Corner Office: Luc Levesque of Trip Advisor, on Frequent Evaluations

Q. You’re the second executive I’ve interviewed who gives employees a “user manual” to help them understand your leadership style. Tell me about yours.

A. I started thinking about it two years ago. I had a great team, we had worked together for many years, and we were in a groove where everybody’s running at full capacity and really working well together. But I was hiring about five new people, and I remember talking to my executive coach about it and thinking: “Now I have to go through that whole process again. This is going to take forever.” And that’s when I went back and forth with my coach, and we thought, “Wouldn’t it be great if you had a blueprint to give someone on Day 1 that encapsulates what works with me and what are some of the quirks about me that you’re just going to have to accept?” So I wrote it up, and started sharing it with my team. It’s worked really well.

Q. Can you give me some examples of what you included?

A. The whole blueprint in my case is all about speed. I like doing things quickly — if somebody has an idea, test it a bit first and then commit further if it makes sense. And I need to trust you. People wouldn’t think of that as a speed thing, but if you don’t trust somebody, then you find yourself constantly double-checking and following up.

Probably the biggest quirk of mine is that I really like quick responses to e-mails. Why? Because we’ll move faster. I get that some people can’t always be on e-mail at all hours, and it’s not a ding against them if they can’t always respond quickly. But wouldn’t it be just great for people to know that about their boss?

Another is no finger-pointing if something goes wrong, so fall on your sword. We’re all in this together. We move very fast and we’re going to make mistakes. That’s O.K. Just own up, find a solution and move on. I also value people who follow through. It will drive me completely nuts if I can’t follow through on a commitment and I value that tremendously. If you say you’re going to take on a project, then you’re all in.

Q. What else is unusual about your culture?

A. I started doing performance reviews differently. I thought about a new approach after I did a performance review for one of my guys last year, and it was a good review. The next day he came to my office and I could see he wasn’t happy. He said, “We left all these things out, and I feel like you didn’t represent how good a job I did.”

And I said: “I agree. We left some stuff out; I don’t remember it all. But you’re right, you did a lot of other good things.” He took out a list and he walked me through it and said, “I want to include all these things.” So we put them in. I also told him that my coach had been asking me to start monthly reviews, and I asked him if he would help me try that. He said, “Sure, let’s do it.” So I opened up a Google spreadsheet and put his goals down. Every month, he fills out his goals. This approach is supposed to speed us up, and it creates alignment every 30 days, and you’re constantly giving feedback.

The meeting every month just facilitates a conversation, and it captures all of the great things they’ve been doing. And I think the most important questions at the end are: “What can I expect for the next 30 days? Anything I can do to make things go faster?”

It’s so good that I don’t how you run a team without it because those conversations can be very hard to have otherwise. It’s great for them to get positive feedback. It creates some structure, because we’re so busy as leaders that we might not be doing it otherwise. And the beauty of it is that the year-end conversation is a piece of cake, because it’s all written already, and you know exactly where you stand throughout the year. If you do all of that well, good things are going to happen, because if you’re hiring the right people, they want feedback.

Q. I’ll keep asking. What else about your culture?

A. The way we use iPads is a little different.

Q. Tell me about that.

A. One of my engineers moved to Calgary. But we’re big on speed and a piece of that is being face-to-face, since there’s no e-mail misinterpretation or trying to get hold of people. So he had an idea — “Why don’t we get an iPad and put it on my desk? And that way you’ll see me.” So it’s really no different than if we had a window to his desk in Calgary. We use a wide-angle lens, and it’s always on. So if you want to have a chat, you just lean over and say, “Hey, Mike, how’s it going?” We call it the iMike, and it really changes remote working at a very deep kind of human level. It’s like you’re connected again.

Q. How do you hire? What questions do you ask?

A. I’ll start by asking right away: “Tell me a bit about you. Walk me from the last page of your résumé to the front page. How did you transition from job to job? I really want to understand, why did you leave? What was the motivation? How did you find the next job? Did you get poached? Did you get bored?” So I want to really understand the transitions between jobs and paint a picture.

I’m looking for what I call “signals of excellence.” I’ve had by far the most success with somebody who’s very talented and has these kind of signals in their history. So did they graduate with honors? Did they have a side project, like a start-up? Are there certain things they’ve done that they excelled at — things that make them better than everyone else? If somebody was at a job, and their boss left to go to another company and came back to hire them away and join them, that’s a signal of excellence. Nobody knows better than your boss how good you are. So if that happened, that’s big for me.

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?

Q. Did you have the entrepreneurial itch early on in your life?

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.

This interview was edited and condensed. (The New York Times shares content with Flipboard through a revenue-sharing agreement.)

Corner Office: Jed Yueh of Delphix on Learning to Manage Yourself

This interview with Jed Yueh, chief executive of Delphix, a software company that streamlines data management, was conducted and condensed by Adam Bryant.

Q. What were your career plans in college?

A. I was an English and psychology major at Harvard, so I had no plans to be an entrepreneur or in technology. My friends from college and high school who were interested in computers all scratch their heads and wonder, “Why are you the tech C.E.O.?”

Q. So what happened?

A. There’s so much money in Silicon Valley to create new technology companies, and I was one of the little particles on the fringe of the carpet that got sucked into the vacuum. I learned how to program in Excel, and built a couple of models for some friends. They got me some contract work for this one company, and I looked at their technology strategy and products and I learned about the industry. That gave me the idea for my first company.

Q. What were some early leadership lessons as you built that first company?

A. My biggest lesson was that you could be technically right and management wrong, and I learned that early on. I can articulate and debate a viewpoint from many angles, and I found that I could be technically right and force somebody into a viewpoint. But then they would slowly spiral into a place where they’re not really working hard because they feel demoralized. So I lost wars by winning battles.

So the first of my three management principles is that you’ve got to learn how to manage yourself. You have to understand how to win wars, not individual battles. If you don’t manage yourself very well, it’s hard for you to maximize the performance of a team. And managers can either increase or decrease motivation for their teams. They can either increase or decrease clarity for their teams. They can either build cultures that are highly collaborative and capable of solving problems quickly, or they can create cultures where you have a lot of paralysis and it’s very difficult to make decisions.

My other rules are hire right and fire right, and that’s pretty much all you have to do to be a great manager. It’s really not that complex at the end of the day.

Q. So let’s talk about hiring.

A. Hiring is the moment when your biggest lever exists for defining the culture. If you don’t know the traits you’re looking for and you haven’t hired around those traits, then you are effectively hiring a wishy-washy culture.

Q. What are the qualities you look for?

A. My two highest-level traits are clarity and creativity. Let’s talk about clarity first. When you’re building a business, there are so many things you can do, so many avenues you can chase, that you have to very quickly find the optimal path. If you can’t separate the signal from the noise, if you can’t find clarity, it’s going to very hard for you to manage a group. It’s also going to be easy for you to spend time in all the wrong places. So it’s very difficult to become efficient if you don’t have clarity.

Q. How do you determine whether somebody has that quality?

A. When I interview someone, I’ll often ask them: “Tell me about why you’d like to join Delphix. What do you think is valuable about Delphix?” I want them to pitch Delphix to me. They’ve had to take in a lot of information about us. They’ve probably read things from a number of sources, and read our Web site. They might have talked to a number of employees ahead of time, and they’ve been synthesizing the information.

So what I want them to do is to present to me how they think about and try to understand something that is new to them, which in this case is Delphix. Some people will immediately dial into the most important elements in the exact right order, and it’s not as simple as it looks. There are a thousand ways you can tell a story and only a few ways that really hone in on what’s important.

