Q. Did you have the entrepreneurial itch early on?
A. I always wanted to just try new things, and I think it was probably in my DNA or something. As a kid, I would see something I didn’t like, and I wanted to make it better. So, for example, we had a phone in my house that was a one-line dial phone, and I had to get a second phone line for my computer. So I rewired the phone to handle two lines. I was really proud of that phone.
Q. And what about your high school years?
A. I had lots of side interests, but I wasn’t very interested in studying in high school. My grades were pretty much all D’s, and I didn’t apply to college. The only reason I went to college was that my parents found out I could go to state school for free because of my SAT scores. I had a day job and I went to school at night. But I had a different job every 12 to 18 months because I’d get bored and I’d want to learn something new.
Q. Once you launched your career, what were some leadership lessons you learned?
A. The most important thing I learned is something I’m still actually working on, which is how to be really blunt with feedback. It’s the most difficult thing for a manager to do. But I worked hard at it, because when managers were blunt with me, it hurt a little bit, but I’m very grateful to those few managers who helped me.
I developed this technique over the years. When I gave people their performance reviews, I would literally take a crinkled envelope, and I’d write five words on it. I would take them out to lunch, and I’d say to them, “Let’s say I left this company, and five years from now I was sitting in a bar and someone said, ‘Hey, what’s that guy like?’ What I would tell them is what I’m going to tell you. And there are two or three words that are positive, and there are two or three words that are really negative.” I would give examples and I would give them the piece of paper, so I had no written record of what we had talked about. One guy in particular e-mailed me 10 years later, and claimed that he still carries that piece of paper around. That really reinforced for me the idea that the best way you can help someone is to be on their side and to be honest with them.
Q. You were a co-founder of Kayak nine years ago. What’s unusual about the culture?
A. We’re a little bit reckless in our decision-making — not with the business, but the point is that we try things. We give even junior people scary amounts of power to come up with ideas and implement them. We had an intern last summer who, on his very first day at Kayak, came up with an idea, wrote the code and released it. It may or may not have been successful, but it almost doesn’t matter, because it showed that we value speed, and we value testing ideas, not talking about them.
It’s all about fast iteration. When you push down decisions, and you don’t require people to write up plans and do designs by consensus, enormous amounts of work just disappear. We cut out all the middle layers and you let the designers talk to the customers. Otherwise, something gets lost in translation with a lot of layers.
Q. What else?
A. We’re known for having very small meetings, usually three people. There’s a little clicker for counting people that hangs on the main conference room door. The reason it’s there is to send a message to people that I care about this issue. If there’s a bunch of people in the room, I’ll stick my head in and say, “It takes 10 of you to decide this? There aren’t three of you smart enough to do this?”
I just hate design by consensus. No innovation happens with 10 people in a room. It’s very easy to be a critic and say why something won’t work. I don’t want that because new ideas are like these little precious things that can die very easily. Two or three people will nurture it, and make it stronger, give it a chance to see life.
Q. How do you hire?
A. You always have to be recruiting. When I meet somebody who’s amazing, I’ll often say to them, “Who’s the smartest person you’ve ever met?” My team might be sick of me asking the question, because I’ll keep asking. Finally, after the third or fourth time, they’ll say, “You know, there was this person.”
Then the two criteria I really look for are productivity — which is about speed and judgment and drive — and the second one is fun. A lot of companies have the no-jerks rule. But I have the “no neutrals” rule.
Q. Can you explain that?
A. We want to be a hyperproductive company and we want to make it fun, and I make a commitment to people that in 20 years they’ll look back and say this was the most fun job they had. If you surround them with people who are annoying or just kind of neutral, it’s going to make the job a drag. And you don’t ever want to hurt someone’s creative energy.
Certainly, annoying people will hurt them, and so will people who are just kind of boring. They’re nice, but they don’t ever provoke the creative person in a fun way. That diminishes their productivity. If I have a commitment to improving people’s productivity and fun, then I have to surround them with people who are fun and who will challenge them.
Q. So how do you get at that in an interview?
A. I know how to assess people about their speed and their product sense and their technical skills. The area that’s much harder to assess is culture. So I’ll look at the résumé, and find something that’s interesting. Then I’ll have them describe to me the team they worked with, and I’ll ask them about each person on the team — “Tell me something they did that blew you away and tell me something they did that annoyed you.” I make them talk about real people and the real product. From that, I can figure out their values and how they see other people. That gives me a really good sense about whether they will fit on my team.
