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School superintendents are perfectly situated for community-wide impact in and across schools and may exert effort, either directly or indirectly, on cultivating character in youth. With the aim of helping aspiring superintendents to develop such a motivation and capacity, we need to learn from existing superintendents. This paper reports on focus groups with existing superintendents in Alabama to explore a.) their experiences leading districts and how they contributed to developing character in schools; and b.) how a virtue ethics character education approach might be developed in schools. Findings suggest the character of superintendents themselves is foundational and that a coherent approach to character education is currently lacking, as is targeted professional development for teachers in this regard.