I also will ask them about successes and achievements in their career, and then dig deeper. “Why were you successful when you were doing this specific project?” And you’d be amazed at the range of how people answer that. Some meander around, and they cannot get to the point. They don’t really know why they were successful, in which case I know they actually never had clarity. Can they find the story? That really is how you identify clarity in an interview.

Q. You said the other quality was creativity.

A. They have to be able to solve a lot of problems, because the problems you’re going to encounter in a start-up are in every direction. So we have to have people who are creative. It has to be core to a technology company, too. In the technology industry, the chessboard continues to unfold and change.

So I’ll ask people to describe to me how my product works. You’ll find that a lot of people have no creative curiosity. But let’s say you’re one of these engineers who is creative and curious and you’ve figured out how the product works. It’s guaranteed that you don’t understand how every aspect of the product works. So I’ll push somebody until they enter an empty space, in terms of their knowledge, and I have an unfair advantage, because I know how it works. If they can’t answer it, I’ll say, “How would you fill that space?” Some of them will actually problem-solve on the spot, and nail the design, in which case we have a winner. You can do it in all industries and roles, too. You can ask a salesperson, “Tell me about a complex deal that you worked on, and how you got stuck and how you solved it.”

Q. And your third rule is “fire right.”

A. We’ve all made mistakes in hiring, and you know you’ve made a mistake when you keep investing more and more time in an individual, and you’re not getting a return. You have to invest in new talent. You have to coach them. You have to help them. But if you are not seeing a return, then you have to make changes.

Q. Anything you have a particularly low tolerance for?

A. My pet peeve is people who think in silos. You want people to think globally and execute locally. But a lot of people just want to think about their own little world and not connect it to the broader picture. We can’t afford that in a start-up.

This interview has been edited and condensed.

Corner Office: Jon Oringer: Jon Oringer of Shutterstock, on the Power of the Hackathon

Q. Did you show an entrepreneurial streak at a young age?

A. In high school, I used to teach guitar and fix computers by the hour. I was looking for some way to make some cash, so I actually learned how to play guitar in order to try to teach it. It turned out to be a pretty good business for a 15-year-old who had to get dropped off to his job by his mom.

I actually liked playing the guitar, but I started to realize that I could charge more to fix people’s computers, so I moved on to that. It was kind of fun just to try to figure out how to make money. It was a good challenge. As I started college, I started to build software products that I could sell to people over the Web.

Q. And you’ve started how many companies?

A. It’s hard to say because they all kind of blend into one another, but it’s probably around 10, and a lot of them were just me, before I started Shutterstock.

Q. So your company now has about 250 employees. Tell me how you evolved as a manager.

A. It’s interesting, because I never had a boss before I started this company. I had never worked in an office. I didn’t know about politics and how to build culture. I didn’t know what culture was. So as I started to hire people, I was looking for the skills I knew I needed to build the product I wanted to build. I didn’t think about a lot of the rest of the stuff. I figured managing people was obvious — I’d tell someone what they needed to do and they’d do what I wanted. It turns out that’s not the case. It was frustrating at first.

Q. As the company grew, were there certain break points you noticed when the culture shifted?

A. At around 50 employees, you get to the point where you can’t see what’s going on all the time. So you start to have weekly check-ins, and you have days that go by without knowing exactly what’s going on. But you need to be sure that everyone is kind of moving in the right direction and thinking about things the right way.

Q. So what’s different or unusual about your culture today?

A. We have a bunch of agile teams that work on different components of the company. At the end of every two-week period, they show everyone else what’s been done. It’s a good way for the whole company to see how we’re progressing.

We also do daily stand-ups for each team. People quickly say what they’ve done and what they’re going to do next. And by keeping these teams small, they can also be self-starting and entrepreneurial.

The whole thing is designed so that meetings are minimized and people can get back to work and push stuff out quickly and then report back to the team. It’s like this daily heartbeat of updates to make sure everybody’s moving forward.

Q. What else do you do in terms of culture?

A. We have hackathons, which are pretty fun. A lot of people get really excited about them, and they can build whatever they want for the company — it could be crazy, practical, whatever. We actually wind up implementing a lot of those things throughout the year. It pushes a lot of thinking. It’s pretty amazing what people can get done in 24 hours. Sometimes we talk about a new product feature and it can take three months to build. Then someone will prototype it overnight.

Q. And why is that?

A. Sometimes as a company you tend to overthink things. If you just sit down and try to do it, it turns out to maybe be easier than setting up meeting after meeting to get it done. So it’s a good reset point for us every year to remind us, “Yeah, we can just get things done quickly.”

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

A. We look for people who are entrepreneurial, who can think in ways that will extend the product in the right direction. We look for people who are “growth hackers.” I’m not sure who came up with that term, but it makes sense to us. It’s the kind of person who can build features and products that market themselves.

Q. So how do you find growth hackers?

A. It’s difficult. I’ll usually show them something that we’ve built and ask them what they can do to improve on it. I’m looking for what their thinking patterns are in terms of whether they can figure out a way to make a particular feature grow in a way that it perpetuates itself.

They also have to be able to mesh with others in the organization. You want people who will push the thinking but not cause trouble. It’s hard to explain, but it’s a feeling you get. It’s easy to find people who will be disruptive thinkers who are reckless, but it’s hard to find disruptive thinkers who are productive. We try every day to make each dollar we spend go one penny further than it did yesterday. That’s the kind of person I’m looking for.

Q. How do you tell if they’re going to fit in to the culture?

A. If you start to challenge them, what happens? Do they come back hard at you? They have to be open to having their thoughts challenged. They have to be open to the fact that maybe they’re not right.

Q. And if hiring were like speed dating and you only had like five minutes to ask one or two questions, what would they be?

A. In your day-to-day job functions, how will you take risk? Like I said before, we want to make that dollar go one penny further every day. I’m not looking for you to double the dollar. I don’t even want a 25 percent return because on a day-to-day basis that’s too much volatility. I want a 1 percent return daily. If the risks are small enough, they can kind of do them on their own without getting themselves into too much trouble. If they are taking fewer but bigger risks, that’s a problem. So I would be looking for how they do that.

Q. What else?

A. If you were going to start your own company right now, and you had to go make one dollar on the Web, what would you do?

Corner Office: Bill McDermott: Bill McDermott of SAP, on Knowing What You Want

Q. Were you in leadership roles early on as a child?

A. When I was around 11 years old, I was the assistant coach to my dad, and we coached my brother’s basketball team. My dad was a huge basketball guy, and my grandfather, Bobby McDermott, was a Hall of Fame basketball player.

Q. In that role, did you help with strategy?

A. Every timeout, my dad would always ask my opinion. And I was always quick to give him one. Sometimes I had a different play in mind than he had, and he was quick to listen and try it. Sometimes he wouldn’t take it, but very often the debate led to an even better answer.

Q. What about your high school and college years?

A. I had three jobs in high school. And then I traded all those jobs into one, when I went to work at this delicatessen. About a year later, I ended up buying that delicatessen. I was 16.

Q. That must have been a lot of work.

A. I came from a working-class family, and wanted to have my own money. I wanted a car. I also wanted to do what I could around the edges to give something back to my family. Plus, I loved to work. I put myself through four years of college on the back of that delicatessen. I took all my classes on Tuesdays and Thursdays, and every other waking hour I was there.

Q. And after college?

A. I sold the delicatessen, and at the time I believed strongly that I had to get with a company that provided great training, that would give me the professional polish I needed. I wanted to work for Xerox.

