Will friends insurance cover him on my motorcycle?

My buddy rides my minimally-insured beater motorcycle occasionally. If he crashes into someone, could I have his insurance cover everything? I'm not worried about the bike at all, only damage to other property. I'm thinking maybe I would need to talk to him beforehand and make sure that he has his own personal insurance card with him. Also he would need to make sure that his insurance would cover that? Or is this an option at all?