[thefivetoes]

I lead a team of 6 designers and developers, and have frequently told my team that I understand they won't work for me forever, and if they ever decide to leave I would be happy and excited for them (and I honestly meant it).

A few days ago one of my best developers told me she is talking to another shop, and while it stung for a second ("oh man it's going to be hard to replace her," "this is the worst time for someone to leave," etc.) I was genuinely excited for her and I talked to her about her options and helped her weigh the differences. I tried as hard as possible to be unbiased.

I think if you have this sort of expectation with your boss, you should talk about it - a good leader has a responsibility to be a mentor and a coach, and should help you work through decisions like this.

Of course, if you have any concerns about repercussions, or believe that talking through it would only help your employer, don't do it.