12/02/2021 by Charlie Britton |

13 Essential Questions to Ask Yourself Before Becoming a Head of School

illustration of multiple colorful question marks Stay connected with CS&A
FacebooktwitterlinkedinyoutubeinstagramFacebooktwitterlinkedinyoutubeinstagram

Twenty years ago, I signed my first contract as a head of school. I remember the exhilaration I felt at the promise of leading a school community and the anxiety of wondering whether I was prepared for the task ahead.

I still wonder how I made the decision to become a head of school. It was certainly a blurred mix of emotions: service to others, the desire to shape a school, the hope of helping students and adults grow and prosper, ambition, and yes, naiveté. Most of all, I think about the questions I should have asked myself before taking such an enormous step at the age of 39, even though two decades later, I have few regrets and many wonderful memories.

While the responsibilities of being a head of school have always been enormous, in recent years with fractured school communities, the pandemic, and DEIB work, the position has grown increasingly complex and uncertain. Yet, those moments as a head when you were able to help change a student's life or work with others to build a vibrant and supportive school culture and know that you were making a huge difference in the lives of others, were priceless and incredibly joyful.

Knowing What to Ask Yourself

What are the essential questions to ask yourself as you ponder becoming a head of school? First, be honest with yourself. Are you prepared to work incredibly long hours, deal with problems that have no definitive answers, and, day in, day out, carry the fortunes of a school on your shoulders? Are you able to be optimistic in the face of adversity and joyful in your work despite the myriad of challenges? As we know, being a head of school is not for the faint hearted, the blindly ambitious, or the romantic.

In thinking about taking the leap to becoming a head of school, here are some questions that you should ask yourself and share with a trusted friend, colleague, mentor, or spouse.

  1. Does your desire to be a head of school come from an overwhelmingly profound sense of service?
  2. What are your core values? How do you align them with the school community you hope to lead?
  3. What are your strengths and weaknesses? Where will you need the most support?
  4. Are you able to continually place the needs of others before your own?
  5. Is your spouse or partner and family accepting of your desire to be a head and realize the time and sacrifice it will take to do the job well?
  6. What kinds of traits do you seek in a board of trustees?
  7. Does the school you are interested in have a history of strong leadership and solid financial footing? If it doesn't, are you willing to lead a school that needs extraordinary care and attention?
  8. Are you being patient and discerning, waiting for a great opportunity, or scatter shot in your search, simply wanting to be a head somewhere, someplace? Have you thought about the implications of leading a school that may not be an ideal fit? Do you have an ambition to “be” or an ambition to “do”?
  9. Are you prepared to feel alone when the community looks to you to make important decisions or disapproves when you make unpopular ones?
  10. Do you have the desire, ability, and patience to build an extraordinary team around you and the ability to accept criticism when people tell you things about your leadership that are difficult to hear?
  11. Along with the desire to see students flourish, do you have a desire to help teachers and administrators develop their talents and careers?
  12. Do you have the ability to delegate and trust others?
  13. Do you have a keen sense of perspective and the ability to find joy, humor, and fulfillment even in the most challenging leadership environments?

Remaining Authentic and True

Looking back, I realize how large of a learning curve I had in those first few years and how those early experiences shaped my vision and leadership philosophy. I began to understand that I needed to find my own sense of self and develop my own style of leadership. I had great mentors, but I soon realized I needed to be me. I wore rumpled khakis and rolled up shirt sleeves my whole educational career before becoming a head, so I soon learned to jettison the suits and wingtips for the comfortable and down-to-earth appearance I had my entire professional life. I dropped the unnecessary formalities of a head of school and became true to myself. Once a teacher, always a teacher, and I needed to remember that I wasn't working at a law firm or on Wall Street. I soon found that I was far more at ease, far more relational, and far more confident about leading a school.

There are so many unknowns as an individual ponders whether to become a school head. Taking the steps to become a head is a leap of faith. But if you truly reflect on why you want to be a head and the mission of the school you hope to lead, you will be in the best place possible to decide.

Most of all, be honest with yourself. Becoming a head of school is a pivotal decision that will change your life trajectory as well as your family's. The position can be wonderfully fulfilling but takes a special mindset of service to others, personal insight, persistence, optimism, courage, and joy to do the job truly well.


Charlie joined CS&A from McDonogh School (MD) where he served as Head of School from 2007-2018. Before McDonogh, he served for five years as head of school at Casady School (OK). He began his career as a teacher and coach at Trinity-Pawling School (NY) and has served as English department chair at the St. Mark's School of Texas and head of the senior school at Shady Side Academy (PA).

Carney Sandoe's Coaching and Mentoring team offers cutting-edge support that helps incoming and current heads, key administrators, and trustees develop greater self-awareness and knowledge, improve communication skills, heighten emotional intelligence, and leverage strengths for their personal and professional benefit, as well as the success of their schools.

Share this:

Back to Blog

Leave a Comment

1 Comment

Kirran 12/30/2021 at 2:10pm

Beautiful. Thank you for writing and sharing.