A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up")

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 going to 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 going to drastically change the cost and the time and everything. What we need to do in a, in a shaping session is we come out with some kind of diagram where engineers, product and design, they're saying, we understand that. So the first thing is we are not, 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 37signals, and through his experience of building Basecamp and his 17 years of building products at 37signals, he wrote a book called Shapeup, 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 Shapeup 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 Des 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@lenny'snewsletter.com with that, I bring you Ryan Singer. This episode is brought to you by work OS. If you're building a SaaS app at some point your customers will start asking for enterprise features like SAML authentication and skim provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by work OS, including ones you probably know like Vercel, Webflow and Loom. WorkOS also recently acquired Warrant, the fine grain authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role based access control or other enterprise features like single sign on, skim or user management, you should consider WorkOS. It's a drop in replacement for Auth0 and supports up to 1 million monthly active users for free. Check it out at workos.com to learn more. That's workos.com this episode is brought to you by Merge Product Leaders. Yes, like you cringe when they hear the word integration. They're not fun for you to scope, build, launch or maintain. And integrations probably aren't what led you to product work in the first place. Lucky for you, the folks at Merge are obsessed with integrations. Their Single API helps SaaS companies launch over 200 product integrations in weeks, not quarters. Think of Merge like plaid, but for everything. B2B SaaS organizations like RAMP, Dorada and Electric use Merge to access their customers accounting data, to reconcile bill payments, file storage data to create searchable databases in their product or HRIS data to auto provision and deprovision access for their customers employees. And yes, if you need AI ready data for your SaaS product, then merge is the fastest way to get it. So want to solve your organization's integration dilemma once and for all? Book and attend a meeting@merge.dev Lenny and receive a $50Amazon gift card. That's merge.dev Lenny Ryan, thank you so much for being here and welcome to the podcast.

Hey, 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 Feels like there's just an increased interest in exploring different ways of working and specifically feels like there's been a rise in interest and Shape up the stuff that you talk about. So I am really excited to basically help people understand what is this way of working? Is it right for them? What are ways to start implementing it? What are maybe some pitfalls you may run into? And as much as possible, get into a lot of real talk about how things are actually going on. Product teams that 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, you know, 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. 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. 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. On an online forum, you know, So I think there's also some reasons why it's been word of mouth kind of slowly gathering steam.

That's something I struggle with on this podcast. You know, it's. As you said, it's a product, and product teams don't want to be sharing that things aren't going great. That's why I introduced Failure Corner on the podcast, where it's like, okay, but tell me at time things didn't go well.

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, 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 exist.

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 going to talk about that. Just like it works for companies that are not nothing like Basecamp. Maybe maybe just touch on that briefly.

Well, I mean, that came as a surprise to me, you know, I mean, when I wrote the book, I had been in Basecamp at that time, I think 15 years, and I actually didn't even know the outside world. You know, I mean, it was Jason's idea to even write the book because he said, look, like a lot of people are going to want to know about this. A lot of people are struggling. And I'm kind of like, well, okay, Like, I knew our inside story of we had some growing pains and we had to be able to formalize the way that we were working and shipping so that as we brought new people in that they could participate in that and we could stay fast, you know. So I knew our, like, internal struggles, but I honestly didn't know anything about the outside world. And it was only after the book came out 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, you know, significantly bigger, like 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, like, a lot of my focus today is actually kind of closing those gaps and helping people figure out how can I make this work for me or for our team.

And you specifically told me you now call it instead of Shape Up. It's shape up in real life or Shape up for real life?

Yeah, well, you know, my wife heard me saying the same thing over and over again on every phone call, and she's. She's overhearing me, and she's like, you got. You have to make a course. You have to do something, because you're just. You always are saying the same thing. So then this. 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 going to.

Get into the nitty gritty of how this actually works and the key elements. But can you just give, like, a very short, over overarching summary of how shapeup 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, that. 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. You know, it just kind of happens on its own. Right. But there was always this really intense urgency from both Jason and David. Like, 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 kind of big things that got fuzzy and started to drag. There was always this, like, 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 the. 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, you know, 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. And cycles of waste.

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

37, 10 hours a week. Yeah.

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

I. Well, Rails came out of. Of. Of the first. So. So he told, he told Jason, I want to try building this in Ruby and. 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. 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. I don't know what he was doing the rest of his time.

You know, probably something great. Something.

But he's always, he's always been like that. You know, he's always doing something interesting like he's either racing or who knows what, you know what I mean? Like so. But all I knew was that we got 10 hours of. Of that time.

I love that. That was like a constraint to design a way of working that uses engineering time most efficiently.

Yeah. I mean, put that, put that together. So David's constraint of 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? And 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 getting to something that we can celebrate and get excited about?

