When Ella Young Flagg, the first female superintendent of the Chicago Public Schools, proposed that educational leadership was a woman’s “natural field” she could not have predicted that one hundred years later women would have neither a majority of school leadership positions, nor would they be proportionally represented when compared with female teachers (Grogan & Shakeshaft, 2011). Unlike the school leadership positions of the principal and superintendent that have been traditionally dominated by men, female leaders have achieved greater parity in special education administration (Keefe & Parmley, 2003). Although female special education administrators represent an exception to this phenomenon of underrepresentation in school leadership, limited research has been done on this specific population. The purpose of this qualitative study with phenomenological interviewing was to understand the leadership experiences of female special education administrators. The central research question asked: How do female administrators in special education understand their leadership experiences? Eight female special education administrators shared how their personal history and their current leadership experiences influenced their leadership behaviors. For the female special education administrators, their leadership experiences were understood as (1) collaborative-relational, (2) instructional, (3) activism, (4) political, and (5) balanced. Parallels between women’s leadership and the foundations of special education offer an explanation for the success of women leaders in the field. A model of the ways female administrators of special education lead is included. The model demonstrates how collaborative-relational leadership is central to female leadership in special education. Recommendations for future research are included.