From a questionnaire some months ago that a prospective employer send one of my old boss’s boss:
Finally, please list what you think his greatest strength or attribute was and something he may be able to improve on? Strength is broad knowledge of software, the Internet and initiative. In terms of improvement, Rob is a very principled person. Something I respect. But at times, staying true to his principles, he would say what he really thought (and what many other people thought as well). I would coach him on the fact you should not always do that. It was never a problem for me and most secure management. Some of the new management had an issue with that.
I don’t like the question (I don’t like questions that are that damn ambiguous) – but I liked my friend’s answer – because what he is saying is, “Rob will tell you when he thinks you are screwing up – even if you are the boss”. And he’s right. I told him on a couple occasions I thought he was wrong. I did it respectfully (which was easy, because I do respect him). But I didn’t just shut my mouth and walk away. He may have been the big boss, but he reported to the same stockholders I reported to.