- Expert Insights
So You Want to Be a Head of School: Guidelines and Guardrails for Independent School Aspiring Heads
You understand the assignment, as today’s kids say. You know the Head’s role well, perhaps as a member of your school’s senior leadership team. You recognize the pitfalls and opportunities, the lows and highs, and the potential wins and certain losses. The value proposition is clear and you believe you can deliver. Above all, you are aware of the care and nurturing you’ll need to demonstrate and deliver 10 times out of 10 at a level 10 for the adults and young people in your community. And, yes. Adults being first on the list is intentional. Today’s independent school communities are brimming with grown-ups: board members, faculty, staff, and parents, and multi-hyphenate-role colleagues whose needs are equal to, and, at times, greater and more complex than the needs of students. Their often charged voices will compete volubly for your attention, drowning out the joyful noises of the playground just outside the Head of School’s office.
As you consider your options for the immediate (July 2025) and longer-term (July 2026) Head of School search season, you may be wondering, “Just because I believe I’m ready, how will I convince a demanding Board, a skeptical faculty, and challenging parents that I’m their ‘one’?” Well, first and foremost, you’re not in the “convincing” business. Be a little Zen. Think about being in the space of “opportunity meets opportunity.” You should be evaluating each prospective Head role in real time, in context, and with perspective, just as the search firm and board are evaluating you within these same parameters. It is okay to kick the tires on an opportunity to assess whether it’s a match, and if not, to move or or withdraw from consideration in the early stages.
Keep in mind, as well, that applying for headships has become a high-wire act. Whether the search is open or closed, people will be watching. But, becoming a Head of School is not exactly like being one. Becoming a Head of School is a bit like discussing the all-school community summer read at the beginning of the school year. A school community may agree (or concede) that they need a new leader, much like they agreed to read the selected book. But, like a worthwhile literary experience, the reviews will be mixed, diverse, and, perhaps, polarizing.
Being a Head of School is one of the loneliest, most isolated jobs around and performed in front of a live audience. Community is everywhere, but rarely present at the moment you’ll make the hardest decisions with urgency — with the most information available to you while weighing the consequences of each option. So here are some questions to contemplate on your way to becomingone:
WHO ARE YOU?
What kind of leader are you? Or, more specifically, what skills have you sharpened in your leadership toolbox? What experiences have shaped you? What qualities have been required and rewarded in your current and previous schools or organizations? As a leader, you’ve been thriving and growing, and you’re ready for the next step. As you enter a search process, know your worth, potential, and areas for growth.
LEADERSHIP IN THREE DIMENSIONS
In my experience, there are three domains of leadership that most often emerge. These domains can be overlapping, and with a growth mindset, you may find that you’ve led in each of these ways. Not surprisingly, these leadership approaches align with what most schools declare they are seeking in their next Head of School.
Tacticians: Leaders who are built to solve highly complex challenges in the near- and long-term.
These may be academic program demands, enrollment and staffing deficits and surpluses, building projects, budget concerns, accreditation processes, and logistical conundrums. No challenge is insurmountable, and no detail is too small to warrant their attention. These leaders are likely to begin a conversation, “The problem is…” and before you know it, their closing comment contains a beautiful, efficiently designed solution laying out the very steps needed to resolve the dilemma. Schools do not survive, let alone thrive, without several tacticians on staff.
Strategists: Leaders who work within the existing framework to execute new, bold, and high-risk/reward ideas.
They never lose sight of the mission unless the strategy happens to involve examining or tweaking the mission. They value fidelity to place, purpose, and people while being willing to question authority, challenge paradigms, and advocate for new thinking. No one way of doing things is sacrosanct, especially if it’s not working. These leaders are likely to enter the conversation happening around them asking, “How are we going to achieve that goal now that we accept this reality?” Schools need at least a strategist or two on staff. Current Heads of School often describe these kinds of leaders on their senior teams as being most highly skilled at thought partnership.
Visionaries: Leaders who thrive in a future-state of possibilities and potential and speak almost exclusively in aspirational terms.
These leaders’ greatest appeal is their capacity to see us in the most favorable light. In their eyes, we are parents who make selfless sacrifices for our children’s education, we are teachers who see and unearth our students’ greatest potential, we are coaches who take our young athletes from good to great, we are staff who uphold the highest standards and create the best outcomes. The status quo is a temporary state; there are new and greater challenges ahead and the future is discernibly bright! These leaders are likely to start a conversation declaring, “What’s possible?” No matter the answer, and even if there is no current answer, they remain focused on this question and in pursuit of its potential answers, often inspiring those around them to join them on the journey.
Oh, and every leader in schools today needs to be this:
Talent Whisperer: Leaders who are most experienced in any of the domains listed here must possess the capacity or develop the skill to identify and utilize the talent within their school community. No person is an island, and the Head’s job – if it is to be successful – cannot be a solo act.
WHAT SHOULD I KNOW AS I ENTER A SEARCH?
Here are some answers to the most commonly asked questions we get from candidates:
What are schools looking for? What are boards looking for? Often, until they are presented with multiple options, neither boards nor schools are as sure as they appear to be about the “who” or the “what.” It is common for a board to land on a chosen candidate who doesn’t “check all the boxes” that were non-negotiable at the start of the search. The pendulum swing factor is also real. Choosing a candidate who appears to be the opposite of the outgoing Head of School may be tempting for a board, especially if that head’s tenure has occurred during a difficult period in the life of that school or if the head’s relationship with the board has been fraught.
What can I do to prepare myself for these unknowns? Use your (perhaps nascent) relationship with the search consultants to help you glean these answers with this framework in mind: Do they need a doer- a tactician? Do they need a fixer – a strategist? Do they need a builder – a visionary? Might the board need one kind of leadership in year one (or years 1-3), and could they evolve in their understanding of what they need more narrowly or broadly in those out-years? And, consider what leadership approach you have practiced most in your current and past contexts. Your expertise in context is invaluable and uniquely yours. Have you been able to flex different muscles by facilitating a formal change process, steering a strategic direction, or leading a visioning experience? Do you even want to have done more than one of these? Knowing what kind of leader you are and what you’re working on in your own personal leadership syllabus is essential. Knowing what each school you’re submitting your materials to needs most at this time in its history? Priceless.
Pro tips:
- An executive coach, behavioral health expert, or constructively honest colleague, partner, or family member may offer helpful guidance around your specific, demonstrated strengths and opportunities for growth. There are many leadership assessment tools, as well.*
- If your Head of School is not your sponsor or mentor, be sure to find a school leader who is willing to be one or the other. There is no substitute for guidance from one who has sat in the Head’s seat.
By Staci Williams Seeley, Managing Director
Storbeck Search | Diversified Search Group
Staci Williams Seeley is a Managing Director at Diversified Search Group | Storbeck Search. Her practice is dedicated exclusively to independent school leadership transitions, and to helping schools grow and thrive with experienced and emerging leaders. Staci is also an associate certified coach (ACC) for leaders across diverse sectors.
* Resources for leadership assessments without endorsement:
Intercultural Development Inventory (IDI)
DiSC Personality Assessment (available on several platforms)