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This interpretive qualitative study utilized person-job fit and person-group fit theories to explore the knowledge, skills, and dispositions of assistant principal candidates valued most by those who select and hire them; principals (n=15) and human resource (HR) administrators (n=10). Findings from this study could inform faculty on how to address more nuanced aspects of administrator preparation and selection to include what is prioritized most by principals and HR administrators who select and hire them into the ranks for the first time, which typically begins with the role of AP, by determining potential “fit” for the position and administrative team during the application, interview, and selection processes.