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Principal supervisors coach principals by providing feedback, modeling practices, brokering resources, and helping principals prioritize instructional leadership development. Most research available to inform this change process focuses on findings from large urban districts, which have structures, organizations, and role conceptions not easily translated to mid-size and smaller central offices. In this retrospective qualitative study of five mid-sized districts, we explore how district leaders conceptualize and develop roles similar to that of a principal supervisor, select from personnel to fill these roles, and then support them in their work with principals in underperforming schools. We find that superintendents prioritize support over accountability, prefer instructional leaders but rely on longstanding professional relationships, and reorganize strategically to emphasize personnel strengths.