I'm somewhat of in a pinch and I'd appreciate your insight on how to solve things for the best. We've been operating like a company for about 1 year, and I say "like" because we haven't really got around constituting it as such. We are four partners bound only by our word and we all agreed to certain responsibilities, all but one of us has responded, the COO.
The problem lies in that he seems to forget his position and chooses (perhaps unconsciously) to focus on mundane work. This has gotten us in serious control, organizational and managerial issues and has really gotten to the point that I've personally taken charge for his responsibilities (mainly PM, for 1-2 week periods) where he asks me "what's next?", when it is supposedly his job to answer that. I've told him this personally.
The thing is that he is excellent at doing the everyday work, we are resource crunched and, given that we've all endured all sorts of stuff during all this time, the fact of cutting him loose just because he has an employee's attitude rather than a partner's seems like the wrong thing to do. He is a great worker, but he brings no value to the company other than his work.
It also feels like he is more comfortable asking "what's next" instead of determining it by himself and telling all of us what to do, which we are open and almost begging him to do it.
I'm not really sure how or what he should be doing instead of being a COO. Perhaps we are asking him more than he is ready to give, but I see no scenario where he is demoted (by position and/or equity) and doesn't leave the company. I also have the suspicion that he might have the intention of looking for another job (or at least is thinking about it).
Oh, and he is my best friend.