In my personal experience, folks who reach fairly lofty positions in companies do not want naysayers around them, at all, ever, it's career suicide to do so. Most really think they got there because they are so much smarter and more capable than anyone else. Most I knew got there because they were brown nosers. The rest knew when to shut up and play ball.
Some of the bosses I had 2-3 levels up were plain vile, you really had to watch what you said around them. Or try.