How to Prank Your Boss (and Keep Your Job)

Photograph by Per Dahl/Getty Images

Take a long, hard look at your boss. What do you see? Notice the bloodshot eyes, constant hand-wringing, and nervous facial tics? Believe it or not, your boss is seriously stressed out. According to the global consulting firm BPI, 82 percent of supervisors or managers are suffering from higher-than-average stress. In other words, they’re a ticking time bomb, just one bad day away from a fatal heart attack or stroke.

What your boss needs now more than ever is comedy. And what better way to tickle their funny bone than with a prank? Imagine their relief at discovering their desk wrapped in aluminum foil, or their car filled with polystyrene balls, or their entire office covered in balloons. Laughter, after all, is the best medicine.

But it’s never that easy, is it? Stress has a way of blinding people, especially authority figures. Instead of “Thank you for the blood-pressure-lowering prank,” your boss could likely respond with, “I’m having security escort you from the building.”

With April Fools’ Day on the horizon, here’s Bloomberg Businessweek’s three-step system for pulling a prank on Mr. Sourpuss without being shown the exit.

1. Know Your Audience. Margo Berman, a former copywriter at a Miami advertising agency, once hired a stripper to pose as an art director for a job interview with her boss. During the interview, the stripper purportedly undressed while telling Berman’s boss, “I’ll do anything for this job.” It sounds like the sort of gag that would probably result in a sexual harassment lawsuit. But Berman remembered the first—and perhaps most important—rule of office pranking: Know your audience!

“I didn’t get fired, because my boss frequented strip clubs and everybody knew about it,” she explains. “I realized he would be shocked, but I also knew he was a great sport. Later, he couldn’t believe that he didn’t realize what was going on until half of [the stripper’s] clothes were off.”

But just because your boss has a healthy sense of humor doesn’t mean he finds you funny. Warren Lieberstein and Halsted Sullivan, producers for NBC’s The Office, think it’s vital to take a long, hard look at your comedic capabilities before attempting a prank.

“Try to make yourself laugh,” they suggest. “What’s the funniest word you can think of? What’s the funniest cheese? Camembert? That’s 1990s funny. We are looking for 2012 funny. The correct answer is cottage.”

2. Create the Illusion of Productivity. Not every boss likes to laugh. Some of them have mouth muscles so atrophied from inactivity that they’re barely capable of smiling. But even the most humorless boss will appreciate a prank if it’s even vaguely constructive and work-related. Sir John Hargrave, professional prankster and author of Mischief Maker’s Manual, recommends large-scale, contractor-level stunts. “Try covering the boss’s office in Post-it Notes,” he says. “Or gift-wrapping everything in the office, including the furniture. If your boss complains, just point out the teamwork and creativity that you and your co-workers showed.”

Even the most immature prank can masquerade as a team-building exercise if executed correctly. Take, for instance, that old classic: photocopying your butt on the Xerox machine. Hargrave suggests using a program called Rasterbator, which allows you to “blow up a single photo to the size of an entire wall. It will print out pieces of the image on a standard work printer, which you then paste up, mosaic style, onto an entire wall.”

If your boss doesn’t appreciate the ingenuity required in wallpapering his office with a gigantic Xerox of your ass, then maybe he’s not a team player after all.

3. Safety in Numbers. “The more co-workers you involve in your prank, the harder it is for any one person to get in trouble,” Hargrave says. “A mass prank distributes the blame. The boss can’t fire the entire office.”

Jacqui Rosshandler knows this from experience. When she was just a girl, she witnessed a prank on her father, a plastic manufacturer in Melbourne, Australia, that demonstrated the benefits of group collaboration. His employees pooled their funds and hired a woman to play Lady Godiva, who rode “naked” (actually in a skin-colored bodysuit) on a horse through the neighborhood, right up to the front door of the boss’s factory. “Everybody was waiting outside and clapping,” Rosshandler remembers.

To further protect themselves, the co-conspirators also alerted the media. “I don’t know who thought to call the local TV station,” she says, “but there was video of the whole thing on the news that night.”

Remember: If somebody’s around with a camera, your boss will have no choice but to smile and play along.

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