The Puzzle: Blog

The journey to becoming a Head of School is both exhilarating and daunting, and at times, even a little ridiculous. I remember arriving at my hotel after a finalist interview day, electrified by the experience, but so completely drained that I fell immediately asleep, thankful I had pre-set my alarm for the next morning. The process had been intense—back-to-back meetings, presentations to large groups, conversations over meals, and even impromptu Q&A sessions in hallways.

Just when I thought I had nailed it, a parent in the final forum threw me a curveball question: What would you do if half the faculty threatened to resign over a leadership decision? I took a deep breath, gathered my thoughts, and answered honestly. That moment stuck with me—not just because of the challenge, but because it encapsulated what this journey is about: adaptability, authenticity, and the ability to lead through uncertainty. Whether you are just beginning to explore leadership opportunities or actively engaged in the search process, preparation is key. Below are some insights to guide your path from my own experience.

Lay the Groundwork Early

The search for a Head of School often begins 12 to 24 months or even longer before the position starts, meaning your preparation should begin well in advance. Clarify your vision for leadership, assess your experiences, and build the skills that will strengthen your candidacy. Consider what type of school best aligns with your leadership style, values, and personal needs, including location and community fit.

I’ll never forget the moment I realized just how intense the process could be. I had made it to the semifinalist stage for a school I was really excited about. The search firm asked me to record a short video answering a series of questions. Easy enough, right? Well, after recording my first response, I thought, “That wasn’t quite right—let me try again.” Then again. And again. Thirty or forty takes later, I finally had something I was happy with. I hit submit, relieved—until I had the terrifying thought: What if they can see how many times I re-recorded my answer? Spoiler: I didn’t get that job, but I learned an important lesson—perfection isn’t the goal; authenticity is.

Craft Your Leadership Narrative

Schools seek transformational leaders, not just administrators. Your application materials—resume, cover letter, writing samples, and leadership statement—should reflect your unique leadership philosophy and experiences. Focus on showcasing impact rather than listing responsibilities. If you need more experience in areas like finance or governance, seek out opportunities now.

A mentor once told me, “Schools overestimate what they can achieve in a year but underestimate what they can achieve in three to five years.” That advice stuck with me. Schools want leaders who are invested for the long haul. For me, as a Head of School who happens to be gay, a school’s approach to diversity, equity, and inclusion (DEI) was a crucial factor. I needed to know that the school valued belonging—not just in mission statements but in action. Would I feel truly accepted by the Board, faculty, and families? Similarly, location mattered. Some communities are more welcoming than others, and while I wanted to be a leader who could push a school forward, I also needed to be in a place where I could thrive personally.

Engage with Search Firms

Most independent school leadership searches are managed by firms such as Carney Sandoe & Associates. Building relationships with recruiters increases your visibility for future opportunities. Reach out, attend leadership events, and stay engaged to ensure you’re on their radar when the right opportunity arises.

I learned about one opportunity at a cocktail party at an NAIS event sponsored by a search firm. I hadn’t even considered applying, but a recruiter pulled me aside and said, “This school is looking for someone exactly like you.” Sometimes, the best leads don’t come from job postings but from networking moments you least expect.

Prepare for the Interview Process

From initial recruiter conversations to semifinalist and finalist visits, each stage of the search process requires thoughtful preparation. Research each school thoroughly, tailor your materials, and refine your ability to articulate your leadership vision. During campus visits, remember that the school is assessing you just as much as you are evaluating them—ensure it’s a mutual fit.

Finalist visits can be grueling. My schedule was packed from dawn to dusk with meetings, interviews, and Q&A sessions with faculty, parents, and students. Meals weren’t even a break—answering strategic vision questions while trying not to choke on a bite of salad was a skill I never expected to develop!

Be Ready for Rejection and the Offer

Rejection is an inevitable part of the Head of School search. Very few candidates land their first headship on their first try—you will likely apply for multiple positions before securing the right one. I remember the sting of my first rejection. I had fallen in love with a school and made it to the finalist stage, had what I thought was a great visit, and then got the call: We’ve decided to go in a different direction. I replayed every conversation in my mind, wondering what I could have done differently. But with time, I realized that rejection wasn’t personal—it was about fit. Each search is a learning experience, refining your understanding of what you need in a school and what you bring as a leader.

If you reach the offer stage, take time to review contract terms carefully. Consulting with legal or industry experts can help you navigate key considerations such as compensation, benefits, and contract length. Heads of School are often dismissed unexpectedly, so negotiating protections in your contract is essential.

When I received my first offer, I was so thrilled that I almost said yes on the spot. But a trusted mentor told me, “Take a breath.” Asking for what you need isn’t just about salary; it’s about ensuring long-term sustainability in the role.

Resilience is Key

The Head of School search is a journey that requires resilience, humility, and a clear sense of purpose. Rejection is part of the process, but each experience refines your understanding of what you seek in a school—and what you bring as a leader. Stay patient, be strategic, and when the right opportunity arises, step into it with confidence.

For a deeper dive into the Head of School search process, read the full article here: Lessons from the Head of School Search Process: One Candidate’s Guide

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Dr. Roberto d’Erizans is currently the Head of School at The Millennium School in San Francisco and has been appointed as the next Head of School at The International School of Denver (starting July 2025).  Carney, Sandoe & Associates consultants Karen Neitzel and Deb Welch coordinated the ISDenver search.

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