As you practice this skill, you will learn what works and doesn’t work for you. However, read this article for some good tips on Do’s and Don’ts.
My advice with this article is to read it and determine, based on what you know about your boss, what will and won’t work. Actually, this is the best advice for anything you read or hear. Each person is different and these tips aren’t universal.
These will work a lot of the time, but the experienced professional builds a relationship with the individuals so they know what will and won’t work.