The purpose of this research project was to engage in self-reflective analysis of leadership development as an ongoing process of social action towards democratizing education. Four White women connected by their work as educational leaders, teachers and administrators, engaged this topic by conducting a dialogical analysis of their experiences in leadership. They dialogued from what were technically different positions in the hierarchy at their University and implemented a research process to speak across or marginalize those technical differences to produce a text that explored the rich terrain of leading in which they shared experiences of growth, the conceptual frameworks that guide their leading, and their differing interpretations of gender's role in the leadership process.