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Undercover Boss's Eli Holzman Tells Us What Really Goes On Behind the Scenes

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Eli Holzman is having another good year. In the last 12 months, both of the Project Runway veteran's most recent TV creations—CBS's Undercover Boss and Bravo's Work of Art—have found success: Currently in its second season, Emmy-nominated Undercover Boss has become one of CBS's most successful shows, and now Work of Art is headed for a Season 2 of its own ("It hasn’t been, like, officially announced, so I’m being a little bit cagey, but we’re doing it, yeah,” Holzman told me.) And as of this week, Holzman is officially an author: Undercover Boss: Inside the TV Phenomenon That Is Changing Bosses and Employees Everywhere hit shelves on Tuesday. I reached Holzman by phone (and accidentally pulled him out of a project meeting!) to talk about the book and to delve a little deeper into what goes on behind the scenes of the show.

What should people expect from the book? Is it about the making of the show? Some sort of corporate exposé?

The book tries to capture the experience that each of the bosses had on their undercover journeys in a bit more detail, and with the benefit of 20/20 hindsight and the ability to reflect on what they were experiencing. Because it all happens so fast when we’re undercover and going all across the country filming. There are all these words that get bandied about in business circles, where you hear about [things like] "employee engagement." I hear things like that and I don’t even know what they mean. When you see the difference that caring makes, and the difference that taking time to try and really understand someone on their terms makes … those words take on real meaning.

Plus, at least from what I've seen, some extra, producer’s-cut kind of stuff.

Exactly, exactly. You know, we’re out there for a long time, and most of it doesn’t get [into the episodes.] But it’s not an exposé.

The reason I put it that way is that I still have questions about the actual making of the show. Walk me through an episode—what’s going on behind the scenes?

We try to let the boss lead as much as we possibly can, from things as silly as coming up with what their alias will be to the way to the manner in which they’ll change their appearance. ... The only thing they don’t know in advance is exactly where they’re going to go, and they don’t know exactly with whom they’re going to work, because we want them to an authentic experience.

[Whereas] a movie might get shot completely out of order, there are semi-scripted reality shows—and it’s a dirty word to admit it, but it’s true—that are also filmed out of order. Not Undercover Boss. Undercover Boss is filmed in order. It’s a real experience that someone really, really does have. We’ve found that [at the end of the experience, they often] tell us they’re transformed somewhat. And so we want to establish who they are at the top.

They then reveal their plan to go undercover to senior staff. And after that we head out. Generally, it’s a job a day in a different location. And the schedule is a grueling one. Some companies, like Waste Management, where there are trash routes and all that, their shifts might start at 4am. And we have to be there in advance of that to be ready. The boss has to stay in a hotel that’s, you know, what one could afford if they were doing the level of job that they’re doing that day. They head out, they work a long shift, we’re right there along with them. And we watch as it unfolds. And oftentimes they start out the beginning of the process with a lot more confidence about how they’re going to be able to do.

It is pretty shocking how much they can learn on that first day, especially when physical tasks are involved.

It’s extraordinary, yeah. Like, Larry O’Donnell [the subject of the series premiere] said to us, when he worked on the sorter in a recycling facility, he said, “Yeah, you know, I thought I’d just be able to kind of zone out and do it on autopilot with my hand, and that I’d able to use my mind to think about other things.” And instead it was all he could do to use every bit of his focus just to try to barely do the job.

He jammed that machine, like, three or four times.

He sure did. I don’t know that he would have been invited back. I think the bosses are often nervous because they’re going on camera. They don’t want to look like fools, they don’t want to embarrass themselves. They’re sometimes trepidatious about what they might find. So apart from the long hours they’re also the center of attention. They’re on-camera the whole time and it’s a different sort of pressure. So those early days are a rude awakening. And then it turns into a bit of a slog, which I think is a good thing, because at the heart of show it’s about appreciating that the most sophisticated organization in the world is only as good as the person doing a great job in the most humble position in that organization.

And so the boss [does] job, after job, after job, after job along the way. Ultimately, they will arrive generally back at their headquarters, sometimes in an off-site location, where the staff is called together. And individually they go in and our final day of shooting is generally that day where the boss has one-on-one meetings with them and tells them who he really is.

I’m very curious about that end-of-the-show bit. It’s always very heart-warming—the boss has learned how hard it can be to work in his company. But often there’s also a promotion or a lavish gift in store for the employees the boss met while participating in the show. Does the show have anything to do with those perks?

It’s part of the template of the show, the idea that the boss might change something in the business based on what they’ve observed, or now learned. So it’s definitely something that we’ve thought about. With respect to what the companies do specifically, or what the bosses do specifically, it’s very much up to them.

Every company’s culture is different. And so what might seem somewhat modest in one organization is actually really, really generous. And what might seem generous in a different business might seem extravagant in another one. It’s something the bosses actually have to be really, really careful about. And they often will spend time really agonizing about that and talking to their people. You’ll often see them at the end of the show meeting once again with that senior staff to reflect on what they have learned, and to implement changes, and to talk about what they want to do. You know, it sounds great to go in a room and say, “Actually we’re going to now pay for everybody to go to college.” But that might be ruinous for the bottom line, or it might be a program that somehow alienates or is unfair to some constituent of the workforce and backfires. So those are the things that have to be thought through very, very carefully. If they want to do nothing at all that’s their choice and we’ll report it fairly. If they want to do something really lavish we’ll do the same.

Ultimately it’s you who puts the bosses with the individuals who they’re going to work with on each job, right? How do you select those lucky or unlucky few?

It’s a great question. Unfortunately, because of the sort of covert nature of the show and our ability to produce it successfully for many seasons, there are aspects of it, or a level of detail that I should probably stay away from. But suffice it to say that in concert with the company, we work to identify people and job functions within the business that make sense to feature.

