Here are some that come to mind;
Am I pushing my teachers too hard or not hard enough?
Are we going the right direction?
How can I get all my teachers on the same page? How can I influence mediocre teachers to have the same drive and passion as the high fliers? Is this even possible?
When am I going to have that crucial conversation with that staff member?
I do know that I will keep getting up and doing what I feel is right, and that is all I have control over. We need to keep fighting the battle everyday keeping students at the forefront of everything we do. If I can do that everyday I find myself not worrying about some of the items above.
What keeps you up at night?