Everywhere I've ever worked, you can tell any boss things they don't want to hear. What you have to do is do it respectfully. I've told directors and VPs multiple levels up from me that I thought they were wrong about something in large meetings. I said it to their face and respectfully, and that was fine. As long as you understand your place and don't publicly trash your boss, there's normally no problem.
The tweet in question here was... not that.