Dissertation (MA Education)Worldwide Statistics provides that, women are underrepresented in school leadership positions. This study sought to investigate factors influencing women access to secondary school leadership positions in Tanzania. The study objectives were: to examine the nature and type of obstacles preventing female teachers from holding secondary school leadership positions; to find out the gender based challenges facing female school heads in the management of secondary schools; and to analyze the perceptions of stakeholders about women holding leadership positions in secondary schools in Tanzania. The study used the Feminist and Role Congruity theory. Using a descriptive survey design, the study was conducted in Karatu district with sample of 1 DSEO, 6 Headmistresses and 43 secondary school teachers in Karatu district. Sampling was done purposively for DESO and school heads while simple random technique was for teachers. The study used the questionnaire, interview and documentary review as the major data collection instruments. The data collected and analyzed using qualitative and quantitative methods. The study findings indicated that; cultural barriers, family responsibility, inferiority complex, lack of role model and gender stereotype were the major obstacles facing women in leadership positions. Gender based challenges faced female school heads in management were; lack of acceptance and support from subordinates and balancing of multiple tasks. Community perception about women holding leadership positions in secondary school were still negative. The study recommends that women should ensure that they have the necessary skills to work as top education managers, should be willing to take up opportunities, and be willing to maintain the managerial position through good work performance. The Ministry of education and vocational training should introduce application system for being a school heads rather than ad hoc appointment system. This will reduce the possibility of favoritism and corruption. Also women should learn to motivate others and encourage them through different forums, both formal and informal. Socializing agents should work together and ensure that members of the society are enlightened and encouraged to discard traditional beliefs that women are inferior to men and that domestic work and taking care of children are women roles.