The Puzzle: Blog

This spring, CS&A is shining a spotlight on women in leadership. This piece is one of a series of stories about female leaders in independent schools, the importance of mentorship, and their professional journeys. Find the full series here.

CS&A is proud to have hosted the third-annual Women's Institute on June 14 in Boston, an event designed to support women and their allies in the education community. Our Placement and Search Groups are dedicated to increasing the number of women in leadership roles as part of our commitment to diversity, equity, and inclusion.

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Peter O’Neill, a former head of school and now a Senior Consultant and executive coach with Carney, Sandoe & Associates, likes to tell the story of meeting Jenny Rao for the first time. Peter was head of Garrison Forest School, an all-girls school in Baltimore. Jenny was a candidate for the dean of the middle school. “Two minutes into the conversation,” he says, “I switched from thinking of this as an interview and started thinking of it as a full-on recruiting effort. I knew instantly that I wanted to hire and work with this person. Jenny has all those qualities we try to teach our students — intelligence, perseverance, and grit. She had the skills for the position and then some. And she just embodies drive, energy, and focus.”

What he didn’t know at the time is that hiring Jenny would be the start of a professional mentor-mentee relationship that would last years and see her rise from a teacher and middle school dean to the head of the middle school, to the director of academic affairs, and finally to head of school at Emma Willard School, an all-girls school in Troy, New York.

To bring things full circle, Jenny, as the incoming head in 2017, hired Peter to serve as her executive coach for 18 months, starting six months prior to starting at Emma Willard and lasting through the first school year.

Jenny isn’t the only aspiring school leader that Peter has mentored. Peter was originally hired for a one-year appointment as Garrison Forest’s interim head in 1994. But this one year turned into the third-longest tenured head in the school’s 100+ year history, ending in June 2014. During that time, Peter was a strong national advocate for single-sex education for girls, leading Garrison Forest’s largest campus expansion and establishing one of the nation’s leading experiential-learning programs for girls: the Women in Science and Engineering (WISE) program and an academic partnership with The Johns Hopkins University Whiting School of Engineering, the Bloomberg School of Public Health, and the Krieger School of Arts and Sciences. During this time, he also made sure to identify, support, and nurture aspiring school leaders.

Peter says he realized early in professional life that the support and guidance of a good mentor can make all the difference in one’s experiences. A mentor of his, a professor from St. Michael’s College in Vermont, led him to undergraduate studies and research in the humanities. Based on this work, at age 22, he was hired to chair a newly-created humanities department in the Worcester, Massachusetts, Catholic schools where he initiated a series of curricular changes to create greater cross-disciplinary connections. From Worcester, he moved to Marvelwood School, a boarding school in Connecticut, where he served for a number of years as a teacher, coach, and dorm parent. With mentorship from the Marvelwood head of school, he rose through the ranks to become the admissions director, director of development, and eventually assistant head. By the time Peter was appointed head of Garrison Forest, he not only knew just about every key position in a school, he also understood the role school leaders should play in bringing along the next generation of leaders.

“As the head of an all-girls school, I knew that a core part of my job was to be an advocate for girls’ education and for women leaders,” he says. “It’s rare, as it should be, to have men as heads of all-girls schools these days. It was an honor to work at Garrison Forest, but it also gave me an important perspective on the need for more women in leadership positions. I took it as an essential part of my job to be a mentor and advocate.”

Peter is also part of the baby-boom generation of school leaders that has dominated the independent school ranks for much of the past three decades. “As a group,” he says, “we understood that we would exit the headship stage more or less together — and that independent schools would need a large pool of excellent candidates to take our places. It was something many of us were deeply committed to doing.”

In this mentor role, he says he was keenly aware with every hire that he was appointing a person who could not only do well in the position in question but also potentially replace him in time. Once these aspiring leaders were hired, Peter knew he also needed to consciously support, mentor, and advocate for them. To the degree possible, he made it clear that he was available for mentorship.

Jenny Rao, as it turns out, fit the bill perfectly — an energetic, talented teacher with a clear interest in education leadership and strategic thinking.

