We investigated and analysed the factors that women teachers consider as barriers to their advancement to headship positions in Zimbabwean primary schools. Specifically, we sought to identify the factors perceived by women school heads to be causes of persistent under-representation of women in school headship positions. Data were collected through structured face-to-face interviews and focus group discussions with 13 experienced women school heads. The findings revealed that although the majority of the women teachers in the study sample were qualified for promotion to school headship positions, they had not attempted to apply for them. The majority of the women teachers in the study sample were adequately qualified for promotion to school headship positions. Indeed, a large number of them either had a university degree or were pursuing degree studies and also had extensive experience. But most of them had not attempted to apply for school headship and hence were still class teachers. Gender stereotypes were shown to be one of the major causes of persistent under-representation of women in primary school headship. The influence of gender role stereotypes was found to manifest in the form of low self esteem; lack of confidence; women's perception that their role in the family overrides all other roles; and lack of support from the home and the workplace.