Existing literature provides newly identified responsibilities of the principal supervisor but lacks in information about how districts should strategically spearhead the process of initiating, implementing, and managing the changes to the role of the supervisor. In this study, I examined the behaviors and actions of one school district's executive-level leaders as they shifted the position of the principal supervisor. Findings could contribute to a new area of research in how district leaders may navigate and manage the complicated process of initiating and managing the changes to the principal supervisor's role.