This paper employs the feminist educational leadership perspective to analyse the ecological context and its influence on the leadership experiences of school head teachers within a patriarchal cultural setting. Methodology: This paper forms part of a mixed methods study that included a quantitative random survey during the first research phase to determine the leadership styles of 350 secondary school head teachers across nine districts in the Punjab province of Pakistan using the Multifactor Leadership Questionnaire. This paper is based on the second research phase that analyses empirical data from semi structured interviews of a purposive-stratified sample of 14 head teachers, selected from among the 264 survey respondents, comprising of seven males and seven females. Bronfenbrenner’s ecological development theory is employed as an analytical framework for thematic analysis. Findings: The study reveals that females must navigate gender stereotypes in a society where they have to fight to establish authority, encounter misogynistic attitudes, rely upon familial support to begin their career, gain spiritual support from a higher power, face work-family conflicts all while practicing educational leadership with high motivation. On the other hand, males assume themselves to be natural leaders and appear to be spared from ecological challenges that impede their leadership journeys. Implications: The findings confirm the prevalence of gender stereotypes that position leadership within the masculine domain in a patriarchal context. The study proposes a complete restructuring of the socio-cultural framework to create a gender neutral society that provides equal educational and professional opportunities to all social members in order to maximize human capital development that is crucial for a country’s economic progress. The findings reflect several subtle and non-subtle socio-cultural challenges faced by female leaders around the world. Originality – This study contributes to enhancing the literature on gender and educational leadership in a patriarchal cultural context.