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The goal of this study was to explore how aspiring school leaders interacted with students in the schools where they worked as full-time administrators. We overlaid principal behaviors identified by the literature as effective ways to interact with students with three leadership theories. Our data come from two sets of interviews and observations of five aspiring school leaders. We found that resident interactions with students fall into three categories: informal interactions that aim to build relationships, informal interactions that aim to prevent or resolve emerging discipline problems, and formal interactions that seek to resolve existing discipline problems. Residents also described two challenges in interacting with students: having most interactions center on discipline problems and working with other administrators with conflicting philosophies.