I think a reason why cockiness is enjoyed by the more thoughtful types is that it gives them an illusion of choice. By restricting the problem down to a couple of different solutions, thoughtful types figure that one has to be more optimal than the other and is therefore the more reasonable solution. The "reasoners" may be good at comparison study, but are often paralyzed when it comes to devising completely new solutions. A cocky leader, while maybe a technical ignoramus, at least narrows the choices down a bit.