For those that don’t know, steelmanning is the opposite of strawmanning.
It means re-stating your opponent’s view in a manner that they agree “yes, that is my view” and only then you express why you disagree with it.
Failure to do so means one of two things: either you don’t actually understand the stance you claim to oppose or you’re not even in the business of finding truth and changing minds to begin with.
Not sure if this is actually unpopular, but it didn’t feel like a showerthought either.
Sounds more like your boss just didn’t understand the business. “By the book” managers often have no idea how the business actually works, so they hide behind vague answers and questions. They tend to be liked by upper management because they’ll just do what’s asked without questions. They tend to be hated by people below them because they can’t answer any questions and often know less than the people they supervise.