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When is it best to tell your manager/boss about a job you applied for?

When you are actively looking or when you’re hired and putting in your 2 weeks notice?
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Depends on the boss and organization really... I have had some bosses that I could talk with and we talked about potential future jobs years in advance before I was ready for them and they help try to educate you.

Other bosses... it's best to tell them absolutely nothing, as they'll hold it against you, make your life harder.

So I think it all depends on the situation and people and organization involved.