Don't bother. He'll just go into Father Knows Best mode, telling you how the real world works and that everything that can be done has been done and it's not constructive to discuss it on a discussion forum (yeah, I know, can't make it up). Then he'll wrap it up by telling you the solution is to send some emails.
With thinking like that, no wonder our athletic department looks like a high school department instead of a Division I collegiate department.