06/12/2019 by Carney Sandoe Staff |

Penny Evins: My Journey to Headship

by Penny Evins, incoming head of school at Collegiate School (VA)

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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. 


I am the youngest of three sisters, and we are all educators. We hold different titles; however, in many ways, my sisters mentored me, and the fact that we chose education as our way of life reflects the phrase that our parents and grandparents taught us: “The gift of an education.” They spoke with and showed respect and reverence for those who listened to this calling, and as such, I deem education important and “big” work. As I head from leading St. Paul's School for Girls (MD) to Collegiate School (VA) as their incoming head of school, I am reminded that my “big” work is to care for the entire community as a lifelong educator.

My first title was upper school guidance counselor. Serving as the first counselor in this school’s division, I was creating and forging a path. I depended upon teamwork, clarity of convictions, and building relationships. Communication and putting systems in place were simultaneous priorities. I have also held administrative positions in lower, middle, and upper schools. I have served single gender and co-ed schools in a range of geographic locations. My thinking and philosophy include a bit of a pioneer mentality, in that I believe at some point, all leaders must take healthy risks—professionally and personally—and accept new positions. I chose to take jobs where I knew no one, remained flexible, and worked hard.

In order to develop new skill sets and practice leadership, one may have to give up some hopes and dreams. I had long-distance relationships and did not necessarily have the luxury of deciding when, where, what, and how much I was paid. I think this is really important and yes, tough to do. There is a time for advocacy and a place for realizing that compromise is a sign of maturity. We are modeling, every day, decisions for the children in our care. Our communities need to see us show the same open mindset, humility, confidence, grit, and purpose that we strive to cultivate in our schools.

Leading means bringing out the best in others, growing the good, shining the light, and partnering with a range of hearts and minds. As a head of school, that means when things go well, I clap for and give kudos to others; however, when something does not go well, it is my responsibility to own it. As I team with others, we all learn from situations—good or bad—and help each other.

Without a doubt, many in my family are mentors. My mother and grandmothers taught me how to be polite and purposeful. They showed me how to wear your flaws, ask questions, love others, know yourself, and trust the journey. I always felt I had a safe harbor. Even when a student in boarding school, I called home for comfort and to talk, listen, receive advice, and simply share stories. To this day, my family buoys me.

Being a head of school is a way of life. In many ways, my husband and children have participated in this role, and we all acknowledge its gifts and messy blessings. Yes, I have had amazing teachers and heads of school foster my growth and inspire me, and trustees and colleagues teach me and six o'clock me; however, it is my husband who allows me to flourish in this role and in my service to others. We met performing cafeteria duty as administrators at his alma mater, and he is my best mentor, partner, and friend.

On that note, as a spouse of a female head, I think he faces unique challenges. When meeting someone, he is often asked what he does. Anyone who understands the pace of headship knows that someone who is willing to support a first family, two adolescent children, pets, and a wife who regularly misplaces her phone (a critical tool for me, as I am not one to sit at my desk all day), and who is always “on the job,” knows that he is truly the captain of Team Evins. He still coaches and helps to fill any gaps at school; but he is, in his words, the lineman and I am the quarterback.

So, the truth is, I can't simply change my tie and instantly have a new outfit for photos and events. Simply put, my advice is to own and wear your gender, whatever that means to you. I tell my board chair when I am going for a haircut—although I sit in the chair and work during this time, and actually get some of my best work done! Yet, I know that seeing me out and about in the middle of the day is something that creates chatter for some. As such, I tell the story. There can be no palace intrigue if you know and claim yourself as a tireless leader who has complicated hair!

In all seriousness, being a woman is simply who I am. Yes, I am a wife, mother, sister, dog owner, and other traits. If more women talk about how being a woman does or does not affect her leadership style, there will be less mystery and more celebration. With more celebration comes a larger pipeline. We must share stories, communicate, and create systems for others.

No matter my role, whether counselor, teacher, coach, division head, school head, or person taking a hike, I believe it is my duty of care to help others become their best selves. It is the highlight of my role to fertilize the occupational soil for others. Opening up opportunities for others to learn about all facets of school leadership grows them, and frankly, creates stronger teaming. Silos don't work for me.

I try to serve on boards that align with my core values, inspire me, and welcome generative thinking. Having the answer is not leadership. In my mind, leadership is more about having a network of people who can partner with you as you collectively determine what is needed emotionally, intellectually, and strategically to move ahead of, next to, or behind others.

Leading is oftentimes lonely, so it is important to know yourself and know what you need to feel restored, readied, and whole in your professional and personal life. I claim these habits and do not apologize for them; however, rarely do they conflict with anyone else's needs. I am getting better at modeling this for others in a more public way. However, I know that sleep, movement, and my faithful dog are, for me, key to my readiness. Know yourself and be yourself.

Different communities, leaders, and cultures have shaped me, no doubt. However, the best professional experience was serving a school when I was “brought to the table” for talent rather than title. I try to practice that, and am honored, humbled, and excited to see what is next for the school I have served and the school to which I am heading.

Close loops with others and model this for your colleagues. Communication is key!

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