High school counsellors serve as role models and mentors for students as they negotiate academic challenges, develop future career and educational plans, and explore their identities. Though research exists on the gendered experiences of high school administrators, there is a dearth of scholarship on school counsellors. To provide a framework for understanding gender dynamics within school counselling, we combined the feminist critical scholarship on K-12 educational leadership, with the sociological research on gendered experiences within women-dominated professions. Drawing upon in-depth interviews with 20 school counsellors, we examined the role of gender in leadership aspirations and experiences. We found that although women and men did not want to pursue leadership positions, men discussed internal and external pressure to take on leadership, while women received little encouragement. These findings confirm evidence of the glass escalator within the school counselling field and offer insights into the continued existence of traditional gender identity roles.