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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)

“Or the product person is going to be looking in and saying, "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.”

— Ryan Singer

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

Transcript context

…And that's the input to the framing session or sorry, the shaping session. Exactly. 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, and where is the value in this? But let's suppose that that's happened, 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, 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 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 stuck in one idea and now you're going in circles around little details of one idea for three hours, but to really step back and say, "Here's an approach. What if we had the scrolling agenda view, okay? And that's idea A. Then what's a very different way of doing this?" Do you know what I mean? If we didn't want to have the agenda view there, is there a way to do this where it's just a month view? Let's see if we can draw that. So that's the thing that's happening. You asked about the time, and I started with people aren't used to just going all the way in to actually trying ideas. So there is a little bit of learning how to just face that blank page and start trying things together. What we find is that a three-hour session can be very, very productive to help you figure out what do we already have that are possible approaches to this? What are some major missing things? Like, okay, I've got the calendar dot grid, I've got the agenda idea, but what about multi-day events? Do you know what I mean? So there can be these things, these what abouts. So then maybe we break and we think for a little bit, and somebody sketches some ideas on that and does a spike or two on something, and we come back again for another three hours or we come back the next day. And what I would say is if the project that you're trying to do is doable with, let's say, your existing technology, 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 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 if the problem is clear and the time is now, you will be able to come to a conclusion about what's possible to build in three sessions, something like that. The key thing is leaning into those sessions and really wrestling with each other. now, you will be able to come to a conclusion about what's possible to build in 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 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 and you have to go back to the drawing board. We need to have all the necessary information in the same room for these sessions to go fast.…

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