SEASON 2 - EPISODE 111 - MAY 29, 2024

The Subtle Art of Staying Out of It

In this episode, REWORK host Kimberly Rhodes, talks with Jason Fried and David Heinemeier Hansson, co-founders of 37signals, about the importance of stepping out of the day-to-day operations as a founder. Giving employees room to call the shots can spark new ideas and get things done faster. It also inspires people to think beyond just following orders.

Watch the full video episode on YouTube

Key Takeaways

00:34 - The result of holding your grip too tight in your organization.
02:36 - Find the middle ground between projects you should be directly involved in and those that can be managed by others.
08:38 - Giving employees the freedom to make decisions can lead to increased productivity and better ideas.
10:20 - Stepping in when it’s necessary to realign urgency or quality.
12:54 - Not all opinions weigh the same.
15:28 - Trying to be involved in every task or decision reduces the organization’s effectiveness.
22:48 - Intent prompts people to think independently instead of just following a set of instructions, as described in the book Turn the Ship Around.

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, and I’m joined as always by the co-founders of 37signals, Jason Fried and David Heinemeier Hansson. A few weeks ago on LinkedIn, Jason wrote a post about the Subtle Art of Staying Out Of It and he said he’s quote, “been practicing the subtle art of staying out of it for a few years.” So let’s talk about it. Jason, do you want to get us started? I’m sure there’s a fine line between jumping in and having opinions on everything running in your company versus letting things happen. Kind of talk us through this.

Jason (00:35): Yeah, it’s subtle, which is the point. You can definitely stay too far out of it, but I’ll start with a little story that just kind of hit me actually a couple days ago. I’ve been learning how to play drums again. I bought a drum set and the same thing happened to me when I learned how to try to learn how to play guitar. I say try because I’m not good at either, but is, especially with drums, is that you tend, as someone who’s new, you tend to grip the stick really hard. And the same thing is true when you’re playing guitar. You tend to hold the neck too hard. You’re too tense. You are literally gripping this thing and when you grip it, a lot of bad things happen. You get fatigued quicker, you don’t have as much actual control. You feel like you do because you’re gripping it so hard.

(01:17): You feel like you’re fully in control, but you actually, you can’t articulate the stick as much. You can’t do as much. You don’t get the same feel, you don’t get the same sound. This kind of one note, and this is a weird parallel, but it is sticking with me to some degree, sorry for the stick pun there I guess. But this feeling that if you grip something too tight, you don’t get as much out of it and actually you can’t do it as long and you can’t do it as well and you don’t have as many degrees of freedom. So I think that in some ways is sort of what I’m trying to get at here, which is that especially in the early days when it’s just two or three or four of you, you are involved in everything because you have to be. But as you grow a company, as you hire other people, as you try to grow other people, as other people grow for themselves, you’ve got to let up on your grip a little bit, I think, to allow other people to flourish and to have more degrees of freedom inside the organization.

(02:10): Otherwise everything’s going to keep always falling back to you, waiting for you to make the decision. People are going to be afraid to make their own decisions. So that’s sort of the metaphor I’ve been thinking about lately is just loosening up on the stick, loosening up on the grip a little bit, and that’s equivalent to sort of this subtle art of staying out of it when you need to.

David (02:29): I think it relates really well to building a more resilient organization. As Jason says, you can suck up a lot of oxygen in the room if you as a founder or an executive step into every conversation and want to referee it, it’s not even just making the decisions. Just your presence in a conversation in a thread is going to change the nature of that thread and people are going to be more likely to delegate to you and like, alright, well this senior person is in the room, they’re going to make the choice. And you are just not going to get the kind of decisions that someone’s going to learn from nearly as well through that. Not that you can’t learn from other people’s decisions, you certainly can, but you probably learn more from your own decisions, particularly if you’re allowed to make some mistakes. And I think this is where the subtle art comes in.

