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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“Yeah, thanks a lot. You had amazing questions. You know, it's a subject that can go in so many directions, and you kept bringing us onto some kind of a main track. So I'm really pleased. It was really nice. Thanks a lot.”
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
“Who do we need to get to do this work? Who are the right people? How do we bring them into a pilot project? Narrowing down, doing some framing work on the pilot so it's going to be clearer in the shaping and then giving some guidance on how to get through that shaping with some feedback rounds. This is usually a good approach.”
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 it basically starts with either often first CPO or CTO often reaches out first. And when it works well is when we actually get them together. And then they understand that they need to change something or we have like a head of product and a head of engineering, that kind of a thing. If those two are both seeing eye to eye that there's a problem, then we can start a conversation around, okay, so who would be the right people for a pilot team? What are the things that are going on business-wise that could be a good pilot project? And then I can kind of help to figure out like, how do we actually, so almost like guiding through, like narrowing down that pilot project framing so that they have the support that it's going to be successful in shaping, you know, and then coaching the team so that they actually learn those shaping skills so that they can get through a session and come out with much more clarity? Like how do they actually run those sessions? So it's kind of first working with leadership.”
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 got through it They can find me on my website. That's ryansinger.co. I'm also on xrjs. I'm on LinkedIn, you know, so just reach me there. And how can people be useful to me? I love hearing from people who are having these problems. If you're having these problems where it's like things are dragging or we can't see the end and we're not getting the quality we need and all this stuff like, man, this is, I mean, this is how I learn. All this stuff is by talking to people who are in it, you know? You know, even if it's not clear, what's the next step yet? You know, if that problem is real, it would be cool to hear about it. I'd love to chat.”
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, it's kind of like the jobs would be done book that's a bit more tactical, you know If you're really curious about the general spirit of jobs to be done, then competing against luck is a really good intro. That's the one that Clayton Christensen wrote with a lot of, I think there's a lot of stuff that Bob worked on that's in there. But for a little bit more tactical of what's it look like to do the interview and how to think about the struggling moment and stuff like that, this demand side sales is good for this strategy stuff.”
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 know what's interesting about it is that it's very, very pointy for like if you are trying to make progress on sales, then it's this other kind of sales, this demand side sales, you know. So I think maybe it's more for us who are kind of using it for different purposes. Like we're the product people trying to pull something out of it that it's a little bit less aligned, but it's. Still useful”
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
“Actually, the one that I recommend the most is a demand side sales 101. And it's funny because it's like sales, you know, especially for a product person, like you're like, I'm the product person, not the salesperson, but it's such a good dive into what are people really trying to solve and getting into that mindset of what's the struggle, what's the problem. I think that's a really good entry point for that.”
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 this question of what's the demand? Where are people struggling? Where is really the place, the itch they're trying to scratch, you know? And then a lot of the shape-up stuff is kind of when I have something where I think there's an opportunity or I think there's something meaningful there because of what we learned from customers or the job to be done research or whatever it was. Now how do I turn that into something that we can actually go do and ship in a reasonable amount of time? That's kind of the supply side. That's where the shape-up part fits in. So maybe it just might be cool for people to sort of see a link there.”
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
“One thing I could throw out there is sometimes people reach out to me because their projects aren't shipping. There's a lot of struggle. There's a lot of lack of clarity. But the root cause is actually that the input at the very beginning of the process is too unclear or we don't actually know what's important to customers or we're not actually sure where the value is or this kind of a thing you know so there is this link this framing stuff that we talked about of what is really the problem before we go into shaping this this is the link to product strategy also and this is the place where it can be really useful to reach for a lot of for example Bob Mesta's stuff with the jobs to be done and the demand side work of trying to get clear about things so that's the tool that I reach for at that phase and you can think of kind of this you know before the problem definition”
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
“Is they like to really show a clear example, not like this is how you could do it, this is how some people do it, but like this is how we do it. And I think it's their strength that they are very, very clear, like this is how we do it and kind of take it or leave it. And what I understood was that if I did another version of the book that was just kind of how Basecamp does it, I think it would leave so much opportunity on the table. Like there's so many people where what they need to learn is more like how can it come closer to where I am If I have the wall today between product and engineering, how do I bring the right people together into a shaping session? How do we actually do that? How do I overcome all of these little challenges because this is so far from our current way of working, you know? So the work that I'm doing, for example, with shaping in real life is kind of all about those gaps. And then I don't know what's going to be in the second edition, you know, because they are, I guess, someone there is going to be working on that.”
