Development and The Head of School

I don’t often get a school tour from the Head of School. Usually, my work is with the Development or Admissions Director, and my initial tour of the school is with them or a member of the team. I learn a lot about what the school and its leaders value and the professionalism that they bring to the role. I’m also looking to see how they engage me in the narrative.

I had the great pleasure of touring a boys’ school with the Head of School. He wanted to show me the Upper School, which had been completely renovated. We admired the architecture and spaces to house specific programs or classes; we stopped to look in on classes in progress and walked across campus to attend Senior Speeches. The Head used all of it as a backdrop for his illustrations of the many ways the school serves boys. He drew me in through storytelling, the way he engaged the students and teachers we encountered, and how he brought me into each conversation. He has been a Head for a long time and was masterful as a guide for this development-focused tour.

Every school that is actively and successfully advancing their school through transformational gifts has a Head of School who embraces their role in stewarding the relationships with a few donors, the donors who can and will invest in the school because they see the vision and feel alignment with the mission and the Head of School.

These key relationships are delicately balanced and can cause consternation among the development team or the development director. At some schools, the Head actively keeps the key relationships away from the development team, and at other schools, the Head has no relationship with major donors and leaves all development efforts to the staff. The most effective development programs have a combination of development leadership, board members, and the Head of School working in tandem to steward the relationships with the school’s most cherished friends and investors.

In considering the role of the Head of School in advancing your school, here are three things to keep in mind:

The Head of School is part of donor relationships. The development director is not likely to be successful at teeing up perfect scenarios for the Head to walk into a lunch meeting, for example, having never met the donor before and asking for a major gift. The Head can be more effective if she is part of several conversations that would lead to that meeting.

Use events strategically. If the Head attends an event, whether for friendraising or fundraising, learn who will be in attendance and plan for conversations with a few specific people. Create a strategy for follow-up for every event, particularly ones where the Head was present.

The Head is a member of the development team. Every outward-facing member should have a portfolio of donors for whom they are responsible for the stewardship of the relationship. That portfolio will look very different depending on the size and age of the school, the size of the team, the individual team members, and the initiatives in progress. The Head will also have a portfolio. It will be a short list and intentionally chosen.

New Heads of School have been named and are preparing to move into their role in July. As a new Head, are you excited about development and your increased visibility and responsibility in that realm? As the Development Director, are you ready to guide your new or development-resistant Head of School and new trustees to prepare for the inevitable campaign on the horizon?

Encouraging, building, and navigating relationships with donors can be intimidating and fraught with a spectrum of peril. But it doesn’t have to be. Let’s talk about the possibilities within your advancement program and how to get there together.

The author, Jill Goodman, is a consultant working with independent school leaders to advance their school’s mission, enhance their processes, and bolster their skills. Learn more about all services here.

Image credit: Getty Images