The day of my interview, my father drove me to the Long Island Rail Road. As I got out of the car, I said to him, “I guarantee you I’m coming home tonight with my employee badge from Xerox in my pocket.” My dad said: “Bill, don’t put that kind of pressure on yourself. Just do your best.”

So I went to Xerox’s hiring center in New York. I made it through all the interviews to meet the district manager. We had this extraordinarily good interview, and he said, “I really enjoyed this conversation, and the H.R. department will be in touch with you in the next couple of weeks.”

To which I replied: “I don’t think you completely understand the situation, sir. I’ve never broken a promise to my dad in 21 years, and I can’t start today. I guaranteed him I’d have my employee badge in my pocket before I got home to Amityville tonight.” He just looked at me for what seemed like an eternity, and he said, “Bill McDermott, as long as you haven’t committed any crimes, you’re hired.”

Q. So what’s the broader take-away, say, for a class of graduating seniors?

A. Two things. A lot of people might play the field, or try to figure out what they want. But I knew exactly what I wanted. Second, you’ve got to want it more. If you want something badly enough, everybody around you can see the passion. And people will make bold bets on people who have an unwavering passion to succeed or a passion to do something. I think that can get totally missed in the world of academia, but that’s the real world.

Q. You moved up quickly into senior leadership roles at Xerox — how did you get started?

A. I basically moved up to become the sales operations manager for the New York region, then became the district manager for Puerto Rico and the Virgin Islands. Our region was ranked 86th in the company out of 86. And I said, wow, this is very interesting.

So now the challenge was, how are you going to make these guys winners? I spent two weeks interviewing everybody and listening. I’d sit there and just say, “What do you think we need to do?”

After doing that for two weeks, I found out the three things that were unanimous in terms of what people thought we should do. No. 1, they wanted to be motivated. A previous boss, they told me, had been very financial in his orientation, and focused on cutting expenses. The second thing was that they wanted to have a holiday party, because they had lost the holiday party. The third thing is that they needed clear direction on what they were supposed to do. “Just tell us what to do,” they said.

So we basically gave them three things that we were going to focus on in the business. Then we gave them inspiration and pageantry at every turn to celebrate the victories as we made progress against those three goals. And then we had the holiday party, which was the most important of all. By the end of the year, we ranked No. 1 in terms of beating our plan.

Q. How do you hire?

A. I always try to hire somebody who’s got a vision at least as big as mine. The main question I ask is, what do you want? If you ask somebody what they want, you’ll know everything there is to know about them. We’re looking for people who have a clarity about who they are and what they want, and where they want to go. They should have a keen understanding of how the job they’re interviewing for fits into their personal passions. So I want to know that they’ve got the talent, the bandwidth, the acumen and the intellectual curiosity to keep getting better. But I also want to know that they really want it.

Q. Are there things that you have particularly low tolerance for?

A. People who play office. They come in to basically play the corporate game — here are my PowerPoints, here’s my pitch, and I’m going to pound you with my corporate-speak until you acknowledge my point of view. But if you want to have a conversation and interest me in what it is you need to get the win, then I’m incredibly interested in you.

I also have a problem with wasting time. You need people who have a sense of urgency and passion, and they come in with a desire and a stated goal, they have a point of view, and they’re looking for some support because they’ve got a game to win. That’s what I want.

Corner Office: That’s a Good Idea. But First, Can You Put It in Writing?

A. No. When I graduated from the university, I went to work for the Lawrence Livermore National Laboratory, and was just sort of plopped into one of the most outrageous engineering projects. I worked on the laser fusion machine, and it was one of those rare situations where you’re an engineer with no budget constraints.

And so in that process of infinite budgets and the early days of computers, I think I got a sense of just the raw creativity when you have a clean slate and lots of flexibility. So I didn’t start out as an entrepreneur, but I think in those early working days, I was lucky to have that kind of freedom to work with brilliant physicists and big budgets and to kind of push the boundaries. Then I decided after working for two years as an engineer that I didn’t want to spend my life being bossed around by a physicist, and that kind of pushed me more into a traditional business career.

Q. And when you were younger, were you in leadership roles?

A. Early in my life, and really to a degree even today, I was a total introvert. I was more of a quiet kid, and I was one of the math geeks, and I was often more doing my own thing. But I also had a bit of a creative streak. It was clear early on that I could write.

Q. So you had the potent combination of having both math and English skills.

A. I did. In fact, I always tell people that I think I advanced in the earliest days of my airline career because I could use a calculator and talk. I kept being mentored and moved up and I had no idea why it was happening. To this day sometimes I wonder. I think it’s because they needed this quantitative skill set to help understand an industry that was deregulating. The work was more about creating direction than being given instructions. It’s also my nature. When I was a youngster, I wanted to go into the military because I wanted to fly fast airplanes, but I quickly decided that would probably be a bad idea because I’m not good at taking direction.

In fact, I remember the day when one of my favorite bosses told me I’d been promoted to vice president of American Airlines, and I said to him, “I really enjoyed working for you.” And he said, “You know that you were never working for me for one day.” I had to laugh because I was just doing what I thought was right, and sometimes that was a good thing. Sometimes I got pounded on the head. But I did what I think is right, and I still do.

Q. Tell me about your approach to leadership today.

A. To me, it’s all about having a thoughtful strategy and recruiting talent, and if you have those two things, you can really make a lot happen as a leader or as a team. You can make almost anything happen. I don’t think it’s a guarantee, but without them, it’s very hard to thrive and be successful, and frankly to enjoy yourself.

I’ve even had examples when I didn’t follow my own advice. I started my own little company, called Travel Game, and tried to make a go of it for 18 months before I shut it down. I had no team. It was all contractors, and really there was no strategy. I just thought, “Let’s throw it out there and see what happens.” And of course it flopped. I thought: “Wow. What if I had followed my own advice?”

Q. Orbitz was your first time running a start-up. Did you have specific thoughts on what you wanted the culture to be?

A. My first thought was that we may not be here in a week or a month or three months. So we’re going to be really candid and we’re going to be really about excellence, and doing what we say. So my rules began to be about transparency and honesty and integrity. I would tell people: “Look, you can make any mistake, and I guarantee you it won’t be a fraction of the mistakes I’ve already made, and you won’t be chastised for failure. But if you tell a lie, you’re fired.” And it was that black-and-white for everybody who was new to the organization.

The culture was really about candor, too. I wrote them an e-mail every Friday. It was called, “Good Morning, Orbitz.” It went to all the employees, and it just talked about what I thought was going on, what I was personally doing, and there were kudos here and there. There were slaps here and there. I wouldn’t name the person, but I’d say this certain thing didn’t go so well. I still do it at Wize Commerce.

Q. How do you hire?

A. First of all, I will acknowledge that I have made a ton of mistakes, so I wish I had a better formula. Mostly I take a lot of time. Track record is important because it’s a demonstration of something that they were involved in that worked. Or maybe it failed, but it was failure in an area where learning is very relevant.

And I look for problem-solving skills. The people I interview usually are in roles where their impact is important. So I like to be around problem-solvers, and I think the more problem-solvers you have, the better. So I usually discuss big problems with people — the kind of problems where I don’t know that there’s a right answer, but I can understand better how their brain’s machinery works, and maybe how it works with my machinery, to see whether we can work collaboratively to come up with solutions. I’ll also say: “Look, would you think about this problem and get back to me? How would you launch this product as a marketer? How would you tackle this problem?”

Q. So you ask them to do a writing exercise.

A. When you ask people to write, they have more time to think carefully about something, so I’ll see what careful thought creates. If there’s an inability to string thoughts together, that’s good to know. Or maybe they’ve done their research, and their passion and interests are also reflected a little bit more. It’s just a way to dig in slightly deeper.

