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Shortages of diverse education leaders are particularly pernicious in urban areas, but traditional pathways to leadership positions pose barriers for diverse candidates. There is a growing need for culturally responsive leaders who are better able to retain diverse teachers, more likely to stay in urban schools, contribute to higher achievement of diverse students, and create inclusive environments. This qualitative study uses narrative inquiry to examine the leadership pathways at 28 intentionally diverse charter schools across five locales. We explore leaders’ motivations and find that for some, segregated school experiences led them to seek leadership positions in diverse schools, while others were motivated to give back. Implications are particularly relevant at this time of civil unrest and demands for amplified voices.