Ryan Singer: commitment

Transcript context

…No, I wouldn't do that. 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. Oh, so much of the challenge is getting to the point of aligning between product and engineering that we cannot have projects that are dragging and dragging and dragging. We can't keep ending in a place where this is the end of a sprint or the end of a cycle and we still can't see the end of it, 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... Also by the way, this is surfacing at the exact level. Imagine, you're the CPO, you're the CTO, and you are supposed to be answering to, "How's that work going?" And it's like, "Well, actually, we're working on it. I can just think of a couple of 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. And that feeling when you are with top leadership in the room and you don't have a good answer for where you are on something is like... Oh, it's brutal, right? And then from the CEO's perspective, it's like, "Where's the movement? We're running a business here. Really, nothing is shipping still?" This can't just keep happening. So there's some recognition somewhere either at the higher levels or within the team of, we don't want to keep dragging, we don't want to keep being lost in the weeds, and then this can be the activation energy. You gather the power to be like, "Okay, we actually want to try something different." And in that case, what I would say is what usually works best is, okay, we're going to try a pilot project, and what we want to do is, as you said, choose a problem that's important enough to all of us that we think it's meaningful, it's going to be worth 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 three week thing for the first time. What's important is just matching these things together. 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, and it's big enough that it's going to feel like we really achieved something. 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 getting to a place where 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? , I don't know. And then getting to a place where 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, and that's another real life thing, is sometimes we talk about if... On the one hand there's this universe 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. Do you know what I mean? That's a little bit more the real scenario when you're actually in this aligned world of we want to ship something now. Yeah, real life constraints. That's a really helpful way of telling you how much time you have to do this. For people that are just like, "I don't know, any friends that are using this. It's like weird, this way of working. It's not a thing I hear about all the time." What can you say to them to help them be like, "Okay, I should actually give this a try. Here's how many people are using it. Here's impact that you've seen." Anything you can share that would help them get over that hump?…

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