Your Head of School Search: Five Considerations for a Candidate’s Deep Preparation

PictureBy Autumn Graves, Head of St. Annes-Belfield School (VA)
I’ve been named a head of school three times and a finalist nine times. Granted, if I were a major league baseball player, I could be considered for the Hall of Fame with my “batting” average, but in no way am I an expert in securing a headship. Nonetheless, I have spoken to many search consultants, read hundreds of pages of position descriptions, been interviewed by several doctoral students writing about the path to headship, and been asked all sorts of professional and personal questions by search committees.
 
There are many pieces of advice that candidates are given as they approach headship for the first time: prepare your resume with the job in mind, have a succinct and authentic personal statement, consider what sort of school and what sort of philosophy will match your purpose.  We hear these a lot.
 
There are other considerations that could provide an even deeper level of preparation.  Here are five subjective observations that I’ve figured out about this process along the way. I hope they will help someone considering being a head of school.
 
  1. Involving Your Spouse/Partner in Deciding to Apply: Engaging in a search process as a single person with no children at 34 years old was very different from engaging in the process at 47, married, with two school-age children. I learned that being the head of school is a family decision and not just a professional one. You need to make sure your partner understands that you are both going to be cast into the limelight. Both of you are being interviewed, and your relationship is also being evaluated as a fit for the school community. In the process, ask questions about the community’s expectations of your partner regarding event attendance, event logistics management, travel, and fundraising. Is your partner the official host of school events in your home? Are they expected to travel and attend fundraising meetings with you? If your partner has other significant personal or professional obligations, be sure to talk about how those will be honored in your new community.
  2. Recognizing the Importance of the Board Chair/Head of School Relationship: Falling in love with your prospective school’s mission, students, and faculty is just as important as your relationship with the board of trustees. Ask questions about trustee leadership succession plans, so you can get to know the likely board chair after your initial one. Ask to spend time with the current chair and incoming chair. The board chair and head relationship is critical to your professional success and experiencing happiness along the way. Some of the most impactful adult relationships I have had have been with a board chair.
  3. Discerning Fit for You: Realize that you can leave the search process at any time, even after the finalist visit. The interview is like the dating period before a marriage proposal. A successful dating relationship is not just one that ends in a proposal (or an employment offer). The process is equally successful if you realize that something about the school’s culture, board culture, finances, or operational practices is misaligned for you. Yes, even after you finish your finalist’s visit, it’s not too late to gracefully exit the search. Love yourself enough not to continue in a process that doesn’t feel right. The mantle of leadership is too great and, at times, too heavy for you to be carrying it for a school that just doesn’t feel right for you. You want to be in a place where you feel that you belong and your gifts and talents are valued and needed.
  4. Being Prepared for The Talk:  You need a contract or labor lawyer who understands schools. Independent school head contracts are a bit unique compared to other CEO contracts and the most unique of any other employee in a school. Before accepting an offer, you should secure an attorney. Talk about some of your own personal and financial needs and expectations. If the school is using a search consultant, ask what the school considers parts of the package. You should be prepared to share some of the high-level, broad strokes that you are expecting - tuition remission, housing, health care, club membership, housekeeping, car allowance, cell phone allowance, deferred compensation, yard maintenance, moving assistance, housing support for aging parents or other dependents. Make sure your legal counsel or accountant helps you understand how the IRS will view these forms of compensation through a lens-specific to you. You don’t want an unexpected tax bill on April 15. Competent legal counsel can cost upwards of $10,000-20,000. Consider it an investment in your peace of mind. And see if you can negotiate the school paying for your legal fees upon the contract’s execution.
  5. Talking About the End, at the Beginning: You will want a potential termination and severance agreement to be considered in the contract negotiation. It’s better to figure out what the ending could be when everyone is excited about the beginning.
 
Being a head of school is also one of the most dynamic, creative, nuanced, challenging, emotional, and fun servant leadership roles you will find. Leading independent schools is also really hard. We are working to balance two bottom lines: a financial bottom line and a mission bottom line. The intersection of these dual bottom lines can cause friction, but that friction creates incredible pearls that change their world.
 
I love being a part of supporting children in exploring their passions, their identities, and their sense of self as they launch into adulthood. It is my honor to work each day (and night) to support an incredible team of educators and support staff in delivering our mission and value proposition to our students. I am passionate about the role of independent schools in bringing people together around a shared set of traditions and expectations about the purpose of education and a life well-lived. And while I can imagine a life doing something else, I envision leading independent schools for many years to come. It’s a role that I hope more talented educators will consider, especially women and people of color. And I hope that sharing my personal experience and observations will be helpful to some of you in your journeys in independent school leadership. It truly is one of the best jobs on the planet.