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Kenny Chesney Shows Appreciation for Employees With Respect and Free Trips to the Virgin Islands

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Mike Coppola, Getty Images

A gig on a Kenny Chesney tour is one of the best jobs you could land, and not because he makes great music and seems like a cool guy. Chesney appears to be quite a generous, caring and fun boss — a luxury most working stiffs don’t enjoy. The singer spoke to the New York Times about the business of Kenny Chesney, which entails touring, merch and more, and about being the boss of an operation that employs 120 people on the road and 30 off.

Chesney’s Golden Rule of running a well-oiled machine? Communication.

“It’s important for me to be sure that everybody knows what everybody else is doing,” he said. “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.”

His other top priority? To treat his people well. Chesney said, “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. ”

Chesney sometimes institutes a merch lottery where everyone’s name is tossed in a sombrero and whomever sees their name pulled out of the hat wins the merch take of the night. The largest pot totaled $300,000! That’s beyond generous. But beyond his generosity, Chesney said the crew is such a tight-knit family that they split the booty amongst themselves. “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,” Chesney said.

A merch lottery isn’t the only way Chesney demonstrates his appreciation for his staff. At the end of each year, he takes his crew, merch, catering and management staff to the Virgin Islands for a week. Girlfriends and wives are also invited, on Chesney’s dime. He’s done it every year since 2002.

Chesney also admitted that he is hands-on with everything, from the color of his tour bus to what he eats for dinner to how the lights are hung. But it’s his brand, and he has to make sure that dollars and cents add up, financially and reputation-wise.

The toughest thing he learned as a boss is how to be “everybody’s friend” and how to instill the idea that “this is the way it’s got to be.” He said, “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.” He also learned to handle confrontation, rather than avoid it. He admitted, “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.”

The singer also revealed the criteria he uses when interviewing someone to join his crew. He often asks them about their family and their down time. “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,” he said.

That aside, Chesney is looking to learn about people’s characters before he puts them on the payroll.
“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,” he admitted.

No wonder there isn’t much turnover on his staff.

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