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Ryan Singer: evaluation

30 Mar 2025 Lenny's Podcast A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

“There's a reality check that happens there and very often, there's 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 like, "No, we can't do that," or, "Actually, it doesn't work like that.”

— Ryan Singer

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Speaker
Ryan Singer
Attribution
Verified speaker
Claim type
evaluation
Recorded
30 Mar 2025
Publisher
Lenny's Podcast

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…I love that. I love that point. Okay, coming back to shaping, maybe one way that would make it real easy for people to understand, what's the output of the shaping session? The output of the shaping session is, and by the way, about shaping session, maybe we can talk a little bit about what shaping is not because we need the contrast sometimes. So, very often, when people try Shape Up, what I see is a product team creating either a lot of Figma files or maybe a lot of documentation, 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 this is what we shaped, what happens is it blows out. So, 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 and very often, there's 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 like, "No, we can't do that," or, "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. How do we flow from here to there? What are the different cases of logic? In which case do we move from here to here to here in the flow? What is happening behind the scenes? It's like the engineering team, they have to put on their x-ray goggles and study this thing to try and understand what's happening underneath. I often use this analogy of if you're doing a home renovation, you can have the most beautiful rendering of here's the new bedroom, and we're going to have these lamps on the side of the bed that are coming out from the wall, 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, 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. So, what we need to do in a shaping session when it's going well is we come out with some kind of drawing or diagram where engineers, product, and design are all looking at that and they're saying, "We understand that. I know exactly what to go build." I'll use the example of the calendar from the book. So, what is a calendar? 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 are not going to just build calendar, which is 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. 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 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. 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, that's a good indicator that it's clear enough that it's shaped well. So, in this case, when you go to an airline and you want to book something, you see this two-month grid. 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 a free day or not, if there's something in that day or not, like 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. 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, 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 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? That's going to 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.…

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