The New York Times recently caught up with Kenny Chesney, however this interview was a bit different as they discussed the business side of things. This is a great interview that really gives you an inside perspective on Kenny Chesney and his role as a leader to a solid crew. It is because of Chesney and his amazing crew that makes everything happen so fans can enjoy the fantastic shows they put on night after night.
Q. So, you’re the C.E.O., in effect, of Kenny Chesney Inc. How big is the business?
A. I have 120 employees on the road every day, and about 30 other employees off the road. I remember being on the bus a couple years ago, and I looked out the window of my bus and said to myself: Who’s paying for this? And it hit me: You are! I was in charge of making sure that we get from Point A to Point B, that we all do it seamlessly and that we all do it effectively, and we all do it on time.
Q. Tell me what’s important to you in setting a tone and a culture among your employees?
A. It’s important for me to be sure that everybody knows what everybody else is doing. I want there to be a level of respect between everybody. You get that many people out on the road at once, and all of a sudden agendas sometimes can become a part of that. And sometimes they’re not your own. There’s this idea that somebody’s job could be more important than somebody else’s, and to me, that’s not true.
Q. So how do you make that real — everybody should have respect for everyone else — rather than just a slogan?
A. I want all the people out there who work with me to feel as appreciated as possible, especially the people who are the first to get up in the morning and the last to go to bed — my crew guys. Sometimes we do a “merch” lottery. We put everybody’s name in a huge sombrero and whoever’s name I pull out gets all of the money from merchandise sales for that night.
Q. How much money could that be from the merchandise?
A. Probably the biggest check was three hundred grand. But do you know what those guys did? This is why I think this kind of thing works: They waited until the end of the year and I wrote one big check to the crew and they divided it up 13 ways. Doing things like that just motivates people.
Q. What else do you do?
A. At the end of each year, I take the band, crew, the merchandise people, catering people, my management team, their wives, girlfriends, whatever, down to the Virgin Islands for a week to thank them. I pay for everything, and we’ve done it every year since 2002.
Q. I imagine a lot of artists just focus on the music and let others worry about the business. Obviously, you’ve not done that.
A. I don’t have the computer chip to say, “O.K., I’m just going to write my songs and sing them and the business is up to you guys.” I’m so hands-on, from the color of my tour bus to what I eat for dinner at 5 or the way the lights are hung. I mean, you could only imagine what diesel fuel costs me as an overall expense for this year. It’s exhausting, but that’s me. And my name’s on everything.
Q. Over the course of your life, what do you consider as some important leadership lessons?
A. An important mentor for me, in terms of teaching me that there’s a right way and a wrong way to do things, was probably my football coach. And playing football was one of the first times in my life that I realized nothing is given to you. You have to work really hard. I was a very short, slow wide receiver on a very mediocre football team. And we had to work really hard to be as mediocre as we were.
Q. What made you decide to get so involved in managing and leading your business?
A. For the first five years on the road, I didn’t make any money at all, and I had no idea what I was doing — none. I was fresh out of college, and I didn’t really think that this was going to last. But there were moments when I thought: What if it does last this long? What if this is going to be my life? And if it is, how am I going to approach it? And I realized that I wasn’t saving any money. I couldn’t afford a house. I had no investments. I had nothing.
And I sat down with my manager, Dale Morris, and told him what I wanted to do and realized that I wanted this to be my life. He had been in the business a long time, and he had a great business mind. That’s when I realized I didn’t just want to be a singer-songwriter and let everybody else take care of everything. And from that moment on, I started really paying attention to a lot of detail and to what I was making every night.
Q. What are some of the more subtle points of leadership you’ve had to learn?
A. It can be hard to be everybody’s friend and still show them that this is the way it’s got to be. And I’ve gone both ways. I’ve been everybody’s buddy and then it was tough because you put yourself in a position that’s not the best when you have to let people go. That was tough for me. I’m still kind of everybody’s buddy, but they know I’m the boss. I think it is possible to be friends with employees, but there has to be a respect level where you’re not taken advantage of, either.
Q. When you’re on the road, you’re spending a lot of time with your employees.
A. I don’t think there’s a better laboratory for human behavior than being out on the road with a lot of people for a long period of time. You know, you see the best of people and you see the worst of people. When you get 120 employees out there, you see every one of those people go through ups and downs in their life. One thing that I learned that helped me deal with human behavior is confrontation, and I’m not that great with confrontation at all. But once I started to be O.K. with that, the better everybody’s life got. We didn’t have a lot of those problems after that because I try to talk to everybody as much as possible to clear the air. If you don’t clear the air, with that many people together on the road, it can be just a mess. I think it’s helped me as a person. I think it’s helped my business. It’s helped the morale out on the road, and it’s helped everybody communicate better.
Q. How do you hire?
A. There hasn’t been a lot of turnover. My band has basically been the same, except this year we did hire another guitar player. I let my band leader do the hiring, but I had to approve it. I knew what I was looking for. I know that, with spending as much time together on the road as we do, they have to be a great player but they also have to have a certain mentality, and they have to be almost a better person than player.
And that’s because when you live with people out there, and you have as big a family as we have, attitude is so contagious. You take a couple of people who have hidden agendas or bad attitudes or feel entitled or whatever the negativity is, and it just spreads like a cancer. So they’ve got to be a great player, but they also have to bring something else to the table other than that.
Q. So what do you ask people in an interview?
A. I want to know about their family. I want to know what they do in their down time. I want to know what their dreams are. I want to know what they watch on TV. I don’t care about their religion or their political views. I don’t care about any of that. But I do have to know if, deep down, they’re a solid person, and that they’re not on drugs and don’t have those kinds of problems. I can’t have any of that stuff in my life. I’m too healthy, and I’m too focused. I want to know if these people are focused.
And are they dependable? I mean, that’s the main thing. I don’t really have a lot of rules, but I need to know they’re dependable, and that they’re on time. That’s the two things that can just drive me crazy. I don’t want to have to worry that something might not get done when I ask them to do it. I don’t like that because then I start second-guessing myself and I’m just too busy in other areas. I think that no matter what business you run, people have to be dependable.
Q. And if you could ask somebody only a few questions to decide whether to hire them?
A. I would want to know how close they are with their family. No two days are ever the same on the road. And it’s really important to have people out there who can roll with the flow — who don’t look at every situation as a life-or-death thing — and take each day as it comes. So I would ask them about their family, and I would ask them if they’re able to roll with the flow. You don’t know that until you see people behave in certain situations.