I had a really bad boss who didn't understand IT, but even worse, he didn't understand the company. He had grand plans and big goals that did not fix the organization at all. That was the worst. Now, I have a boss that is completely disconnected from what I do. On average, I communicate with him once a month. It only happens when something major fails or I need capital for a project. Otherwise, he is completely hands off. While I like to think that speaks of the confidence he has in me and the team, I still feel a bit like Dilbert on occasion.