Beware of experience asymmetry
There are things you’re going to do just once. Get your tonsils out. Pick a caterer for your wedding. Raise money from a venture capitalist. Apply to college.
In these situations, the institutions and professionals you’re dealing with have significantly more experience than you do. Not only that, but they know that you’ll be gone soon and they’ll still be around.
In these asymmetric situations, it’s unlikely that you’re going to outsmart the experienced folks who have seen it all before. It’s unlikely that you’ll outlast them either.
When you have to walk into one of these events, it pays to hire a local guide. Someone who knows as much as the other folks do, but who works for you instead.
Students come and go, but deans last for generations.