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

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 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 going to go the other way around and we're going to 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. and through his experience of building Basecamp and his 17 years of building products at 37signals, 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. I've noticed more and more teams adopting the Shape Up 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 going to give you everything you need to give Shape Up 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. Also, if you become a paid subscriber of my newsletter, you get an entire year free of Perplexity Pro, Notion, Superhuman, Linear and Granola. Check it out at Lenny's newsletter.com with.

That, I bring you Ryan Singer.

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Yeah, 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, 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. It 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 in Shape Up, the stuff that you talk about. So I am really excited to basically help people understand what is this way of working? 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 in product teams that people often don't like to hear. So first of all, just do you have you also seen this increased interest in Shape Up?

Yeah, I think it's interesting that we're talking now. You know, I mean, the book came out in 2019 and it's just I've been hearing more and more like, oh, we know somebody who's trying it or we're hearing it when we go talk to other companies, you know, like, so I think it's a wave that's slowly building. And it's funny, you know, like, When it came out, I even tried to have like an online forum to get everyone 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 shipping, especially, you know, CPOs and CTOs don't like to go on 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, it's not an easy community topic 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 a time things didn't go well. Oh, yeah, that's great. Yeah, because it's so hard to get to that. Right. And it's not all just this golden path, Rosie, 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 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, there is a lot of struggle.

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 never do waterfall. And then there's like the startup way of just like ship and maybe one or two week cycles, and then there's Shape Up. So it feels like it's one of the rare other options 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 think it's always been connected to Basecamp. We're gonna talk about that. Just like it works for companies that are nothing like Basecamp. Maybe just touch on that briefly.

Well, I mean, that came as a surprise to me. I mean, when I wrote the book, I had been in Base Camp at that time, I think 15 years, and I actually didn't even know the outside world. I mean, it was Jason's idea to even write the book, 'cause he said, Look, a lot of people are gonna wanna know about this. A lot of people are struggling, and I'm kind of like, well, okay, 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. So I knew our internal struggles, but I honestly didn't know anything about the outside world. And it was only after the book came out 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 Basecamp, like VC funded, significantly bigger, very different pressures, different team structure, different skills who are doing it. And at the same time, there's 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 A lot of my focus today is actually closing those gaps and helping people figure out how can I make this work for me or for our team.

You specifically told me you use now call instead of Shape Up, it's Shape Up in real life or Shape Up for real life.

Yeah, well, my wife heard me saying the same thing over and over again on every phone call. She's overhearing me and she's like, you have to make a course, you have to do something. You're always saying the same thing. This led to this 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 if my designers don't code? If, you know, if I have actually, 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 can you just give like a very short overarching summary of how Shape Up is different from how other product approaches are?

I think the way it's different starts with kind of how the way we were working was a little bit different. So I started working with Jason and David on the first version of Basecamp, you know, which was like the flagship product of 37signals back in 2003. And we were a team of three. And we were, I mean, I think it's 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 kind of happens organically because you're together, you don't have to explain it to other people. It just kind of happens on its own. But there was always this really intense urgency from both Jason and David, like, we've got to get to something we can ship. We have to finish this and move on. We have to get to something that's done. There was just no tolerance for big things that got fuzzy and started to drag. There was always this sharpening to get to what is this thing really and when are we going to get to the end soon? And on top of that, even when we were building V1, David wasn't actually full time as our only technical person. He was programming 10 hours a week. So we had this really intense pressure of like, how can we really use David's time well? We don't want to ever kind of give something that this is the thing we want to build, and then it turns out not to be what we want. We have to throw it away and then come back again. Or, you know what I mean? Like those kind of Bad cycles of waste.

Let me actually ask about this, because this is really interesting. So this is DHH. He was working part-time when he started 37signals.

10 hours a week.

Yeah. Was he working on Ruby, basically, and that whole thing?

Well, Rails came out of the first... So he told Jason, I want to try building this in Ruby. Because before they had done some collaboration and David had done things in PHP before that, And he had this new idea he wanted to try Ruby, this language he fell in love with. And then, you know, the framework Ruby on Rails, he ended up releasing that after Basecamp was standing, because it was kind of extracted from the things that were necessary to get V1 of Basecamp to stand up.

So that's what he was doing the.

Rest of his time instead of- I don't know what he was doing the.

Rest of his time, you know?

Probably something great. But 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? But all I knew was that we got 10 hours 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 together. So David's constraint of 10 hours 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 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. 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 get into something that we can celebrate and get excited about?

I love that. That's an attribute, I think, of a lot of successful founders. So that makes sense to hear that.

Totally, totally. And that's why where I come back to you, like this is the part of the story where I think so many companies would say, yeah, I know that experience, right? Because I think that's probably the seedling of a lot, as you said, of successful companies, is that combination of urgency and also that those guys were so talented and that they had a clear vision of what they wanted to do and all of that is this amazing time actually these early days.

