You will have to do a flight plan involving the most sophisticated aircraft on the AOC. You could either get a simple flight from a-b-c or if he doesn't like what he sees or hears you may get A-B-C...... all the way to Z. Manifests, fuel loads, W+B each destination. WX, notams (don't forget HO notams).
If you're capable and competent and safe and have taken a genuine interest in the Regs......you'll do fine. If you don't know an answer let him know, don't guess.
Good luck