Steve was a huge asshole to a lot of people, when he had power over them. There's eccentric behaviour, and there is being a jerk. One's harmless, if odd - the other goes out of the way to ruin someone's day. You don't want to be the second one.

Consider the interaction between John Carmack and Steve Jobs that was posted the other day:

> One time, my wife, then fiancée, and I were meeting with Steve at Apple, and he wanted me to do a keynote that happened to be scheduled on the same day as our wedding. With a big smile and full of charm, he suggested that we postpone it. We declined, but he kept pressing. Eventually my wife countered with a suggestion that if he really wanted “her” John so much, he should loan John Lassiter to her media company for a day of consulting. Steve went from full charm to ice cold really damn quick. I didn’t do that keynote.

Do you really want to be remembered for anecdotes like that?

It doesn't take guts to be blunt to people you have power over.

People that (potentially will) have power over you, often respect you being blunt to them. That does not make it easier as there is a significant group of egomaniacs that cannot stand it so you need to know who you have in front of you.