I wish I could quantify it like Robb has, but I can't. For me it's instinctual or something? I don't know how far to lead them, it's just when it looks right.
But I agree with the respondent that said he was generally reluctant. I don't do it until what I see, body language, tells me he isn't going to offer a better shot. This usually means multiples.
Good hunting. LB