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As generative artificial intelligence (AI) expands in K–12 education, superintendents face pressure to respond amid limited policy guidance and ethical uncertainty. This qualitative study investigates how superintendents in a Midwestern U.S. state navigate AI integration across instructional, operational, and policy domains. Drawing on a socio-technical perspective, it examines how leaders make context-sensitive decisions and respond to stakeholder concerns around equity, trust, and responsible use. Data include interviews with 15 superintendents and district artifacts, analyzed through multiple coding cycles. Findings suggest that superintendents act as mediators of AI adoption, balancing innovation with caution and adapting existing frameworks to local needs. The study offers implications for designing leadership frameworks that reflect real-world decision-making and support more responsive and grounded AI implementation approaches.