A. I always wanted to just try new things, and I think it was probably in my DNA or something. As a kid, I would see something I didn’t like, and I wanted to make it better. So, for example, we had a phone in my house that was a one-line dial phone, and I had to get a second phone line for my computer. So I rewired the phone to handle two lines. I was really proud of that phone.
Q. And what about your high school years?
A. I had lots of side interests, but I wasn’t very interested in studying in high school. My grades were pretty much all D’s, and I didn’t apply to college. The only reason I went to college was that my parents found out I could go to state school for free because of my SAT scores. I had a day job and I went to school at night. But I had a different job every 12 to 18 months because I’d get bored and I’d want to learn something new.
Q. Once you launched your career, what were some leadership lessons you learned?
A. The most important thing I learned is something I’m still actually working on, which is how to be really blunt with feedback. It’s the most difficult thing for a manager to do. But I worked hard at it, because when managers were blunt with me, it hurt a little bit, but I’m very grateful to those few managers who helped me.
I developed this technique over the years. When I gave people their performance reviews, I would literally take a crinkled envelope, and I’d write five words on it. I would take them out to lunch, and I’d say to them, “Let’s say I left this company, and five years from now I was sitting in a bar and someone said, ‘Hey, what’s that guy like?’ What I would tell them is what I’m going to tell you. And there are two or three words that are positive, and there are two or three words that are really negative.” I would give examples and I would give them the piece of paper, so I had no written record of what we had talked about. One guy in particular e-mailed me 10 years later, and claimed that he still carries that piece of paper around. That really reinforced for me the idea that the best way you can help someone is to be on their side and to be honest with them.
Q. You were a co-founder of Kayak nine years ago. What’s unusual about the culture?
A. We’re a little bit reckless in our decision-making — not with the business, but the point is that we try things. We give even junior people scary amounts of power to come up with ideas and implement them. We had an intern last summer who, on his very first day at Kayak, came up with an idea, wrote the code and released it. It may or may not have been successful, but it almost doesn’t matter, because it showed that we value speed, and we value testing ideas, not talking about them.
It’s all about fast iteration. When you push down decisions, and you don’t require people to write up plans and do designs by consensus, enormous amounts of work just disappear. We cut out all the middle layers and you let the designers talk to the customers. Otherwise, something gets lost in translation with a lot of layers.
Q. What else?
A. We’re known for having very small meetings, usually three people. There’s a little clicker for counting people that hangs on the main conference room door. The reason it’s there is to send a message to people that I care about this issue. If there’s a bunch of people in the room, I’ll stick my head in and say, “It takes 10 of you to decide this? There aren’t three of you smart enough to do this?”
I just hate design by consensus. No innovation happens with 10 people in a room. It’s very easy to be a critic and say why something won’t work. I don’t want that because new ideas are like these little precious things that can die very easily. Two or three people will nurture it, and make it stronger, give it a chance to see life.
Q. How do you hire?
A. You always have to be recruiting. When I meet somebody who’s amazing, I’ll often say to them, “Who’s the smartest person you’ve ever met?” My team might be sick of me asking the question, because I’ll keep asking. Finally, after the third or fourth time, they’ll say, “You know, there was this person.”
Then the two criteria I really look for are productivity — which is about speed and judgment and drive — and the second one is fun. A lot of companies have the no-jerks rule. But I have the “no neutrals” rule.
Q. Can you explain that?
A. We want to be a hyperproductive company and we want to make it fun, and I make a commitment to people that in 20 years they’ll look back and say this was the most fun job they had. If you surround them with people who are annoying or just kind of neutral, it’s going to make the job a drag. And you don’t ever want to hurt someone’s creative energy.
Certainly, annoying people will hurt them, and so will people who are just kind of boring. They’re nice, but they don’t ever provoke the creative person in a fun way. That diminishes their productivity. If I have a commitment to improving people’s productivity and fun, then I have to surround them with people who are fun and who will challenge them.
Q. So how do you get at that in an interview?
A. I know how to assess people about their speed and their product sense and their technical skills. The area that’s much harder to assess is culture. So I’ll look at the résumé, and find something that’s interesting. Then I’ll have them describe to me the team they worked with, and I’ll ask them about each person on the team — “Tell me something they did that blew you away and tell me something they did that annoyed you.” I make them talk about real people and the real product. From that, I can figure out their values and how they see other people. That gives me a really good sense about whether they will fit on my team.
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