(03:17): What are the kinds of decisions that you are okay failing and that’s even too overstated. Okay being slightly different than what you would’ve preferred in some ideal world where you made all the choices. Looking at a spectrum of decisions and inside of a company like our company that’s close to 70 people, there’s probably hundreds of decisions every single day that you potentially could be a part of. You could potentially referee, first of all, you’d go crazy, you’d drive everyone else crazy, it would not be sustainable in any way. So you have to pick any way. There’s a hundred daily decisions, how many can you weigh in on? Maybe in a very tight grip you’re weighing in on 25. What would happen if you weighed in on 10 or five or two or none that day or that week or that month? Would the whole thing fall apart?

(04:10): If so, that should be telling you something. You know what, this is not a resilient organization. If I step out of it, I don’t make all these decisions, like the whole thing is just going to not run well. But as Jason said, I also think you can do the other thing. I’ve seen that too. Twitter for years was kind of the poster child of the absentee leadership organization. You had this large organization, a bunch of people being busy showing up, well busy or not busy. Some of these tiktoks and the day in the life of a project manager at TikTok or at Twitter was hall of fame cringe, what the fuck are you doing stuff. But let’s just assume that there were a bunch of people working on a bunch of stuff and it didn’t kind of go right, it didn’t go in some direction that moved the thing forward when you look back upon the year.

(04:58): So there’s some place in between those things where you’re like, you’re never there. No one is ever injecting the major risk that usually has to come from founders or executives or you’re there in all the stuff all the time and no one but you can make any decisions. There’s a sweet spot in there in between. And I think, I remember when Jason first wrote about this, I really went like, oh, do you know what? That’s a really good point. I got to literally step out of some rooms that I actually feel like I have something to add to. There’s more being added by me not being there.

Jason (05:30): And by the way, to get back to the stick metaphor for a second to that point, there’s a place, it’s very subtle where with the drumstick, at least if your grip is not tight enough, it’ll just fly out of your hands. And that’s the problem David’s talking about, which is if it flies out of your hands, you’ve sort of your absentee. And so you’ve got to find that middle ground. But it’s counterintuitive because I think a lot of entrepreneurs especially feel like they need to have a tight grip on everything. If I go out of town, everything’s going to fall apart, then you’re a shitty founder. If you can’t leave your own organization, you’ve built a terrible organization. It can’t just be you.

David (06:07): And I think that’s one of the reasons why I really enjoy the fact that we embrace not working 80 hours a week, embrace having vacations, embrace having sabbaticals. When I first moved to Denmark in 2020, I took seven weeks off I think it was. Probably the longest stretch of uninterrupted time away from the company that I’d had in maybe ever, and came back after that and went, do you know what? I’m really pleased with that. I’m really pleased with being able to step away for seven weeks and seeing a bunch of good work happen, a bunch of people just taking initiatives, filling in and so forth. And I think teaching the organization that it’s self sufficient, that it doesn’t have this learned helplessness that we can’t do anything unless the top boss is there, is just really empowering and it’s more fun for all involved. I think it’s even more fun for the kind of person who do like to be involved in a lot of things.

(07:08): I like to be in a lot of things because I care about a lot of decisions. I care about a lot of the tech. I care about a lot of the things. That’s great. But also sometimes it’s great just to pull the plug, two weeks or seven weeks and then come back and go, do you know what this is kind of like? I dunno if it’s an odd metaphor, an orchard, right? You plant a few seeds and you go like, oh, okay. And then you come back three years later as in our case we literally planted some seeds for some fruit trees and there’s all these lemons. They’re delicious. How did that happen? Oh, well it happened because three years ago you planted some seeds and then there was some watering and all the things came together. You weren’t there micromanaging that seed all every day we got to cut this little leaf and we got to just add this little nutrient. No, no, no. You just let things be for a while and that in itself can be the nutrient, especially for an organization simply just the step away.

