I don't know if I would call this "devastating," but something that I have always had to deal with is how to support teachers but also keep parents and kids happy. To tell you a story, I had a student many years ago who was a graduating senior. He needed to pass a marine biology class if he wanted any hope of graduating because he needed the science credit. Well, the kid not only failed the course (with a low 50), but also purposefully skipped the final exam. The school has a policy that an active skip like this is an automatic zero and the kid is not allowed to make it up. Well, this ...
This solution discusses an instance of leadership ethics. It describes one case where an administrator had to make a very difficult call regarding the well-being of a student, even though is violated school policy and angered the teacher. It shows how difficult school leadership is and the ethical and moral decisions that are constantly being made.