This interview has been edited and condensed.

Corner Office: Paulett Eberhart: Paulett Eberhart of CDI, on Gaining the Boss’s Attention

Q. Were you in leadership roles early on?

A. After I graduated from college, I was hired as a billing office supervisor of about 30 people.

Q. That’s a big step for a first management role.

A. It’s one of those moments where you show up at the right time and they needed someone, and I think my college education was important to them. I had the good fortune of working for a woman who taught me a lot. Most of the people who worked there were older than me and they certainly had a lot more experience.

So how do you deal with that? You have to learn to become very humble, and you have to recognize that they know a lot more than you do. I spent a lot of time walking around getting to know them, spending time sitting with them, learning what they were doing, how they were doing it. I think they appreciated that.

Q. You said your boss at the time was a good mentor. How so?

A. She knew that I really wanted to learn, I was dedicated, and I was working really hard. I have found that if people think you’re working really hard and trying, then they’ll spend extra time with you. I learned very early that you’ve got to ask for help, you’ve got to go in and say: “Look, I’ve got this situation and I’m not sure what to do. I want to run it by you.” If people think you’re really trying, they’ll go the extra mile to help you.

Q. Tell me about some aspects of your leadership style today.

A. I tell my team that I expect them to be very honest, brutally honest with me, but in a respectful way. I like to have strong people around me, and they have to be very open and very honest and very candid. So you can’t just tell me once and assume that I grasp it.

If it’s critical and important, you’ve got to come back, you’ve got to tell me, you’ve got to come into my office and shut the door. I don’t care if you have to pound your fists on the table and say, “Paulett, I don’t think you’re comprehending it, I want your full attention, listen to me, this is what I am telling you.” We, at a minimum, need to discuss it or whatever the situation is.

And so I encourage them to be very aggressive with me because I work and I run at a fast pace, and sometimes you have to stop and take five minutes. You’ve got to invite them in and sit down and say: “O.K., what are the issues? You’ve got my full attention. Let’s talk about it.”

Q. You were brought into your current company to turn it around.

A. The board decided it needed someone from the outside who could bring more of a growth culture, which is a lot of what I like to do. I like transforming businesses and then figuring out how do we get a new strategy and start really growing. A lot of that goes back to my early days at E.D.S. because we grew so quickly there.

Q. What have you done to change the culture?

A. I was surprised to learn how many people in the company really didn’t know the company’s history. So I had some people re-create the history and we put together a video, because I think it’s good to know the past that leads you into the future.

I also saw a company that had really talented people, but they didn’t really talk to each other a lot. They were in different silos, and there were actually a lot of silos, given the size of the company. One of the things I heard from talking to our clients is that people from CDI don’t even know who each other are. That told me we weren’t maximizing our opportunities with the client.

So we tore down a lot of the barriers and really got people to think that if it’s good for the client, and good for CDI, then we’ve got to figure out a way to make it happen.

The other thing that I really focused on was accountability. You have to be accountable for your actions. And if you sign up to hit an objective, whatever that objective may be, then the rest of the organization and your client, or whoever else it may be, are counting on you to hit that goal. I felt we needed to push that more. Culture is a hard thing to change. It takes a long time, but you’ve just got to keep repeating things and practicing what you preach.

Q.  I’ve heard a lot of leaders talk about the importance of repetition.

A. People don’t spend enough time communicating. People love to know what’s going on, and you’ve got to keep communicating day in and day out. Sometimes I’ll think, I’ve said this so many times — surely people would get it. But then you’ll go into a meeting and you’ll think, wow, O.K., they don’t get it yet, so we’ve got to continue reinforcing it.

Q. How do you hire?

A. I try to get them to talk about what’s not on their résumé. Part of it is just getting a sense of the person. I’ll say that we’ve all had a lot of successes in our life, but we’ve had some things that we’ve learned from as well, so what are some of those?

And I’ll ask them, “If I were to talk to a group of people who’ve worked for you in different roles, what would they say that’s good about you, and then, what are the two things they would change about you?” And so it’s not so much about the answer — it’s just how thoughtful were they about it and were they really honest?

Q. What career advice do you give people?

A. I think accountability is important. People have to be able to count on you to deliver on what you committed to deliver, whatever that is.

I also talk to people about what I have learned in my career, and what I would do differently in some areas. One of the things I should have done earlier in my career is network more. I thought, just keep your head down and keep working and everything will work out. And I’ve done well, so I have no complaints.

But the advice I give people is to really keep those networks alive and truly stay in touch with people.

Corner Office: A Good Manager Is Much More Than a Messenger

Q. You’ve started more than five companies. Did you have the entrepreneurial itch when you were a kid?

A. It’s funny, because the likelihood of me sitting here today and talking about these companies was exactly zero when I was a kid. I lived in Communist Czechoslovakia, and when I was 15, I was sent to vocational school to study accounting. When I was 18, I decided to study computer science, but we didn’t have access to any computers. So it was more science than computers. The first time I saw a computer or had access to a PC was when I was almost 25.

Q. Tell me about your leadership style.

A. A big part of my leadership approach is about confidence, and confidence comes from understanding. If you have a deep understanding of the industry you’re in, and of the problem you are solving, and you are ahead of everybody else in your space, then you can give your team the confidence to trust you. So if people are questioning what you’re doing, and the task looks impossible, you have to give them the confidence that we have a vision, and we understand the space better than anybody else.

The second thing is the importance of communication skills. Having a vision and having confidence doesn’t mean anything unless you’re able to communicate it to your team, investors and customers. The ability to communicate well didn’t come easily for me. I always assumed that everybody would see things the same way I see them, and now I understand it takes a lot of time to get people aligned.

Q. What about the culture you’re trying to foster?

A. The No. 1 thing for us is openness. It’s about trust — people can trust me, and I can trust people. So we have open calendars, for example, and certain rituals. Most Thursdays, I get in front of everybody to answer questions. Leading up to that, people will put questions online and then vote on the most interesting ones.

Q. And the open calendars?

A. Anyone at the company can see my calendar. Sometimes I’m surprised by how many people ask me what a particular meeting is for. You can never underestimate how curious people are about the C.E.O.

Q. What else have you learned about culture?

A. You can never be out of your role as a C.E.O. You always have to be careful about how you carry yourself and how you act with people because, again, it’s about confidence. For me, any start-up is one big, giant mood swing — every bit of news is extremely bad or extremely good and that’s what makes it so difficult for some people to work in that kind of environment. That’s why the C.E.O. has to demonstrate confidence, so they can say, “Here’s the bad news and here is what we’re doing about it.”

Q. Anything you have a particularly low tolerance for in your organization?

A. I have a really low tolerance for people making comments, especially managers, without actually positioning them.

Q. What does that mean?

A. Somebody might say, for example, that our competition has a new product. But is it good news or bad news? Should we do something about it? I always expect my managers to have an opinion and they should not be just messengers. A manager is not a messenger. I don’t like my managers essentially talking to their people without being able to express their opinion and position what they’re discussing.

Q. Anything else?

A. People know that I hate long e-mails and that all of the e-mails they send me, with a few exceptions, should always be short enough to fit on the screen of my iPhone. If you send me an e-mail, and I need to scroll down to read it all, you’ve lost me.

Q. Let’s talk about hiring. How do you do it?

A. I’m usually the first person to meet with a new candidate, because I’ll do the selling. People have options, and when they come to us, we’re not the only company they look at. We want them to be extremely committed to the process, even the process of hiring. They have to come and interview with 10 people and do homework. The best way to do that is to get them excited about the company and for me to sell them the vision and talk about the culture and why we will win. Then I’m usually the last one who sees that person again and then it’s a real interview.