Kimberly (08:02): Well, it sounds like taking the step of stepping away is a conscious decision. I want to go to this question that someone posted on a YouTube video. It was a clip from a previous podcast episode talking about letting employees make some of their own decisions. And someone wrote in and said, I’d like to hear Jason’s take on when to take a risk on not overriding potentially small mistakes versus how to make the call to override a potentially big mistake. It says Jason, but David, feel free to chime in as well. How do you know when it’s time to step in to prevent something bad from happening versus letting it go?

Jason (08:38): Well, I think first of all, you don’t really know if something’s going to be great idea or bad idea anyway until it happens. So part of this is a bit of humility going, well, if I suggest this, it’s going to be better than what they suggested. Now in some cases you might have the experience, you might have the insight and the fortitude to figure out that this is actually a better decision, but it also may not matter that much. And by stepping in and making the better decision, you’ve actually cut off something else from someone else, which is their willingness to step up and make a decision. Now they’re going to wait for you to make the decisions next time. So it’s almost like in many cases the outcome probably doesn’t matter as much. Sometimes it does, sometimes it doesn’t. I can’t really give you specifics there, but there is a trade off and there is a cost to you making the call that didn’t need you to make the call.

(09:28): And that is that this other person now feels like they can’t make the call. They weren’t given the latitude to make the call. They weren’t trusted enough to make the call. And so you made this stupid decision that didn’t matter anyway, but you took it away from someone else. That is a pretty big deal and can have pretty large negative downsides there. So that’s how I think about it more so than I know the right way and their way is the wrong way. I mean there are some calls where you’re going to make some of those, but most of them don’t matter as much as you think on the upside. But they matter a lot on the downside. And so be careful is what I would suggest people do.

Kimberly (10:07): It kind of sounds like it’s kind of crossing over into the line of when are you micromanaging versus not.

David (10:14): I think micromanagement is one way of looking at it. Another way is who’s the guardian for quality? And that is usually the part where I feel like there is a line somewhere. It’s fuzzy because as Jason says, sometimes your perception of quality is one of those moments where it doesn’t matter and other times it kind of sort of does. And the dynamics I’ve found sometimes where stepping in as a founder and executive to just realign either urgency or quality. Those are usually the two barometers where this is just taking too long. Someone might be making the decisions, but we got to speed it up. It’s not running at the right clock frequence, so maybe you need to make more mistakes, but you got to make 'em faster. We can’t spend another six weeks on getting this little part of the way. If we’re going to spend another six week of this, we got to get this part of the way.

(11:06): So setting those boundaries of like, alright, so you get to make the decision but it’s within this scope, you figure out how to do it, but by six weeks you got to have something and it’s got to be good. I think the few times where I felt like I wanted to sit back and then didn’t was this feeling of we’re going to ship something that’s not good enough. The bar here is for whatever reason on this particular thing, has been allowed to slip to a point where people sometimes just like, I want to ship. I want to get it off. I want to do another thing next cycle. I would do something else. Let’s just get it out there. And sometimes you’re literally the only one left going like, no, wait a minute, no, that’s not good enough. Let’s rather can it, one example I remember was we worked on this sidebar concept for Basecamp where you had this particle come in that was kind of yours and navigation and so forth.

(11:57): And we had worked on it for quite a while and then we had given it even more time and the people who were on it were obviously eager to ship. When you already have something that feels late and then you put more into it, then you were even more eager to ship and it had to not ship because it wasn’t good enough. But that decision is a difficult one in a lot of cases for employees who haven’t gotten used to making those kind of decisions to make because it’s sort of one of those sunk cost things. Well, we’ve already spent eight weeks, if I say now we shouldn’t ship, am I responsible for squandered the eight weeks? Where does that line go?

Kimberly (12:34): Yeah. So my question, David, from a technical perspective, I would imagine, I don’t know, I think about the design side and so much of it is subjective. I’m assuming on the tech side it is less subjective and there’s either a right or a wrong. So maybe you would want to step in more or is that not true?

