137. Rethinking Fundraising: Smarter Strategies for School Advancement with Barbara Barron

Every spring, schools pour weeks of staff time and thousands of dollars into a gala or auction because that’s what has always been done, even as the return on all that effort keeps shrinking. Barbara Barron joins us in this conversation to talk about why that model is running out of road and what a school might do instead if it actually let it go.

We also get into how many separate asks a family absorbs in a single school year before the annual fund even launches, why alumni giving looks so different for day schools than it does for boarding schools, and what it actually means to bring mindfulness into a fundraising conversation instead of running through a script.

In This Episode, We Discuss:

The approach Barbara uses to get marketing, development, and admissions rowing in the same direction

Why galas and auctions have some of the lowest ROI in school fundraising, and where she recommends looking instead

How alumni giving realistically differs between day schools and boarding schools, and why that changes the strategy

Why the months leading up to the annual fund can quietly work against it

What actually gets a school’s email opened when families are drowning in their inbox

Why being a little imperfect in donor communication builds more trust than a polished message

How reframing interruptions as “the work” changes what a fundraising conversation feels like