:30 If I have the wall today. Between product and engineering. How do I bring the right people together into a shaping session? How do we actually do that? How do I overcome all of these little challenges because this is so far from our current way of working, you know? So

1:37:45 the work that I'm doing with for example with shaping in real life Is kind of all about those gaps. And then I don't know what's gonna be in the second edition, you know, because they are uh I I guess someone there is gonna be working on that. But what I'm guessing is it's gonna be an update on

1:37:59 You know, kind of up on top of the mountain over here. This is this is what Base Camp is doing. So hopefully it'll be kind of a cool thing to look at as like here's a model. Uh What they're doing. And then the question is, what can I take from that and what do I need in order to actually be able to make it work?

1:38:16 in the real situation I'm in. You know? And that's kind of where Well, that's my focus. This is so interesting. Thank you for sharing. Sounds like a fork fork he forked it and uh and these go going potentially in different directions, but inspired by each other.

1:38:29 Mm-hmm, totally. So interesting. Ryan, is there anything else that You want to share it? Before we

1:38:36 Wrap up. One thing I could throw out there is um Sometimes people reach out to me because They're Projects aren't shipping, there's a lot of struggle, there's a lot of lack of clarity.

1:38:48 But the root cause is actually that the input at the very beginning of the process. is too unclear or You know, like we we don't actually know what's important to customers, or we're not actually sure where the value is, or this kind of a thing, you know, so there is this link. This framing stuff that we talked about of what is really the problem.

1:39:09 Before we go into shaping. This this is the link to product strategy also. And this is the place where uh it can be really useful to reach for a lot of, for example, Bob Mesta's stuff with the jobs to be done and the demand side work. Of tr trying to get clear about things. So that's the tool that I reach for at that phase.

1:39:28 And you can think of kind of this You know, before the problem definition, there's this question of like what's the demand. Where are people struggling? Where is really the the the place the itch they're trying to scratch, you know?

1:39:42 And then a lot of the shape up stuff is kind of When I have something where I think there's an opportunity or I think there's something meaningful there because of what we learned from customers or the job to be done research or whatever it was. Now, how do I turn that into something that we can actually go do and ship in a reasonable amount of time? That's kind of the supply side. that's where the shape up part fits in. So maybe it just might be cool for people to sort of see a link there.

1:40:06 That's a great uh Plug for our f Bob Mest episode. We talked in depth about the jobs to be done framework and how to actually apply it. What's the book you'd recommend there? Sounds like basically it's like Shape up plus Uh, this book gives you a lot.

1:40:19 Actually the one that I recommend the most is uh Demand Side Sales One O One. And it's funny because it's like sales. You know, especially for a product person. Like you're you're like I I'm the product person, not the salesperson. But it's It's uh it's such a good dive into what are people really trying to solve and and getting into that mindset of what's the struggle, what's the problem. I think that's a really good entry point for that. Yeah, I don't love that title. I feel like

1:40:45 feel like you could have m done better there with that book's title. 'Cause they think that's the right. You know, what's what's interesting about it is that it's very, very Pointy. For like if you are trying to make progress on sales.

1:40:58 Then it's this other kind of sales, this demand side sales, you know? So I think maybe it's more for us who are kind of using it for different purposes. Like we're the product people trying to pull something out of it that it's a little bit less aligned, but it's It's still useful. Yeah, but basically it's like the the jobs to be done book. Yeah, it's kinda like the Jobs to be done book that's a bit more tactical.

1:41:17 You know? If if if you're really curious about the general spirit of jobs to be done, then competing against luck is a really good intro. That's the one that Clayton Chris uh Clay Christensen wrote. Uh with a lot of uh uh uh I think I think I think there's a lot of stuff. That Bob worked on that's in there. But uh

1:41:35 But for a little bit more tactical of like what's it look like to do the interview and how to think about the struggling moment and stuff like that, this demand side sales is good for this strategy stuff. Awesome. And we'll also link to his episode where you could get The gist of it in one hour's time. Oh, that's right. You did that that episode was great, by the way. That's Yeah. Thanks, Ryan. Okay.

1:41:54 We did it. This was amazing. I think this is gonna help so many people. We got through it. Uh we're not we're not done yet. Two final questions for you. Where can folks find the book, find you if they want to work with you, anything else that you want to share? And how can listeners be useful to you? Well they can find me at my website. That's RyanSinger.co. I'm also on on X RJS. I'm on LinkedIn, you know, so just reach me there.

1:42:17 And uh How can people be useful to me? I love Hearing from people who are having these problems. You know?

1:42:24 Like if you're having these problems where it's like things are dragging or we can't see the end and we're not getting the quality we need and you know, all this stuff, like Man, uh, this is I mean, this is how I learn all this stuff is by talking to people who are in it, you know? So You know, even if it's not clear What's the next step yet? You know, if that problem is real, it would be cool to hear about it. I'd love to chat. Be careful what you wish for. Bob Mesta was just on the podcast and he

1:42:49 Uh told me he's got over a hundred LinkedIn DMs with people. Sharing their struggles with their job search. So here you go. Oh yeah, but job moves, that's a big one, you know. I think that's a broad appeal. Yeah. Yeah, that's true. Uh yeah. I'm gonna ask you to Explain the when you do consulting work, just like how does that work? Who's that for? Just'cause I know that's something else you do.

1:43:10 So it basically starts with Uh either s often first CPO or CTO often reaches out first, you know. And uh what I'm what when it works well is when we actually get them together. You know. And then they understand that they need to change something, or we have like a head of product and a head of engineering, that kind of a thing.

1:43:27 If those two are both seeing eye to eye that there's a problem. then we can start a conversation around, okay, so who would be the right people for a pilot team. What are the things that are going on business wise that could be a good pilot project? And then I can kind of helped figure out like

1:43:43 How do we actually n sort almost like guiding through like narrowing down that pilot project framing so that so that they have the support that it's gonna be successful in shaping, you know? And then coaching the team so that they actually learn those shaping skills so that they can get through a session and come out with Much more clarity. Like how do they actually run those sessions, you know? So it's kind of first working with leadership. Who do we need to get to

1:44:07 do this work, who are the right people, how do we bring them into a pilot project? narrowing down doing some framing work on the pilot so it's going to be clearer in the shaping and then giving some guidance on how to get through that shaping with some feedback rounds. This this is usually a good approach. Amazing. And they can find us on your website if they want to explore this. Yes. I'm easy. Ryan.

1:44:27 Thank you so much for being here. Yeah, thanks a lot. You had amazing questions. You know, it's a subject that can go in so many directions and you kept bringing us on to Some kind of a main track, so I'm really pleased. It was really nice. Thanks a lot. Do my best. Yeah. Thanks, Ryan. And bye, everyone.

1:44:45 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 Lenny's podcast dot com. See you in the next episode.

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