Asking questions and knowing what you don't know and being honest about it is super important. But so is moving forward, getting things done and leadership and sometimes constantly questioning your world with fresh eyes every morning can mess with these things. It's also exhausting.

I find folks who have been surrounded by extremely smart hands-on analytical types most of their lives are slow moving and not great leaders because they question absolutely everything. It's a reflex that develops because if you're working with 20 other engineers building a rocket you don't want to be the guy who said "lets just assume" or "screw it, lets just get it out the door".

Sometimes though, it's useful to have an arrogant ass around that makes a few assumptions and keeps kicking the can down the road. Steve Jobs comes to mind.