I gotta say that 9/10 times when I talk to a former player turned exec, they tell me they tell me they started training during their career. Of the guys who battled injuries, that's more like 10/10.

Guys like Jordan and Magic are kind of the exceptions. Sure they were into the business side of things but maybe not the front office specifically. They were given the gig based on their pedigree as players. Is that going to happen with Hill, who is like 15 years removed from stardom? Doubtful.

Hill had plenty of down time to study up on the business side. Even if he did not have that time, he still could have prepared adequately, especially if he started early.

I cannot do anything more than speculation on his level of preparedness but if I had to guess, he's not a bad pony to back.