When do you tell your boss you're applying internally? Our HR system automatically alerts managers late in the process, but I want to be the one to tell him. We have a great relationship, and he knows my goals, but I don't want to tip him off too early if I end up applying to a few things. Do you give a heads-up before hitting apply, or wait for an interview?

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You should probably mention it sooner than later. I would expect internal applications to result in the hiring manager going immediately to your manager to ask about you.

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And then it’s awkward and they get their feelings hurt you didn’t give them a heads up

In cases where there is a good working relationship, I would bring it up and ask about the positions you are looking at. That person can be a great sounding board to find a good fit for you.

For the most part, I would advise to do it the same day you apply so that it doesn't catch them off guard.

Now…If you have a good working relationship, and he’s a good leader, he will ask how he can help. Maybe he knows someone or will be a reference. In the past, my leaders have encouraged me to go for new roles and been cc’d on my internal interview follow-up emails as references.

Our internal system doesn't alert the manager at all, at least that is what my manager told me, I think they only find out if a job offer goes out to the individual and is accepted.

My manager knows I am interested in moving on from my current role. It has come up a few times in our 1:1's. My manager has said that he would give a reference to the hiring manager if I wanted him to.

I guess it all depends on how the relationship is between you and your manager. If it's a good, then let your manager know sooner rather than later.

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