Corner Office: Paul English of Kayak, on Nurturing New Ideas

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. 

Corner Office: Andre Durand of Ping Identity, on Setting Reachable Goals

Q. Were you an entrepreneur early on?


A. As far back as I can remember. My mother says that when I was about 4 years old, I was selling my toys. Later on, I had a paper route, but I didn’t stop there. I started selling synthetic motor oil to the people on my paper route. I figured that if I was already collecting the money for the papers, I could sell them oil, too. I also rebuilt and sold bikes that I pulled out of the Dumpster. Then, when I was about 19, I got my first PC. I just fell in love with software.


Q. You’ve started a few companies. What were some early leadership lessons you learned, particularly about culture?


A. My aspirations were always bigger early on than our resources. The way that manifested itself was that I never raised enough money early on to make money less of a factor in the way we made decisions. That meant I was either always pressured to ship software that wasn’t quite ready, which is a little bit of a death spiral, or I was always raising money within a few days of payroll — and asking the employees to trust me and to not quit.


So I was trying to be bigger than I could afford to be, and your decision-making is always convoluted by these factors. That was a big early lesson. It ingrained in me the importance of matching the entrepreneurial aspirations with the resources. Those all have to be aligned. And ever since, I’ve always raised money when I don’t need it ahead of time, for a rainy day. I just never put myself in that position again.


Q. Other big lessons?


A. I would say the overarching lesson is that there are no shortcuts, no Hail Marys, no silver bullets. It’s easy, early on, to think that you can somehow just jump right to the endgame. I can tell you that kind of thinking is pretty dangerous and unhealthy. In my experience, when you reach the goal you’re after, more often than not it’s fairly well deserved by the time you get there.


Here’s another lesson I learned. When you’re younger, you create a lot of expectations about who you’re going to be, where you’re going to be when you’re 40. It’s as if life past 40 doesn’t exist. So when you think of your relationship to time in that construct, you’re very impatient. My mind-set at 20 was that I had self-imposed deadlines that ended at 40.


But here’s the paradox. When you get to 40, a couple of things happen. You look at the second half of your life, and you realize that life is not endless, and that it is very finite. Yet somehow you can learn patience. I became very cognizant of the relationship between patience and time and decision-making. When I became patient, I simply made better decisions.


Q. So much of leadership is about finding the right balance point. Other thoughts on that?


A. One of the things I’ve really come to appreciate is that you tend to work harder when you’re winning. So you have to make sure that when you’re setting goals for people and the organization, they aren’t so far out that they’re unachievable, which will leave people demoralized.


You have to be careful and thoughtful about the way you set expectations. You don’t want them to be slam-dunks, but you don’t want them to be unattainable, either. They need to be within the realm of attainable. Even though you don’t have every step of the way figured out, you’re pretty confident that you’re matching the resources and the talent and the goals, and that all of those are aligned.


You can either create a circumstance where you build this positive vortex where everything right out of the gate is leading you toward more and more success, where you’re more motivated to not miss, or you can become trapped in what I call a cyclone of doom. And they start with these very small, seemingly innocuous decisions almost out of the gate and then they build on one another. So you’re either heading down or you’re heading up.

Q. How do you hire? What qualities are you looking for?


A. There is a subtle but important difference between people who want to work at a company to do something great and people who want to go to a company because they want to join something great. One group wants to pull and one group wants to ride.


Q. What questions do you ask to determine that?


A. I listen carefully to the language they use as we’re talking. I haven’t distilled it to a question yet that embodies the difference between these two, but oftentimes it just shows up in conversation in little ways. Somebody might say: “I’ve always liked what you guys were about. I’ve taken a look at what you’re offering and I can see how I can help.” They’ve identified a need and they’ve assessed their own skill set and they see how they can bring value.


Q. And what’s the off-key version of that?


A. I’ve had conversations where people will say: “I’ve visited your ‘About’ page and your ‘Culture’ page and your ‘Career’ page and it looks like a lot of fun. You guys look like you have a great culture.”


Q. What advice would you give aspiring entrepreneurs?


A. Everyone talks about the role of persistence, and I’ve come to like this one-liner: “The world filters out the uncommitted.” It’s not just entrepreneurship — it’s true about anything you want to do.


I also see a lot of brilliant people overthinking. They overanalyze an idea before it’s even off the ground. They have a smart idea, but they spend all their time thinking about all the what-ifs. By the time they’ve done their risk assessment, they don’t do anything. It’s like, “Well, what’s the point?”


