Women in school leadership have experiences that, when reflected on, can reveal challenges and enabling factors for their success. Leadership comes with a host of challenges for anyone, yet women experience added challenges unique to their gender. This study centres on women’s reflections of their experiences in school leadership positions and the ways in which they cope with school leadership dynamics. Their reflections and insights can shape and inform the career trajectories and leadership styles of other women and have a bearing on the educational institutions and communities they lead. In this way, their reflections can contribute to the continuous professional growth and development of fellow teachers. They can also inform the development of mentorship programmes, leadership training initiatives, and Department of Education or school policies to enhance gender equality and support the advancement of women in educational leadership roles. Social Role Theory (Eagly, 1987) informs this study. This theory foregrounds the intertwined identities and experiences of human beings, such as ethnicity, socioeconomic position, gender, and aptitude, as well as the sociocultural variables that contribute to certain behaviours in various contexts. The theory is well suited to the aims of this study, which seeks to examine the reflections of women in school leadership positions so as to understand the status quo in South African schools. This research is qualitative and based on an interpretive paradigm. To generate data, 40 women in school leadership positions—departmental heads, deputy principals, and principals—were purposively sampled and interviewed in focus groups. The generated data was analysed thematically.