David (12:54): I don’t think that’s true. I think it’s actually quite similar. Most technical problems can be solved in about a thousand different ways and a lot of the distinction between which way is better or not just have some subjective quality to it. But subjective is a really interesting term because subjective kind of implies that it’s all the same, just different preferences. That’s not what subjective means to me. Subjective to me means an individual’s gut is making those decisions. All guts are not trained equally. Someone who has been working for three years will have a very modestly trained gut. Someone who’s worked for 15 years will have a very distinctly trained gut. That doesn’t mean the more training is always better, it just means they’ve seen more things, they’ve been in more situations and their subjective analysis is probably worth more, not in every situation, but in most situations by default that person is going to have more experience as long as that experience is kind of marinated in competence.

(13:54): There’s plenty of people who’ve worked the same year 10 times, they’ve had 10 years of experience, but it’s the same year repeated. But if you’re doing your career well, let’s put it like that, you’re not repeating the same year. So 10 years is worth more than one year. And I think that we got to pull subjective out of, it’s like it’s all the same. It’s just your preference. That’s not what that word should mean. It should mean, hey, it’s grounded in an individual’s perspective, but those perspectives are not equal. And it is sometimes I can imagine, well, I can not even imagine. I know that it is frustrating when I for example, step in on a project and go like, this is not good enough and I’m saying it’s not good enough on the basis of my perspective and so on. Someone else who doesn’t have that will go, why is it not good enough?

(14:43): This looks fine to me. And I go like, no. One of the reasons I’ve been talking about lately is aesthetics. Sometimes people will come up with a solution that works. Customers will be none the wiser. Whether we ship this that is right now or we ship something else that I find very aesthetically pleasing. But that’s part of that quality bar. We are not just in the business of shipping software, we’re in the business of making good software that I want to look at again in three years because we’ve been around for 20. If every single time we had to, let’s just ship it, it’s good enough. We’d end up with a ball of mud that’s Basecamp and we wouldn’t want to work on it anymore. So that’s a lot of here, there and everywhere.

Kimberly (15:26): So my question is, Jason, you’d mentioned early on when you first started, when the team was much smaller, you felt like you needed to be more in it in the day to day. Was there a tipping point for someone who’s listening and thinking like, I’m building this business. At what point can I step more away and have the team run it? Was there a point for you guys?

Jason (15:48): I don’t remember exactly the point, but it’s a gradual release of, I mean you just simply can’t handle it all. I would say you probably are making some bad decisions because you’re jumping back and forth making them too quickly trying to decide on too many things and you’re not giving certain things deliberation that they need. And I dunno, to me it’s just a feeling. It’s also probably one of the best things. Again, like David was saying, and I’ve done the same thing, not for seven weeks, but I took six weeks off and you just realize I don’t need to be involved in all these things that I thought I needed to be involved with. But there is definitely a size where if you feel like you’re a bottleneck, I would say this is another place. If you feel like you’re a bottleneck, you probably are. And you don’t want to have any bottlenecks in your company, certainly not you. You’re probably the worst one to have too, because billion things can happen. You can hit by a bus, whatever. If you are the most important bottleneck in the business, your business is a bit in trouble, pretty risky, pretty flimsy actually all things considered. So I guess that’s how I would answer that question.

David (16:53): Yeah, I think there’s a tipping point when your organization’s capable of doing more things than you can keep in your head at one time. You simply cannot be involved with all the things at a level of quality of involvement that makes sense and adds value. And I think that level is probably, I don’t know, three things. You can be really involved in like three things, maybe four if you’re stretching it by the time you add a fifth thing to pay partial attention to, that’s getting a very thin slice of your attention bandwidth. And that’s the time where, alright, so this project can either have me very heavily involved with 10% of my attention or it could have a hundred percent of someone else’s attention to it. Are you literally 10 times better than that person at making these kinds of decisions? Maybe you are, maybe you’re not.

