This paper is organized as a dialogue between two female administrators, the superintendent of program and the superintendent of operations, from the Wellington County Board of Education in southwestern Ontario, Canada. After describing Wellington County and the organizational structure of the school board, the superintendents describe the nature of their positions, including departments and programs for which they are responsible and specific duties they perform. Next, both women explain their early school experiences, their educational and professional goals, and the sequence of events and positions that led them to the superintendency, with mention throughout of instances of sexual harassment and sex discrimination. After reviewing the changing roles and opportunities for women in administration, the presenters discuss the realities of the superintendency and offer suggestions for coping with domestic and professional responsibilities to women aspiring to that position. Last, essential traits of administrators such as political acumen and common sense are examined, the importance of leadership development programs is discussed, and ideas for helping women move into higher level administrative positions in education are presented. (CLA)