This paper explores the ways in which gender may lead to conflict between women superintendents and members of their elected boards of trustees. The report draws on the perspective of three female former superintendents. A qualitative case-study approach was used that relied on indepth interviews and a focus-group interview with all three participants. The results show that the three women described similar scenarios in their school districts: they were selected by a progressive school board that was replaced when opposition grew enough to force them out. The women described gender as a factor in all stages of the evolution of their experiences: gender operated at personal, community, and societal levels with their board members and made it difficult for these board members to support the actions of the female superintendents. None of the women had received training on gender-related issues in their university-preparation programs, and these issues were never discussed with the school boards. The concludes that members of educational institutions must work toward understanding the operation of gender in superintendent-board relations. (Contains 38 references.) (RJM)