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How to Give Your Boss Constructive Criticism and Still Keep Your Job

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If you think you’re the only person who’s ever dreamed of chucking a ninja star at your boss, think again. The sadistic smartphone game Beat the Boss has been downloaded eight million times and spawned two highly popular sequels.

Beat the Boss is billed as a game to relieve pent-up workplace aggression, but let’s be honest: Sometimes, you still need your voice heard. Many managers create an environment where contrary opinions are squelched, but no matter where you work, you need to feel free to contribute your ideas.

Here’s how to tell your boss what you really think — without getting fired:

1. Time it right

If your manager already looks pissed off, it’s probably better to wait for another time. Also be mindful of meetings, projects and other big events on your boss’s schedule. It’s probably not the best idea to tell your boss everything he’s doing wrong as he’s on his way to an important presentation or speech, unless you’re planning on filming an epic “I Quit!” YouTube video.

You may have a boss who’s always in a bad mood. In that case, there’s no better time than the present to discuss his attitude with him.

2. Pick your battles

It’s OK to criticize your boss, but it’s best to do it one-on-one. Joining in on a break room bitch session could be dangerous. The business world is filled with sharks, and you never know when something you say could make it to the manager’s office.

There’s a stark difference between someone with initiative and personality (who companies want to keep on staff) and dissenters who destroy the company from within. You don’t want to develop a reputation as a backstabber.

3. Support your ideas with facts

Just because you think something is a good idea doesn’t make it so. (Click here to tweet this thought.) If you tell your boss you work more productively when she’s not around, you’d better have an hour-by-hour breakdown showing the correlation.

But even if you bring the facts, there’s no guarantee management will seriously consider your idea. Be prepared in the event the conversation doesn’t go your way.

4. Be playful and gracious

Graciousness and playfulness are attractive qualities in people. These qualities build trust, and when you hit an inevitable rough patch with your boss, that trust will come in handy.

When approaching your boss with criticism, keep your tone friendly and playful. It sometimes helps to reference a movie or TV show you both enjoy to illustrate bad behavior while keeping the conversation light.

It’s also helpful to be self-deprecating. Conan O’Brien is the king of self-deprecating humor, and he gets away with insulting so many public figures because he’s not afraid to take jabs at himself. Keep an eye on all the late-night hosts, comedian roasts and morning radio shows. Practice mimicking the humorous tone they use when insulting celebrities.

Just to be clear, humor doesn’t have to negate the criticism you dole out. In fact, humor can keep your boss from going on the defensive and lead to a more productive discussion.

5. Keep it clean

While playful jabs at coworkers help foster a creative and trusting environment, watch your mouth. People aren’t robots. Even if they know you’re joking, your coworkers might be offended by certain taboo subjects.

Remember you’re at work — not on stage at The Improv. Avoid offensive jokes and swear words to keep it professional. You’re not Samuel L. Jackson, motherfu —

6. Know when to stop

The scariest part of flying is the takeoff and landing. Criticism is no different. The anticipation can be overwhelming. But once you start, it’s easy to get on a roll like you’re giving an Academy Awards acceptance speech and telling people off when you should be thanking them.

Say your piece, and move on before you say something you might regret later. Remember what goes around comes around, and you’re not without faults yourself. Treat people (even your boss) the way you’d want to be treated, and don’t dish it out if you can’t take it.

If you offend someone, apologize and redirect. If tensions heat up, table the discussion for another time.

Rather than bottling up your work rage until you get home (and snapping at your significant other), take responsibility by giving your boss a much-needed reality check and improving the office for everyone. When done well, standing up to your boss can help you release frustration, bring problems to your boss’s attention and maybe even earn your boss’s respect.

Nicolas Gremion is the CEO of Free-eBooks, a popular online source for free ebook downloads, resources and authors. Nicolas is a culturally curious traveler and entrepreneur who lives in Costa Rica with his wife and his dog Frankie.

Brazen powers real-time, online events for leading organizations around the world. Our lifestyle and career blog, Brazen Life, offers fun and edgy ideas for ambitious professionals navigating the changing world of work.

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