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Principals are charged with evaluating teachers. Some contend this disqualifies them from being effective at supervision. Research suggests positional power accorded the title of Principal creates barriers to trust, causing teachers to perceive principals as always in evaluation mode, unable to distinguish between looking to judge and looking to support. This argument is not always without merit. The assertion that trust cannot be established, allowing supervision to support growth between a principal and teacher, is challenged in this work. Superintendents have a significant role to play in ensuring best practices in supervision, where professionals trust each other, and provide meaningful support toward teacher’s attainment of goals. This paper speaks to the Superintendent’s role in establishing best practices in supervision.