Why Undercover Boss Should Make Us Want To Cry

Undercover Boss— now in its seventh season — is a reality show that maintains an average viewership of over 7 million people. It stands with The Profit, Shark Tank, and Kitchen Nightmares in a growing category focused on the joys and sorrows of running, and most importantly fixing, a business. The show is so popular and (and predictable) that it was parodied this month on SNL. And by the end of every episode, without fail, the boss, the employees, and presumably the audience, are all in tears.

Everybody’s crying, but not for the right reasons.

In the show, a CEO or top executive from a major brand goes undercover (often wearing a disguise) and works inside the rank and file of their own business. It’s understandably formulaic. They struggle to excel at the very repetitive, but deceptively challenging activities that make their business hum. They learn powerful lessons about what’s working and not working. They meet a few unsung heroes in their workforce and learn of their personal, often heartbreaking struggles to make it in America.

Why are we drawn to this?

Undercover Boss works because it represents a chance to right the wrongs of modernity. We can’t wait for leaders to come down from their ivory towers to “see what’s really going on” and “do something about it.” And we empathize with the lowly worker who has never had a voice in the future of their business, until now. We love this. Why? Because 21st century work life is so $&@#ed up. 100 years have passed since Taylorism gave us the manager-worker (aka thinker-doer) dynamic. By many measures worker engagement is at an all time low, and bureaucracy and shenanigans are at all time highs. We’re desperate for change, and if the only way we can get it is by dressing up a CEO and making them serve Cinnabon out of a gas station for a day, then so be it.

Further, the show offers us a sorely needed redistribution of wealth. At the end of each episode the boss meets one-on-one with his/her trainers from the week prior and reveals the stunning truth: it was the boss all along. Then, apparently moved by their plight, the boss rewards each of them with cash, vacations, money for tuition, debt forgiveness, you name it. The employees are almost always brought to tears over this generosity (so far has the middle class fallen that a $10,000 gift is a truly life-changing experience), and the boss is often moved as well. We cry too (or at least I do). We cry because seeing people that are giving their all get a hand up is a powerful thing, and it speaks to our deepest nature as a generous and collaborative species.

Why it’s not nearly enough.

The problem with the show is, of course, the small scale on which it operates. While the boss might spot a few things to fix and hear a few employees’ opinions, this pales in comparison to the overall amount of trapped creativity and passion hiding in the business. If visiting 3 stores gives them good ideas, we have to ask, what about the other 1,000+ locations? Indeed, we are so reliant on the boss as “fixer” we can’t even imagine what might happen if we allowed the system to self-regulate. But don’t even get me started on the benefits of (and barriers to) self-organization.

In terms of just basic humanity, if three of your employees are facing hardships but “kicking ass” so they deserve a $10,000 bonus, what about the thousands of other people that work for you? Chopped liver? Leave it to social security? We can’t believe that the three angels we met in tonight’s episode are the only people of merit in the whole organization, so we’re left to assume that the show (and the world) is just unfair.

Kylo Ren as Undercover Boss

No one boss can fix the problems of modernity — it has to heal itself. But neither are they unaccountable. No one should amass so much wealth on the labor of employees that they feel guilt-bound to save them once they actually meet them and understand them as people.

The ultimate problem with Undercover Boss is right there in the title. We don’t need better bosses, we need something different altogether — to create and protect the space for autonomy, inclusiveness, and humanity in the workplace.

So the next time you watch the show, and the waterworks inevitably begin, ask yourself, am I crying because of what’s happening, or what isn’t happening?

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