Jenny’s path to independent school leadership is anything but typical. She was born and raised in Mexico City to a Mexican mother and British/American father. When it came time to apply to college, she studied a list of American colleges and universities and liked what she read about Bates College in Maine. So, without a college counselor to advise her, she applied sight unseen and was accepted. Bates turned out to be a great choice. But Jenny realized early on that she needed to improve her English speaking and writing skills, so she took a bold step: she joined the debate team where she’d have to debate in English only. In her senior year, she represented Bates at the World Parliamentary Debating Competition in Greece.

After graduating from Bates, Jenny worked from the Boston-based consulting firm Cambridge Associates, but quickly realized that wasn’t her calling. Recalling the joy she took teaching classical ballet in Mexico City, she decided to get involved with education in this country. She taught Spanish at the Fessenden School in Massachusetts for a few years, but her interest in systems thinking drove her to enroll in the school leadership program at the Klingenstein Center at Columbia University’s Teachers College. After finishing the program, she applied for the middle school dean position at Garrison Forest School, where she met Peter O’Neill for the first time.

The choice of Garrison Forest turned out to be ideal for Jenny. For one, Peter had, as she puts it, “a habit of leading in a mentoring way” — supporting and encouraging aspiring leaders to develop their skills. “He made sure I had opportunities to lead, trusted my decision-making, and stood by me when I needed him,” she says. He also supported her decision to take part in the NAIS Fellowship for Aspiring School Heads — a yearlong program designed to guide and train future heads of school and to create leadership support networks.

Following her fellowship, Jenny applied to be the head of Emma Willard — and Peter served as an enthusiastic reference.

Jenny recalls that period as a time of some doubt. “Typical of too many women leaders in independent schools, I thought at first that I was too young to apply for a headship, that I didn’t have enough experience. I also thought it would be difficult to pull off, since I had two young children.”

In time, she worked her way through the doubts, knowing she, in fact, had both the skills and interest to head a school. She then applied to two schools and was a semi-finalist in both. But it was the Emma Willard post that excited her the most. “The school just felt like a great match,” she says. This being her first headship, however, Jenny and the Emma Willard board agreed that it would be beneficial for her to have an executive coach during the transition and first year.

The first name that came to mind? Peter O’Neill.

This formal coaching relationship was different from the informal mentor-mentee relationship back in Garrison Forest. For one, at Garrison Forest, Peter was Jenny’s boss. At Emma Willard, Peter was hired to serve Jenny’s needs. She called the shots. Jenny says she was uncertain about this switching of roles at first, but quickly came to see its value. Starting six months prior to Jenny officially taking over as head of Emma Willard, she and Peter would have bi-weekly phone calls to work out the details of making her transition as smooth as possible. During that time, Jenny was in communication with the current head of Emma Willard, the board, and the senior administrative team — and Peter offered both advice and a sounding board.

“As a new head, and as a woman, I suffered from the imposter syndrome. It was hard to trust myself. But Peter helped me learn to trust myself and work through the steps that would make it possible to hit the ground running.” The work included getting clarity about Jenny’s approach to leadership and what she needed to focus on at the start of her tenure at Emma Willard. Peter, as he puts it, mostly helped her trust her instincts. On occasions, he would offer direct advice.

What is great about having an executive coach, especially one who has also served as a mentor in earlier years, Jenny says, is that she could be completely open with Peter. “I could be vulnerable and messy. I could raise all my worries and doubts. And doing this, we could work our way to greater clarity and focus. When I still had doubts, I could borrow Peter’s confidence in me — until I could earn it for myself.”

Through conversations with Peter she was able to keep the 30,000-foot view of the school front and center and identity her priorities. She could learn both the importance of balance in her work and life and how to find it. As a head of school, she has clarified her view that what matters most is focusing on the school culture and environment — creating a climate where students and adults thrive. This big-picture thinking has even distilled itself down to a simple guiding principle: “To look within and see beyond.”

Now, finishing up her second year as head of Emma Willard, Jenny says she has confidence in herself — and can see that all the decisions she made in the first year, about her approach to leadership and about personnel and policy changes at the school, are paying off.

And she is clear about the value of a mentor and coach in helping her find her way to this point.

Jenny is also a vocal advocate for other women stepping into school leadership. “Headship is the most rewarding work,” she says. “If being a head of school is something you are interested in, trust yourself and your training. Seek out leaders who can support you. Make the leap.”

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