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 and I was doing hands-on coding as well. So we're very, very integrated. Everybody kind of does a little bit of everything. All of us were coding. 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 bulk of the programming. And Jason and I were having these 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, and all of a sudden you'd be like, oh yeah, that's the idea. That's the thing we want to go try to build. And for me, those sessions with Jason, they were these short, very, very intense sessions where you're trying to crack the nut together. Where's the idea? What's the concept? How can we go? What's this thing that we're going to go and 10 hours later, David's going to come back and we're going to be like, this is awesome. This thing works and it does something we're excited about. That was really the seedling. I mean, actually that continued over years and years and years, those sessions. And that's the seedling of this word in the book Shaping. What does it mean to do shaping? It wasn't sitting alone 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. It was this super intense, really exciting, collaborative, like, what about this? What about that? Oh, maybe this. So that was a really big part of how we worked also. Very intensely collaborative sessions to figure out what the idea is and getting it sharp enough and crispy enough that 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 so that we would kind of keep going and we wouldn't have to reverse or go back to the drawing board.

What it sounds like is essentially you're trying to maintain the startup way of working as the company grows. Everything you're describing is how it feels to be at a startup, and this is a method to keep that. Does that sound right?

That's exactly what became Shape Up was how do we hold onto that as much as possible. One big ingredient we had an advantage also, which was that Jason and David hired so deliberately slowly. And this is kind of a fortunate side effect of the fact that they didn't take investment money. So there was kind of, there wasn't, 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 one more person, you know? And so this, this natural way of working, it was It was organically spreading. There were, I think, maybe 10 years before we had the first kind of like, wait a minute, what just happened? Like, that's not like that project didn't go well. That's not how things normally run. You know, I mean, we really, it was, I mean, of course there were always like ups and downs, but there was, it was about 10 years later when we had the first project I mean, I remember the project. I remember being at the end of 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. And I remember we had a review session and there was a fairly new person who was leading the, 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, 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, as we're asking, and what we're starting to realize is, oh, not only is this not going to ship, but we can't even see the end of this. you know? And, and that was like one of those moments where you're like, oh, this isn't going to automatically organically just keep spreading as we hire forever. You know what I mean? We did reach a point where it's like, oh, this, we're going to have to figure out when this goes well, 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 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 kind of like three, maybe big things. 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 take a big concept and then say, what's the estimate for this thing? We're not going to say, oh, we need 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 going to go the other way around and we're going to say, what is our appetite for this? 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. At least this, if not the whole project, this meaningful piece we can literally walk away from. So then what we found was that there was a lot of experimentation. We found that six weeks is kind of the maximum that we can see into the future. 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, what can we do? What could we shape so that after that amount of time, we've gotten to somewhere we want to be? You know, it's kind of like if you're going to buy a car or you're going to you're gonna buy a house or you're gonna rent a new flat or whatever, you have to have like a budget in mind, right? And 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 want the faster engine, you know, but I can't, you know, but I have to give this up or, you know, I wanted 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 second piece is this work that we call shaping. And the shaping work is how do we actually 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 that's going to work in the amount of time that the business is interested in spending? so 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, 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. 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, this is what we want to go build. So it's not just calendar or dashboard or, you know, newsletter builder. But it's like this idea of how we're going to tackle this problem about the calendar request. Right? So that's the shaping. And then the third piece is when we've actually carved out a fixed amount of time, when we've shaped a solution that is From a experience standpoint, from a functionality standpoint, from a technical standpoint, doable and desirable something that we can make happen in that amount of time, then we can give it to a team and we don't have to do the sometimes called Scrum, the paper shredder. You know, that's where you take an idea 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 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, 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 that makes sense. And now you're going to have freedom to figure out how to actually make this a reality. There's going to 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.

One of the core elements of this that I want to confirm is that you can pick and choose these things into your team. You don't need to do this wholesale. Correct.

You don't need to do, yeah, any of it. So this is where we kind of, it helps to look at like what's going wrong and what are we trying to fix? 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 want to give the team, let's say six weeks, and I want to give the team more latitude or let's say more creative freedom that they are going to be responsible in the six weeks to figure out how to make happen, right? And usually a lot of the drive for that is, I'm getting tired of having so many meetings and rituals and things that are not actually working on the problem and doing the work, you know? I mean, especially Scrum teams, they often complain about that. So what they sometimes see in this is like, oh, I love this idea that the team is just going to be cooking for six weeks and they're not going to, you know, we're going to meet as needed and we're going to workshop things, but we're not going to be busy with all these rituals all the time, right? Now, the thing that's tricky is that if you want that reality of the team happily buzzing and humming like some happy bee colony for this six weeks, they need to have a lot more clarity around what's the thing that we're solving, right? 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 going to have the clarity that they need to take over that responsibility, you know, 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, the worst is that sometimes see cases where people are like, okay, we're doing shape up. So you guys are going to 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? because I think I'll quote Bob Nesta, who's been on your show a couple times. You can't put 10 pounds of crap in a five pound bag. So, you know, it's a high academic statement, you know, and 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 ship something meaningful in six weeks by cutting away scope. Right. So it starts, 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 going to build? 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, okay, we're going to, we estimate this little, this landing page is going to take a couple of weeks. Great. Let's work on it and then ends up being six weeks. 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. And scope is not allowed to go beyond that. Makes total sense. Like, this just makes so much sense as you listen to this, especially for people that have just fallen into the problems of estimates not being accurate. Then there's a six week element. And the key there is you're, you're, and this is kind of counter to maybe two week sprints like Scrum. Is that kind of the, where this comes from?