Q. And so what are you looking for in that interview?

A. Raw I.Q. is No. 1, but the second quality is the ability to be part of the team. So the question I most consistently ask people is, “Tell me about a time in your career when you felt in the zone, where you felt you performed the best. It doesn’t need to be the most recent experience. It doesn’t need to be the most high-level job. I just want to understand when you were most excited, and at the top of your game. Who helped you to develop that? What was the environment? Why did you feel like that? What was the company? What was special about the company, about the product, about the space, about you?”

I usually focus on that moment because I want to understand how people got there and whether we can replicate that with this person.

Q. What is your very best skill — the thing that sets you apart from others?

A. I’m not a developer, and I don’t write code, but I have the ability to see where technology is going to be in five years. I can see it ahead of most V.C.’s and most analysts and most customers. If you look at all of my companies and my track record, the results show that I was more right than not. My secret thing is that I can see stuff that nobody else can see.

Q. And where do you do your best thinking?

A. Part of working in the big mood swing of a start-up is that you have to somehow get out of it. So every Saturday and Sunday, I’m on a bike for at least a couple of hours. I bike alone because those are the moments when I organize my ideas. Being alone is very helpful for a C.E.O. and I have very few of those moments. I also like long flights.

Corner Office: Brad Garlinghouse of YouSendIt, on Clear Leadership

Q. You joined YouSendIt with a mandate to turn it around. What changes did you make in terms of culture?

A. I think any great culture is born out of transparent, authentic communication. You almost can’t overcommunicate. You can try, and you might think, “Oh, do I really have to say this again?” And the answer is yes. One thing I started doing was to send out every Sunday night an e-mail to the whole company. The e-mails aren’t particularly structured, and they might be on all kinds of topics, like what’s really going on with our monthly results.

We also started a free Monday lunch to bring everybody together to share a meal. The first Monday lunch we did, some people got their food and went back to their desk. So I started to talk at these Monday lunches for a few minutes and then just take questions. I set the tone that all questions are fair game. The third thing I did was require everyone to do what we call a “fly along” with our customer support desk for several hours so they could really understand our customers.

Q. How did you develop these ideas about culture?

A. We are all products of our experiences, good and bad. Sometimes you learn as much from the negative experiences as you do from the positive. I’ve had the good fortune of working for a number of profound leaders. But I’ve also been in companies where the communication increasingly became noncommunication — where the C.E.O. would do an all-hands meeting, and at the end of it I would be wondering: “What did they just say? I don’t even know what that meant.”

I was most engaged with leaders who made it clear to me what we were trying to do, and where we were trying to go. I became invested in that. With people who didn’t do that, you feel a little bit alienated because you don’t internalize what they’re saying.

Q. Other steps you took?

A.We rewrote the company values. So our three values are: be in, be real, and be bold.

Q. Can you unpack those for me?

A. “Be in” is all about passion. Life is short. There are so many interesting things we can do in our life, and I feel like if someone is just kind of showing up, it’s not worth it for them or for us.

The second value, “be real,” is really about being authentic in our communication. I have seen different cultures in my career that I felt had atrophied and needed revitalization, and they were the ones where you just didn’t feel like people were being real in terms of their communication. You’d sit in a meeting and work through something and think you got somewhere, and then you walk out of the room and someone’s putting the parking brake on and you don’t even know they’re doing that.

And the last one’s about being bold. As some companies grow and develop, that instinct is almost beaten out of the system. To me, if we’re not failing a little bit, we’re not trying hard enough. I think great cultures encourage risk and are tolerant of failure. If you don’t do that, you’re going to end up with a culture that is stagnant and not thinking about the next generation of products and experiences.

Q. How do you hire?

A. I think there’s a certain amount of serendipity that is healthy to acknowledge. You spend a few hours with someone, and no matter how deep you go, you don’t know what it’s going to be like to work 60, 70, 80 hours a week with them.

The thing I look for more than anything else is passion. If someone brings passion to their work, it compensates for myriad potential weaknesses, and that passion manifests itself in hard work and commitment. It manifests itself in authentic communication. For really passionate people, it’s hard for them to keep their opinions to themselves because they feel so strongly about something.

Q. So what questions do you ask?

A. One of the questions I love to ask is, “How would your friends describe you in college?” And then they’ll say a few words, and then I’ll say, “All right, so after you graduated from college and started working, how would your first group of colleagues describe you?” I think you get more real answers that way than if you say, “Hey, describe yourself.” You definitely see some evolution as people mature.

For another question, I’ll start by saying that any successful leader, if they have been bold, has had some detractors over their career. And I will tell them a story about someone who was a detractor of mine. And then I will ask, “If you’ve had a detractor in your career, and I don’t need their name, who was that person? Why were they a detractor? What was it about that relationship that didn’t work?” It’s just interesting to see how they talk about it. If somebody tries to pretend they haven’t had one, that’s actually a warning sign. It’s also a warning sign if they say, “Oh, I’ve had 10.”

Q. What other qualities are you looking for?

A. Humility is certainly something I look for. I try to find someone who is self-aware and confident, but not to a fault. So one of the things I like to ask about that is: “Have you ever had to fire someone? How did you fire them? What was that experience like?” And you get from that a sense of their empathy. I think when people are empathetic, they’re less likely to be high on the hubris scale.

Q.What career advice do you offer people?

A. My dad told me at a relatively early age about this idea of “take the professor, not the class,” meaning just seek out the best professors, whatever they’re teaching. And the idea of taking the professor, not the class, applies to your professional life, too.

I think one of the mistakes people make is to go and work for the “hot” company. By the way, I’m guilty of this at various times in my career. But if you go work for the hot company, you could end up working for a 26-year-old who’s never managed anybody and is not thinking about how to make you a better employee, better manager and better person. But if you have a fabulous mentor or an engaging leader, that experience can help you launch a career.

This interview has been edited and condensed.

Corner Office: No Longer the Loudest Guy in the Room

Q. You’ve started several companies. Where did you get the entrepreneurial DNA?

A. My stepfather was a successful entrepreneur who built a sizable business and then sold it for a lot of money. And my father became a senior partner at PricewaterhouseCoopers. So I had an Ivy League-educated father with an accounting background who is very detail-oriented, and I had a stepfather who barely finished high school who built this massive direct-marketing company. All of that converged in me in a very fortunate way, in that I’m very analytical, but I also know how to sell.

Q. Other mentors?

A. John Sculley [former Apple chief executive] and I have worked together for at least 15 years. One of the things he taught me was style. I used to be much more brash. I remember the first time we went on a West Coast swing. I had just started a company called InPhonic/Wirefly. John was our first investor and took on the role of my mentor. We went to the West Coast and had 10 or 15 client meetings. I remember we came out of the first meeting and John said, “David, there’s a West Coast style and there’s an East Coast style. We need to work on your West Coast style.”

Q. Explain that for me.

A. Soften it up. Take it down a number of notches, and just listen instead of always talking. Up to that point, I had always been a person who could muscle my way through anything. He taught me how, from a leadership perspective, to step back and take in the landscape. And it’s something he does exceptionally well. He will sit in a room for an hour before he says one thing, but when he says that thing, he is so right.

Q. As you’ve expanded your companies, have you noticed there are certain break points or key milestones?

A. To me the first break point is when you hit $1 million a year in sales. It’s very different below that. The next jump is $10 million, then $25 million, then $100 million. At that point either the wheels come off or you get some business process expertise in your company. Very few entrepreneurs think about financial controls. Very few entrepreneurs think about balance sheet. They’re really all about the P.& L.