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 also saw the tweet. And I have to admit I was a little surprised when I saw this tweet. But I had had a conversation with Jason a year earlier. And he reached out and he said, hey, we're thinking about doing a second edition of the book. And my first reaction, I mean, I was imagined I was actually really in the middle of learning, you know, all these things that teams need to learn in order to kind of catch up to what was natural for Basecamp to do. And so for me, it was like interesting. I have a lot of new things. I have a lot of new ideas. Maybe a second collaborating on the second edition could make sense. But what I understood was that what he wanted to do was to kind of make it updated version of how they work. Because that's always been kind of a big thing of how should I use the right name, 37 signals, of how they market and also how they lead.”
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 didn't appreciate it, took me a while to realize like there's no engineer in the picture here. And it was when we started to actually do the course. I did actually a couple projects where I helped teams hands-on. And I learned that it was the first actually consulting project I did where I helped a team who was stuck. And what we did was we chose the engineer who was best suited to come over to product and be there in the shaping. And that was the moment when it was like, ah, now I'm in the world I know again. When we had all of that mixed in the same room again. And so that was kind of like, that was really something, I mean, it was a total learning curve for me, you know? And there's a lot of things like that, but that was, for example, a really big one. It's like, oh, we have to get engineering in there.”
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 wasn't that this doesn't work. I was just in a foreign country. You know, it was like we tried it and it didn't work, you know. One of the common things I would hear is the projects kept running over. You know, we weren't finishing them at the end of the cycle. They kept running over and running over. And then I would be like, huh, so can you show me your shaping work? And then they would show me a PRD. I'd be like, like, well, that's not, that doesn't look like what's in the book. And then again, like, can you show me your shaping work? And they'd show me like a bunch of Figma files, you know? And then what I started to understand was like. We have some people in a role who are used to making a certain artifact at a certain step, and they just kind of kept doing that, 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
“Yeah. And then so, for example, like on the book, it says shape up and there's a base camp logo on the bottom, not a 37 signals logo, you know. But then they since I went back. So it's 37 signals again. So I sometimes struggle with, I don't know what to call it, you know, but it's both whatever people can recognize. It's the same powerhouse”
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, I mean, so it's just like the timing of when I left, you know, we were originally 37 signals and then Basecamp became so big that we renamed ourselves to Basecamp”
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, imagine you never, no such thing as a request from sales. No such thing as pressure of like we need this thing in order to upsell, right? Or to close this deal. Never.”
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
“Again and again and again, years without end, you know, keeping that engineering capacity focused on readiness for product and totally leaning into what's exciting to do to build for the product and not getting lost in all this refactoring and new infrastructure and technical debt and stuff like that. I mean, those are amazing. So those are some really big differences. And it doesn't mean that you have to be basecamp to do shape up. But what it does mean is that when we say, oh, just have a shaping session. And if you have the pressure of the time box, then you can make trade-offs together. It's like, well, if we are used to having a big wall between, for example, engineering and design, then we're going to have to learn somebody who wants to start shaping is going to have to learn like, well, oh, I need to figure out kind of who to bring together and how to have that session and how do we interact with each other.”
