1. Timing is everything.
Unless it’s impossible for you to complete your work until your issue is resolved (and I mean it’s actually impossible, not just that you’re too lazy to do it), it’s not a good idea to bring up your concerns with your boss during a busy time. In most office buildings, the busiest time is Monday morning, whereas it’s a down time in retail and restaurants.
2. Keep it private.
When at all possible schedule time in advance. You don’t have to tell your boss you want to meet to criticize them—just ask for a meeting at their earliest convenience. If they ask what about, explain it’s something you’d rather speak about in private. There are very few bosses in the world that won’t understand and respect your request.
3. Stick to the facts.
Avoid being petty, and avoid opinion-based judgments on your boss. Telling your boss they’re stupid, for example, won’t get you anywhere. Instead, have graphs and reports to back up your claims. Does the morning meeting make your job harder? Do you need a second monitor or extra break? Show your productivity statistics to prove it.
4. Ham it up.
When bringing bad news to the boss, injecting humor is a great way to lighten the blow. It helps if you already have a good relationship with your boss—also keep in mind the general tone of your workplace. Some companies are more serious than others. No matter how serious things are, there’s at least one joke for every situation.
5. Play nice.
Although a little comic relief is necessary, remember you’re not on a Comedy Central Roast. No matter how funny you think insult comedy is, you want to be nice to your boss. This is the person in charge of your paycheck and livelihood, so treat them like a mentally slow child who doesn’t understand any of the words coming out your mouth.
6. Keep it clean.
When criticizing your boss, avoid using foul language. It’s okay to tell your boss that it bothers you when they make your job harder, but telling them they’re an asshole isn’t the best idea, especially if they actually are an asshole—they’ll prove you right. In the business world, using profanity with your boss will make them focus on how you react to issues rather than the issues themselves.
7. Stop while you’re ahead.
After you’ve said your piece, you’re done. Don’t linger on it, don’t keep reiterating, and don’t keep pushing into other issues. There are only so many hits your boss is going to take before they start to hit back, and they can hit you where it counts—your wallet. Be gracious and let the criticism begin and end in that moment like an adult. Beat the Boss may be a fun game on your phone, but if you do it in real life, you’re going to be arrested at best. Rather than planning some Horrible Bosses-style revenge against your boss, talk it out with them. So long as you respect everyone’s time, approach the situation lightheartedly, and discuss your concerns like an adult, you should have no problems. If you do run into problems, criticize your boss to your boss’s boss. If things still don’t get better, blow the whistle and turn them all in. They probably deserve it.
