Independent schools need to address the pending leadership crisis as well as the gender gap in leadership due to the growing need for new leaders. With the high turnover of independent school heads in the next decade due to 68% of sitting heads reaching retirement age, schools are in competition with one another for qualified leaders (Kane & Barbaro, 2016).

This study focused on the leadership pathway for female independent school senior level administrators. This project used a qualitative research design to understand the experiences of female senior level administrators in independent schools who are on the pathway to becoming a head of school.

Findings support the need for multiple levels of support to push women forward on their pathway as well as opportunities for women to be “tapped” and invited to step forward. Additionally, women are held back due to family responsibilities and gender bias regarding “good” leadership. Developing confidence and risk taking in women encourages women to be seen as “good” leaders and to self-promote. Finally, senior level administrators perceive the head of school job differently than heads of school in two key areas – board relationships and student contact. The head of school job is seen as a barrier to senior level administrators due to the demands of the job, which contributes to senior level administrators not moving forward into the head of school role.

The crisis in independent school leadership needs attention, as there is a shortage of qualified candidates to become heads of school, creating intense competition for leaders among schools. Although there are experienced senior leaders in independent schools, the number applying for head of school positions is low. This research contributes to the literature on leadership in independent schools in at least three ways. First, this research examined perspectives on the senior level administrative pathway to head of school jobs. Secondly, this study adds to the research on how to address structural and personal barriers for women pursuing leadership. Finally, this study adds to the literature and conversation about the head of school job as perceived by senior level administrators and experienced by heads of school and how the perception of the job affects women pursuing head of school positions.