A central theme that dominates most studies on gender and leadership in education is the emerging tendency towards mitigating pervasive forms of discrimination against females. Yet, women still remain, for the most part, a minority within leadership positions in education. Despite policy initiatives emphasising gender equity, discrimination, prejudice and stereotyping continue to perpetuate the myth of women's submissiveness and remain a redoubtable barrier for impeding women in acquiring leadership positions. The awareness of gender politics combined with challenges related to gender equity in organisations 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 perspective. Findings indicate that stereotypes concerning female inadequacy as leaders persist and act to distort perceptions of male and female performance and potential.