Q: What would your way be to approach a deal with a General Supt. that honestly does not have the field experience or knowledge to do his job. But honestly believes that he is the shit. I am straight forward finding no reason to sugarcoat anything.
A: Sounds like it is an ego problem that is blinding him to the need for his own growth. One path with those types is to choose inquiry, not confrontation. Ask him for ideas on things that are clearly over his head. Ask him for technical assistance that he cannot provide. Get him to acknowledge (without being an asshole about it) that he needs input, as well as your direct assistance. Make sure that when he does take input, thank him for it. Tell him you respect him for being open. A lot of times that kind of behavior is defensive and insecurity and its your job to “manage-up” even if it feels like dealing with a kid.