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 it meant that there was so much clarity all the time around what we're solving and why and why we're making time for it. And then, of course, on the engineering side as well, I mean, imagine you have. Have no marketing That all of selling and marketing is happening by the unicorn founders. So it means that there isn't contention for engineering time, that there isn't kind of like all these different sources of requests that you have to wrestle with. And David did such an extraordinary job of, I mean, the more I see the world world, the more I'm amazed at how every six weeks there was clear runway in engineering of like we have time for whatever we agree together is the most important thing. Just blank check like six weeks at a time, not a blank check, but you know what I mean? Like a blank six weeks. Yeah.”
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, every designer codes, where's the wall between design and engineering? Where's the moment where you arrive with the Figma file and then all of the disappointment and all of your hopes get destroyed because the engineer is telling you no, right? Like those moments don't even exist, right, in that world. And then also, I think also there was this lack of distance between sort of the business objective, the thing that we're trying to, the reason we want to maybe do this project, and the blessing of the founders and the like, there wasn't this kind of, you know, executives far away with some big targets and then some layer of PM and then some building. I mean, the founders were always there right there in the problem definition still. I mean, I can't say today, but I mean, up until 2021 when I was still 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
“I got to tell you, I had no idea how unique we were until I was outside. And there's so many things. For example, it's a lot of the things that people ask me about that are kind of not in the book that started to reveal those things to me. You know, so many things that I was just taking for granted. I mean, every designer codes. Imagine if every designer codes, and not, and I don't just mean HTML, I mean like running the app locally, going into the place where that view is rendered to make that thing look the way that they want it to look or whatever, right? I mean, like really codes, every designer.”
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 PM is less busy with how I get this project to like not be in a bad state when it's getting built. And they're way more in how do I understand the business context? How do I narrow down the problem? How do I negotiate back and forth with maybe the CPO who kind of brought this to me to understand where the core of it is, that really getting deeper understanding of the business and the problem and the customer domain and like what problem is worth solving and what's even slice of that problem is the valuable slice to argue that we should spend a few weeks on that PMs can really contribute a lot in the shape-up world. That's kind of what they do rather than shepherding the process or being a ritual master or something like that.”
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, there's one key thing, which is the role of the PM. Think what we see today out of necessity in a lot of teams is that the PMs spend a lot of time kind of chasing around inside of the build phase, inside the time box to try and make sure that people aren't stuck and getting lost in the weeds and try and keep things moving. And it can sometimes be too close to project management rather than product management. And what we see in really in shape-up teams when they hit their stride is that the PM moves upstream.”
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
“But I think I really think honestly, I think it starts the first project where, for example, the founding engineer is hands off and then the new hire is taking over responsibility or the person who was like sort of founder slash CEO is like first giving it to a PM to kind of thinking they're going to carry it through. And then it's not exactly meeting their expectations of what they thought was going to happen. I think that's when those disconnects actually start. It's the first step away from the work where the seeds of all of these problems actually start.”
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
“When they show themselves, you know, and I think if someone kind of hears this and it all starts to make sense and they're earlier in that wave, then of course the earlier that you can anticipate it, the better, right?”
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 sometimes have the how the heck do I hire the first PM and what do they do conversation? But usually it's later than that. It's after they hired the first PM, after they hired the second PM and maybe even the third, you know, and they're kind of getting to like the product and engineering together are like 30, 50 people, you know. And it's like we thought we put everybody in the right roles. We kind of did what we were supposed to do and everything is just grinding. And like, why are we so slow?”
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
“Actually, it's been so far a lot of the folks who still remember what it was like to be fast and their kind of newly too big and they don't like being slow. I've had a lot of that. I actually think that there is, I think that your intuition is right that the market for the last category is the biggest, but it's hard to reach them. It's not easy to talk about these things. These are sensitive topics. Do you know what I mean? Our engineering team isn't shipping, you know? And like, it's like, and it's happening at leadership level. There's a ton of complaints happening deeper in the org, but none of nobody down in the org can change anything. At the end of the day, it's actually the interface at the executive level of being able to say, how are we using our time? Like, we have to change something.”
