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Too few leaders of color reflect communities’ and student populations’ increasing diversity. Much work on diversifying the leader pipeline targets large urban districts while most districts are small to mid-sized and lack relevant systems and structures. This paper presents the results of Town Hall discussions to learn what unique challenges such districts experience, within and among 7 regions of a state, and the solutions devised to better recruit and retain more diverse leaders. School and district leaders and higher education faculty discussed common challenges and the need for collaborative solutions to enlarge the aspirant pool, mentor and support new leaders, and reduce implicit bias about working conditions and about leader qualifications.