You have to remake your business constantly. And you’ve got to be willing to fail. Most people are not, so they’ll change direction but keep doing what they were doing simultaneously. If I see a division that’s not working, I will shut it down or sell it. Revenues end up going down? No problem. Because if you don’t get rid of that dead limb, management still wants to prove that they can make it work, even though you’re focusing on the new direction.

Q. You also invest in a lot of fledgling businesses. What are you looking for when you’re sizing up entrepreneurs?

A. I ask a lot of basic questions. Even though I might already know the answer, I want to see if they know. Like what were your revenues last month — not last quarter, but last month?

Q. And some people don’t know?

A. It’s shocking. They might round to the nearest $10,000, and these are small businesses. I want to know to the dollar. I’ll ask how big their market opportunity is and what is the market. I always like to hear how they came up with the idea for the business. What data points did they bring together that made this an interesting opportunity for them?

Q. Tell me more about the qualities you’re looking for.

A. I don’t run institutional money. It’s primarily me and three partners. The most important thing for me when I look at a new business to buy, control or invest in is, do I like the person sitting in front of me. That’s it. I’m an extremely dyslexic person, and when you’re not good at one thing I think you more finely tune other skills. I’m a very intuitive person and I try to understand different personality traits so that I can watch for patterns in other people. You can learn a lot about people and understand them if you’re more open and inquisitive. You’ve got to ask a lot of questions.

Q. How is your leadership style different today from when you were younger?

A. I listen a lot more. I will also often let people make mistakes even though I know they’re about to make a mistake. When I was younger, I always had to be right and I always had to be the loudest guy in the room. I will now literally sit in our weekly management meeting and let my chief operating officer run it. I could never have done that 10 years ago.

Q. What’s your approach to creating a culture of innovation?

A. It’s allowing people to fail. But you don’t let them fail too big. For example, we have a great guy who works with us. He loves the fashion business, and he wanted to start a fashion Web site. He gave a presentation to management, and many people in the room came to my office after and said it was a horrible idea. I said, “He’s one of the best guys we have in the company. Who cares? He’ll do it in his spare time. It won’t cost us much money, and when it doesn’t work he’ll abandon it.” That’s exactly what happened, but he felt empowered that he was able to go out and build that.

Innovation to me doesn’t have to be about creating the light bulb or the telegraph. Innovation can be very important small changes to something that’s already working. That’s the stuff that’s overlooked, and it can take things to the next level.

Q. What’s your best career advice to someone who wants to be an entrepreneur?

A. I’d give the same advice my stepfather gave me — which I didn’t take. Go work for somebody who you can really learn from in the field you want to be in.

Q. Any expressions you use a lot at work?

A. I say, “It’s a love story” a lot. It’s a great thing when I see somebody who loves what they do. I also say, “Time is the enemy of all deals.” The longer you wait to get a transaction done, the less likely it is to get done. People get deal fatigue and they start looking for the next shiny thing, and then they’re focused on that.

This interview has been edited and condensed.

Corner Office: Steve Case on Risk-Taking, or Lack Thereof, in Business

Q. What were some early leadership lessons for you?

A. The earliest ones probably related to just understanding that everybody is wired a little bit differently. Just because you think a certain way or are inclined to react a certain way doesn’t mean everybody thinks and reacts the same way. I think people just naturally presume that they look at a problem in a certain way and frame the issue in a certain way and that everybody else would look at it the same way.

I learned in my 20s that there are a lot of different ways to look at things, a lot of different filters that people put on, partly based on how they analyze the circumstance but also based on their own history and perspectives and biases and instincts and so forth. You have to be open-minded about that and listen to what’s being said — but also to what’s not said sometimes. Those discussions can lead you to different places.

Q. Other big leadership lessons?

A. The core one is a Thomas Edison quote that summarizes my perspective on things, which is, “Vision without execution is hallucination.” I do believe in vision. I do believe in big ideas. I do believe in tackling problems that are complex and fighting battles that are worth fighting, and also trying to, in my case, create companies or back companies. That can change the world. The vision thing is really important — but the execution thing is really important, too. Having a good idea is not enough. You’ve got to figure out some way to balance that and complement that with great execution, which ultimately is people and priorities and things like that. You have to strike the right balance. If you have those together, I think anything is possible. If you don’t have both of them working together in a complementary, cohesive way, you’re not going to be successful.

Q. What about mentors?

A. One of the co-founders of AOL, Jim Kimsey, said something when I was about 26. My view, in the early part of my career, was that appearances mattered, that looking like you’re working hard mattered. I remember Jim saying once — and partly I think it relates to some of his training in the military — that really the art is trying to set the priorities and assemble a team so you wake up in the morning and actually have nothing to do. It’s impossible to achieve, but it’s a good goal to have the right priorities and the right team in place so they can execute against those priorities. It’s almost the opposite of how I was approaching it. 

The objective should not be looking busy, but actually creating a process that allows great things to happen in a way that you can be less involved. So it was sort of a process of letting go, which is hard for entrepreneurs. But at some point you’ve got to let go and you’ve got to step back. Ultimately, that is about trusting the people you’ve got — but also trusting yourself, that you’ve set the right context in terms of the vision, the priorities, the team.

Q. With the benefit of time and hindsight, thoughts on the AOL-Time Warner merger?

A. They were both terrific companies. I think everybody saw it as a big idea to bring them together and help Time Warner move into the digital age and help AOL move into the broadband age. Well, it didn’t happen. The reason it didn’t happen is because the execution wasn’t up to the vision — going back to the Thomas Edison thing — and the primary reason was there were not the relationships and trust with people.

Ultimately, it came down to poor execution of what I thought was a good idea, and that was largely attributable to people and relationships and resentments and pride and egos. There were some substantive strategic debates, but it was mostly about people and trust and relationships. I’ve seen where it works well. It can really accelerate and animate a company to do things that nobody thought was possible. When it’s not working, you can’t get much done.

Q. On reflection, what should you have done differently?

A. It goes back to the people side. Both of the answers are probably somewhat impractical, but I think it would have resulted in a better company. One would be that if we’d brought these companies together — and I say this somewhat in jest, but it makes a point — we should have fired the top 50 executives, myself included, and hired 50 new executives who brought new perspectives and could look at this through the focus on the future, not in the rearview mirror. It would have done better. There is a reason why that happens whenever a new president is elected. They bring in an entirely new team to get behind their vision and execute that vision. If it were the same 50 people from the prior administration being asked to implement new policies for the new president, it would not work.

Corner Office: Liquidnet’s Founder, on Saying Goodbye to Titles

Q. Tell me about some of the values of your culture.

A. One is personal responsibility. I tell this to our new people during orientation, but if you see something that we’re not doing right and you don’t say something, then it’s on you. If you think that everyone on the leadership team is taking into account everything that could possibly go wrong, you’re wrong. It’s everybody’s responsibility to help us run this company better than we can do it by ourselves.

One of our philosophies is that I would much rather have everyone assume that everything we do here is wrong and that it’s your responsibility to help us fix it. That eliminates all the ego, or it should eliminate all the ego. Since we’re trying to constantly improve ourselves, you’re helping us by giving us some suggestions about what we can do better.

Q. Some people must be a bit skeptical at first. It’s one of those policies that sounds good in theory, but how do they know you mean it?

A. Well, first of all, we don’t have any titles. And the reason is that I do not want a junior vice president to be at a meeting and not say anything because they have a senior vice president in the room, which I believe happens quite often. Having no titles is symbolic, but it really works. Just to give you one example: we had an intern, 19 years old, and there were a bunch of us in a meeting. I was giving everyone my latest and greatest idea and he took me on and he disagreed with me. It turned out he was right, and I told him he was right at the meeting. So we have to practice it at the top.

