Two words.

GRAVITY BONG.

The only people who I've ever heard say they got high their first time said they took gravity hits. It makes sure you get a fat hit, and makes sure you inhale. If he still don't get high after 3 gravs...hes not gonna get high. Just make him pull them for himself until he feels done.

I'm convinced that is a fool-proof method to getting new smokers high. You'll be able to tell when hes havin' trouble packing the bowl and pulling it.