Have you ever encouraged a high-performing employee to resign?

Yes because it's the right thing for the person.  Typically because they'd outgrown us in some way.  I think if I hadn't had those conversations with them they'd have become frustrated, maybe even disruptive, and they'd have left on their own accord with on a negative note.  I would also try to help them find something suitable - in a parent company, or a customer etc.

I recently talked to a frustrated high-performing seller (#2 this year in her big company) who feels disrespected and not fully appreciated. Not the first time - I've talked to other high performing folks about this. Ultimately they will leave. If you are a leader, appreciate, encourage, and coach your team members - that is part of the job!

yes, because i always want to do what's best for the employee. If i've seen reps hit their ceiling and they have greater potential elsewhere, I've encouraged it. If they're high performing but not loving what they're doing, I dig into what they care about most and push them in that direction. 

When someone cannot holistically be who they are and I know a company that they will thrive and grow then I always help them do that. I

I had a very high-performing individual on the team, and business indicators were charting very negatively. I knew we were going to have layoffs come in the next few months, and as such I encouraged them to resign but with full transparency of what I believed was coming.

Jobs come and go, but people remember people. If I didn't encourage them, they would've been out of a job. It costs nothing to be kind.

We still meet for drinks whenever I'm in the US, and the relationship is still very strong.