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

Totally, totally. And that's why, where I come back to, 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 that combination of Urgency. And also that those guys were so talented and that they, 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 was. 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. 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, like, that's the idea. That's the thing we want to go try to build. And for me, like those, those sessions with Jason, they were these short, very, very intense sessions where you're trying to crack the nut together. Like, where's the idea? What's the concept? Like, how can we go, what's this thing that we're going to go and like 10 hours later, right, 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, right? That was really kind of 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. 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 kind of trying to maintain the startup way of working as the company grows. Like 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 kind of became Shape up was. How do we hold onto that as much as possible? I mean, one big ingredient. We had an advantage also, which was that Jason and David hired so deliberately, slowly. And this is kind of like 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. They. 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, it was, I mean, of course there were always like ups and downs, but there was, it 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, new person who was leading the, the who's doing half of the work on that team. And 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, you know, as we, as we're asking. And what we're starting to realize is like, oh, this is 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, 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, a big concept and then say, what's the estimate for this thing? We're not going to say, oh, we need to be to build a calendar and then do a whole bunch of figma files or write a whole bunch of requirements and then ask for an estimate. We're 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, you know what I mean, it works. We got somewhere. We. This, 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 going to, you're going to buy a house or you're going to rent a new flat or whatever, you have to have like a budget in mind, right? And the, the, the budget then is how you choose between all kinds of alternatives and make a lot of hard Choices and trade offs to figure out. Like, well, you know, I, I, I, I want the faster engine, you know, but I can't, you know, but I have to give this up. Or, you know, I, I want it to be fun to drive, but we also need space for longer road trips. And you know, you're making all these trade offs, right? So this is kind of this 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 room in front of the whiteboard 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, we understand 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. That's where you take an idea and then you split it into a hundred tickets and you hope that it all glues together still after you've done that step. 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, and 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, 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, 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 it happen. Right. And usually a lot of the drive for that is I'm getting tired of having so many meetings and rituals and things that are not actually working on the problem and doing the work. You know, I mean, especially scrum teams, they, they often complain about that. So 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 a, you know, like some happy bee colony, you know, 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 at the worst is that I 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 crue because I think I'll quote Bob Mesta 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 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, and ship, ship something meaningful in six weeks by cutting away Scope. Right. So what start, 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, this landing page is going to take a couple of weeks. Great, let's work on it. And 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 to 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 company.

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 going to 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 the 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. Right. It doesn't mean that we can't use this technique to do a two week project. You know, especially if you're on a growth team, you don't want to wait six weeks or, you know what I mean, you're going to have to artificially bundle things together to do six weeks. It's like, look, I've got, 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, it's, it's more a question of what we're trying to take on. You know, it's really that upper limit.

Okay. So it could be a two week cycle and 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, the other thing, the other side of that is when it comes to feature development or, you know, building something that's going to be needy enough to sell, you know, then there's very few things that are going to 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. You know, if you get to that end of that six weeks and something is going wrong, you know, it wasn't shaped, we can't see the end of it. It's more complicated than we thought 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 basecamp which was this notion of the circuit breaker. Like if a project is not on track to actually finish after the six weeks, we're just going to cancel it and rethink. You know, almost no teams have the stomach for that. But the, the version of that that's more stomachable is, look, we can't just, we can't just cancel the project and then say, let's see what comes next. Right? But what we can do is say we're not going to keep reinvesting in something that we don't understand, you know, so let's take this out of build mode and bring this back into shaping mode, which might mean different people, a different conversation, asking different questions, you know, doing a different kind of work to suss out, like, what is it that's fuzzy here? What is it that we couldn't see? Like, what do we not understand? That's right. How do we get to the clarity that we need so that we can actually say like this thing is going to happen if we give it another whack.

I love just how real this approach is. Not this like theoretical. Okay, cool. After six weeks, you just descope 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, it's, you know, it's, it's. That's, that's not the way we. 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. How do we narrow down our understanding of the problem and how do we identify what the moving parts are of the solution and what actually connects together for this feature to work, 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 going to turn, you know, that's the place where we can say, oh, this is well shaped, you know, and that's a, that's a, it's a different kind of work. In shaping in real life, we call it, you know, 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 kind of 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 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 npm. So add anything else there and when do they happen is at the end of the. Do you call it a cycle by the way, or sprint? The 6ish week period.

What I actually like is Timebox, 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 at like. Like, what's the ideal company stage for Shape Up?

It can function in very large companies. We have, for example, I have some friends at a. At a. They're a. What is. What is it called? They're doing clinical trials. So they're in the pharmaceutical industry. And I mean, the companies, 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 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 going to get pulled away onto something else. If you can kind of carve out, oh, 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 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 like a four week plus two week or like, so they'll do like a, like five week and then one week of cooldown in between and then they, they, they time it so that it adds up to a quarter. You know, 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 you know, a VP in some area. But you're coming to the table where you're supposed to be reporting of what your group is doing. 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 leave you alone. That makes sense.

