I understand, it is boss(or super boss in the case) responsibility to be able to encourage feedback and open conversation. There is big difference between making small talk and using that time to be on the soap box , no boss should need feedback for that line.
It is just that as a manager, I have been surprised how people think I would take offence on something and not mention it for a long time. I always considered it my responsibility to encourage my team even if they are 3-4 levels down to be able openly talk with me and tell me what I am doing wrong and how can i help them do their jobs better, if they are not able to do that, it is on me.
That is fair. Unfortunately, politics, like religion, can be deeply personal, and it is very difficult to predict how someone will react.
If the company had a proper feedback mechanism- whereby I could have left feedback for him anonymously (so that only his boss would see my name) I might have felt more comfortable bringing it up.
It is just that as a manager, I have been surprised how people think I would take offence on something and not mention it for a long time. I always considered it my responsibility to encourage my team even if they are 3-4 levels down to be able openly talk with me and tell me what I am doing wrong and how can i help them do their jobs better, if they are not able to do that, it is on me.