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A central theme that permeates studies on gender and leadership in education is the move towards eroding discrimination against females. Yet, women remain a minority gender in terms of leadership positions in education. Despite policy initiatives enforcing gender equity, discrimination, prejudice and stereotyping continue to perpetuate women’s submissiveness and remain a barrier for women in leadership positions. The awareness of gender politics combined with challenges related to gender equity in organizations remain a thorny concern in education circles. This paper examines the barriers South African women experience. A qualitative approach was employed using a post-colonial feminist lens. Findings indicate that stereotypes concerning female inadequacy as leaders persist and act to distort perceptions of male and female performance and potential.