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, you know, but it can, you know, there are a lot of There's reasons why all those things got there, but there comes a point where we have to figure out how to cut through it and make some hard choices so that we can carve out time to build the stuff that's actually going to be needle moving again and not just sustaining us where we are to like run in place.”
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 actually start to negotiate around how we spend time and we can't just have endless refactorings and infrastructure projects, but we need to be actually building things that we can sell again.”
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
“Go after. So I have to babysit them all the time. You know what I mean? Like these kinds of things. There is another extreme, which is We've already gone past that. You know, we've been Scrum or whatever for years. You know, the company has been growing, like revenue is coming in, like sales is doing their job. Like things are running, but, man, nothing is getting out the door. And we're years in and we have an entrenched development. We have like an entrenched engineering team, which is a wall away from an entrenched kind of product team and everybody's apart and this thing is like we're like stuck. And that is more where there's going to be some tensions that are starting to appear at the executive level. There's going to be some finger pointing. There's going to be some like, why isn't this moving? Why isn't this happening? How can we be spending so much money in all these engineers and we're like, don't have anything to show for it, you know? And that's a point where there can be kind of a so hard, some hard conversations need to start happening about”
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
“Then you start to hire the first other people. And then for the first time, you try to delegate some of those things and the founders try to be less involved. And that's often where a lot of these problems start to appear. And the founders start to ask themselves, like, we used to be fast. And now we hired people because we needed to scale, but now we're slow. So like, how will we be fast again? Because we know what it's like. If we just got back in there as founders and got our hands dirty, like we could make this go. But how do I get these, like the people that we've brought in to make these trade-offs and make these decisions? And how do I get the work to flow again? So that's something that we definitely see there. So that's a really good moment. I'm onboarding new people. I don't know what to tell them how to work. I don't want to introduce a bunch of scrum rituals. Just winging it on Kanban isn't working because they don't have enough clarity on what's going 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
“We didn't formalize it until we had to, and there was a long time where there wasn't a fixed length for projects. There was just an understanding of the urgency and kind of a feeling of what too long felt like, you know, and it didn't actually click into, oh, this is a cycle length and this is six weeks. And then we pause and this is how this is who comes together to make the decision of like what's the next project and here's who is mainly doing the shape. You know what I mean? Like all that stuff didn't get solved until we had reached a certain size. Usually the main tipping point if we start from smaller to big is there's a phase when the founders are still involved in everything. And so it doesn't matter what your process is. It's going to be fine.”
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
“End, I'm losing my, like I'm feeling burned out. You know what I mean? It's not exciting to work on this anymore, like all that kind of a 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
“Yeah, well, I understand what the feature factory critique is supposed to be. It's actually to the framing point of we're not negotiating the value and the outcome we're trying to get from something. We're just kind of taking it and building it. And then, of course, in the end, according to the feature factory critique, we just built it because somebody said we should build it and then people didn't use it and didn't value it and the product is just getting bloated, right? The thing is that like I would say if you have a feature factory meaning you're continually cranking out features, you're probably quite healthy. All you need to do is feed a different input to the beginning of the factory, right? What most teams are struggling with is that they can't, they don't have predictable, repeatable shipping of things. I mean, at least from my experience, the bigger, really widespread struggle is like stuff isn't moving, it's dragging, I can't see.”
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
“More questions coming out, you know, more and more unexpected complexity, things that we didn't anticipate. And it's just, it just doesn't feel like we're getting warmer and coming closer. It just feels like it's getting harder and harder. Those are all the signs that whatever process you use, you know, that there's a lack of clear shaping and there's a lack of clear framing because there's a lack of clarity around what it is that we'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
“Try to read it because it wasn't shaped and we didn't get down to it's this, it's that, it's that, and that's how it works. It's hard to walk away from reading that and kind of have anything that's in your head, you know, as like this is what we're going to go build. It's kind of like a million puzzle pieces that you're going to have to solve, right? So what we see is either, you know, there's the figma file and then there's the pushback from engineers. There's there's the PRD, but then it's like, okay, but we still don't actually know what to build. There's kind of all those things where instead of moving forward, there's like more and more questions, more and more pushback, more and more going back to the drawing board. So that's another kind of big indicator that something is going wrong. And then when we're in the building and we thought we knew what we agreed to, we thought we all said, yeah, this is what we want to go make. And it's just more.”
