If you’re feeling like the role of Head of School has become more complex, more demanding, and more layered than ever before, you’re not alone. This work is rewarding, fulfilling, even invigorating, and yet, over my four years as Head of School, I’ve heard many others discuss how challenging and complicated Headship has become–especially post-COVID. Inspired by Al Adams’ article 31 Windows, I crafted a simple survey this summer to explore how the role of Headship has evolved. I was also recently introduced to a 2023 UK report by RS Academics called The New Art of Headship 2023. Both support what many already believe: being a Head today feels like a juggling act, a marathon, and, at times, an emotional rollercoaster, more than ever before.
The New Art of Headship 2023 from RS Academics explored the changing nature of Headship in UK independent schools. It paints a picture of how the role has shifted in the last decade. Stakeholder expectations are higher—parents want more personalized attention, and staff expect well-being and balance. Social media amplifies everything, and schools are expected to be front-line guardians of mental health. We’re managing social changes while also spending more time on external-facing work like fundraising, alumni relations, and external partnerships.
Sound familiar?
The study highlighted the critical need for Heads to build emotional resilience and care for our well-being. Without that, no amount of skill or strategy will see us through the increasing demands. In particular, the study suggests that we must focus more on “leading self” and “leading others,” noting skills like requesting and using advice, accepting support, and managing conflicts. Lastly, the study suggested the need for the role of boards to evolve, that schools might benefit from “a little less emphasis on holding Heads to account and a little more emphasis on providing reassurance and support.”
Many of the findings in my study matched the UK report. My survey was emailed to various Head listservs over the summer and completed by over 80 Heads across the U.S. The survey focused on the evolution of tasks and roles of Headship in the form of metaphors. Heads who completed the survey described how the traditional roles of “Head Learner” or “Head Teacher” are no longer relevant to their daily work. Instead, Heads spend the majority of their time assuming roles like CEO, Ship’s Captain, Lighthouse, Politician, and even Magician. One respondent offered a particularly poignant addition to the list, that of “Time Traveler.” We each are expected to honor our schools’ histories, steward their present, and plan for their futures—all at once.
Complimentary to the conversations about how complex our work has become is the increasing concern that our school communities don’t fully understand the depth and complexity of the role. Respondents confirmed a similar lack of understanding in their schools.
- 87.5% of Heads said parents have no idea what the role really entails.
- Only 19% felt their Senior Leadership Teams fully grasped the role.
- Just 8.9% thought their Boards clearly understood the complexity.
The disconnect between the challenging nature of the work and the lack of understanding some Heads feel from their school communities can be overwhelming. It can make the work feel particularly isolating, especially when paired with the emotional strain we’ve all felt post-pandemic. Many respondents expressed that parents are more confrontational, enrollment pressures loom large, and the emotional needs of students and staff are constant.
While the job has grown in complexity, Heads continue to express that it is still deeply meaningful work. For many, that complexity is part of what makes it rewarding. One Head shared that they love how every day is different, how they engage with so many constituencies each day, from 4-year-olds to alums, and how the work stays true to a larger mission. The survey results suggest that many of us feel the same way.
So, what do we need to thrive in this role?
- Advocate for realistic expectations. It’s okay to educate your Board or your community about what your role really entails. Many Heads cited transparency as instrumental to their success.
- Lean on your leadership team. Delegation isn’t just wise; it’s necessary. Building a senior team with complementary skills is one critical part of navigating this work.
- Find your people. Whether it’s an affinity group, a mentor/coach, or a peer consortium like The Heads Network, having others who truly understand what this job is like can make all the difference.
- Take care of yourself. Emotional resilience and self-care are our survival tools. Build time for reflection and renewal into your routine.
Perhaps most important, find the right place to lead. One Head said it beautifully: “Pick a place where you can bring your full self with authenticity and energy and a place where you are surrounded by a board and leadership team who truly have your back. This work cannot be done well in an adversarial environment. It’s all worth it when you’re in the right place.” There are many schools out there, and you are amazing - you deserve to be somewhere you can flourish.
Headship is more complex than it’s ever been, AND it’s still a pretty incredible job. Both are true. We get to shape the lives of children, lead outstanding educators and staff, and build exceptional educational communities. The role of Head is unlikely to become less demanding and complex in the near future. Therefore, we need to implement strategies and supports to promote our success and well-being, which, in turn, ensures the success and well-being of the schools we lead.
Nola-rae Cronan has more than two decades of experience in independent schools, including her current role as head of school at Carlthorp School, the oldest independent school in Santa Monica (CA). Nola-rae has served in a variety of capacities in education, including as a teacher, dorm parent, coach, school counselor, and administrator. Her vast experience touches all aspects of school life, including curriculum development, technology integration, professional development for faculty and staff, Diversity, Equity, and Inclusion, student leadership, and student programming.
The independent school world is part of her family life as well; her husband, Ara Brown, spent twenty years as an independent school educator and is now an educational search consultant, and her children, Kalah and Noah, both attended day and boarding schools. Kalah is in her second year teaching at an independent school in VA.