Yes, there are all sorts of unknowns. I like to say the first step is not nearly as big as you think, and success takes a lot longer than you might think. It’s that weird dichotomy. The first step literally is just to say you’re going to do it, and then start doing it. 

Corner Office: So Who Says a New Business Has to Be Small?

A. I did. My parents were entrepreneurs. They ran a small ad agency in upstate New York.

Q. What were your high school years like?

A. I never did particularly well in school, but I did get really into things. I used to build robots, and dove right into computers to the point where my schoolwork suffered. Then I really became inspired by people like Steve Jobs and Bill Gates. In high school, I started my first company, called M Cubed Software. We named it that because it was me and two other guys named Mike.

Q. So did you bypass college?

A. My dad died from cancer when I was 18, and my mom was in a really tough spot. So I wanted to try to help at home. I had started doing some technology consulting. Then a friend of the family got me an interview at I.B.M. They hired me basically as an intern, and they told me not to plan on being there beyond the internship. They also said they don’t hire anyone who doesn’t have a degree.

But I was determined to make sure that I became so valuable that they couldn’t let me go. And that was what happened, and they eventually hired me full time. I.B.M. was my college education, effectively. They were very good at teaching you management.

Q. And the next big step?

A. I left I.B.M. in 1989, when I was 22, to start a company called Paper Software.

Q. What did you learn from that?

A. The first lesson was that I’d bought all these business books because I hadn’t gone to school. And I really got into the theoretical aspects of starting a company. Then what I finally realized after about six months is that I just needed to do it. I just needed to actually build something. And that was a good lesson — do something, build something and everything will happen from there.

I was able to recruit three really awesome I.B.M. engineers. I had to pay them a lot of money to join. One day, two of them said, “Hey, can you come outside and go for a walk with us?” They told me they were going to quit and start a company that was basically going to do what we were doing. I had two other guys working for me who were up-and-coming engineers, and I was paying them a fraction of what I was paying these guys. I came back to the office and I pulled my small team together and said: “O.K., I have good news and bad news. The bad news is, we just lost half of our engineers, but the good news is we kept the best half.”

And that was a great moment, when I learned how you rally people around hardship, and give them the opportunity to step up. You can actually get better output from people when you give them more than what they normally would be expected to handle.

Q. You eventually sold Paper Software to Netscape and moved to the West Coast to join Netscape. Lessons from that experience?

A. One of the biggest mistakes I made at Netscape was to focus too much on competition. Microsoft was trying to kill us. And that caused us to think about what we were going to do about Microsoft. What we really should have been thinking was: How do we focus on what our users want? Why did they love our product? How do we make it more of something that they love? So my advice is, every time you have a thought about the competition, replace that with a thought about your customer and you’ll do far better as a business.

Q. Other lessons for would-be entrepreneurs that you’ve learned over the years?

A. I think a lot of entrepreneurs go into building a start-up thinking they should focus on a niche, and do the simplest thing that can be done. But there is a problem with that approach. In fact, it may be even harder to build that kind of niche company than it is to build a giant company that might someday be able to change the world. It’s going to take the same amount of life force. You’re going to get up in the morning, work 12 to 15 hours every day. You’ll make huge, hard decisions, hire and fire people and build teams. It literally takes the same amount of energy.

So what I think is counterintuitive is that if you focus on the big idea, the biggest thing you can possibly do, that’s actually somewhat easier, because you can attract more investment that way. You can attract more talent that way. It’s more fun, and you have way more room to maneuver.

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

A. I ask people what’s driving them, and what’s motivating them. I’m looking for answers along the lines of: “I want to be a part of a great team. I want to learn from really great people. I love the people I’ve met here, and I’d love to just be part of this.” I also look for people who are into doing something really meaningful and great. So I’m looking to see if their answers are centered around those two pillars. I’m trying to build a culture that’s focused primarily on the camaraderie of the team, because we’re going on a really big, important and giant journey together.

I don’t hire anyone who doesn’t genuinely share that motivation, no matter how good they are on paper. Because you have to have a durable team so that when you do hit hard patches, people are just as motivated to continue to drive forward. The team sticks together. That’s what is really required in building a company. You’re going to hit those hard spots, and you’re actually defined by how you come out of those at the end.

Q. What other questions do you ask?

A. I’ll ask them about the hardest situation they’ve ever been in, and how they navigated through it. I’ll ask: What’s your greatest triumph? What’s the thing that you’re most proud of that you’ve done in your career? And then: What are some of the core lessons you’ve learned? You can have a 90-minute conversation just with those questions.