So, you know, actually it turns out that the six week is only a maximum. 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 what piece of this do we really think we can land? Because if you try to say, you know, in six months, we're going to 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 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 a size of something where we can actually shape it and surface enough unknowns and reveal that complexity before we're in the middle of it. It doesn't mean that we can't use this technique to do a two-week project, especially if you're on a growth team. You don't want to wait six weeks or, you know what I mean? You're going to have to artificially bundle things together to do six weeks. It's like, look, I've got something I want to 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 it's more a question of what we're trying to take on. It's really that upper limit.

Okay. So it could be a two week cycle and that- It could be a two week thing.

Cool.

So it's like we're going to build this new landing page. We're going to give it two weeks and then do a shaping session on that.

Now the other thing, the other side of that is when it comes to feature development or building something that's going to be needy enough to sell, You know, then there's very few things that are gonna be a substantial value add to a product that you can do in two weeks. Right? 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, the question is kind of, 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 are not on track to hit that, instead of extending the date you cut in order to still hit it.

This is a tricky one. So you're right that it's implied, but the thing is, in real life, if you make a commitment and you get alignment that we are going to spend six weeks of engineering time building this thing, if you get to that end of that six weeks and something is going wrong, it wasn't shaped, we can't see the end of it, it's more complicated than we thought, 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, 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 managed to ship inside of six weeks. That's going to kill everybody's morale. Everyone's going to feel disappointed. We're going to feel like, this wasn't really worthwhile. And now we go into the next cycle with this kind of like debt feeling, you know, that we didn't actually finish the thing we were kind of supposed to finish. So now we're like overtime, you know, none of that is good. And if we also go the other extreme and just say, well, like we actually we say in the book, you know, we had this principle at base camp, 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 going to cancel it. and rethink. Almost no teams have the stomach for that. But the version of that that's more stomachable is, look, we can't just cancel the project and then say, let's see what comes next. But what we can do is say, we're not going to keep reinvesting in something that we don't understand. So let's take this out of build mode and bring this back into shaping mode, which might mean different people, a different conversation, asking different questions, doing a different kind of work to suss out, what is it that's fuzzy here? What is it that we couldn't see? What do we not understand? How do we get to the clarity that we need so that we can actually say, 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 just did the scope and it's all, that's cool.

Yeah, you just cut the scope, you know?

Yeah, no problem.

I've seen some shape up adoptions that looked like that, by the way. And that's, you know, it's not the way. The shaping step is crucial. And you know what you mentioned with your landing page example, by the way, it's so seductive. because we can imagine, you know, oh, 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. But if you give me two weeks, you know, then I'll stop after two weeks. But when it comes to real product work, 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 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 and how do we identify what the moving parts are of the solution and 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, that's the place where we can say, oh, this is well shaped, you know? And that's a different kind of work. In shaping in real life, we call it, we actually teach it as doing live shaping sessions. And this was how I did it for years 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 the senior engineering person who isn't just senior in title, but the one who actually knows where the bodies are buried, how the old stuff works, and what's truly possible, and what's hard, and what's easy in our infrastructure. The person that really knows, right? You bring that person together 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 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, 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 NPM. So add anything else there. And when do they happen? Is at the end of Do you call a cycle by the way, or a sprint? That's the six-ish week period.

What I actually like is time box, actually. Because the thing is that some teams need regular cycles because they have parallel teams and they need that cadence in order to kind of reduce management overhead, 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 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, there's dependencies and timelines launch, go to market dates and all these things. What's like the largest company this this approach has worked out? Like, what's the ideal company stage for ShapeUp?

It can function in very large companies. We have, for example, I have some friends at a, what is it called? They're doing clinical trials, so they're in the pharmaceutical industry. And I mean, the company's, you know, thousands of people. 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. And it's completely possible in that context, if you have someone who's at a senior level on the engineering side, who is able to make the right architectural choices and also do some negotiating and kind of be the backstop to make sure that someone isn't gonna get pulled away onto something else, you know, you can kind of carve out this system can be worked on independently of that system. This was actually what David at Basecamp has always been 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, 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 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 going to protect this team from that other work for this number of weeks, you know, you can really get a lot done.

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 kind of like the adapter, and I want to come back to the actual shaping process, but 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 in a two week, sometimes six weeks, sometimes four week cadence. Advice on how to, like, what's the adapter that connects those two cadences?

So there's kind of two different things. So like I've seen cases where they've decided on a four week plus two week or like, so they'll do like a five week and then one week of cool down in between, and then they time it so that it adds up to a quarter. I've seen that. The other thing I've seen is when the team is just continuously delivering meaningful things, it doesn't have to line up because from the executive level, if you are CPO or CTO, or I mean, in these bigger cases, it's more like 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. And when you are consistently saying, we said we were going to do this and nothing finished, and now we're doing this and it's going to finish. And the next time you say, we said we were going to 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?

