Leaving your job is stressful. You feel guilty about burdening fellow employees with more work. Saying goodbye to a great boss can weigh on your heart. And, you might feel loyal to the organization, whether you should or not.

In the middle of this complex scenario, you wonder when, or if, you should tell your boss you are looking for another opportunity. It’s not a clear-cut situation.

Here is some advice to follow if you, or someone you know, plans to leave but does not know what to do:

Do Not Tell Your Boss You Plan to Quit If:

Your boss has proven to be unsupportive, unreliable, or flat-out terrible. They will likely use the information to make your life more difficult.

Your company has a policy of walking employees to the door upon termination. Your employment may be in jeopardy if they find out you are ready to leave.

You cannot trust your boss to keep the information confidential.

Do Tell Your Boss If:

There is ample evidence that your boss is trustworthy. A great leader will encourage you to grow in your career in any way that suits you. They can support you when you need to go to job interviews, and you will feel less conflicted about your exit.

You are motivated to train your replacement. This might seem nuts on the surface, but you’ve worked hard to create solutions and positive relationships in your current role. You might enjoy protecting the investment you’ve made as you move on.

Your boss is an important part of your professional network and will be willing to open doors for you. A great boss has taken the time to get to know you and understands your strengths. They can be an important ally in your search and in your career over the long haul.

Most people feel they need to keep their job hunt secret, and as I mentioned, sometimes this is the best choice. But take a moment to step back and ask yourself if an honest, transparent conversation is warranted. It can reduce your stress and give you more creative energy to make an amazing transition.