The school leadership landscape presents an array of challenges and opportunities for women. This study explores women's experiences in educational leadership in one region of South Africa. Qualitative data was collected from three focus groups comprising 30 women school leaders—10 principals, 10 deputy principals, and 10 departmental heads—from schools in the Pinetown and Umlazi districts of KwaZulu-Natal. The aim was to identify and examine the key enablers and constraints shaping their professional journeys. Data was analysed using thematic analysis, revealing that robust support systems, professional networks, ongoing personal and professional development are enablers that significantly enhance women's leadership efficacy. Conversely, gender bias and discrimination, work overload and difficulties with time management, patriarchy and cultural constraints, and systemic issues pose substantial barriers that detract from their leadership efficacy. The findings underscore the importance of fostering supportive environments and equitable policies to empower women in leadership positions. Recommendations for policymakers, schools, and communities include leadership training tailored specifically to the needs of women, mentorship programmes, the promotion of gender equity, and adequate resource allocation. This research contributes to the broader discourse on gender and leadership in education, offering insights that can inform strategies to enhance the participation and success of women leaders in schools.