Yeah, if you're doing great, people will leave you alone. That makes sense.

For sure.

I love that point. Okay, coming back to shaping. One, maybe one way that would make it real 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 we need the contrast sometimes. So very often when people try Shape Up, what I see is, a product team kind of creating either a lot of Figma files or maybe a lot of documentation, you know, 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 when you give that to a team as like, this is what we shaped, What happens is it blows up. So, I mean, you probably know about what happens when the Figma file 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 solutioning all the way down to detail without engineering involved, usually that's a painful recipe, you know? And then it's kind of like, no, we can't do that. Actually, it doesn't work like that. 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, how do we flow from here to there? What are the different cases 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 and like study this thing to try and understand like what's happening underneath. You know, I often use this analogy of like, if you're doing a home renovation, you know, you can have like the most like a beautiful rendering of here's the new, here's the new bedroom and we're going to have these lamps on the side of the bed, you know, that are coming out from the wall. These like, you know, and you can have the perfect rendering and the perfect lamp in the perfect color. But if you haven't checked if there's electricity in that wall there or not, right? It's going to drastically change the cost and the time and everything. If you're going to have to rip open those walls to feed some lines up to those lamps, right? So what we need to do in a shaping session when it's going well is we come out with some kind of drawing or diagram where engineers, product and design are all looking at that and they're saying, we understand that. I know exactly what to go build. 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 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 in the book, there's a chapter called Setting the Boundaries where we get into this. And it's like, look, 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. 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. Then what are we actually going to build? We came to, here's a good rule of thumb. If it's shaped well, you can usually describe it in less than 10 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? That's a good indicator that it's clear enough that it's shaped well. So in this case, we had a, you know, when you go to an airline and you wanna book something, you see this like two-month grid. Right? So it's like there's gonna be two months side by side, but they're just gonna have dots in them to indicate 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 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 gonna be an agenda view that slides underneath, 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, right? And that's more or less it. So what you can see here is it's not like, what is a calendar? You know, it's not a calendar. It's a two month dot grid with scrolling and gender view underneath, right? And the ability 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 practical, realistic conversation about, is that a thing we can do in six weeks? You know, that's gonna be a real conversation and not looking at a whole bunch of mockups 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 kind of like the user experience with just like wireframes slash sketches of the screens and the key buttons and flows. So it's kind of like the architecture with key components, not like a doc of spec and not final design, and also not just like a user story. As a user, I need to be able to see empty spaces.

Exactly. So, 'cause that's the thing where it goes wrong. If we're going to commit engineering time, and it's like we believe there's some way to see empty spaces, but the way is a question mark. It's a really risky way to spend that time.

'Cause you're committing, right?

It's like, yeah, 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, 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 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 work on.

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That's really interesting. I gotta tell you, the dominant failure case that I see in the real world is always again and again, not enough detail. And it's also the most common failure mode where the engineers run back to the product folks and say, I'm not getting enough from you. It's really like that. But I can understand why the hair stands up on the back of the neck a little bit, thinking about it, because Of course, if you give a senior engineer, here's how I want you to go implement the schema for this database change for this model. They're gonna be like, what are you? Who are you? You know what I mean? But what's really interesting is it's not a universal thing. The amount of detail that the team is gonna feel 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 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 going to do this and I would suggest approaching it like this, this, this and this.

Right?

That junior person is when they don't know how to do it, they're not going to ask. because they don't want to show that they don't know. And they're going to hide the fact that they're lost and it's going to blow up later in the project. 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 give less detail and see how they handle it. Right? So you can really give people bigger shoes to grow into and help them to be successful. And then of course you can also do it the other way around where 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? But 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, then a better solution would be to actually bring them into the shaping and have them play that technical role in the shaping session. 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. It's all about 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 are able to apply the maximum creativity, 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 the risk, the biggest risks and address the biggest unknowns as much as possible. Like, there's probably this 80 of here, the risks. Let's just. understand them deeply before we commit to this appetite.

That is exactly right. There are these, 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 had a step of onboarding in a FinTech product. Okay. And there was this step of onboarding and they would lose a lot of people in the funnel at that step. 'cause you had to fill out a whole bunch of information. And they figured out that they could actually pipe that data in from one of the partners that they had 'cause 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 fix conversion, we're gonna eliminate a step from our user experience. It's gonna be great, right? You know, the thing that they didn't look at was if you go into the code on that step of the onboarding, It's not actually one step. There's like three different branches of that step, depending on which bank the customer is integrated on, 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, 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? You did all these beautiful drawings, by the way, and now you're finding this out in week four. That's a bad place to be. But if we're in the shaping room and we didn't kick this thing off yet, we didn't even greenlight the project yet, 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, 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 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 it's not like, okay, now we're screwed and the project is going to be bigger. No, 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. 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? 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, 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 are 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 on this 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, but a few questions. How long do these usually take? Is it like sounds like a whole day kind of experience? and then it sounds like you invite as few people as possible, but not too few people. What's your guidance on who should join?

