Corner Office: Jay Walker on Why Leaders Don’t Always Make Good Managers

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Corner Office

By ADAM BRYANT

This interview with Jay Walker, chairman of Walker Digital and founder of Priceline and Upside, was conducted and condensed by Adam Bryant.

Q. What were your early years like?

A. I grew up in Yonkers, N.Y. From an early age, I was an entrepreneur. I delivered papers. I shoveled driveways. I sold greeting cards. I sold everything.

I had that start-up gene, like some entrepreneurs do. You get knocked down and get back up. If something doesn’t work out, you try something else. I definitely had that persistence and a desire to understand customers and persuade them to buy products or services.

Tell me about your parents.

Both of my parents were highly entrepreneurial. My mother fled the Nazis when she was 6, so I’m a son of a German on one side, and my grandmother on the other side fled the Russians. I’m the son and grandson of immigrants.

That pretty much shows in my outlook on the world, because immigrants are largely entrepreneurial. You have to leave your country behind, go to a new land, a new culture, across an ocean, and you’re determined to make it work.

I got the willingness to take risks and fail from my father’s side of the family. He never talked about succeeding or failing. He would ask: Are you learning? Are you experiencing things? Are you paying attention?

And from my mother’s side I got analytical skills and attention to detail. So I have this amalgam of two heritages.

I was very fortunate. My father had done well financially, relatively speaking, and so I got to travel a great deal. Before I was 15, I had been to Europe five or 10 times.

I could travel by myself. I was one of those kids who was a little older than his age. My parents would let me go places, so I spent six weeks traveling in Europe when I was 12. Travel teaches you to be independent, make decisions and learn how to get by.

What were some early management lessons for you?

I’m not a manager, and you wouldn’t want me to manage anything you were running.

Because?

Because management is a set of skills and desires, neither of which I’m strong in. Management is the art of accomplishing objectives through others, and that’s different from leadership, which is more the art of inspiring others and getting them to want to do things.

I’ve never thought of myself as a particularly good manager. A manager’s job is to develop the people they work with. It’s about process. I’m not a strong process person. I’m more an out-of-the-box guy.

I’ve always hired managers to do the job of management, which is no insult at all. It’s not beneath me in any way. It’s just not my strength. Create things? I’m your guy. Solve unusual problems? Maybe. Dream up whole new ways to approach things? I’m your guy. Manage? Not so much.

Let’s say I came to work for you. What should I know about what you’re like as a boss?

I would correct you right out of the box. My style is not to perpetuate a false illusion that you work for me. You work for you. You get up every day and you come in here because you want to be here. We’re not having a discussion about who’s in charge. If you have a better idea, great. Let’s hear it.

I wouldn’t try to encapsulate a set of rules and regulations to say here’s how I do things. But I will tell you that I’m highly collaborative and interested in the best thinking. If you can express yourself well, that’s good. If you can’t, that’s a big problem.

My style would be to say: What are you trying to accomplish? How are you going to do that? How can I help you? You might say: “Jay, what I need to succeed is for you to never talk to me. Just send me emails. And I’ll deliver in spades what you want.” Then I’ll say, “O.K., let’s see if that works.”

Like any entrepreneur, I’m highly adaptable. You work with what you’ve got, not with what you want. And what you’ve got is often an incomplete set of facts, an insufficient amount of capital, an insufficient amount of knowledge about the key things you need and insufficient people to do that job. Other than that, welcome to the job.

How do you hire?

I’m looking for the things you would expect — people who are thoughtful, passionate, adaptable and who have failed, preferably two or three times. If you haven’t failed, that’s a big problem.

What is your single best interview question?

Tell me how you’re going to make a great deal of impact on our organization, and how you’re going to make us both a lot of money. In a small firm, there is no room in the rowboat for somebody who can’t pull the oar, because everybody else has to pull that oar.

What career and life advice do you give to new college grads?

The No. 1 thing that young folks often misunderstand is that they use money as a scoring system for the desirability of the job, which is understandable when you graduate with $200,000 in college loans.

But the fact is that you’re going to do much better financially if you find a job where you love what you’re doing, even if you have to create the job yourself.

The second thing I tell them is you need to start learning. They haven’t learned anything. Most new graduates think they’re ready for their career, and they’re not. They need to start with a clean sheet of paper. You need to start reading more, not less.

You’ve got all this stuff to learn, and by the way, you’ve got to learn it in a dozen fields, not just the one you’re working in, because it’s all about cross-pollination. It’s all about taking good ideas in other areas and bringing it into your area.

It’s all about adding value above your job description, not just doing the job. You’ve got to exceed that by a substantial margin if you really want to get ahead.