Q. And what made you decide to do away with titles?

A. We eliminated them early on because we started getting all this title creep. Someone came to me once and said we had 15 titles or something, and I said: “That’s it. We’re done. No more.” I don’t want people to aspire to get a higher title. I want people to aspire to take on more responsibility. More responsibility gets them more recognition.

Q. How did people react when you told them you were eliminating titles?

A. It was very divided. A lot of people felt that it would be very difficult to attract people if we couldn’t give them a title, because that’s what goes on their résumé. Quite frankly, that really was not my concern. We found it turned out to be a good differentiator for us, and it helps us attract the right people. If somebody wants to come here but is determined to have a managing director title, then go to a place that has a managing director title.

Another thing I did from Day 1 was to set a no-suits-and-no-ties mandate. That, too, is a measure of informality. When we’re sitting around in jeans, or whatever people want to wear, that’s the kind of interaction I want. I want to have a casual interaction. I want to be able to say whatever I want to say and have them do the same.

Q. But you must have some hierarchy.

A. Everyone has managers, but the elimination of titles means that everyone has a right to state their opinion. We define levels by the responsibility you have in the company. So I am a “shape.” Most of the folks on the leadership team are shapes. We help shape the direction of the company. The people next level down are “guides.” The level below that are “drives,” and below that are “solves” and then there are “creates.” A working group came up with those levels. I just think they nailed it.

Q. What else about your culture?

A. We have something that I call a very efficient organ-rejection mechanism. If somebody comes in and just does not fit the culture, we reject them. Firing is a very big and an important part of who we are, as well. I think firing is much harder than hiring but it’s every bit as important. If you make a mistake, try to fix the mistake as quickly as you possibly can.

Q. Where did you get these specific ideas about culture? Were there experiences early in your career that affected your thinking?

A. I hated one of my bosses when I was in my early 20s. He was just nasty. There was nothing that anyone in the firm could do right. If you came up with a new idea, he would just beat it out of you.

Q. What are some things you do to spur innovation at your company?

A. We have a “skunk works.” Once every six months, we ask everyone to come up with ideas. It could be anything — a new app, a new process, whatever. And we have a committee that vets them and reduces them down to a specific few, and then we give people some time and resources to go and develop them.

Q. What advice do you give aspiring entrepreneurs?

A. First, find something you’re passionate about. Don’t do some kind of “furniture.com” business just because the furniture industry is big. Pick something you’re passionate about and define a very large problem. And if I were you, I’d define a very large problem that people know is a problem.

So take on a large problem, and see what you can do to fix it. Most people have not spent the time to figure out what is going to be their company’s value proposition. How do you win? If you don’t, it’s like going into a marriage knowing that there are problems but hoping that somehow, some way, it’s going to resolve itself. That doesn’t happen. So if you don’t spend the time to figure it out, why would you spend your money doing it, or somebody else’s?

I think that’s a common pitfall. Somebody creates a new app and puts it out there on a wing and a prayer. The true personality of an entrepreneur is not of a gambler. It’s somebody who goes for a sure thing. You have to figure there’s going to be a whole bunch of things that are going to come at you that you never expected. You’ve got to try to control as much as you possibly can control by anticipating that stuff up front. Those are the basics I leave people with.

Corner Office: A Start-Up Spirit, Without the 18-Hour Days

Q. You started working in Silicon Valley early on in your career. Tell me about that experience.

A. The first real start-up I was involved in was Epinions.com in 1999. I was employee No. 1 and my husband was employee No. 2.

Q. What were some lessons from that time?

A. A huge lesson was that we needed more experience when it came to the hard business skills. I think the oldest person was 29. How do you hire people? What’s legal? How do you think about culture? What’s right? What’s wrong? Without that, a culture evolved that wasn’t healthy. It was based on face time — “Just how loyal are you? Well, I slept under my desk. You went home?”

After a year, I left because it was just crazy. We had hired 100 people. No one really knew what they were doing. It became very cutthroat — kind of like “Mean Girls,” but in a company, with people telling on each other. Meetings were conducted at 2 a.m., and even if you were in charge of the project, decisions were made without you if you weren’t there.

Q. You eventually wound up returning to your hometown, Eugene, Ore., and took over the C.E.O. role from your father at Palo Alto Software, the company he started. Tell me about the transition, particularly in terms of the culture.

A. When we first came into the company, I just remember wondering, “Is there a factory bell here?” Because when 5 o’clock came, the office would empty out. My husband, Noah [the chief operating officer], and I struggled with that a bit. We didn’t like the Epinions approach of “Be here all the time, no matter what.” At the same time, we felt like Palo Alto Software was maybe too much of a lifestyle company.

So we started thinking about how we could get more of a Silicon Valley start-up sense here. How do you take the good and not the bad? I mean, working 18 hours is ridiculous. You can’t be creative and innovative. I didn’t want that environment, but I wanted an environment where people were more committed to results, and they were excited, wanted to innovate, were O.K. with uncertainty, and had enough pride in their work and their careers that they would do what needed to be done, and we weren’t going to have to baby-sit them.

Q. So what did you do?

A. We had to make a change with some people. We probably should have moved more quickly, but we were conscious of being respectful of my father, and we also knew all these people. It’s a small town.

But we just had to say: “The company’s changing, and certain people aren’t going to have the skill sets, and that’s just the way it is. We need to move in a different direction or we’re not going to survive. We’re a technology company. It’s grow or die, and innovate or die.”

Q. What were some of the other changes you made?

A. One of the important things is how you hire the right people. We definitely made mistakes and learned a lot from them. One of the things we want is someone who’s able to figure things out, and become an expert. You don’t say: “Oh, I can’t do that. I don’t know it.” You say: “How do I figure it out? What do I need to do?” We live in an information world and you can find out everything, and usually inexpensively. So we want people who aren’t afraid of that.

You can’t really ask that question in an interview, because you’re just going to get the answer they know you want. So we’ve changed our interview practices. Everyone who interviews with us, no matter what position, gets homework. We do an initial phone interview, and then they get homework before the in-person interview. It’s two hours of work. And the purpose of it is not to find the correct answer, but more to see their thought process. But more than 50 percent of the people you send the homework to never even contact you again. It’s great, because we don’t want that person.

Q. What other changes have you made in terms of culture?

A. We started having metrics meetings every Tuesday. They absolutely help us run the company and not have disagreements. If we look at data and metrics, it’s easier for us to make decisions and it’s easier for us to not argue about decisions because it’s all in the numbers. When you’re running a company that sells software, there are so many metrics that help you decide.

Not everybody has to come to the meetings, but they’re all invited, and it’s about sharing all the information. We focus primarily on financial metrics, like sales and expense, and then we look at unique visitors, and time on site.

Those meetings are about flagging the anomalies with all the right people in the room. It’s about recognizing the bad and the good, and then also understanding why, so that we can re-create the good. You want to be anticipating changes, but also reacting really quickly to changes. For the people who don’t attend the meeting, we also send out a confidential recap. And each department has its own metrics meetings. So it really trickles down.

Q. Any other big changes you’ve noticed in the culture?

A. There was a time at Palo Alto Software when we would say, “This company’s so great to work for that people stay here forever.” And that was considered a positive thing. And that’s not something we say anymore, because it’s not true. That’s a culture thing we wanted to change, because just because someone’s been here forever is not really a measure of a great working environment.

