Stephen Cloobeck believed he knew the inner-workings of his company, Diamond Resorts International, from the top-down.Cloobeck, the CEO, placed his business cards at the front desk of more than 177 branded hotels. The goal was that when a customer was upset, he’d email him and Cloobeck would respond in less than 10 minutes.
He preached to his company “the Meaning Of Yes,” which at its essence meant never telling a customer “no.”
So when CBS approached the CEO to be on the third season of its primetime reality show “Undercover Boss,” at first Cloobeck declined.
He was the face of Diamond Resorts International, so his employees would definitely recognise him. Cloobeck also serves as the chairman of the entity responsible for marketing U.S. tourism abroad.
He “surprise attacked” his resorts all the time. Everything was under control, he thought.
Cloobeck’s right-hand man, David Palmer, president of Diamond Resorts, pushed the experience on Cloobeck after talking with other CEOs who went through the “Undercover Boss” experience.
“Stephen’s expectations about customer service are pretty unrealistic,” Palmer said in an interview at the episode’s premiere in New York City this week. “That is what I like about him, but I felt like the snapshots he was getting during the surprise visits were still very varnished. He needed this.”
So after an hour of makeup each morning, Cloobeck posed as Jack Fischer, a middle-aged man who wanted to quit his day job and venture into the world of hospitality. Fischer would shadow four different Diamond Resorts employees to find out what it was really like, and if the career change was really for him.
Yesterday, Cloobeck saw the episode he starred in for the first time along with friends, colleagues and the media at the Eleanor Bunin Monroe theatre in Lincoln centre. He hid his face during parts of the show where he said silly things such as “I feel my abs getting stronger, flatter,” after performing physical labour with his team members.
What Cloobeck found during his ruse caused him to turn red in the face, scream and even blow his cover at one point. It wasn’t because his employees were bad; they were “improperly trained” to carry out Cloobeck’s company motto, “the Meaning Of Yes.”
“I realised my company was nowhere near as efficient as it could be,” Cloobeck said. “I also understood after my experience that everyone in my company needs to communicate better, which means they’ll communicate with our guests better.”
In one scenario, a repairman was still using sandpaper by hand, when using a sandblaster would have cut the job’s time by a fourth. In another, the front desk attendant was still logging information by paper, and not using the computer matrix. And the representative at the call centre didn’t properly understand how to roll over a customer’s points to use for next year’s timeshare.
Despite the flaws Cloobeck discovered in his company during the show’s filming, he enjoyed getting to know four of Diamond Resort’s team members, who came to work every day to support their families, despite hardships they had endured.
The hotel engineer had a business deal go sour, so he and his wife each had to work two jobs to pay for their retirement. The 22-year-old front desk attendant had a sick mother whom she cared for and contributed to the family food fund. The worker at the call centre was drowning in student loan debt.
Cloobeck rewarded the team members who trained Jack Fischer and taught him about his company with gifts that brought the employees and some members of the audience watching the episode to tears. The hotel engineer’s mortgage was paid off. The handyman received a new truck, and a new freezer because he told Jack he liked to cook. The call centre representative’s student loan was paid off. The hotel front desk attendant received help with her mother’s hospital bills.
And those were only some of the gifts they received.
“I’m really proud of my team members,” Cloobeck said. “This was such a great experience because the company starts and ends with me, and now I know the work that goes into every aspect of it.”
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