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The answer to this question seems straight-forward from a human resources perspective; it’s almost laughable to ask. But alas, outside of HR, this is a question that is often overlooked.

The best answer is no — you should not be friends with your boss in almost all situations. Even your weird situation you’re about to start explaining.

Before your outrage gets out of hand, let me be clear: being friends with your boss is quite different than being friendly with your boss. Your friends are people you can be uniquely you around. They like you just as you are and hopefully don’t judge you for that. Your friends don’t have enormous power and influence over your career trajectory, compensation or general work/life happiness.

Still not convinced being friends with your boss is a bad idea? Consider these four potential consequences:

1. Compensation Questions are Awkward

Asking for more money is difficult regardless of the situation. But when you’re friends with the person who controls the money, the awkward meter skyrockets for both of you.

Your boss generally wants you to get as much money as possible, particularly if you’re a great employee. Sometimes they don’t have the choice or the money available to give you what you want. Having to say no to a friend, when they have heard you complain about how expensive rent is, is a difficult situation for them to be in. More importantly, you can almost never recover from it.

2. Special Treatment Isn’t Good for Your Career

Being friendly with your boss means that you two get along and you’re able to connect with common language, but you keep things professional. Sure, you’ll go out to lunch together every now and then or perhaps you get assigned a special project, but it won’t be their natural reaction to favor you.

Subconsciously, you want your friends to succeed, so your boss may provide additional opportunities to you if you’re their friend. I know that doesn’t sound like a bad thing — in fact, it may be your master plan — but you don’t want your friendship to be the reason you’re given opportunities.

You want your work and capabilities to stand on their own merit, not be tarnished by being perceived as “teacher’s pet.” In your next role, you’ll be expected to perform at an even higher level — will your experience and expertise shine through without getting special treatment?

3. Egos and Competition

Our work environment is set up to at times encourage us to compete against each other — who’s the best candidate, who’s the subject matter expert, who’s a better fit. It’s in our nature to step up to the plate and compete when it’s a position, project or thing that we want.

Your boss may want the same thing you do, and their ego may prevent you from having a fair competition. How do you recover your friendship and career after that?

Another competition is one for your talent in general. If you make your boss shine — which as their friend you will try even harder to do because you’re just that awesome — they won’t want to lose you, almost at all costs. They finally have an employee they trust and they know can deliver, and they will be very hesitant to let you go. If you express interest in a new position, be prepared for them to be less than supportive.

4. The “Always” Rule

I try not to use absolute statements with career advice because there can be exceptions to every rule. Except for this one. This is always true: It is never ok for you to get drunk, party or otherwise engage inappropriately with your boss. Ever.

See? You thought you could still manage being friends with your boss until reason four. Gotcha with that one.

One last thought to consider: Giving notice to your friend, telling them they weren’t the best boss, is a crucial conversation you never want to have. Instead, be friendly with your boss, but make your friends outside of your reporting structure.


This post originally ran on CareerMeh: smart, actionable advice for Millennials, by Millennials.