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. These cases cover a wide range of topics, including: teacher evaluations, educational reforms, school safety, cultural differences, undocumented students, and social media. Each case study has three alternative responses written by experienced educational administrators and academics. The respondents were asked to identify the primary problem, along with secondary problems, and to provide a strategy that will address the problems identified. By providing three alternative responses to each case, a diverse range of problems and solutions are available for each case study. Mr. Jeffers as the new principal at Wilson Elementary School, he concerned about a number of things, however, he will address the three things that concern him the most. He will inform staff of his plan to visit all classrooms and work areas for the purpose of visiting/observing performance.