Cloobeck undercoverWhen Stephen Cloobeck, ceo of Diamond Resorts International, was approached to appear on CBS TV’s Undercover Boss–in which bosses show up disguised as a new worker in order to get a front line view of how the company functions–he initially said 

“Thanks, but no thanks,” to the offer: His relatively young company, made up of 180+ resorts around the globe, was doing just fine, and he didn’t think it was worth the risk to the brand and to the company to do the show. But his executive team convinced him it would be a good exercise, so he agreed. What he learned was eye-opening: Yes, the company’s philosophies were in place, but they weren’t consistently generating the guest experience that Cloobeck intended. Becoming an Undercover Boss helped him to see the real issues and also, the right solutions. 

CloobeckStephen Cloobeck, CEO of Diamond Resorts International, in disguise for Undercover Boss (first photo) and as he usually looks.Probably the most important lesson Cloobeck learned was that often what stands between a guest and a great experience is an employee’s stress, and they are often stressed about things unrelated to the job. At the conclusion of the episode, Cloobeck cemented new relationships and offered financial relief to team members in need so they could focus on doing their personal best. 

For Cloobeck, being on the program was a risk, but ended up being a lesson well learned. So, when CBS asked if he’d shoot a second episode, Cloobeck agreed.

A Risk Becomes Reward
But why repeat the experience? Starring on Undercover Boss “was the most miraculous journey a CEO can take,” Cloobeck said. Being on the show helped him develop “tremendous appreciation for the team and the brand.” But there was another great benefit: It helped him to accelerate “the journey of improving the business.” 

So when the company recently added five new hotel groups–with five different cultures, processes and sets of standards–to the DRI family, Cloobeck very clearly saw that the way to integrate them quickly and effectively was to go undercover. 

Being on the show a second time “let me assimilate the new properties into the company,” Cloobeck said. “It usually takes a year to get [the new properties] on line, but being on this show let me get them on line in three months.” For Cloobeck, being on the show is an all-around win. But is it a win for guests and team members?

Creating Excellence–From The Top Down
Cloobeck believes so. In his first round on Undercover Boss he learned that when team members have issues–from financial stress to family pressures to career struggles–this can impact the guest experience. “And [employees] are the core of the business,” said Cloobeck. “On balance sheets we don’t have a line for human capital, but they are the most important asset we have.” Cloobeck learned from his first go-round on the show how to help his team members get past their personal issues so they can excel on the job. In the second episode, he continued that path. At one of the new properties he met a team member “who we did something special for, that was not about money, but about saving a life. It’s amazing that if not for the show, this woman perhaps would have died.” Cloobeck also learned something about himself: “On the second show learned that I should not do blow outs and wash hair. It’s not one of my strong suits. I’m not good at that!”  The episode, which aired on November 30th, can be viewed here.  

DIR Sedona“Undercover Guests” could win a trip to one of Diamond Resort International’s many properties; pictured here, DRI’s resort in Sedona, Arizona Another Undercover Invitation: Undercover Guests
Cloobeck believes so much in this journey of discovery that he recently announced DRI’s own program, ‘Undercover Guest,’ a contest that will bring ten families to a resort for a week, at the end of which they will report to Cloobeck about their experience (entry information can be found on DRI’s site, While this contest won’t be front and center on CBS, it will help DRI to further polish guest experiences by getting ideas and opinions straight from the best source: their guests.