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This qualitative study explores superintendent leadership development in the context of a university-led applied learning network focused on equity. The central questions are, “How do superintendents frame problems of practice for school district improvement?” and “What questions do superintendents seek to answer in collaboration with peers focused on enhancing equitable student outcomes in their districts?” Superintendents normally have little opportunity to deeply examine how district systems are enhance or inhibit equitable student outcomes. District leaders push for improvement centered on equity, while assessing “the how” of shifting school and district culture in order to realize high quality education for the diverse students served by schools; cultivating instructional leaders and building school culture to produce equitable district systems.