For sure.

For sure. I love that point. Okay, coming back to shaping one maybe one way that would make it really easy for people to understand. What's the output of the shaping session?

The output of the shaping session is so, and by the way, about shaping session, you know, let's maybe we can talk a little bit about what shaping is not. You know, because 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, 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, when you give that to a team as like, this is what we shaped, what happens is like, it, it blows up. So, I mean, you probably know about what happens when the, the, 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, 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, in a shaping session when it's going well, is we come out with some kind of 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. Right. 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, we, we're not going to 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 going to have this, this, this, this, this and this and that's how we're going to let people see the empty spaces. You know, that's a good indicator that it's clear enough that, that, that it's, that it's shaped well. So in this case we had a, you know, when you go to an airline and you, and you want to book something, you see this like two month grid, right. So it's like there's going to be two months side by side, but they're just going to have dots in them to indicate if there's, if there's a free day or not. 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 going to be an agenda view that slides underneath which is going to 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 agenda 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, that's going to be a real Conversation and not looking at a whole bunch of mock ups and, 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, 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 dock of spec and not final design and also not just like a user story. As a user, I need to be able to see empty spaces.

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

That time because you're committing, right?

It's like, yeah, we're committing and that time is really valuable, right? That's six weeks of engineering 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 engineers run back to the, 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, if you give a senior engineer like, here's how I want you to go implement the schema for this database change for this model, they're going to be like, what do you like? 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 going to 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. And on the other hand, if they are given more guidance, they're going to be able to be successful. They're going to learn about, you know, this is how this person who knows well kind of approached it. And then in the next round or a few, you know, a few projects later, you can dial it back and say, well, let's, let's give less detail and see how they handle it. Right? So you can really give people bigger shoes to grow into and, and, and help them to be successful. And then of course, you can also do it the other way around where if, if you've got some really stellar talent on the team and you have a long history and you have a lot of trust that they are going to be able to understand and solve it, then of course you can leave things out. Right? But the, the, the thing that I often see is if there's someone on the build team who really feels that they should be involved in the fundamental decisions about the approach, then a better solution would be to actually bring them into the shaping and have them play that technical role in the shaping session. You know, if they're re. If they have the right skills and the right perspective and the right knowledge to play that role well, then just bring them into the shaping, right? So it's all about how do we bring people into a moment where, 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 de risk the biggest risks and address the biggest unknowns as much as possible. Like there's probably this. 80% of here are 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 the team and they, 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 because you had to fill out a whole bunch of information. And they, they figured out that they could actually pipe that data in from one of the partners that they had because they were partnered with banks. And they're like, oh, we don't even need to be asking people this, right? So we're going to we're going to fix conversion, we're going to eliminate a step from our user experience. It's going to 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. 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, like that's a bad place to be. But if we're in the shaping room and we didn't kick this thing off yet, right? We didn't even 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 going enable us to really ship something that's successful later.

Well, let's go one level deeper on the shaping session because clearly that is so core to this working. And I know you have a whole book about like how to actually do this. So we're not going to 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, 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 like Katya and I will be running the session and we have to like people aren't used to working so fast you know, to like, like what are we actually doing right now? What's the decision? Like what's an idea? Like right now we're not going to go away and, and, and, and draw something and then, and then I'll comment on a document and then come back and get together tomorrow. Like what ideas do we actually have right now? Like starting from zero. So like imagine, imagine like we, we, we've narrowed down the calendar problem to. 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 how you, that's the input to the framing session or sorry, the shaping session.

Exactly. So that's, so that they 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 going to, you know what I mean? This isn't going to work because of this reason. Or the product person is going to be looking at 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, like is there a way to do this where it's just a month view? Let's like see if we can draw that, you know, so that's, that's the kind of thing that's happening. You asked about the time and I started with like people aren't used to just going all the way in to actually trying ideas, you know, so there is a, a little bit of 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, what about multi day events? Do you know what I mean? Like, 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, you know, for another three hours, we come back the next day, right? And what I would say is if 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, new AI model. It's more about like, how do I use the APIs and the frameworks and the tech stack that we have? How do I put that together to build something? You know, 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 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's, 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. Yes, like, let me. Yeah, that's fine, let's go.

More concreteness.

Very concrete, very like in, in depth. And then 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, yeah, 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 you know, one other thing that I would mention is that we can't be drawing Figma files. It. By the way, I'm, I'm, I'm, I'm being very mean to, to, to Figma. You know, 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, you know, the. 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 want to 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 like very evocative of what this whole session is about, is like 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, from a fat marker sketch for it to be valuable to us as, as builders is it has to really communicate the idea. So when I look at that, I'm like, oh, now I get it, right? And if it's kind of more this sort of general wireframe of like, you know, dashboard goes here and there's going to 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 like 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?