Most schools have an annual fund, but few have a clearly defined leadership giving program within it. Without intentional structure, leadership-level giving can stagnate, rely on a small number of loyal donors, or lack clarity around expectations, recognition, and growth.

The head of school is the most influential partner in an independent school’s advancement success. While the role spans every aspect of institutional leadership, a head’s effectiveness is directly tied to the strength of the school’s advancement efforts.

For years, independent school leaders have asked a deceptively simple question::

As schools move beyond early experimentation with AI, new challenges emerge: overlapping initiatives, unclear authority, faculty fatigue, and difficulty translating values into consistent practice.

Many schools are experimenting with AI in isolated, reactive ways often driven by individual enthusiasm, external pressure, or emerging concerns about risk.

Many development offices are highly productive but still struggle to make meaningful progress toward their goals.  The issue is rarely effort or commitment.

Too many strategic plans stall because they lack two critical companions: a financial roadmap and a philanthropic plan to fund them. A strategic vision only gains traction when it is translated into a clear, time-bound fundraising program with defined priorities, targets, timelines, owners, and measures of impact.

Join ISM’s Scott Wilson for a candid conversation with two successful and innovative independent school heads about the challenges they (and their peers) are facing today and in the immediate future.