About Rachel Skiffer

I do this work because leadership can be both rewarding and profoundly isolating. Throughout my career, I have found that the most important decisions rarely involve a single right answer. They require leaders to navigate competing truths, incomplete information, and complex human dynamics. I am drawn to helping leaders build the confidence to trust their judgment, strengthen key relationships, and lead with both conviction and humility.

I have coached and mentored teachers, department heads, division directors, senior administrators, and Heads of School. My approach combines deep listening, thoughtful questioning, and practical problem-solving. Rather than offering prescriptions, I help leaders clarify their thinking, examine assumptions, and identify strategies that fit their values, institutions, and circumstances.

I have served as a Head of School, Director of Admissions and Financial Aid, Dean of Policy and Strategic Planning, attorney, and management consultant. I have led enrollment and financial aid strategy, strategic planning, governance initiatives, major capital projects, fundraising efforts, personnel matters, and institutional change. Having worked across both the academic and business functions of schools, I bring a systems-level perspective to leadership challenges and organizational decision-making.

My perspective has been shaped not only by professional leadership roles, but also by the responsibilities of parenting, navigating personal transitions, and managing uncertainty. These experiences have reinforced my belief that effective leadership begins with self-awareness, resilience, and the willingness to learn from both success and setback.

I hold degrees from Harvard University and Harvard Law School and have pursued ongoing professional learning in leadership, governance, organizational development, strategic planning, and equity and inclusion. I will be working toward a professional coaching certificate to further develop my coaching practice and strengthen the support I provide to leaders. My greatest education, however, has come from leading schools and working alongside talented colleagues, trustees, students, and families.