Make him a phonetic cheat-sheet for the callsign so he can just look at it.
Add a script of things he should say for various common requests from callers (his name, your state, city, grid, county, his name in phonetics, your name in phonetics) that you can just point at the correct response and he can read it.
If you do this on a dry erase you can add in the RST numbers for him and he won't have to understand and estimate those...though in my experience they will ask about it pretty quickly.
Be sure he understands there is no real pressure on him, he can just wing it if the caller asks for his favorite hobby or requests naval gunfire.
The looser they get the more fun they have with it.
I have gotten my daughter on a few SOTA activations, though I am not sure she will go on any new ones without serious bribery.