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Scholars have increasingly focused on the practice of central office administrators who supervise school principals. This study draws upon interviews with 20 principal supervisors conducted over three academic years to examine the role tensions that arise as central office principal supervisors assume a coaching orientation. Findings indicate that principal supervisors have difficulty balancing the expectations associated with their supervisory role with those required of a leadership coach. Consequently, data suggest supervisors tended to rely on directive supervisory behaviors. The findings have implications for the understanding of the supervisor’s role, the efficacy of coaching as a professional development approach, as well as the ways in which leadership preparation programs might better prepare candidates for central office supervisory positions.