When you first meet Undercover Boss Stephen J. Cloobeck, Chairman and CEO of the Diamond Resorts Corporation, you kind of want to hate him because he has everything you probably don't: a Maserati, a buff body-builder physique, a smoking hot model/actress wife, and of course, a luxurious palace-like home. But as the premier episode of the third season of the CBS hit progresses, you rapidly realize that this guy is amazingly down to earth and eager to make things right.
He allows himself to appear on national TV in a ridiculous wig, pretty much bungling every task he's assigned, no matter how menial. He almost sets a roof on fire. This season's cover story, so employees don't get suspicious about the cameras, lights and producers, is that some poor guy is on a show trying to decide if he should quit and go after his dream profession, or keep his day job. Most of the employees Cloobeck worked with suggested the latter.
Now, I know a lot of viewers are skeptical about this show, wondering how they can fool the employees, and how they can find so many people with difficult backgrounds and challenging stories. But I have gone behind the scenes at "Undercover Boss," interviewed all the bosses and many of the producers, and I can tell you that this is one reality show that's truly the real deal. Of course there's some savvy editing done, and you don't see all the boss/employee interaction that takes place. But their stories and rewards are 100 percent authentic.
For example, for this episode, Cloobeck told me all about his great mortgage payoff: "I decided to do it on the spur of the moment. I asked Randy, 'What's your mortgage?' I think he told me about $1,200 per month. And I said, 'No, I don't want to know your monthly payment, I want to know how much you owe on your mortgage.' And he told me. I wanted to do something great for this guy. There's no reason he and his wife should each have to be working two jobs like that...so I told him I was going to pay off his entire mortgage. He fell like a big old piece of timber to the ground, crying." You just can't script that kind of stuff.
Believe it or not, that was just the tip of the iceberg regarding the bonuses and rewards Cloobeck dolled out to the employees he worked with -- even the incompetent one who came perilously close to being fired. You really have to see this episode to believe it. But be forewarned: You'll need a big box of Kleenex, and you'll find yourself glued to the television at 8 on Sunday nights from now on.