This chapter presents a complex, real-life, accessible case study in expecting the best to provoke and stimulate conversation around practical problems an 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. The organization and unique approach of Educational Leadership in Action allows for flexible use in courses for aspiring leaders to supplement core readings, reinforce central concepts, exemplify theory, and provide grounded examples to encourage learning.