The study described in this paper elevates the role of community and educational stakeholders in building purposeful and meaningful relations with school district superintendents in the state of Kentucky. The purpose of this survey-based research is to explore superintendents' experiences with various educational stakeholders including school district, professional organizations, teachers, parents, and students. Emergence of special interest groups, factors influencing political action in the district, and the extent of superintendent community involvement are reported in this paper as well.