Reason why I'm not a boss. Sorry you had to deal with that.

Well done, you sound like you handled it as well as anyone could expect. I know not everyone has the ability to completely compartmentalize stuff like that the way I do, which is why it's absolutely vital that people like me are kept far, far away from power while people like you make the world a better place. =)

Sometimes it's not the wrong person for the job, it's the wrong job for the person.
I bet six months or five years down the road, he tells you that changing jobs was the best thing that he ever did.
More people could use a boss like you.

I've found people tend to know when things don't fit. I've never fired someone who hadn't seen it coming. Still it's never a pleasant thing to do. It's great that he found something else.

Thanks everybody, for your kind words.
When I fired him, he did say that he'd expected it, but not for a few months, so it wasn't a complete shock. He's a designer, we're a small web dev shop, and he'd been chafing at the bit a lot about having his designs changed or rejected, etc. He wasn't happy, we weren't happy, and he asked for a raise.
Didn't really see any other way out.

People know when it's not working. It stings, but unless it's a layoff, it's rarely a surprise. Even so, it is the worst part of being a boss.

I've fired four people in my career. It stays with you. It was the right decision each time, but it is never, ever easy.

I've had to fire three people in the last couple of years, fortunately for my conscience, the reasons have been pretty clear-cut cases of malfeasance, to wit:

1. A driver who hocked his truck to a drug dealer for speed.

2. A driver who got in the face of a customer and cursed at them.

3. A driver who gambled away company money at a slot machine.