Do it wrong, seriously.
medium.com
medium.com
No one's fond of anyone who "frequently" challenges them for the sake of challenging.
This little nugget encourages the classic "I'll be an ass like Steve Jobs and everyone will love it" line of thought. While I think it's useful to be frank with the goal of helping yourself and people grow, Steve Jobs is admired because he was insanely successful, not because he was just an ass. If he was just an ass, no one would even know his name.