In this case, I share my process of analyzing data in a multiple case study. The study looked at the interconnections between contexts, leadership, and educational equity to better understand how superintendents lead systems that offer equitable educational experiences for all students. Data included 16 one-on-one interviews with four superintendents, as well as secondary data. My initial plan to analyze the data was unsuccessful, and in this case, I explain the difficulties I encountered and how I changed my approach to successfully analyze the data and write up the results. Throughout the process, the value of critical colleagues and the benefit of flexibility in methods supported me in rethinking my approach to data analysis within a multiple case study.