(17:45): And I think the more of that, I mean I sometimes marvel when I look at the daily recaps I get from Basecamp one every day I get all the activity that’s in all the projects that I have access to and I go like, holy smokes, are we just moving on so many things, so many decisions, so many problems, issues, features. At the same time I’m like I can’t keep even a thin sliver of this in my working memory. I can keep, I don’t know, 2%, 5% of that. First of all, I better pick, well if I’m going to be worth something here, I got to pick the 5% of all the stuff that’s going on that can really benefit from me being involved. And then realize that the other 95%, you should just lean back and marvel at the fact that you have an organization that can do that.

Kimberly (18:36): Jason, in your writeup, one of the things that I love that you said said quote, this means getting used to being okay with decisions I wouldn’t have made or designs I wouldn’t have drawn up or provisions I wouldn’t necessarily have put into place. I would imagine when you found a company and you started being okay with some of those things is a challenge, was that ever a challenge for you guys or letting go was no big deal?

Jason (19:00): Yeah, I would say, well, when I was doing all the design, you’re naturally making all the decisions, but I’ll give you a quick example. I’m working on this new Once product right now. I sketched up an idea for JZ, who’s one of our designers on how I thought this particular interaction should go. We looked at it early on that way. He built it that way. I kind of liked it. I went away and didn’t pay attention for a few weeks and I asked to take a look at where we’re at last week or whatever it was, and we walked through it and it totally changed. And actually it’s better. It’s better. What he did was better, it was simpler, it’s more direct. We had this general idea that we should make things more direct, like fewer things that are sort of hidden behind this and hidden behind that.

(19:40): And he took that to heart and moved this thing out of this thing. Even though I was really proud of this little thing we all were, it’s like, you know what? It wasn’t worth it. He moved it up there to be more in harmony with the other fundamental decisions about making things more visible. And I’m glad he didn’t ask me about it. I’m glad he just did it because then I saw it. I go, yeah, that’s better. I think would he have asked me or had he have asked me, I probably would’ve tried to talk him out of it because I was so enthralled with the previous decision we made and the fact that we already did it, but it’s better. So it’s sort of a roundabout way of, it’s a specific example of I’m glad that I wasn’t even involved in that decision. And I love seeing people make decisions like that where something comes out the other end, you’re like, that’s actually better or more coherent or whatever than I would’ve made. Now this decision, this is one of those examples where it probably didn’t matter anyway, but it’s not going to make or break anything.

(20:43): But it is better because it’s more in line with the general direction we’re heading with other things and that makes it more coherent. And here I am repeating myself and talking about coherence. But anyway, that’s an example of I’m glad I wasn’t there. I’m glad I didn’t ask me.

David (21:04): And I think that’s really a good example because you mentioned several weeks and I think or part of the time, the problem with partial involvement is that you’re still tethered to the thing, alright? You’re not paying a hundred percent attention to an all time, but if you’re constantly there on a regular basis to do it, that presence is just going to suck on a lot of oxygen. What I’ve found is, and I think Jason, you’re better than this than I am. I am more binary in my involvement that if I get involved with something, it’s very difficult for me to just do the 20%. There’s a tipping point for me personally where I go like, all right, I’m all in a hundred percent. Like Campfire, when we were launching that for a long time, I was like, all right, I’m going to sit back, I’m going to sit back, I’m going to lean back and then lemme just look at this one little thing and then it pulls me in and then suddenly I’m bomb all in and then it does end up being a little all consuming.

(22:01): I really enjoyed that experience and I hope that the product benefited from it and the people learned on something from it. But now we’re working on the ones product number two and I’ve really gone, do you know what? I don’t want to do that one again. Here’s particularly one person, Kevin, who I’ve been working with on the one-to-one, he got a front row seat to the full a hundred percent engagement, setting the tone, this is where we’re going to go. Do you know what? I think that’s enough of an injection of me into that process. So now Kevin can really run with it on the Once two thing and then I have to have the disciplines to go, do you know what? I shouldn’t even open it. Not for right now. I’ll open it in a bit. I can’t open it right now. If I open it, it’s going, I’m going to get sucked right in.