So we run in this Shaping in Real Life course, we've been doing workshops where we try to help people to learn what it's like in a shaping session. And one of the things that's always interesting to me is how, so Katya and I will be running the session and we have to People aren't used to working so fast, you know, to like, what are we actually doing right now? What's the decision? Like, what's an idea? Right now, we're not gonna go away and draw something and then I'll comment on a document and then come back and get together tomorrow. What ideas do we actually have right now, like starting from zero? So imagine. Imagine, like, We've narrowed down the calendar problem too. It's about empty spaces, 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?

And that's the input to the framing session, or sorry, the shaping session.

Exactly. So that's, so 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. So now what we need to do is try out different ideas. And this is the real thing. We have to try to break them. So I want to draw an idea, and then I want the technical person to find like, oh, this isn't gonna, you know what I mean? This isn't gonna work because of this reason. Or the product person is gonna 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 one of the things that we also coach people to do in a session is 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? Okay. And that's idea A, like then what's a very different way of doing this? You know what I mean? Like, if we didn't want to have the agenda view there, is there a way to do this where it's just a month view? Let's see if we can draw that. So that's the kind of thing that's happening. You asked about the time, and I started with, people aren't used to just going all the way in to actually trying ideas. So there is a little bit of a learning how to just face that blank page and start trying things together, you know, 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? What are some major missing things, you know, like, okay, I've got the, I've got the calendar dot grid, I've got the agenda idea. But like, what about multi-day events? Do you know what I mean? So there can be these things, these like, what abouts? 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 for another three hours, and we come back the next day. And what I would say is, if the project that you're trying to do is doable with, let's say, your existing technology, 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 a 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? Then, you know, if the problem is clear, and the time is now, like you will be able to come to a conclusion about what's possible to build in, you know, three sessions, something like that. You know, the key thing is leaning into those sessions and really wrestling with each other. You know, if you have just the product and the designer there and then it's kind of like, well, we'll show this to the technical person later, then 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 and it like sits on top of human nature. One is just you, you need to actually spend, like go into the deep edge cases and nuances and not just like, let me, yeah, that's fine. Let's go.

More concreteness.

Very concrete, very like in, in depth. and the appetites, there's just like so many elements of this that just connect with the way humans work versus a theory of just like, yeah, well, I see 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, you know what I mean? It kind of has to do these things, but in this time and One other thing that I would mention is that we can't be drawing Figma files. By the way, I'm being very mean to Figma so far in this conversation. There is a time, right, when it's the right time for the Figma file, right? What we want to do is have that clarity around, let's say we already know where the sink is going in the kitchen. And now we can make final calls about the tile and 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? But in a shaping session, you can't collaborate 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 and fat marker sketching. These are tools to help us express an idea very, very clearly in detail. You know, we're going to 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? 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 is more this kind of breadboarding level.

Fat marker session is very evocative of what this whole session is about. It's very high level sketches. That's a great term.

The danger there that I often see is that what we don't want is to say, oh, Figma isn't the right thing at this level. So instead we're going to do fat marker sketches. And what you get is the equivalent of a blurry Figma. Do you know what I mean? Just less detail. What we need from a fat marker sketch for it to be valuable to us as builders is it has to really communicate the idea. So when I look at that, I'm like, oh, now I get it. 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. 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 shaped 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 gist, and obviously if they want to actually implement it, they can get the book. and dive in or work with you, which will point people to. Say someone's like, this is awesome. I want to 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. 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 Dev teams, they like the idea of not having the scrum ritual. So they want to take in the six weeks, but unless the engineering and product come together to figure out how to collaboratively shape, like we talked about before, you know, that time box isn't going to go well.

So I think they're going to not have to do stand-ups, but now it's like a day of hard thinking.

Well, it kind of turns into even more meetings because we don't know what to do.

And the more meetings is just that shaping session specifically.

No, I mean is that if we didn't, if we didn't, oh, right. If we only adopted the, if we only adopted the six week cycle and said, 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 scrum rituals, but we can't say that we are you know what I mean? Knocking the champagne bottle on the boat because we're celebrating the launch, you know.

Or whatever, you know, again and again, right? It's a good actually time to maybe talk about there's obviously the sprint kickoff in Scrum.

Yeah.

What's like the main difference for people?

'Cause they may be thinking, oh, that's just like a sprint kickoff. Oh, that's a good one. That's a good one. So what you often see in a Scrum team is that there's somebody who creates these, Tickets of like, these are the things that are gonna happen inside of the sprint, you know? And really, in my opinion, too many cases, it's not the person who's doing the building who's creating those tickets.

It's like a product owner.

So there's a big, big gap there. There's, we could talk a lot about that. But 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, but they weren't really created by the person who understands the work that needs to happen, you know? So the key difference is two things. So in Scrum, you have a person who's not the builders making tickets. And this is what in the cruel picture is the paper shredder. In the Shape Up world, you have a single idea that was shaped. This is the thing we shaped, right? With the two months in the agenda view and da-da-da. Go make your own tasks because you're the professionals. Do 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? That's their expertise, right? So in a shape up world, a kickoff is here's the well-shaped idea and now this time box starts. And at Basecamp, it was really, really loose 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. I mean, they're very technical, really, really skilled people. And 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 kickoff, take whatever was shaped and just draw a grid with nine boxes and give me nine boxes of the nine major chunks that you think have to get implemented from an implementation standpoint. So translate this into nine major scopes of implementation that need to somehow happen over the time box. It's a really, really useful exercise to kick things off. And we have a lot of teams doing that now. If you take six weeks, that's like 30 business days. You divide that by nine, it's like kind of like four days per box, 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, 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, bye, 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, 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.

