Ode to CIOs: One Answer to Head of School Shortages

This article was originally published in April 2023 in Intrepid Ed News.

As an experienced independent school technology leader and strategist and the current board chair of the Association of Technology Leaders in Independent Schools (ATLIS), I have observed a troubling trend in independent schools. A revolving door of school heads is eroding the stability and culture that define these institutions.

Independent schools are a community that seeks to catalyze change in the ways we learn. We’re a “sandbox” for innovative practices in pedagogy, curriculum development, and 21st-century assessment. And it’s crucial that we elevate leadership who deeply understand these issues in our succession planning and for the future of our institutions.

In my frequent talks on the “indy school” speaking circuit, I often reference the pandemic and everything that has happened since as “VUCA,” which stands for volatile, uncertain, complex, and ambiguous. The challenges we faced during COVID-19 shook the “this is the way we’ve always done it” mentality right out of our schools at a pace that resembled a fierce agent for change and for questioning the status quo.

Despite the pandemic’s extreme difficulties for schools responding to unprecedented needs, it was exhilarating, enlightening, and one of the single most productive and collaborative times in my entire independent school career. COVID-19 flattened the organizational hierarchy in a way that allowed diverse voices in our school's internal community to share their talents and insights quickly and transparently. Finally, we became an agile team. This was happening all over the world. We saw independent schools globally pivot, shift, adapt, collaborate, and solve problems more quickly than in the 15 years prior and with great success.

Independent schools are seeing a resurgence of waitlists because they were able to “handle” the challenges of the pandemic so well in support of their students. Despite this proof that independent schools have the talent and strength to sustain uncertainty, heads of schools are unfortunately departing in large numbers.

I get it. It was exhausting. I too experienced an unquestionable shift in the way I felt about my chief information officer role after the pandemic. Yet instead of suffering the burnout that plagued so many of my colleagues, I was inspired by my technology team’s critical role in moving an entire community online. In many ways, knowing that I could endure these professional challenges actually gave me the courage to pursue a lifelong ambition to start my own technology coaching practice.

It’s time for schools to recognize that there are high-potential leaders in your institutions now who have the necessary skills, adaptability, and whole-school mindset to successfully step into the head of school role.

And more often than not, these individuals are in your technology departments.

Instead of searching externally for candidates, I challenge the leadership teams of independent schools and recruiters to rebuff the persistent status quo to the headship and take a closer look at the heroes in your IT department who led the pivot of entire learning communities during a pandemic and survived. Many are well-positioned, more than ever, to lead a school.

K12 technology directors and CIOs are uniquely positioned to take on the role of head of school because of their expertise in the operational and strategic challenges of running a school. In their roles, they spend time in every department in the school at one time or another (usually concurrent with systems changes). They know people in every department and know how they operate. An academic head would not be able to say that.

Tech leaders have more experience with Trustee committees than faculty members or traditional academics. They understand finance and budgets better than most staff. They develop strategic plans instead of just participating on strategic planning committees. They frequently take part in professional development and networking outside the school and as a result often have larger networks, while being well-versed in trends and issues to come. They also know all the academic and operational departments, their goals, and how they plan to meet them with relevant tech tools. And they routinely balance competing priorities, work well with uncertainty, and oversee teams of professionals. These are all skills that are essential for leading a school.

All of these reasons and more are why schools trying to stabilize the current trend associated with heads departing should consider looking within the ranks of technology departments.

While writing this article, I learned that the source of the word “headmaster” was born out of teachers being called masters. IT professionals I’d say are the ultimate “masters” at learning and teaching on demand. They learn to relate to all roles in the school’s ecosystem and teach every constituent group how to engage effectively with the myriad systems and tools available.

Today’s independent schools would gain much to employ the skillsets present in an IT professional. More and more, to prevail in this VUCA, ChatGPT, AI, AR, VR—and all the other acronyms—world, practical, in-the-trenches experience outweighs theory every time. And technology professionals know how to translate and leverage resources on demand.

What our schools need are astute organizational and strategic leaders to lead with vision, understanding, clarity, and agility. And if you really want to sustain and create the schools of the future, seek out those technology leaders sitting in your schools who are culturally competent and represent the diversity that independent schools require to remain relevant. If they’ve been able to claw themselves into the ranks of managing your school’s most precious technology assets, including cybersecurity and the backbone that supports the whole operation, while simultaneously overcoming the invisible and systemic challenges they face as an underrepresented professional within the independent school community, then you’ve got a real go-getter with rock solid perseverance sitting behind the curtain.

They might be an introvert (if the stereotype of the technology professional holds), but I’ve met some incredible leaders who lean toward introversion and have created incredibly successful results for education in my technology strategy work across the country. With a bit of executive leadership and development coaching, a K12 technology professional can be ready to lead a school better than the typical head of school scholar track candidate.

While some might say I’m biased toward tech professionals, the real truth is I am biased toward agile-oriented, culturally competent leaders with a growth mindset who care deeply about how they support children and are willing to step into challenges with compassion, curiosity, and collaboration to solve the systemic challenges present and persistent in independent schools. Those are the people you want leading your school.

P.S. ChatGPT didn’t write this article!