The Constitution of the Republic of South Africa, 1996 confers equality on all South African citizens regardless of race and gender. It has been reported that, under apartheid, gender inequality was a way of life and even social liberation movements observed it. Education is not exempt from gender inequality; the Department of Education in 2003 produced the Gender Equality In Education policy. The then Minister of Education committed to the policy and adopted the mainstreaming of gender and the training of education administrators in the implementation of gender equity programmes. Despite these efforts, male dominance continues in areas such as educational leadership. This paper employs a case study approach to investigate the role of institutional culture in undermining the constitutional aim of attaining gender equality. Using feminist critical policy analysis theory to study the mentoring and management style employed in a South African rural high school, the article concludes that despite the policy imperatives, the conservative and patriarchal tendencies within educational leadership undermine the attainment of gender equality. To attain success, implementation of gender policies needs to be strictly monitored.