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Women's representation in school leadership positions in India, and of Black women in the United States, remains unexplored. This chapter addresses the realities and complexities of women leaders in school education and develops a narrative based on current trends and anticipated challenges for the future. Existing research in educational leadership in schools, case studies, and interviews tend to focus on developing a coherent understanding of the topic. The representation of women in the school, from teachers to leaders, is an inverted pyramid. This chapter aims to provide an overview of how women school leaders from India and the USA manage crises, navigate politics, establish policies and budgets, and where the constraints lie at the school board and family level. Finally, using the grounded theory framework, the authors will present a pattern of women's leadership similarities, differences, and uniqueness in the context of both countries.