Given the challenges of the workplace and the historic exclusion of women and people of color from positional leadership, this dual case study explores women's experiences in two graduate programs designed to support transformational learning of educational leaders. Data included participants' structured reflections on learning about leadership, examined through the lens of two adult learning theories: self-authorship (Baxter Magolda, 1998, 2004) and transformational learning (Brooks, 2000; Kegan, 2000). Cross-case analysis indicated that participants developed confidence in their own knowledge, articulated the importance of personal support and collaboration, gained voice to advocate for themselves and their students, and experienced a fundamental change in their sense of themselves as leaders in their schools. These findings have implications for the provision of systematic graduate instruction that supports reflection and critique, offers multiple opportunities to step into leadership roles, and integrates informational and transformational learning.