Well how about this one then, because this is one part of the show that raises my skeptic’s flag...

Have at it.

The format shows us the boss at home, in his real-life environment, at the beginning of each episode. And at least with the ones I’ve seen, it seems like the people he then encounters always have some sort of coincidental tie-in to his real life. To go all the way back to Larry O’Donnell, he has a mentally handicapped daughter. And then he meets a mentally handicapped customer when he’s out delivering trash.


And on an episode that aired recently, the boss had a son who struggled with drug addiction, and he met a worker who used to struggle with addiction and now ministers to recovering drug addicts.


They can’t possibly all be coincidence.

They can’t all be coincidences, you’re 100 percent right. We do curate the list of who is being featured on the show. And we look for people who typify maybe the experience of somebody in that position, just the way you might curate if you’re conducting a poll, to make sure you have people that represent a mix of people that accurately reflect what the broader sample looks like. And so we do that, we absolutely do that. And we look for people, yeah, who have a great story. If there are two people who do the exact same job in the exact same way, and one of them as soon as you see them, you laugh uproariously or cry because their story’s so amazing, and the other one it’s crickets and you’re really bored, we’re going to go with the really good one.

But I will say this: More than you would expect, those are coincidences. And that was the case with Larry O’Donnell. There were several people who wanted to come out and acknowledge that driver on her route because—I don’t know how much back story we got into in the show, but she had been a nurse, and there were a lot of elderly people. The weather’s incredibly cold in Rochester in the winter, and so she would go and check on the elderly people on her route because it was hard for them to come and take their trash out. And because her training and background was in looking after those people, that’s what she would do. It was just her thing.

As a result, there were lots of people on her route when we were following her around that said, “I would love to speak and acknowledge her. Oh, you’ve got cameras, can I come out and do something?” And we said sure. One of them happened to be that woman. Now we rolled tape for however many days. We can ultimately feature only the best 42 minutes. So we’re not showing you the other eight people that said nice things, because that wasn’t as touching and moving as the one that made Larry cry, because coincidentally she was handicapped and reminded him of his daughter. But we actually didn’t set that up. … We just happened upon it. All things being equal, if someone is funnier, or has some story behind them that sounds like it might touch the boss in some way, we’ll absolutely go with that. But often it’s an accident.

I know a bit of healthy skepticism is appropriate in television in general, and certainly in reality television. But we’re only showing you the best bits of the documentary, and we’re not showing you the other eight people who might not have been that interesting. So it isn’t that every single interaction the boss has is fascinating and heart-warming, but those are the ones [who end up in the] 42-minute show.

How many people does each boss typically work with?

You generally see four or five. And in the pilot we shot far more than that, to be safe. You know, it comes down to time. [Now each boss will] generally do five or six jobs over the course of their journey. We try as best we can to include them all, but there might be one that doesn’t make the final cut.

How do you go about selecting the companies you infiltrate? Are you at a point yet, now that you’re in Season 2, that they are coming to you? What kind of restrictions do you face?

We probably reached out to a few thousand companies to get one to agree to do the pilot. And that’s not an exaggeration. For the first season it was an extraordinary amount of outreach to get a few different companies to agree to do it. Sometimes I get on the phone with a boss or a company and they worry about how they might look because of a problem they’ve been having. And I have to be frank with them and say, “Are you sure you should be doing Undercover Boss? We’re going to go in, we’re going to roll. If you don’t want it on TV, then don’t give it to us on our camera because…”

They have nothing to do with the episode once filming is done, right? The contract they have to sign must be huge.

They see the show for the first time when it broadcasts. So they have to trust us, and they have to be brave, and then they have to have some luck. For the second season, yes, we’re much more on people’s radar, and many, many companies have come to us—and many get offered up and proposed to us.

We get down to the nitty gritty of what’s really involved, and some will then bow out and say, “Oh wow, that’s too much time for our Chief Executive to take out of a schedule,” because it is a real time commitment. I think in a good way, because you kind of can’t just do it as a publicity exercise. You either really believe in the merits of what you’re going to get out of it, in which case you can justify it because it’s at least a full week of the boss’s time.

There are also basic practical considerations. If the company is too small, if it has too few employees, the boss may simply be too recognizable. If the functions are not especially visual it might not make the best episode. If someone worked in a white room with white equipment making, I don’t know, blank pieces of paper, that might be pretty dull after a while.

We also have worked very, very hard aggressively recruiting for minority bosses, for example. I frankly had no idea that it would be so much of a challenge. But it was something that we considered incredibly important. You know, on a subconscious level alone I don’t want a little girl to watch our show and come away thinking that you have to be a man to be the boss. Or child of color to think, “You have to be a white person to be the boss.”

And so we wanted to make sure to feature some of the great and more diverse executives that are out there. I’m proud to say that we were able to pull it off in several instances this season—this second season. But we didn’t manage to the first season, and not for a lack of really, really trying.

Do you have any dream companies that you’re targeting? Who would love to have on the show at some point?

There’s some that I can’t reveal coming up that I am incredibly, incredibly excited about. My dream is to see Leslie Moonves go undercover at CBS.

Do you worry that someone like Les Moonves would be too recognizable? I suppose if a company is big enough, there’s always going to be somebody who doesn’t recognize the top dog.

Yes, I completely agree. And context means so much. If it’s someone who you’ve met once or twice, even if it’s someone important like your boss, and all of a sudden they’re in a completely different role, I think most of us are a lot more susceptible to getting fooled than we realize.

Undercover Boss airs Sundays at 9pm on CBS. Undercover Boss: Inside the TV Phenomenon That Is Changing Bosses and Employees Everywhere is in bookstores now.

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