Women in South Africa face significant challenges in attaining—and thriving—in school leadership positions, despite global efforts towards gender equality in educational leadership. Although strides have been made in promoting women’s participation in leadership, barriers rooted in systemic gender biases, cultural norms, and institutional constraints persistently hinder their advancement in schools. This study offers a reflective exploration of women’s experiences in school leadership positions, examining both their achievements and challenges. It adopts a qualitative research approach, examining the enablers that have facilitated their success and the constraints that continue to impede their progress, using focus group discussions with 30 purposively selected women leaders (10 principals, 10 deputy principals, and 10 departmental heads). Through thematic analysis, the study sheds light on the strategies employed by women leaders to navigate gender biases, promote institutional change, and foster inclusive educational environments. The effectiveness of gender equity policies has been mixed, and barriers persist. Top-down approaches and lack of transparency affect school management, while selective policy application and discrimination undermine meritocracy. Comprehensive reforms are needed for fair processes and an inclusive culture, as are professional development, mentorship, and networking. In addition, gaps in support for transgender and minority groups highlight the need for more comprehensive policies, staff training, and inclusive practices.