
As the Creator of Ruby on Rails and Founder & CTO of Basecamp, David Heinemeier Hansson shares with me what he wishes he learned earlier as a leader.
We chat about empathy, illusions of disagreement, and why
Claire: Hi, everyone. Iâm Claire Lew, and Iâm the CEO of Know Your Company. Today, Iâve got a super special guest with me. Iâve got David Heinemeier Hansson who is the co-founder of Basecamp, along with the founder of Ruby on Rails, which I feel like half the internet is built on, including Know Your Company. Iâm lucky because David actually sits on our board, so weâve gotten to work pretty closely over the past few years. I know Iâve personally benefited as a CEO from a lot of your insights. Iâm excited to have you here and ask you this one question about leadership.
DHH: Awesome. I canât wait to be surprised.
Claire: Yes haha. Hopefully, itâs a question that youâre ready for. My question for you, David, is:
Whatâs something you wish you would have learned earlier as a leader?
DHH: Yes, wow, thatâs a good question. Thereâs definitely tons of things. I think one, I got exposed to, early on, from leadership training was the negative end of it. I got to see a lot of really poor leadership. I got to see a lot of poor management, and I learned a lot from that, but there werenât so many positive examples from that to draw from. I mean itâs great to learn what not to do, but itâs also sometimes good to have some idea of what works.
Claire: Yes.

DHH: I think one of the early principles I took from that was just like, oh, I experienced all these bad leadership moments where Iâm like, âAt least Iâm not going to do that.â Let me just try to be more authentic in the way that Iâm acting as a leader, which means how would I like to be treated, right?
Claire: Mm-hmm
DHH: That was where a lot of it got driven forward. I just got it going in that group and thinking like, âWell, at least if Iâm acting in ways where if I was on the other side of the table, I would feel good about it.â Thatâs good, right? I think that goes a long way. That goes, I donât know, half the way maybe, right?
Claire: Yes.
DHH: Then, the other half of the way is then realizing not everyone is like you. Not everyone would react the same way as you would in a certain situation. So you can feel like what we put in forward or what weâre talking about, âIâm being fair. Iâm being on top of it, of whatever because Iâm putting myself on the other side.â
But Iâm putting myself on the other side. Iâm not putting the person necessarily that Iâm talking to on the other side.
I think that, that was probably one of the things that I had to just learn. To see that there are different reactions, that I could propose things or talk to people in a certain way or try to inspire people in a certain way that I knew I would have reacted well to just through the experiences that Iâve had. Then, it didnât work for whatever reason because the person on the other end of this was not me. It was someone else. They had different sensibilities. They had different things that they responded well to. I think sometimes, early on at least, that led to some frustration like, âWhy canât you just get it?â
Claire: Like, âThis should work.â
DHH: Exactly. This should have worked. I donât feel like Iâm being unreasonable. I donât feel like it, because again, Iâm putting myself on the other side. Iâm trying to be empathetic to my own mirror image, which is not actually a very good definition of empathy. You should get into the other personâs shoes, right. Iâm trying to get into my own role somewhere else, which, I think, is one good influence, but itâs certainly not the only one.
Claire: Right.
DHH: Having just to picking up more on whoâs on the other side and picking up on that, itâs not just like someone is not me. Itâs that, that person is different from another person. Itâs different from another person. The way you talk to people, the way you try to motivate them, the way you try to inspire them, theyâre going to be different. Even within the large group of people that are not me.Thereâs all these other individuals.
It sounds to obvious, but I think itâs harder to summarize in just an essay here or single thing or just like, âOh, you should do things this way.â For then some number of people who respond well to that avenue, thatâs going to be totally the right thing, and thereâs just the people who donât. In some cases, itâs like the exact opposite that works for one group of people that doesnât work for another group of people.
Claire: Totally. I think itâs so interesting because to your point of it sounding obvious, treat people the way you would like to be treated, right? Oh, duh, so obvious, and yet, itâs absolutely not because your point is it takes some nuance and awareness to realize that, âOkay, every person isnât like me. They donât have the same experiences, tendencies, personality.â I think, I mean personally, when Iâm thinking about running Know Your Company, it can be hard to feel that way because youâre in your own bubble of things.
I mean for you, personally, was there a moment that happened in the past, 10, 15 years since youâre running Basecamp where it stared you in the face? Youâre like, âOh, wow. I think Iâm putting myself on the other side and not actually thinking about them and not me.â
DHH: Yes, Iâm trying to think of a specific scenario.
Claire: Yes, go ahead.

