This article examines, from a female perspective, the complexities of gender and ethnicity embedded in successful urban school leadership. The authors use qualitative data, collected from female participants in two cohorts of aspiring urban principals in a yearlong experimental leadership preparation program, to discuss issues that arise during the coursework mentoring and school internship components of the program. Recommendations for future programs, drawn from the study, include selecting program participants based on their commitment to social justice, utilizing opportunities to confront gender and ethnic leadership stereotyping, providing the training to conduct school dialogues on social justice issues, and exposing aspiring principals to ethnically diverse urban school environments.