SEASON 2 - EPISODE 150 - APRIL 16, 2025

Picking Priorities

How do you decide what to work on next, without relying on a long, stale to-do list? In this episode of The REWORK Podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson talk about why they don’t rely on lengthy roadmaps to set priorities. Instead, they focus on what makes sense now, not what seemed like a good idea months ago. They explain how working in real time leads to better decisions and thinking that fits the moment.

Watch the full video episode on YouTube

Key Takeaways

00:44 - Priorities aren’t permanent—they’re meant to shift as you learn
03:20 - Ditch the roadmap mentality in favor of real-time decision-making
07:20 - There’s a difference between winging it and planning as you go
09:10 - Why 6-week cycles give you just enough structure without locking you in

Links & Resources

Transcript

Kimberly (00:00): Welcome to REWORK, a podcast by 37signals about the better way to work and run your business. I’m your host, Kimberly Rhodes, joined by the co-founders of 37signals, Jason Fried and David Heinemeier Hansson. This week I thought we’d talk about something I know a lot of small business owners and entrepreneurs struggle with, which is how to choose what to work on first or simply picking your priorities. This is something 37signals knows a lot about as we’re building new products, working on current products, working on a new version of Shape Up, so many things going on all at the same time. So I thought we would talk a little bit about some of the ways that we choose what to work on first. Jason, I’m going to open it up to you. I know you recently wrote something about this on your HEY World and shared some news with the company so you kick it off.

Jason (00:44): Sure. So priorities. Well, I think the first thing is that they don’t need to be permanent. They’re sort of like, what do you think is important right now? And you have to commit to that because you don’t want to keep whiplashing people like back and forth, right? So you pick some things. What do you pick? You pick the best things you can based on who you have, what you want to do, what your thoughts are, what you think you can achieve. I think people probably stress too much over feeling like the things they pick, now like everything else is off the table forever, and so they freak out. This is why we typically work in six weeks cycles where we pick things to work on every six weeks, we get that done, we commit to that, we get that done, then we choose what to do next. That’s on an existing product or a new product, and so that way you don’t really worry too much about maybe picking the wrong thing.

(01:26): There isn’t really necessarily a wrong thing in that case, it’s only six weeks at a time and you sort of figure it out as you go. I think that deciding if you’re going to build a new product or commit significant resources to something, that’s a different kind of thing. I think even those are relatively flexible for most kinds of businesses like ours. Obviously if you’re Boeing or Airbus or SpaceX or one of these, that’s a different story, but when you’re making software, you don’t need to run your business as if you are a business that has to invest in factories and parts and supply chain. You can make things up as you go. You can be malleable, you can tweak as you go, feel things out, see where you’re headed and decide that when you’re into something, if maybe it doesn’t feel right or you just don’t have enough people or someone leaves and you have to change priorities, that’s okay too.

(02:09): Priorities are not permanent. That’s the important thing here. But again, you don’t want to just keep flipping back and forth, then people freak out. Then there’s uncertainty. People don’t know what to do and I don’t think you want to do that. For example, we’ve been working on two brand new products at the same time for a while now, a few months, not a while while, but for a few months and we just had someone leave and we kind of use that as a moment to reflect on can we actually pull this off with one fewer person? And we decided, no, we probably can’t. What we’re going to do is just pick one of those things that we were doing instead of do two, we’re going to do one and we’re also going to put some other resources into something else and pause something and kind of shift some things around and it feels right.

(02:48): You post that message internally and people, yeah, that makes sense. I think that’s how you know you’ve picked relatively good priority is people kind of go, yeah, actually that’s what I think we should probably be doing anyway. In fact, I thought maybe what we were doing before was we’re stretched too thin or we weren’t doing the right things or whatever it might be. And of course sometimes you’re going to make a controversial call which people have to eventually come around to, but I wouldn’t freak out about it and sit around and have months and months and months of meetings and discussions and debates about what you want to do. That’s I think the bigger insight, is you can change your mind if it’s within reason.

David (03:20): I think one of the reasons why people can have a hard time changing their mind is because there’s a sense of professionalism that comes from having a roadmap, having made decisions in a grandiose way at one point, and you set this long time table, it imparted you, you know what you’re doing and I can see where someone would get that from. When you look at the project managers who as Jason say, have to figure out how to shoot rockets to Mars, you probably have to order the whatever shimmagajing two years in advance maybe. I mean, I don’t know anything about rocket science, but I can imagine that, right? I can imagine when you’re building a skyscraper that there’s just certain planning steps that you have to get and you have to get them right early. There’s a lot of foundational work that you have to be spot on with. In software that’s not really the case.

(04:17): In fact, the opposite is the case and Jason’s written about this frequently, that when you make decisions far in advance of when you’re actually going to do the work, you know nothing. Or at best, you know a little. You know much less than you would if you make that decision as close to the point of execution. The day before you’re going to work on a feature, you know so much more about that product, about what customers want, about the current trade-offs, about who you have, about what they’re good at, than you would if you had made that decision nine months ago. Nine months ago, it’s a guess. It’s a guesswork, and I think that’s one of the reasons why we’ve tried, well, first of all, we don’t have to try. We have no intention of seeming professional. We’re not trying to impress anyone. Neither Jason nor I is sitting here in a suit. We don’t have a lot of ceremony to impress other people, so we’re free to just go with, do you know, what works best?

