The purpose of this research was to investigate the main factors that influence the career aspirations of women senior leaders in New Zealand secondary schools. There is currently a significant disconnect between the number of women in secondary teaching and the number who become principals. Despite women dominating the teaching profession, men dominate educational leadership. There are both external structural factors that influence women's career aspirations and personal agency. The research consists of semi-structured interviews with three women senior leaders in Auckland, where they explain their career aspirations and the enabling factors and barriers to achieving them. The most influential factors enabling women were mentoring, experience and flexible workplaces. The major barriers were the pressure to either put career or family first, and the negative perceptions around the role of a secondary school principal. To close the gender gap in educational leadership, women need to be mentored and encouraged into leadership early on in their careers.