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 if the output the team that's building it can come up with nine. And is it like more, like does it have to be nine? Is it like six cool, 10 cool?

What I found is if it's more than 10, then you just get into ticket land of here's a million things I have to do. You know what I mean? If you have 100 things, it's like, that doesn't tell me anything. But if it has to be nine.

Or less, you know- Nine or less, okay.

I actually think I'm speculating here, but you know, the UX designers in your audience will know about this rule 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. And 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, assume it's six weeks to start, try to get into, 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?

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 going to be able to get anywhere.

Yeah. Okay. So you spend like three hours, maybe six hours in the first session. Would you recommend like try to keep it to this many hours when you're first trying it out?

No, I wouldn't do that. You know, I think 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, you are far along. You're doing great if you're at that point. You know, so much of the challenge is getting to the point of kind of aligning between product and engineering that we cannot keep, we cannot have projects that are dragging and dragging and dragging. We can't keep ending in a place where like, 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 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 are supposed to be answering to how's that, how's that work going? Right. And it's like, well, Mm-. Actually, you know, we're working on it. I mean, oh, I can just think of a couple times when I needed to go to Jason 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 were 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 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 shipping still, you know? This is, this can't just keep happening, you know? So there's some recognition somewhere either at the higher levels or within the team, you know, of like, we don't want to keep dragging, we don't want to keep being lost in the weeds. And then this can be the, 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 going to 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 going to be worth, 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. It's timely, something that we would like to be shipped soon. It's not so small that we're not going to actually learn this new muscle, you know, and it's big enough that it's going to feel like we really achieved something, right? So maybe that's going to be four weeks, maybe it's going to be six, maybe it's three, I don't know. And then kind of getting to a place where we have we wrestle a bit with the problem to get the problem narrowed down, we get into our shaping session, 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 for those X number of weeks, that's the upper limit on how long we can spend a shape. And that's another kind of like real life thing is sometimes we talk about like, you know, you know, like, if, if on the one hand, there's this Universe of kind of never ending documents back and forth to get feedback and comments, you know, and then on the other hand, there's like, the team is going to be available. We're trying to actually do this. So actually, we've got a week to shape because engineering needs to kick off next week. Do 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 We want to ship something now.

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, this is like, I don't know, any friends that are using this, it's weird, this way of working. It's not a thing I hear about all the time. What can you say to them to help them be like, okay, I should actually give this a try. Here's how many people are using it, here's impact that you've seen, anything you can share there to help them get over that hump.

I would say wait until it hurts more. If the unfamiliarity is kind of the big problem with it, then maybe the things are fine. I mean, because it's not like this is the only way. It's more like, I mean, changing is really hard. And if there's a good reason to do it, And it's like, look, we've done it the old way. We've tried different experiments. We've even already churned through a new head of product, or we've got a different CTO in, and we're still having the same problems. Then there comes a point where it's like, I know that this is uncomfortable, and I don't know somebody who's done it, but I think we need to try something different because we can't continue this way.

That is a great answer. Falling 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, you shouldn't look into this seriously.

You know, there are pains all along the journey. So, I mean, I think, the, the, the place where it's most obvious is at the end of the line when we thought we were going to 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 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, 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, they have this idea of this thing we need to build, right? or the CEO had this idea in the shower the other day, 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 a source, right, from the business perspective of like, this is the thing we should do next. If we just say dashboard and we don't negotiate what that means, if we just say calendar and we don't negotiate what that actually is, then what do we experience? This kind of fuzzy, fuzzy thing where, you know, like, it's really hard to get to a conclusive answer about, like, yeah, that's what we need to go do. You know, it's kind of like the ever expanding blob, you know? So if we've, if you felt that before, that's already 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. And of course, I don't want to be cruel to the people who are putting their hearts into that work because the Figma file is beautiful. It's just coming a little early. 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. 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, 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 going to go build. It's kind of like a million puzzle pieces that you're going to have to solve, right? So what we see is either, you know, there's the Figma file and then there's the pushback from engineers, you know, there's 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. 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 just doesn't feel like we're getting warmer and coming closer. It just feels like it's getting harder and harder. You know, those are all the signs that whatever process you use, you know, that there's a lack of clear shaping 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 always talk of feature factories. and that rarely are they actually efficient factories. They don't actually work. Talk about that.

Yeah, well, I understand what the feature factory critique is supposed to be. It's actually to the framing point of 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? And then of course in the end, 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, you're probably quite healthy. All you need to do is feed a different input to the beginning of the factory, right? 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 mean, at least from my experience, 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 kind of like the sweet spot stage for a company to start using Shape Up? 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 in this way? or do you find it's more useful later on?