DHH: Iâm trying to think of specific characteristics. I have a high sense of urgency. One of the things that help in this is to get a vocabulary to talk about personality differences and traits and leanings. We did, at Basecamp a while back⌠I donât know what it was called. They never called personality test or whatever, right? Thatâs another thing. Itâs an assessmentâŚ
Claire: Is it a StrengthsFinder thing?
DHH: Yes! StrengthsFinder is one of them, and weâve done another. We used to have an assessment we did with new hires that was even more in-depth than strengths finder, but letâs just say StrengthsFinder, for example, right?
Claire: Okay, cool. Yes, the StrengthsFinder.
DHH: Yes, so StrengthsFinder, that I have a high level of urgency. I then have a lower score on thoroughness, and those things are frequently in conflict. There are other people in the company that have relatively low levels of urgency and very high levels of thoroughness. They really want to make sure that all the Is are dotted and Tâs striped or whatever thatâs called or something. Sometimes, thereâs a tension there, right? I do get a problem or I do get a project and go like, âWe could ship this in two weeks.â They go like, âUhhh, what are you talking about?â
Claire: No, no, no.
DHH: No.
Claire: No way.
DHH: Itâs not because weâre looking at things differently in the sense of how much hourly input in there needs to be. When I think of, âWe can ship this in two weeks,â Iâm not thinking, âOh, we could ship this in two weeks if we work 120 hours and weekends and whatever.â Iâm thinking, âWe could ship this in two weeks because I will cut this corner, that corner and this corner.â Iâll end up with a smaller problem that I need to solve in two weeks that I can solve that in 40 hours a week. Versus there are other people in the company who have a much higher level of thoroughness that will think through all these other, âWell, what about this edge case? What about that edge case? What about this edge case,â right?
Claire: Yes.
DHH: Those edge cases are totally valid. Itâs just in many cases, Iâm just willing to trade off. Thatâs like, âAh, letâs just launch and see what happens,â because when we launch, it might not be worth it at all. Then, you could have solved all those edge cases for something that just isnât done. It doesnât go anywhere, right?
I think even between Jason (my co-founder at Basecamp) and I, we often have some of this tension because we have different sensibilities around these. Jason happens to have also have a very high level of urgency, so there, we have some common denominator thing.
Claire: Okay, alignment, yes.
DHH: We have other sensibilities around experiments and how far or how much to invest upfront in experiment. I have a very relatively low tolerance. I want to put in the least amount I can to just get a trial going, and Jasonâs offering more like, âNo, that wonât be a proper trial. You have to round it up more. You have to spend more time on it. Otherwise, you wonât get a viable result.â
Thereâs just all these inherent traits of thoroughness or urgency that are intentions. You can often come into these illusions of disagreement or of tension or whatever because people are coming from different angles.
When I say like, âOh, we could ship this in two weeks,â and someone goes , âWhat the fuck are you talking about? No, no, we couldnât do that.â Weâre just not talking about the same thing. Youâre talking about a version of the project that is embellished in all sorts of ways, to deal with all these edge cases. Itâs completely reasonable to talk about that. Iâm talking about the version that I have in my head that has half of it cut off and two-thirds of it just stopped out to get something out there.
Thatâs just one example of something where you can get into conflict or tension or miss each other because youâre coming at it from different angles. The way that Iâm posting things, Iâm trying to talk to myself, because thatâs the first bar to clear anything. Most people donât even clear that bar, right? Theyâre not treating others like they would be wanted to be treated themselves. But if you clear that bar, then, the next level is well, you have to treat others like they would want to be treated.
Not just like how you would want to be treated, which requires all that additional level of empathy and insight into, âWho are they? What are their strengths? What are their sensibilities? What do they respond to?â Once you unlock that, itâs just, everything becomes a lot easier.
I mean itâs not even once youâve unlocked that because youâll never truly unlock that. But at least if youâre trying, youâre making an effort to understand who the recipient is.
Claire: Yes, absolutely.
DHH: Itâs funny because I frequently have just internal tension with that like in my writing. You would think some writers think like, âOh, think about the reader and what would they likeâ⌠I never do that. The only way I can write in a productive manner is to think about myself on the other side.
Claire: Write for yourself.
DHH: What would I want to read? Again, that just tops out at some level. Iâm sure thatâs restrictive in some levels, and there are ways. Perhaps some of the messages that we have could reach broader if we were better and more capable of writing for other people, not just for ourselves. I accept that limitation in my writing. I try not to accept that limitation in leadership and management.
