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, 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. The chapter explains that the primary problem confronting Kelly, the business administrator of Brunswick school here is a very serious lack of communication between her and the superintendent, and she needs to take immediate action. A secondary issue is the miscommunication that is happening in the district, stemming from the superintendent's office.