3. Learn how to say NO to him, everybody have a weak spot, if he perceive you as a "yes man" he will lose respect to you.
This is the most important of all: being able to say NO: "we will not go into Aspen and yes others might be but it is not safe!"
There are too many yes man because: a) we want to please and b) we want to get there and c) he pays your bills! This tend to cloud ones judgement and have one say YES too often