I'm drawing a blank on how to proceed here. How would you help a high-C peer through an uncertain process?
Specifically, this is a process for providing estimates to sales for technical services work. By its nature a sales estimate is looser; we do lots of them and they need to be quick. This gentleman is having a very difficult time dealing with the uncertainty. His trend is to delay, take more time, ask for more detail. He wants to do a full blown design every time. When pressed for an answer, he says "I can't estimate this, there isn't enough information." Eventually he gives an estimate, but always seems reluctant to do it.
I'm concerned (both for the company's process and for him) because he or his team must provide these estimates of their work to move forward. He is obviously uncomfortable making a guess, even an educated guess. No other team can do this work, but he is just not being that effective here.
I have suggested that he delagate this to a member of his team, but so far that hasn't been taken up on. My sense is that he believes the process is broken and therefore isn't going to let it out of his control.
Any thoughts on what I can do to help him deal with the uncertainty better?