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Very few articles in the published research literature have considered the clinical supervision of school psychology and even fewer articles explore the administrative supervision of school psychologists. The purpose of this study is to describe the roles, and responsibilities, and challenges faced by district leaders who supervise school psychologists. Using a purposeful sample, participants met criteria for this study if they worked at the district level, supervised at least three school psychologists, and were responsible for hiring and firing school psychologists. Nineteen participants qualified for this study and completed a phone interview that included eight open-ended questions.Participants shared that they primarily had managerial and leadership roles during their busy and unpredictable work weeks. Participants also reported challenges directly and indirectly related to the national shortage of school psychologists, difficulties with large workloads, the need to advocate for the field of school psychology, and a lack of professional guidance and training in their role.Implications for practice include developing a professional organization or community of practice for administrative supervisors, establishing best practice guidelines, and providing a defined role for these leaders. By coming to know the roles and challenges that district administrators are facing, the field of school psychology can find ways to support administrative supervision endeavors.