Reverse Undercover Boss

Here’s a scenario involving you. But it’ll never happen. 

The CEO of your company gets picked to be on the TV show Undercover Boss and goes undercover disguised as a new employee in your company, and you are one of the few people that are selected to mentor and train this “new employee.” All of this, including your amazing abilities and underappreciated insights, are filmed for television broadcast.

The show Undercover Boss was first created in 2009, and has since been produced in localized versions in 14 different countries with 5 more countries planned.

Here’s what happens in each episode. A CEO of a large company goes undercover, disguised as a new employee, and works at various jobs within their own company – by being paired with a fellow employee. It’s a way for the CEO to surreptitiously learn about aspects of their company they might not otherwise experience, and to get to know a few (typically) hardworking and underrepresented employees.

Once the CEO has completed their time undercover, they head back to their corner office, whereupon the employees they worked with are called in for a meeting – “Do I look familiar?” The deserving (and shocked) employees, struggling with work and life issues, are typically awarded generous financial and training bonuses, and sincerely thanked for their efforts in making the company work.

Of course, as with any of the “reality” shows on TV, there’s certainly a lot of “set-up.” But there’s no denying it’s a learning experience for the CEO.

And in my imagined scenario where the CEO is working in a new role with you, she (or he) is a bumbling but well intended fool. What’s more, you point out problems, difficulties and real frustrations in the company that they were clueless about. And beyond the CEO, you impress the heck out of everyone in America watching the show. So thanks for your patience and education!

Truth is… you humble the CEO and you play a real role in making the company work.

Mostly though, the CEO learns about you – that you care about the work, that you have worries and struggles and issues like everyone else. In fact, the CEO is actually a lot like you. Actually, everyone watching the episode is a lot like you.

Which is why, in this scenario… after you’re surprised to learn the “new employee” is actually the CEO (“I thought that long hair looked kind of weird!”) you’re awarded a sizable sum of money and are chosen to run a new company-wide initiative to identify a multitude of problem areas for improvement.

Unfortunately, as was said at the outset, that scenario will never happen. The CEO of your company is not in the process of selecting a wig to spend a few days under your tutelage (though if they were, you’d certainly get the previously mentioned awards).

But the good news is.. you don’t need to wait for the CEO to come to you disguised as a new employee. Here’s a better suggestion that really could actually show some benefits.

Flip it. You put together your own new look as the CEO – and approach your job with a new CEO-like perspective. The disguise or “new look” doesn’t need to be with clothes, though you could try to look more of the part – whatever that means in your company.

Mostly though, the “new look” is the perspective and the questions you bring to your work.

  • What are the things about your job that need fixing?
  • Why is the department doing things this way?
  • How could these projects go smoother? What are all the things you’re responsible for, and which ones matter the most?
  • What things could you do differently, even as an experiment just a few times – and see if there are any improvements?
  • What EXTRA things could you do that would improve the quality of the work?
  • How might the job change in 3-5 years, and what could you do to begin the changes?
  • How could your 8 hours of work get done in 7 (or less)?
  • What could you do outside your job (write a blog, read a list of relevant books, meetup with people in similar jobs to compare and consider best practices, interview industry thought leaders)?
  • What could you analyze, test, trial? Write-up in a report of recommendations?

Doing those things will have you thinking and acting more like the improvement-seeking solution-searching person you are.

You’ll be thinking beyond your normal day-to-day activities. Maybe you can rope-in some colleagues. It might even be fun.

But the reality is…

Your quest for improvements will probably be frustrating. It’ll definitely require extra effort, working through lunches, some late nights. You may be viewed with odd looks or even criticism from your colleagues. Some of your ideas will probably be lame. Many of your suggestions will be ignored. It won’t be easy. And in the end, your work may not have any impact.

But regardless of the outcomes, you’ll be better for the effort. You’ve stepped-up and attempted to make things better. To improve the company and yourself.

You’ll begin to recognize yourself as a CEO, at least of the work and people for which you’re responsible. Soon others will recognize you too. That’s something you can’t disguise.


Tom loves building meaningful businesses and technology (with people who care). Follow him on LinkedIn. Reach him on Twitter @thomastriumph

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