[subroutine]

Have you talked to others on your team about this? Perhaps they find him useful in ways that are not directly apparent to you (also if he is helping others it could be slowing progress on his own tasks).

If your team feels similarly though, I think the next move would be to inform this person that you are considering downsizing the team and there may not be room to keep him around. If he was just being lax from a false sense of security due to his tenure maybe this will inspire him to be more productive. At the least it will give him time to prepare for a possible firing.

This must be one of the worst parts of being the boss - having to fire a nice guy.

[throwaway753647]

I haven't talked to others directly about letting him go, since that doesn't seem appropriate or fair. I do know though that people have had to wait on him for things longer than they should, and follow up with him more than should be necessary. So while he does have useful knowledge and insights, I feel like he may be holding others back as much as helping them.

I'm not sure that (essentially) the threat of firing would be the best motivating measure. If I've made the decision it seems more fair to just do it (along with a good severance).