Man Over Practice
It's great that you are trying to practice this. We do it once in a while to recover someone's hat (in windy conditions). What works for me is as follows: 1. Tell someone to point to the object overboard. and 2. The driver jibes the boat. That puts the boat in a circle and you coast up to the floating object.
You can also do an immediate "hove to" move, and theoretically you'll float back to the object....but I haven't tried that technique.
It's a fun exercise. The real hard part is getting someone back on board.
Anyway, we should all be practicing this.