A democratic South Africa assured equality to all individuals irrespective of gender, religion, beliefs, or race. Nonetheless, women’s representation in leadership roles remains unequal compared to men, particularly in the secondary school landscape. The study used a qualitative research approach, through semi-structured interviews, and respondents were selected through the purposive sampling technique. The study findings revealed that entrenched gender stereotypes, insufficient mentorship, and political and union biases significantly hinder women's career advancement in principalship positions. Despite possessing the necessary qualifications and skills, female principals often confront biases that question their competence and authority. This paper recommended that there is a need for systemic reforms to address these barriers, promote fair and merit-based selection processes, and establish supportive networks for female educators. The findings of this study contribute to the discourse on gender equality in educational leadership and inform initiatives aimed at promoting the advancement of women in South African secondary school leadership roles.
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