LUMINARY: What were some early influences for you?
Stewart Butterfield: I was born in a little town called Lund, in British Columbia. It’s like a fishing village. My parents were hippies. They tried to live off the land, so I grew up in a log cabin, and we didn’t get running water until I was 4. The next year, we got electricity. Then we moved to the city, Victoria, British Columbia, so I could go to school.
I was pretty entrepreneurial as a kid. I had a lemonade stand. When I was 12, I arbitraged the price of 7-Eleven hot dogs; I’d buy the ones that are pre-wrapped with the bun and then sell them on the beach. When I was 14, my dad and two of his friends bought an art-house cinema. I worked the concession and figured out that it was better to take people’s orders while they were standing in line before the movie. Plus I got tips.
LUMINARY: Did you always want to be an entrepreneur?
Stewart Butterfield: I don’t think it ever occurred to me that I wouldn’t be an entrepreneur. My dad became a real estate developer, and that work is usually project-based. You attract investors for a project with a certain life cycle, and then you move on to the next thing. It’s almost like being a serial entrepreneur, so I had that as an example.
LUMINARY: What are some leadership lessons you’ve learned?
Stewart Butterfield: I can tell people a story that they believe in and get behind. So I’m good at the leadership part. But I’ve always said that I’m a terrible manager. I’m not good at giving feedback. People are like horses — they can smell fear. If you have a lot of apprehension going into a difficult conversation, they’ll pick up on that. And that’s going to make them nervous, and then the whole conversation is more difficult.
If you go into those conversations with no apprehension of any kind, that just makes people feel at ease. I’ve tried to absorb that lesson. I’m not able to practice it 100 percent of the time, but it’s definitely something I’ve learned.
You’ve had a couple of big successes, starting Flickr and now Slack. What are your thoughts about culture?
I really admire good restaurants. I don’t necessarily mean expensive ones. I mean restaurants that are well run with a seamless kind of flow. I notice things like whether the servers keep an eye on each other’s tables. If someone needs the check, they’ll tell each other. I think everyone likes working in an environment like that.
I played in jazz bands when I was younger, and I like playing improvisational music generally. You really have to keep your eye on everyone at the same time.
LUMINARY: So how do you try to maintain that feel as your company grows?
Stewart Butterfield: One of our values is that you should be looking out for each other. Everyone should try to make the lives of everyone else who works here a little bit simpler. So if you’re going to call a meeting, you’re responsible for it, and you have to be clear what you want out of it. Have a synopsis and present well.
At the same time, if you’re going to attend a meeting, then you owe it your full attention. And if it’s not worth your attention, then say so — but don’t be a jerk about it — and leave the meeting.
People can go to work every day for a year and not really get anything done because they’re just doing the things that they felt they were supposed to be doing. We just went through this process of canceling almost every recurring meeting that we had to see which ones we really needed. We probably do need some of the ones we canceled, and they’ll come back — but we’ll wait until we actually need them again.
When we talk about the qualities we want in people, empathy is a big one. If you can empathize with people, then you can do a good job. If you have no ability to empathize, then it’s difficult to give people feedback, and it’s difficult to help people improve. Everything becomes harder.
One way that empathy manifests itself is courtesy. Respecting people’s time is important. Don’t let your colleagues down; if you say you’re going to do something, do it. A lot of the standard traits that you would look for in any kind of organization come down to courteousness. It’s not just about having a veneer of politeness, but actually trying to anticipate someone else’s needs and meeting them in advance.
LUMINARY: How else do you hire?
Stewart Butterfield: I used to always ask three short questions — one math, one geography and one history. I didn’t expect people to get the answers right, but I just want them to be curious about the world. The first is what’s three times seventeen. Then name three countries in Africa. You’d be astonished by the number of people who can’t do that. And what century was the French Revolution in, give or take 200 years.
I don’t do that anymore, but I do ask everyone what they want to be when they grow up. Good answers are usually about areas in which they want to grow, things they want to learn, things that they feel like they haven’t had a chance to accomplish yet but want to accomplish. A very short answer to that question would be automatically bad.
LUMINARY: Advice for new college grads?
Stewart Butterfield: Some people will know exactly what they want to do at a very young age, but the odds are low. I feel like people in their early- to mid-20s are very earnest. They’re very serious, and they want to feel like they’ve accomplished a lot at a very young age rather than just trying to figure stuff out. So I try to push them toward a more experimental attitude.
I certainly didn’t have anything figured out by the time I was 25. In a certain sense, I still don’t have certain things figured out.