It's important to look at the relative upside and downside for different parties. If you are the voice of uncomfortable truth for someone you have the possibil

It's important to look at the relative upside and downside for different parties. If you are the voice of uncomfortable truth for someone you have the possibility of a big win (e.g. say out loud that the emperor's butt naked) but are probably viewed as a big meanie and may burn bridges in most typical cases. If you are the voice of sugar coating and go with the crowd, or whatever you think the other person wants, you are unlikely to have a big win, but at least you are considered "nice" most of the time. In practice, no one is all one or all the other. It also depends on who is risking what. In the Dan/Dani case, the surgeons and doctors didn't have to deal with the consequences of a mistaken decision, but they did have to deal with the possibility that someone might label them anti-trans bigots. When nothing is really at stake for you, personally, why not be blandly, gently "nice" to someone and avoid hurting their feelings? On the other hand, if $1M of my own money is on the table (e.g. investing it in a startup), even though I want to maintain good working relations I will ask the hard questions, because there's big downside risk for me if I don't.