YouSaid · the spoken record

Ryan Singer

lines on the record: 126
first: 2025-03-30
most recent: 2025-03-30
sittings or episodes: 1
sources: podcast

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“So there's a big, big gap there. 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. Was shaped. This is the thing we shaped, right? With the two months and the agenda view and da da da.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 going to happen inside of the sprint. And really, in my opinion, too many cases, it's not the person who's doing the building who's creating those tickets.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“No, what I mean is that if we didn't, if we only adopted the six-week cycle and said we're going to 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?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Know what I mean? Just less detailed. 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, 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”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“And grout color. We don't want to have to throw it all away every time something changes. 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 kind of the sort of the level of detail where we can move fast together, but still see something real as more of this kind of breadboarding level.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“And we'll figure it out We're solving a puzzle together 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 the, let's say we already know.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Three sessions, something like that. The key thing is leaning into those sessions and really wrestling with each other. 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Know what I mean? Like, so there can be these things, these whatabouts. 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 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 and, you know.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, is there a way to do this where it's just a month view? Let's see if we can draw that, you know? So 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 into actually trying ideas, you know? So there is 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 do we already have that are possible approaches to this? What are some major missing things? I've got the calendar dot grid. I've got the agenda idea, but like what about what about multi-day events?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. So that's so having a narrowed down problem from the framing work, and this is a whole other topic of 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 Have to try to break them”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 like Katya and I will be running the session. And we have to like. People aren't used to working so fast, what are we actually doing right now? What's the decision? What's an idea? Like right now, we're not going to 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 we've narrowed down the calendar problem to it's about empty spaces.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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? 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. And when you're doing that before the project starts off, that feels like, oh, we're talking about the important things. We're not failing right now. We're engaged in the hard questions that are going to enable us to really ship something that's successful later.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Let's say we've got three different integrations here, three different segments integrated into different banks.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 green light 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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 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 fix conversion. We're going to eliminate a step from our user experience. It's going to be great, right? 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“How do we bring people into a moment where we are using their strengths? 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 going to be able to understand and solve it, then of course you can leave things out, right? 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, right? So it's all about.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“That's really interesting. I got to tell you the dominant failure case that I see in the real world is always, again and again, not enough detail. 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, you know, thinking about it. Because, of course, 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, why are you? Who are you? You know what I mean? But what's really interesting is it's not a universal thing.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. So, because that's the thing where it goes wrong. You know, if we're going to commit engineering time, 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Be a real conversation and not looking at a whole bunch of mock ups 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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? 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. 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 going to.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 it's shaped well. So in this case, we had a, you know, when you go to an airline and you want to book something, you see this like two-month grid, right? 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 a free day or not. I mean, if there's something in that day or not, kind of like the iPhone calendar, I think, still has this, where it's just dots on the month view.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 going to just build calendar, which is like Google Calendar, 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. So we got to that point of like to 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, right? I'll use the example of the calendar from the book. So what is a calendar? 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?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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 and 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”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“The output of the shaping session is so, and by the way, about shaping session, 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,”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 in another few more months or, you know, we're working at it. I mean, that's what everyone wants to see is that movement, you know?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“So there's kind of two different things. So, I've seen cases where they've decided on a four-week plus two-week or like, so. 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“It can function in very large companies. We have, for example, I have some friends 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. 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, 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“I actually like his 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. 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, you know, like how the old stuff works and what's truly possible and what's hard and what's easy in our infrastructure, like the person that really knows, right? You bring that person together 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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? 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 going to 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, 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...”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Seen some shape up adoptions that looked like that, by the way, and it's not the way. The shaping step is crucial. And 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 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, right? But what we can do is say we're not going to keep reinvesting in something that we don't understand.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a 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...”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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, oh, 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 that the question is kind of, what's big enough that we can actually get somewhere with this amount of time, right?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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? It's more a question of what we're trying to take on. It's really that upper limit.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 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.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“You can't put 10 pounds of crap in a five pound bag. That's a high academic statement. 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 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?”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“Buzzing and humming 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 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 enjoy your responsibility. You know what I mean? Which is just cruel, right? Because I think quote Bob Nesta, who's been on your show a couple times.”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source
“You don't need to do any of it. So, this is where we kind of helps to look at what's going wrong and what are we trying to fix. And then, you know, what do I want to bring into this? 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're 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 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 happening,”
2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source