Head of school transitions happen for a variety of reasons. Without a doubt, however, the most stressful ones are those that are not voluntary. In the last few years, an increasing number of boards have decided to let their heads go at nontraditional transition times. In turn, this has left the school leadership staff scrambling to ensure that the school community remains confident in the school for the remainder of the year or longer. This article disucsses some of the main reasons these relationships have ended badly, as well as suggestions on how to avoid these situations. While there are instances in which it is clearly in the school's best interest to fire a head, schools can often avoid these abrupt and disruptive transitions by strengthening the working relationship between the board and the head. Finally, boards that make the decision to go separate ways with a head need to be aware of the potential pitfalls that often appear afterward.