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
“Coming a little early, right? And the PRD is full of a lot of true things that are probably really important for decision making in the project. But the way that it's packaged at that moment isn't something that gets absorbed. You know, I mean, you write this document and who, I mean, who actually, I'm sorry, like who actually reads it. You know what I mean? Like, and I know it's painful, but it's like that, you know. And then even when we”
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 we just say dashboard and we don't negotiate what that means, if we just say calendar and we don't negotiate like what that actually is, then what do we experience, this kind of fuzzy thing where it's really hard to get to a conclusive answer about like, yeah, that's what we need to go do. You know, it's kind of like the ever-expanding blob, you know. So if you felt that before, that's already a first pain. And then, of course, where does it go from there? So we say calendar. So we don't know what it means, but we say calendar. So now we give it to product and we've either got a whole bunch of figma files or we have the PRD with a million requirements about what a great calendar is, you know. And of course, you know, I don't want to be cruel to the people who are putting their hearts into that work because the Figma file is beautiful. It's just.”
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 know, there are pains all along the journey. I mean, I think the place where it's most obvious is at the end of the line when we thought we were going to be done and this thing is just dragging and dragging and dragging, right? Like the teams, like we're not shipping things, we're running in place. We keep going in circles on this. We don't see the end. Of course, that's kind of like the culmination, you know. But there's also a lot of pain points along the way. So there's, if we go all the way upstream. We go to the source of a project, right? Sales talk to a customer, you know what I mean? Or sales talk to a lead and want us, they have this idea of this thing we need to build, right? Or the CEO had this idea in the shower.”
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 would say wait until it hurts more. If the unfamiliarity is kind of the big problem with it, then maybe the things are fine. I mean, because it's not like this is the only way It's more like, I mean, changing is really hard. And if there's a good reason to do it, and it's like, look, we've done it the old way. We've tried different experiments. You know, we've even already churned through a new head of product or we've got a different CTO in, you know, and we're still having the same problems. Then there comes a point where it's like I know that this is uncomfortable and I don't know somebody who's done it. But, you know, like I think we need to try something different because we can't continue this way.”
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 that's another kind of like real life thing is sometimes we talk about If, on the one hand, there's this universe of kind of never ending documents back and forth to get feedback and comments. And then on the other hand, there's like the team is going to be available. We're trying to actually do this. So actually we've got a week to shape because engineering needs to kick off next week. You know what I mean? That's kind of a little bit more the real scenario when you're actually in this aligned world of like we want to we want to ship something now.”
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
“Matching these things together, right? Here's a problem that we actually care about, it's timely, something that we would like to be shipped soon. It's not so small that we're not going to actually learn this new muscle, you know, and it's big enough that it's going to feel like we really achieved something, right? So maybe that's going to be four weeks. Maybe it's going to be six, maybe it's three. I don't know. And then. Kind of getting to a place where we have We wrestle a bit with the problem to get the problem narrowed down. We get into our shaping session, and then we do our best. Do you know what I mean? And usually what happens too is. If we have an engineering team that's going to become free to do this work for those X number of weeks That's the upper limit on how long we can spend to shape.”
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
“What usually works best is okay, we're going to try a pilot project. And what we want to do is, as you said, kind of choose a problem that's important enough to all of us that we think it's meaningful, it's going to be worth, you know, trying to do well. And it doesn't have to be six weeks. It could be something that is a little bit smaller. Maybe you feel comfortable taking on a three-week thing for the first time. What's important is just matching.”