Claire: Sure. Well, and that was literally like the next question I wanted to ask when you brought this topic up. Because I completely agree that I think as a leader, there is almost, sometimes, this fine line between wanting to push the company forward and lead your team and inspire folks in a way where itâs catering very much to the individual taste and preferences of every employee. Is there a line too where you shouldnât do that or canât do that, or in a case of you canât make everyone in the company happy, right, or where you canât fulfill every person and present something in a way where every person whoâââwhether theyâre more thorough or they have a great sense of urgencyâââare going to feel good. How do you find, straddle that line?

DHH: Yes, I think itâs one of the things like the math between two points is relatively simple. Then, you add a third or fourth point, and itâs completely ugly and un-understandable. Iâve not even solved a point-to-point part of the puzzle yet, so I donât try to necessarily solve the 34-point part of the puzzle.
I mostly use this technique when Iâm dealing with people in one-on-ones or in direct approach to developing people. When it comes to broader initiatives on the company level on what weâre doing or whatever, itâs there, but not as prominent. Because then, Jason and I have a tendency. We fall back to like, âAll right. Thereâs two people thatâs there.â Thereâs Jason. Thereâs me, and we have different sensibilities. We know that thereâs some overlap. If between the two of us, we can just have a general understanding and have somewhat of an idea or like how this other oneâs to be perceived, thatâs the best that weâre at. Which is why this is constantly like a curve.
I think that this is also one of those things where it helps to have a somewhat stable company. A lot of the people at Basecamp, weâve been working with for many, many years. We have several people who have worked here for more than a decade. We have tons of people work here for five years and more. You get to you have a better shot at understanding peopleâs preferences and strengths and reactions, anticipate their reactions once youâve worked for them for a longer period of time. I think thatâs one of the ways that having a stable workforce really works into your favor.
Itâs one of those things though, on the other hand, that can throw you off when you then have someone new joining the company. You donât fully understand what they respond well to. Itâs pretty easy to misstep. Thatâs, to some extent, just what it is, like the way you learn about another person is that you misstep and you gauged reactions. You see how well the approach you thought was working doesnât. Then, you calibrate, and then, you try again. At least just being aware of that, itâs a big step forward.
Claire: Absolutely. As you try to keep this in mind and like you were saying, you clear this first bar of, âOkay, I think Iâm treating people how I would like to be treated.â
DHH: Yes.
Claire: Then, you go perch at that second bar, and okay, well, how would they like to be treated? How do you, in your head or in one-on-one interactions or as you and Jason think about how you also present information to the company? Right now, youâve got the all-company meet-up going on right now. How do you try to bake that into how you operate as a leader, David?
DHH: I find it hard to do two explicitly at a conscious level that this calibration become part of the gut reaction system. I think though weâve gone better at that in the sense of letâs say thereâs some announcement we want to make to the company, that first of all, we read it for ourselves and clear that first bar, what I would like to be spoken to in this manner? Weâre like, âOkay, cool.â Hey, letâs think about all the ways this could be interpreted in different ways. People sometimes call this the devilâs advocate or whatever. I just try to misinterpret anything that if we try to put it out there and schemes we put in place.
For example, one of the more, the bigger changes we made on the personnelâs side of things where a couple of years ago, we went to a new salary, pay system. We used to have what most people or what a lot of companies do, which is very individualized. Everyone negotiate, somewhat, their own salary. No two people at the company had the same salary. We just found, for us, that, that was not working well.
I felt like I wasnât treating the company the way I would want to be treated because I felt just a deep sense of unfairness about that. People joined at different times. They ended up with different salaries, even though those different salaries doesnât always match their differences in the scale of experiences. I just felt like, âHey,â I thought through it as in like, âIf the payroll was public, would I be embarrassed about that?â In the few instances, we ended up feeling, âYes, we would.â Then, we went through this whole process of thinking like, âOkay. What are we going to do about that?â
First thing was what is the market actually? We often say like, âOh, yes. I think weâre paying like in market,â but we didnât know. We just had this anecdotal information about someone said, âThis person over at this company is being paid so much.â Thatâs just not a very rigorous way of dealing with something so important as pay.
We went and like, âWell, letâs hire a company.â We ended up using Radford, which is a service that surveys a bunch of different technology companies and just take you through the whole process of what did we want to pay people? We hadnât even thought that up. It just happened. We made it a lot more rigorous about it, which ended that at some point, we had to communicate that like, âHey, we switching from a system business, ad hoc system thatâs not very rigorous and may well be and was unfair in some instances. Weâre switching to this new system where everyone is going to be paid the same if they have the same level of experience and skills and work in the same position.â Thatâs a pretty big change.
