For many educators, the desire to move from the classroom into an administrative role is a natural and admirable next step. After years of teaching and mentoring students, collaborating with colleagues, and contributing to school life, it makes sense to want a broader leadership role—whether as a division head, assistant head, dean of students, or in areas such as admissions or development. Yet while the ambition is clear, the pathway to administration in independent schools is not always straightforward.

At Carney Sandoe, we regularly work with talented teachers who come to us ready to make this transition. They bring deep instructional expertise, institutional knowledge, and a strong commitment to school communities. It can be surprising, then, to discover that moving into administration, especially at a new school, can be more challenging than expected. Understanding why this is the case, and why keeping an open mind is so important during a job search, can make all the difference.

Why the Transition Can Be Tricky

Classroom teaching experience is invaluable, but administrative roles require a different, broader set of skills. Beyond instructional leadership, administrators are often responsible for managing adults, navigating complex interpersonal dynamics, communicating with parents and trustees, handling budgets, supporting strategic initiatives, and responding to crises. These competencies are not always developed fully within the confines of one’s own classroom.

When candidates apply for administrative roles, particularly at a new school, hiring committees are often looking for evidence that a teacher has already begun to operate beyond the classroom. Without that demonstrated experience, even highly effective educators may find it difficult to convince schools they are ready to step into leadership.

The Importance of Leadership Experience at Your Current School

One of the most effective ways to prepare for administration is to pursue leadership opportunities where you are now. Serving on committees, chairing a department, leading curriculum initiatives, mentoring new teachers, coordinating grade-level teams, advising student groups, or partnering with admissions or development offices all help build a leadership portfolio. These experiences signal readiness and show that you understand how schools function as complex organizations.

Importantly, this work also allows current supervisors to see you in a leadership capacity. Their support and advocacy can be critical as you start to work toward a larger goal in administration. In many cases, a strong internal track record opens doors more effectively than classroom excellence alone.

Why an Open Mind Matters in the Job Search

Many candidates begin their search with a very specific goal: a particular title, division level, or type of school. While clarity is helpful, rigidity can be limiting. In independent schools, leadership pathways are often nonlinear. A role that appears to be a lateral move, or even a step sideways, may offer significantly more leadership exposure, mentorship, or growth potential than a more obvious promotion.

At Carney Sandoe, we often see candidates discover that the best opportunity is one they had not originally considered. Keeping an open mind allows you to recognize these possibilities and evaluate them not just by title, but by what they offer in terms of growth, responsibility, and long-term trajectory.

The Value of Expert Guidance

Our team of placement associates brings decades of experience placing candidates in independent schools across the country. We understand how schools think about leadership readiness and how careers typically evolve within this sector. When you work with us, we encourage you to thoroughly review referrals, ask thoughtful questions, and consider opportunities through a wider lens.

Sometimes the right next step involves joining a new team that is willing to invest in you, mentor you, and give you room to grow. Other times it may mean making a strategic lateral move that sets you up for advancement sooner than you expect. Trusting the process and being open to professional guidance can help you see options that align with both your skills and your aspirations.

Looking Ahead

Transitioning from teaching to administration is an exciting goal, and one that many educators successfully achieve. The key is preparation, flexibility, and openness. By building leadership experience at your current school, honing the skills required beyond the classroom, and approaching your job search with an open mind, you position yourself for long-term success in independent school leadership.

At Carney Sandoe, we are proud to partner with educators at every stage of this journey and to help them find opportunities that may ultimately be even better than what they first imagined.