Yes, You’re Smart, but What About Your Topspin?

Q. When you were younger, were you in leadership roles?

A. I was the captain of a couple of teams in high school — basketball and track. It was a great experience. Then I had a short-lived but terrific management experience right out of high school, when I went to the Naval Academy. I stayed for a semester but I learned so much. During a plebe summer at a military academy, you learn more about yourself than probably four years of college anywhere else.

Q. What did you learn about yourself?

A. What you’re capable of, and how you don’t need sleep because you’re not going to get it. You also find out physically what you’re capable of.

I saw leaders who were good role models, too. I liked the leaders who pushed very hard, and they could get the best out of you without being overly tough. They corrected you, but there was just a positiveness to how they approached everything that attracted me to them as leaders.

I’ll never forget that. They’d be very tough on you, but they knew when to take a little bit of a break and maybe whisper something or just let you know that they were empathetic. They knew when they’d pushed too far and they knew how to pull back.

They were a great example of a saying that I use all the time: “You treat people well, they will return the favor. And if you treat them poorly, they will return the favor.”

Q. Tell me how you rose to the chief executive’s role.

A. The agency’s been around since 1968, and I’m the second C.E.O. in 44 years. The founder, Jack Connors, knew that the business would change, but it was important to him that the core of the culture would go on. And he gave me a good period of running room, a few warm-up laps before I became C.E.O.

Q. Did you have explicit conversations about why he thought you were the right person to take over?

A. Nothing explicit. But I knew he trusted that I understood the culture.

I also appreciated what he had built from scratch as a founder. There were those early days in the agency’s life when he wasn’t sure if the place was viable, and I think he knew that I really respected that. I’ve told him that I’ll always know the difference between what I do and what he did. He started from scratch, and in my mind, there’s no comparison. There were times when he was worried about keeping his house. I’ve never had that kind of worry.

Q. How did you learn to be a leader?

A. I was always observing leaders and tried to understand why they succeeded or what their flaws were. I learned that there is a selflessness to really good leaders and that they were willing to sacrifice for the sake of the team.

It was important to have a coach who valued assists and rebounds as much as scoring points to build a winning team. People who didn’t succeed as leaders, or who were short-term leaders, tended to be more selfish, because the people can smell it a mile away when someone’s not supporting them, or someone’s not advocating for them. It’s not hard to tell.

I’ve also seen a lot of leadership skills in people who played competitive sports and were captains of teams at a young age, and who at some point in their life trained incredibly hard and left it all on the field. And you have to learn from your losses. If you don’t take losses seriously and if it doesn’t really bother you, I don’t think that you’re going to be a great leader. You’ve got to lose sleep at night.

Q. Tell me more about the culture of your company.

A. I think there are two kinds of cultures, and then you can subdivide them after that. One is based on a foundation of insecurity, fear and chaos, and one is based on a firm platform where people come to work and they’re worried about the work itself. They’re not worried about things that surround the work and are not important. I’ve tried to make Hill Holliday that kind of environment, where people come to work and they’re not worried about their peers shooting them. If leadership doesn’t provide a forum for that kind of behavior, it dies quickly. People forget about it and they just focus on doing their job.

You don’t want a conflict-free zone, but you want the conflicts to be about the work itself. Sometimes you have to dig a little bit and talk to people, but if you find out the conflict is about the work, then that’s good, because it’s healthy. I think that in a lot of workplaces it’s the opposite — people have to come to a consensus on the work, and so all the conflicts are political.

That’s one thing that the founder, Jack, instilled in the culture. It’s not a democracy. You’ve got to make tough decisions and then you’ve got to move on. “The enemy’s out there,” he would say. “The enemy’s not in these four walls.”

Q. Let’s talk about hiring. What are you looking for?

A. There are people who are smart, and they can assimilate their observations. But then there are people who can turn those observations into insight. There’s just a magic to it. I don’t know where it comes from, but I know it when I do it. I’m trying when I’m interviewing people to see if they have that kind of spark, if they have that kind of tenacity to push, to take what is orderly and then maybe put some incredible topspin on it.

I’ll ask people what they’ve done in the past that they’re most proud of. We’ll dig in deeply into important events in their life about their role and what they felt afterward. You get a sense of who’s real and who’s maybe academically perfect but just may not have that topspin that you need. You want to populate the agency with people who can put a lot of topspin on the ball.