We didn't formalize it until we had to. 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 who is mainly doing the shaping, 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. And so it doesn't matter what your process is, it's going to 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, we used to be fast, and now we hired people because we needed to scale, but now we're slow. So how do we be fast again? Because we know what it's like. If we just got back in there as founders and got our hands dirty, we could make this go. But how do I get these people that we've brought in to make these trade-offs and make these decisions and how do I get the work to flow again? 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? These kinds of things. There is another extreme, which is we've already gone past that. We've been Scrum or whatever for years. The company has been growing, revenue is coming in, sales is doing their job, things are running, but nothing is getting out the door. And we're years in, and we have an entrenched development. We have an entrenched engineering team, which is a wall away from an entrenched kind of product team, and everybody's a part, and this thing is like, we're stuck. 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? And that's a point where there can be kind of a, so hard, some hard conversations need to start happening about how do we actually start to negotiate around how we spend time? And we can't just have endless refactorings and infrastructure projects, but we need to be actually building things that we can sell again.

What an idea.

Yeah, you know, but it can, You know, there are a lot of kind of 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, 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 build the stuff that's actually going to be needle moving again and not just sustaining us where we are to run in place.

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, 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. I actually think that there is, I think that your intuition is right that the market for the last category is the biggest. But it's hard to reach them. It's not easy to talk about these things. These are sensitive topics. Do you know what I mean? Our engineering team isn't shipping, and it's happening at leadership level. There's a ton of complaints happening deeper in the org, but nobody down in the org can change anything. At the end of the day, it's actually the interface at the executive level of being able to say, how are we using our time? like 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 the 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 usually it's later than that. It's after they hired the first PM, after they hired the second PM, and maybe even the third. You know, and they're kind of getting to like the product and engineering together are like 30, 50 people, you know? And it's like we thought we put everybody in the right roles. We kind of did what we were supposed to do and everything is just grinding and like, why are we so slow?

Perfect. So 30 to 50-ish people seems like a good time to, that's probably 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, I mean, 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.

So if you're- so it's when it's too late is when they come out.

I mainly hear about it when it's.

Too late, you know, that's why they're reaching out. Got it. So maybe close to 2:30. Okay. But I think, I really think, honestly, I think it starts the first project where, for example, the founding engineers hands off and then the the new hire is taking over responsibility, or the person who was like sort of founder slash CEO is like first giving it to a PM to kind of thinking they're going to 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 the first step away from the work where the seeds of all of these problems actually start.

I want to 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 Up that you want to add or share?

Yeah, there's one key thing which is 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 kind of chasing around inside of the build. phase inside the time box to try and make sure that, you know, people aren't stuck and getting lost in the weeds and try and keep things moving, you know? And it can sometimes be too close to project management rather than product management, you know? And what we see in really in Shape Up teams when they hit their stride is that the PM moves upstream. 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 business context? How do I narrow down the problem? 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 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 argue that we should spend a few weeks on, you know? That's the place where the PMs can really contribute a lot in the shape up world. That's kind of what they do rather than shepherding the process or being a ritual master or something like that.

That sounds pretty wonderful. I've been doing some thinking about what an AI oriented world does to the role of PM. And it feels very similar to that actually, where the building now is going to happen for you with AI tooling. And that means the bigger question I was like, what the hell should I build? And is the thing I've built right, incorrect and likely to work? And it feels like this is similar. It's like the PM spending a lot more time upfront thinking through what to build, and then the building is 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. Let's see.

I'm also very curious. Yeah.

Oh man, what a wild time. Okay, let's talk about Basecamp. I think we talked about this ahead of the podcast that I think you want people to know that it's, Basecamp is very unique and not everyone can work the way Basecamp works. Just talk about your insight there and your advice there when people see all this advice coming out of Basecamp.

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 that are kind of not in the book that started to reveal those things to me. So many things that I was just taking for granted. I mean, every designer codes. Imagine if every designer codes, and I don't just mean HTML, I mean 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 whatever, right? I mean, really codes. Every designer. So every designer codes, where's the wall between design and engineering? Where's the moment where you arrive with the Figma file and then all of your the disappointment and all of your hopes get destroyed because the engineers tell you no. Those moments don't even exist in that world. And then also, I think also there was this lack of distance between 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 there wasn't this kind of 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 still. I mean, I can't say today, but I mean, up until 2021 when I was still there. So it meant that there was so much clarity all the time 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, that all of 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 sources of requests that you have to wrestle with, you know, and David did such an extraordinary job. of, I mean, the more I see the world, the more I'm amazed at how every six weeks there was clear runway in engineering of like, we have time for whatever the, whatever we agree together is the most important thing. Just blank check, like six weeks at a time. You know, not a blank check, but you know what I mean? Like a blank six weeks. Yeah. Again and again and again. years without end, you know, keeping that engineering capacity focused on readiness for product, you know, 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 debt and stuff like that. I mean, that's, those are amazing. So those are some really big differences. And it doesn't mean that you have to be base camp 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 pressure of the time box, then you can make trade-offs together. It's like, well, if we are used to having a big wall between, for example, engineering and design, then we're going to have to learn. Somebody who wants to start shaping is going to have to learn, like, well, oh, I need to figure out kind of who to bring together and how to have that session and how do we interact with each other So that we are combining all of that knowledge that maybe at Basecamp 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 to do it based on their experience. And there's so many just 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.

