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.