[skue]

This article is full of good advice, but one thing Fred doesn't say which should be added: It's quite possible that the employee is already aware that things aren't working out - especially if it's a smaller startup.

I cofounded a company and hired a friend who moved across the country. I even went to the mat with another cofounder who questioned whether he was the right fit. Turns out he wasn't. It wasn't his fault. He's very talented, but he duplicated existing skillsets (mine most of all), and the hat we needed him to wear was one that he'd never worn before. And this increased the stress of his job, which only made it even harder for him to be productive.

Fortunately, the other founders agreed to be generous about offering him an exit (in line with Fred's advice), and so when he and I had the conversation it was much easier for his departure to be a mutual decision and we've retained our friendship.

I would never go into a conversation like this unprepared and rely on the assumption it will be easy or mutual. And I haven't had to do this often enough to know if this was a rare outcome. But if you look at it from both sides and are willing to be generous with the solution, then it is possible that sometimes the "mutual decision" really is a mutual one.