Claire: Itâs sensitive.
DHH: Itâs very sensitive, right?
Claire: Itâs sensitive. Itâs about money.
DHH: Thankfully, in our instance, weâve had a way of doing it where we didnât have to decrease anyoneâs pay. The only factual change was for that a bunch of people got a big raise.
Claire: Nice.

DHH: Thatâs what you say, right, like, âNice. That sounds nice,â but thereâs all sorts of things that are actually not so nice about it.
Claire: Oh, okay, yes.
DHH: One of the case studies we looked at was thereâs this guy in, I think, Seattle or something running a payment processing company who said like, âWeâre going to pay everyone $70,000. Thatâs going to be the floor.â You ever read something about like, âOh, at $70,000, money stopped being a factor and happiness doesnât increase.â
Claire: Thatâs the threshold, yes.
DHH: Thatâs the threshold, so you want to pay everyone $70,000. He got an incredible amount of awesome feedback and some negative feedback from the outside, right? Youâd think within that company, isnât that only good?
Claire: Okay. Thatâs what I would think, yes.
DHH: Exactly. It turned it wasnât, necessarily. What the floor meant was there was a bunch of people who are, I donât know, making $30,000, $40,000 who got a big raise. Then, there were people making $105,000 who got no raise. They got to see all these people who, they felt for whatever reason, that before, there was a split. Maybe they felt that they were being paid $105,000 because had a law degree or they had long experiences or something else, that there was a relative fix between precisions that felt reasonable. All of a sudden, that relative fix got erased, right? A bunch of people, apparently, ended up leaving because they were not happy with that at all. You go like, âHoly shit. Thatâs fascinating.â
Youâre doing a supposedly just universally good thing by raising the floor, but it has all these secondary effects. That story definitely left the mark. Not in the particulars, just in the fact that clearly, the guy who was CEO and wanted to raise everyoneâs salary did not anticipate that.
Claire: Yes, and he had the best of intentions, right, and wanting to cure that.
DHH: Yes, and I think thatâs really where this is important because I think most business leaders would think in most cases, that they have the best intentions. You know what? Best intentions are just not good enough. Best intentionsâââeveryone says they have the best intentions.
Best intention is bullshit. What matters is outcomes, right, and whether youâre taking actually steps to anticipate those outcomes and mitigate those outcomes the best you can and just think through that whole thing.
When we went through this payment shift or pay adjustment process, that was one of the big things like, âAll right. Weâre going to move.â There were some people who got some very large raises, and I felt like, âThatâs great.â We wanted to set a target that we wanted to pay everyone at the top 5% or the 95 percentile of the industry, based on Chicago or better rates. In some cases, we were just off on that, right? We were catching up, but still. These were some of the things we thought through. Then, we thought through all the ways. We wrote up the announcement.
Then, we tried to just poke holes on it from like, âOh, if Iâm a person like this whoâs sitting in this position where I, for example, do not get a raise, am I going to read this and go like, âWhat a jip. Everyone else fucking got a sack of money, and I didnât get anything?ââ Thatâs one of the strategies we tried to use to get broader perspectives. Again, these are like weâre role-playing, so itâs a pretty inaccurate science, right?
Claire: Of course. Itâs not science.

DHH: Exactly, itâs not science. Thereâs a bunch of things, through the reactions to all sorts of things where we went after whatâs like, âOh, holy shit. I totally couldnât of thought that.â I donât have a vivid enough imagination to imagine other people sufficiently different from me, and their reaction is different from me. Then, in almost all cases, you can still back-trace and then go like, âAll right. I actually understand where thatâs coming from.â
Claire: Right. I think that was such an incredible insight. I mean personally, I find that such an important reminder that yes, your best intentions are not good enough as an employer, as a leader. Itâs not. Itâs what you do, right?
DHH: It is what goes into that consideration. Most peopleâs best intentions just go from there, like little heads, but maybe they cleared the bar on how they wanted to be treated themselves. I think oftentimes, they donât think clear of some romanticized version of what they would have done themselves in that situation, which is just a pretty poor gauge of whether this is good and not good. Your gauge is, âWhat is the reaction?â
Claire: Exactly, yes. Your gauge is, âWhat is the reaction?â Iâll be definitely keeping that in mind, David.
DHH: Cool.
Claire: Thanks so much for your time.
DHH: Yes, thanks for having me.
Claire: I know everyone whoâs watching this, yes, appreciates it.
DHH: This was fun.
Claire: Cool. Thanks so much.
DHH: Thanks!