I don't really think it's about expectations or initiative. It's about accountability. He's simply saying that there are times when the guy on the bottom of the ladder has his hands tied and can say there is nothing he could have done(breaking and entering is not a viable option for a janitor). At some point someone has to take responsibility, Jobs says that starts at the VP level.

I also think people get a little carried away with this due to Jobs' persona. I don't think he means it in a, "you must get X done at all costs". I think he's simply saying, "This is your responsibility. You're accountable. Don't blame someone or something else".