My Boss (the CTO at a mid-sized company) says he really appreciates my candor and ability to ask challenging questions, but based on his reactions when I do so I'm pretty sure what he actually really likes the IDEA of being an executive who invites diverse and dissenting input, more than having people do it.
To be generous, sometimes how one feels in the moment is different than how one feels when given time to reflect. So it may be that your boss really does appreciate it (just not right then).
"Managers often say they'll reward something – perhaps they even believe it. But then they proceed to reward different things. I think people are fairly good at predicting this discrepancy...." - "People can read their manager's mind", Jossi Kreinin - https://yosefk.com/blog/people-can-read-their-managers-mind....
This happened with me -- VP said he wanted feedback but clearly didn't like real critical feedback. Then that VP tried to set up a denied promo, even though I was performing two levels above my then-current level. Finally the company got bought and levels were frozen and he was laid off (as executives are often laid off in an acquisition), so who knows what would happened.