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
“Level. Imagine, you know, you're the CPO, you're the CTO, and you're supposed to be answering to how's that work going, right? And it's like, well, Actually, you know, we're working on it. I mean, oh, I can just think of a couple times when I needed to go to Jason, and he expected me to be making progress on something and I had gotten nowhere on it, you know. And that feeling, you know, when you were with top leadership in the room and you don't have a good answer for where you are on something is like it's brutal, right? And then from the CEO's perspective, it's like, where's the movement? We're running a business here. Like really nothing is shipping still, you know, this is this can't just keep happening, you know? So there's some recognition somewhere, either at the higher levels or within the team, you know, of like we don't want to keep dragging, we don't want to keep being lost in the weeds. And then this can be the, you know, like the activation energy, like you gather the power to be like, okay, we actually want to try something different. And in that case, what I would say is.”
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, I wouldn't do that. You know, I think the key thing is actually if you get to the point where you're trying to hold a shaping session and you manage to get product and engineering into the same room to do it, you are far along. You're doing great if you're at that point, you know, so much of the challenge is getting to the point of kind of aligning between product and engineering that we cannot keep We cannot have projects that are dragging and dragging and dragging. We can't keep ending in a place where like where this is the end of a sprint or the end of a cycle and we still can't see the end of it, you know, or we have to make so many cuts and compromises at the last minute that it's not the quality of or it's not really matching what it was supposed to be in the first place when those problems are happening or you know also by the way this is surfacing at the exact”
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, for sure. The question is what problem are we trying to solve? Because the shaping work is more, what are our options for the solution? And if the problem is too fuzzy and big, if the problem is just calendar, you know, then the shaping is going to be this ever-expanding, never-ending thing, and we're not going to be able to get anywhere.”
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 think I'm speculating here, but you know the UX designers in your audience will know about this rule of 7 plus or minus 2. It's this cognitive science principle that was found about how many things someone can hold in their head at once And so this nine is the upper limit of 7 plus or minus 2. And it basically, you know, it's kind of like, do we actually have a picture of what it means to build this there? We can also hold in our heads. Can we kind of see the whole castle?”
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
“What I found is if it's more than 10 Know what I mean? If you have 100 things, it's like that doesn't tell me anything. But if it has to be nine or less, you know.”
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
“A really, really useful exercise to kick things off. And we have a lot of teams doing that now. If you take six weeks, that's like 30 business days. You divide that by nine. It's like kind of like four days per box, you know. So you're going to get a lot of clarity from a quick exercise. And again, this is done by the builders. This is a really also good exercise for them to notice like, oh, wait a minute, we think there's too much scope here, even though it seemed reasonable when we put it into nine boxes. It's like, I, you know, I don't think we can do this all. Or it's also a good moment where somebody who's more junior might kind of describe their implementation approach. And then someone who's senior can review that and say, actually, you know, we've done that before and we'll run into this trouble if we don't use this other thing. So those kind of really nice kind of coaching moments can happen.”
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 the nine major chunks that you think have to get implemented from an implementation standpoint, so like translate this into nine major scopes of implementation that need to somehow happen over the time box.”
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
“Make your own tasks because you're the professionals. Do you know what I mean? So, like the contractors, you know, like if you're building a house, like they have to know the plans, but you don't have to tell them now take the hammer and go over here, you know, that's their expertise, right? So in a shape-up world, a kickoff is, here's the well-shaped idea, and now this time box starts. And at Basecamp, it was really, really loose because, I mean, they are just stocked with senior people. I mean, they have so many very senior engineers, and all the designers are coding. I mean, they're very technical, really, really skilled people. And what I found is helpful when the team is a little bit more mixed. If they're not all super senior, is a simple exercise of at kickoff, take whatever was shaped and just draw grid with nine boxes and give me nine boxes.”
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