You are not the first one who has this issue with him, and I'm sure he is smart enough, self conscious and has enough experience to know that sometimes people don't understand him and that he has to repeat himself. And as long as you ask kindly and with tact I think he won't mind to repeat as many times as needed. Maybe you just can't really overlook or ignore that, and if you can so just let it be. Don't be so afraid to ask him to repeat himself and don't be so conscious about it.