Research exploring the challenges department chairs face has long suggested the role is difficult and lacks tangible reward (Buller, 2012, 2015; Gmelch et al., 2017). Yet, as higher education demographics, settings, and organizational expectations change and chairs function in more uncertain and increasingly complex institutional environments, it is important to understand how chairs describe the challenges they encounter, the ways in which they respond to those challenges, and the knowledge and skills they draw on to do so. Drawing on 45 interviews with chairs across a variety of institution types, this study focuses on chairs' perceptions of their role, contextualization of their learning, and understanding how orientations toward faculty, staff, and students contribute to their work. Findings suggest chairs struggle to balance their approaches to the work, striving to employ common sense while decision making, humanity when working with others, and savvy when approaching an unavoidable and often overwhelming political landscape, all while possessing limited institutional authority. These are expressed as tensions of task, organization, and role, and the people and relationships that chairs must reconcile, rather than resolve, if they are to be successful.