In Tanzania, many qualified and capable women teachers are not involved in decision making despite the fact that the Tanzania government has affirmed the promotion of women's participation in the decision-making process. Even those few who are in leadership still face obstacles and challenges especially in a rural context. This paper examines the challenges women leaders face and identifies the coping strategies they use to overcome the challenges in Community Secondary Schools (CSSs) in rural Tanzania. The study involved heads of schools, teachers, the Regional Educational Officer (REO) and the District Education Officer (DEO). Data were obtained through interviews and focus group discussions. The findings reveal that women face multi-level challenges with respect to family, society and the education system, most of which arise from early socialisation. Women leaders work in a patriarchal society that does not accept them due to their sex/femininity and there is a lack of trust from their spouses when they execute leadership roles. It was also observed that women leaders face challenges posed by witchcraft and superstition issues in the rural context. In confronting these challenges, women leaders identified cooperation with staff and the community, sharing challenges with experienced leaders, and being creative as useful coping strategies. The study recommends a number of measures for overcoming such challenges at society, organisational and government levels.