To me, this shows radical leadership, and that he is very unattached to societal norms. Radical leadership meaning that this is kind of the antithesis of a follower mentality. I think it's a kind of genius, but also a personal failing. I really appreciate people who are willing to "question everything", because there are a lot of things we take for granted without thinking about why.
The failures I think this comes from are a form of ignorance and arrogance, and possibly a lack of empathy about how they're perceived. I personally know someone like this that is very intelligent, and thinks that they have all the right answers. There seems to be a mentality of, I have this information facts, given these facts, and that as a goal, *this* is the solution.
With the person I know, a significant problem with their reasoning is that they have important gaps in their knowledge (ignorance). They believe other people just aren't as enlightened as they are (arrogance), and if they were, they would have come to the same conclusion.
For my acquaintance, I believe that the mentality comes from a history of often being right, but also a prolonged social isolation that allowed them to build a myth in their head that they are always right.