Unless you’re planning on working for one company your entire life, at some point you’re going to have to tell your boss you’ve accepted a job with someone else. And even though it might have seemed like you were in an “open relationship” where you thought you were free to interview with other companies, as with any breakup, your boss and the powers that be could still feel rejected, disappointed, or even angry.

Of all the conversations you’ll have with your boss, this is probably right up there on the awkwardness scale with the ever popular “raise discussion.”

There are two schools of thought on how much you should communicate about your interest in “seeing other companies.” Some career experts suggest having an open and honest conversation with your supervisor. Others recommend waiting until you have an offer in hand to have the discussion. Depending on your particular situation and your relationship with your boss, both could be right.

If you were in a truly “open” relationship, you’d work for an awesome boss who is totally supportive of your career development and advancement. In that case, there’s a good chance they’ll ask about your short- and long-term career goals during a performance review--obviously a great time to have that discussion. By bringing it up, they’ve opened the door to talk about it.

But, most employer-employee relationships aren’t completely open. When they hire you, they could be looking for a possible long-term commitment. If that’s the case, they might feel betrayed or rejected and end up writing you off delegating most of your projects and responsibilities to someone else. And once that happens, you can say goodbye to a positive performance review or any chance of a future promotion.

“It’s not you, it’s me.”

How you handle the breakup will go a long way in determining if you can be friends. You want to keep the conversation short, but not abrupt. Let them know (in general terms) why you’ve decided to accept another position. For example, are you leaving for a position that is more in line with your long-term career interests? Are you doing it to be closer to family? You want to be general to avoid making any negative comments about the company; these might come back to hurt you later if you want to apply for a position in the future. In the world of dating, you probably wouldn’t like it much if somebody pointed out all of the reasons he or she didn’t want to go out with you. The same holds true when exiting an organization. Finally, thank them for the opportunity. Even in a bad relationship, it’s possible to learn a lot.

“But I can change.”

Okay, so the company doesn’t want to lose you. If they think you’re “a keeper,” management might want to work with you to reorganize your job content to try to get you to stay. They may offer you more money. Or, on the other hand, they could be happy to see you go. Be ready to respond to any situation.

When you break up with someone it’s difficult, if not impossible, to predict how the other person is going to react. So before you have a discussion with your boss about interviewing with other companies, make sure you look for subtle or not so subtle cues that might suggest he or she would be supportive. Best case scenario, the split is amicable and you’re able to remain friends or, in this case, colleagues.