Societal norms and ideologies long prevented women’s initial access to teaching and educational leadership. However, women have persisted in the field of educational leadership. The feminisation of the teaching profession and the bureaucratisation of roles within schools prompted a new stratification within education. By and large, men dominated and continue to dominate administrative leadership roles, while the majority of teachers are women. However, women can and do persist in administration. In order to do so, support for their leadership must be provided, including: increasing teacher pipelines, rethinking preparation programmes to reflect multiple leadership perspectives, development of on the job supports to identify and develop aspiring women administrators, and valuing nontraditional leadership styles and approaches.