Jason (22:49): Another example of this is this podcast. So you come up with the topics we’re going to talk about. You don’t ask David and I what topics we’re going to talk about next show you post something in Basecamp of course, and we’re up to speed, but you come up with that stuff, we could definitely say before you officially make the call, run it by us first and we’ll review it and we’ll go back and forth. But it’s better that we don’t do that. So I think that’s just another example of that. It’s not like a specific example we sat down and decided how this was going to be, you just ran with it. And that’s the kind of stuff I love to see.

David (23:25): It reminds me of the book, Turn The Ship Around, which is really one of my top three favorite business books of all time. We talked about Blue Ocean Strategy a lot. I don’t think we’ve talked enough about Turn to Ship Around.

Kimberly (23:37): I don’t think we’ve talked about it at all.

David (23:39): Turn the Ship Around is basically premised on this exact concept that you will let people in your organizations, on your ship decide what should happen because they probably sit with the most information. They’re going to say, I intend to. That’s the phrasing on the nuclear sub, which this principle has been derived from. It’s like pretty high stakes, right? I intend to fight the torpedo, sir. Alright, you better have the right information and I have to have a large degree of trust for you to make that call. But that intention statement provides that opportunity that the more senior, the CO, I think it’s called on a sub can go like no, can override, but the default is no override.

(24:22): The default is you’re just picking the topics. If you pick a topic that either Jason or I go like, no, I don’t think that’s going to be good, I don’t want to talk about that. You put it out there and we can say like, no, but how often does that happen? One time out of a hundred shows or something like that, if even that. And I think as a general principle in the organization, the I intend to, and then you just go, unless someone stops you, you go, you default to trusting your own fingers and someone else, someone senior, someone, a colleague can step in at some point and go like, eh, but it usually doesn’t happen and your fingers will get better. This is the more you intend to and then follow through on it. The more you learn from that, the quicker the feedback cycle was. This is what Turn the Ship Around is about. It’s about taking the worst performing nuclear submarine in the entire US Navy and turning it into the best submarine in the US Navy by that form of management. It’s a really good book.

Jason (25:19): Some additional color on that too is traditionally someone would go to the CO or whatever and say, may I turn the ship five degrees or whatever. And so that was the traditional way, you’d ask and then they would confirm, so you’d ask for the order and they would grant it essentially something like this. And so he basically said, this is L. David Marquette I think was the guy’s name. He said, I want you to come to me with intention. I intend to turn the ship five degrees. And what’s loaded into that is like, this is going to happen. You have to think about it. You’ve had to think about it in a way where you understand the implications because if you just go ask and someone gives you permission, you don’t really have to think about it like I assume the other person thought about it to give me permission. So it’s a couple subtleties that make a big difference.

David (26:13): And really gives ownership over the whole decision. It’s your decision now. You’re going to turn the ship five degrees. That’s something you did. You’re on the line for it. You’re going to double check your work. You’re going to really own that burden. And one of the things we occasionally talk about is the fact that how do you find meaning in your work? And some of the meaning you find in your work is being responsible, is that it’s on you. That meaningful burden of I’m making the intention, I’m making the call here, it’s my ass on the line, if you will. Usually it’s not so you make a wrong decisions. Okay, well unless it’s firing the nuclear missiles at Moscow and that was the wrong decision, maybe your ass is toast. But in most situations it’s not that dire. The criticality is not that high and you have stated it as an attention, so someone else could step in if they go like, no, we really shouldn’t do this. But you get to own the decision and that just gives you more burden, more meaningfulness in your working environment. It’s not just like all out of your hands.

Kimberly (27:17): Okay, well that is a great place for us to wrap. Rework is production 37signals. You can find show notes and transcripts on our website at 37signals.com/podcast. Full video episodes are on YouTube and Twitter. 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 and we just might answer your question on an upcoming show.

The Subtle Art of Staying Out of It

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