
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. "That is what I like about him, but I felt like the snapshots he was getting during his "surprise" visits were still very varnished. He needed this."

Cloobeck gave up the corporate executive suite at Las Vegas-based Diamond Resorts for two weeks to fix and paint drywall, handle small maintenance projects, and check in guests at a few of his company's timeshare developments.
"I realized 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."
While he saw small things that needed "fixing" in the company, Cloobeck said the interaction with employees helped him understand what workers go through.
Cloobeck would encourage any CEO to participate in the series. "It's important to get into the trenches and see if systems are working properly," he said.
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