Leaders on Leading: Jenny Rao, Head of School, Emma Willard School

Teacher writing on a chalkboard

Jenny Rao, now in her second year of her first head of school position, brings passion and perspective to her role at Emma Willard School.

Kalix: What is the most important quality for a head of school?

Jenny Rao: What motivates you to do the job is really important in guiding you. If kids are in your heart and bottom line, you will be okay. Keeping a sense of perspective that every decision you make is because of your students guides you to the right place. Different constituencies pull at you, and you are always making choices among the good, but if your true north is asking what students need today, you will end up making the right choice.

Another quality a head of school needs is to be optimistic. By design, the toughest problems are going to come your way. Remember that the very existence of a school is an optimistic pursuit. This ultimately sets your tone to lead with a sense of hope.

Kalix: What is the most underrated quality?

Jenny: Being able to identify what you can let fall through the cracks. The job of a head of school is too enormous to do it all full-tilt and perfectly. It is important to figure out what you can let go to give your time and energy to the things that matter most. For some, this may mean a messy desk or letter that you let someone else answer. There is a different approach to this for each person but be sure to pick smartly because everything you let go sends a signal. Delegating and trusting others are essential, but there are things I determine that we are just not going to do.

Kalix: What was your first job in education and what did it teach you about leadership?

Jenny: My first job was teaching Spanish at an all-boys school in Boston. That’s where I decided that education was for me. I didn’t have a classroom and carried all my many supplies in a basket. My set-up was certainly the least comfortable one [among the faculty], and I didn’t get the best schedules, but I learned that hard work and dedication pay off. I discovered that when I applied my best self to the job that was in front of me, I could make a difference in a student’s life and that a sense of purpose and fulfillment will always come. In the end, leadership is not about what you want to do. It is about what needs to be done. It’s an act of service.

Kalix: What is your best advice for other school leaders?

Jenny: You need to have a well-established support system that you nurture. When I first started at Emma Willard, a board member told me that there were three people that needed to be right on my team: 1) my assistant; 2) my board chair; and 3) my spouse/partner. These are key relationships to create the support a leader needs.

I also try to remember that I am not doing open-heart surgery. The issues that we face in schools live in our hearts and minds so profoundly, but most of the issues are not life or death. To do this job successfully and joyfully, you need to do it authentically. I believe that all leadership comes from a place of integrity. When you lead from the heart, the chips fall where they need to fall. People can feel it when it’s real. It’s the moments of challenge that test this truth. But when you can sleep at night during moments of hard decision-making and have a sense of peace with your decision, you know that you are being true to yourself.

Jenny RaoAbout Jenny Rao

A native of Mexico City with a Mexican mother and a British/American father, Jenny Rao attended college in the U.S., receiving a degree in Economics from Bates College. After college, she joined Boston’s Cambridge Associates, but after three years, sought the classroom. Her first job was teaching Spanish at The Fessenden School, a K-9th day and boarding school in Boston. She received a Master’s in Private School Leadership at the Klingenstein Center, Teachers College, Columbia University. In 2005, she began her tenure at Garrison Forest School near Baltimore as Middle School dean of students where she taught English, Spanish and Geography. In her 12 years at Garrison Forest, she was appointed Middle School head and director of academic affairs. In July 2017, Jenny became the 17th head of Emma Willard School.

Sarah Achenbach is Communications Lead for Kalix Marketing.

Catch up on past interviews with Heads of Schools beginning here:

Leaders on Leading: Sister Patricia McCarron, Headmistress, Notre Dame Preparatory School

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Jonathan Oleisky

Jonathan Oleisky

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