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. It sounds like you're kind of in.

This like base camp. By the way, was it called 37 Signals? Like, it's interesting you call it base.

Camp, not 37 Signals. Yeah, I mean, so it's just like the timing of when I left, you know, we were originally 37 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 Basecamp logo on the bottom, not a 37 Signals logo, you know, but then they, since I went back, so it's 37 Signals 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 37 Signals, the current name. Great. Yeah. Yeah. So you said that it kind of felt like you left and it was like this bubble you got out of. 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, 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. I was just in a foreign country. It was like we tried it and it didn't work. One of the common things I would hear is 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. And then I would be like, Huh, so can you show me your shaping work? And then they would show me a PRD. And I'd be like, well, that doesn't look like what's in the book. And then again, can you show me your shaping work? And they'd show me a bunch of Figma files. And then what I started to understand was like, 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? And I didn't appreciate, it took me a while to realize, like, there's no engineer in the picture here. And it was when we started to actually do the course, I did actually a couple projects where I helped teams hands-on, and I learned that it was the first actually consulting project I did where I helped a team who was stuck. And what we did was we chose the engineer who was best suited to 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 had all of that mixed in the same room again. And so that was kind of like, 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 cloud, pontificating about something, and 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 because you've spent so much time doing this and you've actually done the work. You're not just in theory about it. So this is amazing. But we're not done yet. One question I wanted to ask is Jason was tweeting that he's working on a follow-up Shape Up book. What's happening there? Are you involved in that? What's the story?

So I also saw the tweet. And I have to admit, I was a little surprised when I saw this tweet. But I had had a conversation with Jason a year earlier. And he reached out and he said, Hey, we're thinking about doing a second edition of the book. And my first reaction, I mean, I always imagined I was actually really in the middle of learning all these things that teams need to learn in order to kind of catch up to what was natural for Basecamp to do. And so for me, it was like interesting. I have a lot of new things. I have a lot of new ideas. Maybe 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 they work. Because that's always been kind of a big thing of how, I should use the right name, 37 Signals, of 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. 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. There's so many people where what they need to learn is more like, how can it come closer to where I am? 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 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 going to be in the second edition, you know, because they are, I guess someone there is going to be working on that. But what I'm guessing is it's going to be an update on, you know, kind of up on top of the mountain over here. This is, this is what Basecamp is doing. So hopefully it'll be kind of a cool thing to look at as like, here's a model of 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 in the real situation I'm in? And that's kind of where, well, that's my focus.

This is so interesting. Thank you for sharing. Sounds like a fork, fork-y forked it, and these are going potentially in different directions, but inspired by each other.

Totally.

So interesting. Ryan, is there anything else that you want to share before we wrap up?

One thing I could throw out there is sometimes people reach out to me because their projects aren't shipping, there's a lot of struggle, there's a lot of lack of clarity. But the root cause is actually that the input at the very beginning of the process is too unclear or, you know, like 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 this framing step that we talked about of what is really the problem before we go into shaping, this is the link to product strategy also. And this is the place where 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 trying to get clear about things. So that's the tool that I reach for at that phase. And you can think of kind of this Before the problem definition, there's this question of like, what's the demand? Where are people struggling? Where is really the place, the itch they're trying to scratch? 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. That's a great plug for our Bob Mesta 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 this book gives you a lot. Actually, the one that I recommend the most is Demand side Sales 101. And it's funny because it's like sales. you know, especially for a product person, like you're, you're like, I'm the product person, not the salesperson. But it's, it's, 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, feel like you could have done better there with that book's.

Title because it's, yeah, 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, 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 still useful.

Yeah, but basically it's like the jobs to be done book.

Yeah, it's kind of like the jobs to be done book that's a bit more tactical, you know? 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 Clay Christensen wrote with a lot of, I think, I think, I think there's a lot of stuff that Bob worked on that's in there. But, but for a little bit more tactical, 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. Thanks, Ryan. Okay, we did it. This was amazing. I think this is going to help so many people. We got through it. 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 on my website. That's ryan.singer.co. I'm also on X, RJS, I'm on LinkedIn, you know, so just reach me there. And how can people be useful to me? I love hearing from people who are having these problems, you know? 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, 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 told me he's got over 100 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.

Yeah.

I'm gonna ask you to explain that when you do consulting work, just like how does that work? Who's that for? Just because I know that's something else you do.

So it basically starts with either often first CPO or CTO often reaches out first, you know, and 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. 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 help to figure out, like, how do we actually, so almost like guiding through, like narrowing down that pilot project framing so that, so that they have the support that it's going to 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 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 is usually a good approach.

Amazing. And they can find this on your website if they want to explore this.

Yes.

Amazing. Ryan, 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 onto some kind of a main track. So I'm really pleased.

It was really nice. Thanks a lot. I'll do my best.

Yeah. Thanks, Ryan.

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