The rewards of hanging with the ‘Undercover Boss’

When a boss goes undercover for CBS, he doesn’t choose where he is going to work or who is going to train him. In fact, in most instances, the nudge to participate in a reality TV show actually comes from the public relations department.

But what about the personal interactions between the “Undercover Boss” and his unsuspecting working-class employees? When Waste Management’s president and chief operations officer, Larry O’Donnell, took the time to learn how an office manager balanced her four different positions, was that for real?

“Some people win the lottery; I won Larry,” said Jaclyn Pilgrim, 30, of Rochester, N.Y, who was promoted as a result of the day she spent training O’Donnell on the four jobs she was juggling when he appeared at the High Acres landfill in Fairport, N.Y, pretending to be a first-day trainee being followed by cameras for a documentary.

“That’s better than anything for me because who gets to have a relationship where he calls me and asks me how I am, or I call him and say, ‘I sold this today.’ Who gets to have that kind of relationship with a COO?”


CBS also has won big with this wish-fulfillment reality show, which is averaging 18.7 million viewers and, as the season’s most-watched new series, was renewed on March 9 for a second cycle. Its timely premise is about enlightenment for corporate bosses, but it’s striking a chord more because the little people seem to be benefiting. Whether it’s a well-deserved promotion or an all-expense-paid vacation, “Undercover Boss” is recognizing unsung heroes who probably would have gone unnoticed otherwise.

“We wanted the show to be transformational for the company, the boss, and for the people the boss worked alongside,” said executive producer Stephen Lambert. “On the one hand, trying to see how the company could be better by viewing it from the front line without people realizing that they were the boss. But the second part of the mission was always to identify the people who were doing a particularly good job and maybe sometimes in difficult circumstances.”

In separate interviews, Pilgrim, White Castle employee Jose Gonzalez, 17, and 7-Eleven night driver Igor Finkler, 48, said they were approached by producers about appearing in a documentary about their company and then were observed working for a day before the chief executive appeared for duty.

When the production company asked Gonzalez’s parents for permission to film their son, he said, his mother was skeptical and wondered what he would get out of it. “I told her, ‘It doesn’t matter if I get anything or not. If they need help or they want me to do something like this, I’ll do it,’ ” Gonzalez said.

As Gonzalez and White Castle owner David Rife spent a day together, cleaning the restaurant, stocking supplies, taking out orders and removing trash, the boy shared his dreams of being a chef and related that he was already enrolled in culinary classes. After Rife revealed himself as the big boss, he gave Gonzalez a $20,000 scholarship, making the teen the first in his family to go to college.

Although he was pleased with the way he was portrayed on TV, Gonzalez has been dealing with the fallout since the episode aired.

“A lot of my friends and my uncle have been saying things like, ‘Hey, cry baby, how much money did you get?’ ” he said and laughed. “I can’t believe I cried on TV.”

Similarly, 7-Eleven’s chief executive and president, Joseph M. DePinto, saw promise in Finkler, a Russian immigrant who earned a master’s degree in his country and served as a manager there but has been working as a night shift driver at 7-Eleven for 11 years. After they filmed their episode, DePinto brought Finkler to L.A. to attend a presentation and tour some stores.


“I realize now that he asked me a lot of questions to see if I have the potential or not,” Finkler said.

The answer came later, when Oprah Winfrey handed Finkler keys to his own 7-Eleven franchise on her show. The store in Dallas is scheduled to open May 10.