Who Needs Coaching?

Written by Katherine Moncure Stuart, President of The Education Group

Does Your Head of School Need Coaching? Or Does Your Board Chair Need Coaching? 

Running a school is not for the faint of heart. A Head of School is expected to be a strategist, community builder, a visionary, and academic and a crisis manager—often all before lunch or recess. With so much on their plate, it is natural to wonder not only how they do it, but: Does your Head of School need executive coaching? 

The Reality of Leading a School

Heads of School juggle a million things at once—fundraising, faculty support, strategic planning, and the occasional parent complaint about carline, a teacher, or the dresscode, you name it, different day, different question. It is a big job, and it comes with big challenges. That is why executive coaching is often suggested to help leaders refine their skills, gain fresh perspectives, and find some much-needed balance. But before you bring in a coach, ask yourself: Is coaching what’s really needed, or is the school just asking for more visible, engaged leadership?

When Coaching Can Help Your Head of School

A good executive coach can be a game-changer if the Head of School needs help in areas like:

• Strategic Leadership: Strengthening vision, decision-making, and goal-setting.

• Managing Conflict: Handling tough conversations with parents, faculty, or the board.

• Delegation & Time Management: Avoiding burnout while empowering others.

• Emotional Intelligence: Improving communication and relationships.

• Navigating Change: Leading through transitions, whether it’s curriculum shifts or leadership turnover.

If your Head of School is feeling overwhelmed in these areas, coaching can be a great investment to help them lead with confidence and clarity.

When It’s Not About Coaching—It’s About Presence

Sometimes, the issue isn’t leadership skills—it’s presence. If faculty feel unheard, parents feel disconnected, or the school community feels a lack of direction, coaching won’t fix that. Instead, consider:

• Is the Head of School visible and engaged in daily school life?

• Are faculty and staff getting the support they need?

• Are board relationships strong and productive?

• Are families feeling connected to the school’s leadership?

If the answer to these questions is “no,” then the real issue might not be coaching—it might be recalibrating expectations and priorities as well as goal-setting. .

What About the Board Chair? Do They Need Coaching?

Here’s a curveball, and a much discussed topic at TEG: Sometimes, it is not the Head of School who needs coaching—it’s the Board Chair. The Board Chair plays a crucial role in setting the tone for governance, strategic direction, and Head of School support. If things feel off at the leadership level, ask:

• Does the Board Chair understand where governance ends and management begins?

• Are they supporting the Head of School without micromanaging?

• Are board meetings productive, generative and strategic instead of reactive?

• Is there a strong, trusting and transparent partnership between the Board and the Head?

If these questions raise red flags, coaching for the Board Chair might actually be the better move. A well-prepared Board Chair can strengthen governance, improve board dynamics, and help create an environment where the Head of School—and the school as a whole—can thrive.

Finding the Right Solution

Executive coaching is a fantastic tool—but only if it is addressing the right problem. If your Head of School needs support, coaching could be the answer. But if the real issue is engagement and presence, a different approach might be needed. If governance challenges are creating friction, maybe it is time for the Board Chair to get some coaching instead.

The bottom line? Find clarity on the real challenges before jumping to solutions. When leadership is aligned and fully engaged, your school will be stronger, healthier, and more successful. If you’re not sure where to start, a conversation with an experienced executive coach can help you unpack what’s really going on and determine the best path forward.