In this episode of Lead Her Higher, host Emily MacLean sits down with Sarah Fleming, Head of Preparatory at Upper Canada College, to explore what it means to lead with both strength and humanity in today’s educational landscape.

Sarah reflects on her leadership journey across international schools and Canadian independent education, sharing how her understanding of leadership has evolved, from positional authority to influence, and ultimately to leading complex systems with authenticity and care. She speaks candidly about the personal experiences that have shaped her leadership, including her journey through illness and motherhood, and how these moments deepened her empathy, resilience, and sense of purpose.

Together, Emily and Sarah explore the realities of leading in high-expectation environments, the importance of emotional regulation, and the transformative power of coaching in building capacity in others. They also discuss what it means to lead as a woman in visible leadership roles, particularly in boys’ schools, and the responsibility leaders have in shaping how young people understand leadership, identity, and belonging.

This episode is a powerful reminder that leadership is not about position, but about presence, and the impact we have on others through how we show up every day.

Key Takeaways

• Leadership evolves from position to influence to system-level impact.
• Emotional regulation is a critical, and often overlooked, leadership skill.
• Coaching is one of the most powerful ways to build capacity and self-direction in others.
• Personal experiences shape professional leadership more than we often acknowledge.
• Visibility matters, especially for women in leadership and the models we provide for young people.
• High-performing cultures require both high expectations and deep care.
• Great leaders create the conditions for others to grow, not just succeed themselves.

Listen to Sarah’s story and be inspired to Lead Her Higher.

Key Words: Leadership, Women in Education, Coaching, Emotional Intelligence, School Culture, Wellbeing, Independent Schools, International Education