Corner Office: Be Yourself, Redfin’s Glenn Kelman Says, Even if You’re a Little Goofy

Q. What were some important early lessons for you?

A. Two things influenced me the most. I’m an identical twin, and I felt that with my twin brother, we sort of formed this unassailable force and it gave me the confidence to be different. Even if I was a goofball, my twin brother was a goofball with me, so I didn’t have to worry about fitting in as much. I was able to march to my own drummer.

My parents were a big influence, too. My mother was a nurse, and my father was an engineer, but I just think they didn’t know how to fit in. Here’s just one example: We moved into this ritzy neighborhood in suburban Seattle for a little while. We were the only renters, and somebody came by to tell us that we had to mow the lawn, that there were these rules about how short the grass had to be. My dad decided that he wasn’t ever going to mow the lawn. I just felt like we really didn’t fit in in a lot of different ways, and I was constantly in embarrassing situations because of things they did. At one point, my dad used a machete to mow or really just hack back our lawn.

Eventually, I just decided that you couldn’t die of shame and that I could do whatever I wanted to. It made me less risk-averse, and gave me this confidence that I could be myself. I think the corporate world is pretty starved for personality. The reason you have comic strips like “Dilbert” and sitcoms like “The Office” is that people just can’t be genuine human beings in a corporate environment. So if you can really be your own self, even if it’s a little bit different, I think people are really drawn to that.

Q. Did you always want to go into business?

A. I was sort of lost, because I wanted to study everything. At different points, I applied to graduate school. I got into medical school. I thought about being a writer. I thought about being an investment banker. I just didn’t know what I wanted to do with myself. I think the thing that best suits me about being a C.E.O. is that you get to exercise many different talents and wear many different hats.

Q. So how did you get into the world of tech?

A. When I was trying to write a novel, I ran out of money, and I was delivering packages on a bicycle. And I finally connected with these guys who started a software company, and almost serendipitously fell into that. I felt like they were goofy guys and that I was a goofy guy. It was just a really interesting, harrowing environment.

Q. How so?

A. I could hear them arguing in the conference room about whether I should be fired, and the C.E.O. would come out and tell me that a chain is only as strong as its weakest link, and God help you if you’re that link. I went home every night just convinced that I was the worst employee they had ever seen. It was a weird place, but it taught me to be tough, it taught me to be resourceful. I loved that job.

Q. You were one of the founders of Plumtree Software before you joined Redfin. How did that happen?

A. I met these V.C.’s and connected with Redfin, an early-stage company that had hit hard times. It was three guys in an apartment who put listings on a Web site. I was just the fourth guy in the apartment. I loved it.

Q. You now have 800 employees. Tell me about your approach to leadership today.

A. The main anxiety I have as an executive is making the shift as a start-up person to becoming an executive at a larger company. You worry that you need to change your behavior to match the new scale at the company, but you also worry that you don’t know what’s really going on, and that people are muttering, “Does Kelman have any idea how messed up this is?”

The way you find out is to have lunch with people, or go on a long car ride with them or join the running club with them. But the most important thing you can do as an executive is to just ask the most basic question, which is, “What should Redfin be doing better?” People will say, “I think it’s great.” But if you say to them, “Think about it,” and then follow up with them, you’ll hear, “Well, actually, this is really screwed up, and I think you need to fix it.”

Q. What else about your culture?

A. The main project I have at Redfin is to unite two separate cultures — real estate agents and software engineers. One of the ways we do it is by having people do “A Day in the Life” talks during our all-hands meetings, and they talk for 10 minutes about a typical day. Then you hear other people saying things like, “I had no idea how hard it is to be a real estate agent.”

Q. How do you hire? What are you looking for? What questions do you ask?

A. Mostly what I’ve learned about it is, you can’t judge a book by its cover. It’s very hard in an interview when someone talks about their work to judge them. What you want is to have them do the work. So when I interview engineers, I give them a coding problem and I ask them to work through it. When I interview a marketing person, I say, “Write a press release,” or, if you’re in P.R., “Write a pitch.” I want to see the actual quality of their work.

The other thing that I look for is people who are beasts. I was a dishwasher once and I kept falling behind with all the dishes, and this guy in the kitchen yelled at me to get me going — “You’re an animal. You’re a beast.” And I was just a very intellectual, effete kid — I was probably reading Proust at that point in my life — and that experience made me a lot grittier and tougher.

If I haven’t found evidence that someone’s ever done anything hard in their lives, then I just don’t believe they’re suddenly going to be able to jump into a phone booth, come out wearing a cape and learn how to be tough on this job. I want to know about anything you’ve done that’s hard, really hard. So I tend to focus on that.