(05:13): And what we found repeatedly time and again, is that what works best is to make decisions about what you’re going to work on as close to when you’re going to work on it. Now, to prevent that thrashing, as Jason says, we only do it once every six to eight weeks. That’s the cycle work from Shape Up that gives a team some permanence about the next coming weeks that gives them some room to actually implement the things that you want them to be working on in a wholesome matter where they have long stretches of uninterrupted time, all of that good stuff. But there’s not this big backlog of things we have settled on will happen in cycle four of this year. Not at all. There’s the next cycle and then there’s just a bunch of fleeting, floaty ideas that are out there that maybe will make it into the next cycle.

(06:03): I often sit down and think we’re doing a cycle planning, oh, next cycle I think I want this thing, and then by the time the next cycle planning meeting rolls around, I don’t want that thing at all. I haven’t even thought about it in four weeks. This is the magic of reserving dedicated time right in advance of when you’re going to work on something and then saying, I’m not committing to anything else beyond that. Screw what looks professional, screw what customers sometimes ask for. I mean, I think that’s fair too. We’ve occasionally gotten, so what does your roadmap look like? Do you have a 12, 18, 24 month roadmap that we could take a look at? And we always go like, no, we don’t. We have what we’re going to work on next cycle. And I’m not even going to tell you that because we have a tendency of occasionally changing our minds as we work on something and we realize, you know what?

(06:53): That thing is not going to work. And every single time Jason and I have promised to customers that we’re going to deliver something X amount of time from now, we have regretted it with capital R. It’s universally been just a bad idea to commit to a roadmap because we’re committing with less information than if we’re going to do it in time, in part because very often that commitment seems almost silly.

Jason (07:20): The other thing I want to add to this is that people are always like, well, how can you just make it up as you go? Or every six weeks? I dunno, how do you make decisions? Well, we sit down and think about what we’re going to do, and I’m like, that’s what we do too. You guys just do it all at once. And you think because you do it all at once that it’s magical, but actually you just do it along the way. Again, as David was saying, closer to the moment, just do it again. Just do it again. And they’re much smaller sessions and they’re more accurate because you’d really know where you’re going to be tomorrow compared to where you thought you’d be three months prior, tomorrow. So it’s like, you can do this. You already do this. You can make it easier on yourself by not trying to guess the next year’s worth of work.

(08:03): That’s hard and there’s no reason to it. There’s no reason to do that. There’s no prize. And people are like, we set the roadmap and people know what to expect. You can still tell them what to expect just more frequently versus imagining what the next calendar year is going to look like. There’s just no really good reason. Again, unless you have a supply chain situation and vendors, and in some of those cases, those things exist. But let’s face it, if you’re making software, which most of our listeners probably are, you do not need to run a business as if you’re trying to line up a supply chain. You can make things up as you go. And it’s actually, I think, a much healthier way to do things and it’s not a scary thing and you’re still making decisions and you’re still being thoughtful and you’re still thinking things through and you get to do it more frequently, so you’re probably going to get better at it as well. There’s nothing magical about doing it all at once in the past.

Kimberly (08:50): I do think this idea of choosing priorities every six weeks is one of the biggest things that we hear from listeners, from customers that they truly don’t understand. How do you not have a looking forward in two years, here’s our big goal and plan? People are shocked. They’re shocked by it.

David (09:10): Now. I think there’s that, and then there’s also what I’ve lived under, worked under is the extreme opposite. I’m not going to commit to anything. The boss marches into my office every Monday, and he has, or she has a completely new idea of whatever we should be working on, just this constant thrashing. You have multiple things going on at the same time. No one seems to have any patience to actually stick to the decisions that they made and to see them through into shipping software. So I could also imagine someone working in that situation and going like, well, be a little careful. Don’t just give bosses who can’t commit to something for two weeks, for six weeks as we do the license just to barge in whatever half baked ideas that they have. And I think for us, that has been one of the magical things about Shape Up.

(10:02): I think both Jason and I do have this tendency that every Monday a new idea pops in our head and we get very excited about it and we want to see it put to life as quickly as possible. That urgency is part of being a founder and I think a very positive part of it. But you also need some restraint. You need some restraint where you go like, Ooh, I really want to do this, but we’re halfway through the cycle and if I then yank people off something I told them three weeks ago, A, they’re not going to be very happy. B, it’s not a very productive way to work. If you keep thrashing people between projects, they’re just going to lose time in the thrash. And C, you may very well end up not shipping anything at all. So by saying, do you know what? We’re restraining ourselves, that every little idea that pops into the head every Monday can’t get put into reality right away, but every six to eight weeks we have an opportunity. And that makes it easier. It makes it easier to go like, oh, okay, okay, I have a good idea. I’ll park it only for a little while only until the next betting table. And what we find, of course, time and again, is that the idea you were super excited about that week, three weeks from now, maybe you’re less excited or maybe not. Maybe that idea is still just like ding, ding, ding, ding, ding. I want to do this. Great, now you have the answer.

Kimberly (11:24): Okay, well with that, we’re going to wrap it up. REWORK is a production of 37 Signals. You can find show notes and transcripts on our website at 37 signals.com/podcast. Full video episodes are on YouTube, and if you have a question for Jason or David about a better way to work and run your business, leave us a voicemail at 7 0 8 6 2 8 7 8 5 0. You can also text that number or send us an email to rework@37signals.com.