This chapter presents a complex, real-life, accessible case study in expecting the best to provoke and stimulate conversation around practical problems and alternative solutions that confront educational leaders today. As payroll costs consume most of the operating budget, a school superintendent decides to unilaterally reduce staff by utilizing a "Last In, First Out" strategy. As a unified administrative team, the superintendent and school board must face the public and offer an apology for making a bad situation worse. They must begin to rebuild the public trust by assuring the public that the administrative team will begin to methodically address a long-term solution, including recruiting and retaining highly qualified teachers at every campus. As such, should future reductions become necessary, teachers will be dismissed based on classroom evaluations and other objective measures, rather than seniority. The superintendent and school board must set the tone that they will always do what is best for students.