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. The chapter explains from a professional development perspective, the opening of school needs to be reworked so that all staff members are informed about the action plans. The superintendent needs to celebrate the past successes in working with English Language Learners (ELL) students and remind them how they developed a nurturing environment for all students.