Smart people like to move around. There’s nothing wrong with that. And we’ve lost good people in the last three or four years because they’re starting their companies. We say we want to hire entrepreneurial people, so how can you then be upset when they go off and start their own company? And we’re not. We’ve actually worked with ex-employees and helped them start their own companies.

Corner Office: Kris Duggan of Badgeville, on the ‘Getting Stuff Done’ Index

Q. How do you hire?

A. The most important thing is to have a framework that everybody in the company knows. So we said: Let’s just come up with something very simple that is easy to understand and that people can use every day in their interviewing skills.

The first is to hire people who are experts in their domain. It’s really about excellence. So I will ask people, “Are you an expert in your field, and if you are, help me understand your field.” Then I ask, “How did you acquire this knowledge?”

The second thing I’m looking for is “sparkle.” Is this person contagiously enthusiastic? You may be an expert in your field, but if you don’t communicate well, or if you don’t get people excited, or you’re not passionate or enthusiastic, that’s going to be a hindrance. And it’s not the difference between being introverted or extroverted — you can just see it in somebody if they have the magic.

The third thing we look for is people who just get stuff done. We’re very focused on metrics — we have goals and controls, and everybody in the company has them. We even have a rating system we use to score employees, from 1 to 5, based on their “getting stuff done” index every quarter. People take the scoring concept very seriously, and really like the accountability and the transparency around some of these things — and the fact that they’re empowered to get stuff done.

The other critical thing we’ve done in our hiring process is to require every candidate to do homework. It varies by department and by function, but every hiring manager has to have a homework assignment for open positions. We just hired a director-level marketing position, and they had to come in and present their plan for what they would do for the company to drive their marketing strategy.

I’ve found that there are so many biases that we create or imagine when we’re going through the hiring process — this person came from that school or they seem very polished, whatever the biases might be. But when you have them put pen to paper, and compare that against a field of candidates, you get a much clearer picture of how they think and work.

We also don’t set deadlines for handing in the homework. We let them set the deadline, but then we track very closely how they perform relative to that. So we’d never say, “You owe us the homework by tomorrow.” We would say: “We’re very interested in you, and we’d like you to do some homework, and here’s the assignment. Do you have any questions about that? And when would you like to submit the homework?” That’s one way we can test for their behavior — do they get it done on time, or do they make excuses because it’s late? What I’ve found from all the interviews I’ve done in the last 10 years is that whatever nagging suspicion you have during the interview process about their behavior will be magnified 10 times after you hire them.

Q. You mentioned the importance of having shared goals in the organization. Can you elaborate?

A. I think organizations have a hard time communicating up and down the chain of command and getting everybody mobilized to focus on the same goals. I’ve experienced that firsthand — whatever your task or scope of work, you don’t know how that connects to your manager and your manager’s manager, and how that is all kind of interconnected.

So the biggest thing we focus on is this concept of “interlock.” It’s about how we get all the departments connected with their goals — from the C.E.O. to the front-line person — so that all of those goals and controls are transparent. Everybody should know what everybody’s goals and controls are, and everybody should understand their individual ones relative to their department, and their department’s goals relative to the company’s.

This interview has been edited and condensed.

Corner Office: Ryan Smith of Qualtrics, on Building a Transparent Culture

Q. What were some early leadership lessons for you?

A. I definitely had an interesting upbringing. There are five children, and everyone’s been pretty successful. My parents are both Ph.D.’s — they were in academia until the late stages of their careers, when they decided to go into entrepreneurial ventures.

They raised us with the mentality of “if you want it, you’ve got to go out and get it.” I remember when I was 13, my mother dropped us off in downtown Provo one summer, about two miles from where we lived, and said, “You guys are all paying for your clothes this year. Don’t come home till you have jobs.” They instilled in us the idea that “you can be anything you want to be, but you’re going to have to go do it.”

Q. How did you start Qualtrics?

A. I was a sophomore in college and working in L.A. for Hewlett-Packard on a summer program. My father was diagnosed with throat cancer, so I took a semester off school to be with him. He was always tinkering with technology to make the research world better. And when he would come home from his radiation treatments, he couldn’t speak. I bonded with him by helping him with his work. The cancer was very severe, and he needed something to look forward to. So we would work together, and by the time he recovered from the cancer, I had signed up 20 clients and we had formed a business. We’re 290 employees now, and we’ll probably double in size in the next 18 months.

Q. Tell me about the culture you’re trying to foster.

A. We’ve been extremely transparent, but not so that we can be cool. And it’s not about an open environment, because that’s not what makes a company transparent. It’s more around the fact that everyone needs to know where we are going and how we are going to get there.

So we want everyone to understand our objectives and make that available to everyone as we’re evolving, so people aren’t guessing and they’re not internally focused. That’s one obstacle a lot of companies fall into. I believe most companies fail because they’re not focused — they either get focused on other things in the market that aren’t important, so they’re thrashing around without a clear objective, or they’re focused internally on things like politics and bureaucracy. It’s not that these companies aren’t smart companies or lack good businesses. It’s just that there’s a lot of noise.

We want to be transparent because we want to encourage our people to have all the information to keep them focused on what really matters — our objectives and how they’re going to contribute.

Q. Can you give more details about how that works?

A. We took our best product guy and some of our best engineers and built a system internally to help scale our organization by knowing everyone’s objectives in the company. We have five objectives annually for our company, and everyone goes into the system each quarter to put in their objectives that play into those broader goals.

For one of the broader objectives, you might have 230 specific objectives. The reason we’re making all this available is, especially nowadays, you’re hiring individuals to think. We can’t control the way they think. All we can control or have an effect on is the environment around them.

We have another system that sends everyone an e-mail on Monday that says: “What are you going to get done this week? And what did you get done last week that you said you were going to do?” Then that rolls up into one e-mail that the entire organization gets. So if someone’s got a question, they can look at that for an explanation. We share other information, too — every time we have a meeting, we release meeting notes to the organization. When we have a board meeting, we write a letter about it afterward and send it to the organization.

When everyone’s rowing together toward the same objective, it’s extremely powerful. We’re trying to execute at a very high level, and we need to make sure everyone knows where we’re going.

The point is that it’s not like we just said, “Hey, we’re going to be transparent.”  We look at every decision and then say, “Why shouldn’t we share this with everyone?” And we do that instead of the default reaction of saying, “We’re not going to share anything.” It might make some people uncomfortable, but that’s not a good-enough argument. 

Q. Let’s shift to hiring. How does the conversation go? What are you looking for? What questions do you ask?

A. We definitely want someone with a high trajectory. The organization is going to change quickly — we’re not perfect, and we make mistakes. We want to find individuals who align with that, who will add value to the company in whatever role they’re in. Part of that is the disposition to be willing to do whatever it’s going to take, because we feel that if we win as a team, we’re going to win together.

Q. Tell me more about how you get at those qualities.

A. From my standpoint, I’m looking to see if someone’s a “gamer” — that’s what I call it. I want to know the hardest thing they’ve ever done. So if you were in Korea, traveling by yourself, did you go home when things got tough? That’s what I’m trying to figure out because when the ship’s going well, everyone’s good. But when obstacles come up, we’ve got to sit back and rethink, how are we going to navigate these? Will some people want to jump off the ship? Or are they going to be a gamer and want to come in, roll up their sleeves and say, “Hey, this is part of it.”

That’s what I’m looking for. I want someone who’s going to roll up their sleeves when a little bit of challenge comes their way.

I think you can pick that up by looking at someone’s career. When times get tough, do they stick in? Because most good things happen after you hit a rough patch. If things are too easy, we probably didn’t learn enough.

The interview has been edited and condensed.