by Barbara Barron | Posted April 29th, 2026 | Subscribe to this newsletter
I call this challenge: How to Strengthen Giving to the Annual Fund.
A small progressive school contacted me to help them build their nascent development program. Their annual fund was meager, and after a few years, they finally had a part-time development pro on staff. The Board had recently committed to getting involved in advancement, but they weren’t sure what to do or how to go about doing it.
The result of the appraisal of their advancement program I conducted was clear: they needed to be far more personalized and direct in their appeals to families. This meant they needed to stop relying solely on a generic written appeal and follow-up email messages. Their task was to identify the families they believed they could get in-person meetings with during the fall and ask for meaningful (read: leadership level) gifts.
But how to have those conversations? How to ask? They didn’t know. And honestly, how could they know? They’d never done it.
So what would you advise in this situation?
Once you’ve thought about it, let’s compare notes:
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Time for training
The Board chair, two trustees, and the Head committed to learning the asking skills and practicing them. It was a vulnerable moment. At first, it was awkward and embarrassing.
We’re all going to stumble, talk too much, get lost, maybe even forget to ask for the gift.
That’s why we practice – so we know where we are and can remain clear about our purpose.
This group did that, but what I really respected about them was they were willing to trust me and follow my advice: do it the way I modeled until they were so comfortable and confident that they could start to modify my approach to make it their own. After all, these are conversations, not scripts.
They also invited me to debrief with them part way through their campaign and took course-correcting advice. Varsity level!
In just a couple of weeks, they met with ten families, asked for and received gifts 5 and 10 times larger than last year (because they asked for an amount), and are now reporting that their annual fund is up by 15%. Reminder: that was only with 10 families. And there were several additional steps to the process that I am leaving our here. But they were excited about this solid start and are committed to do it again, earlier, and with more families next year. They told me they felt guided and supported (and pressed, too) to fulfill their commitment to this fine school.
Bravo!
Barbara Barron
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BARBARA BARRON is one of the most respected and highly sought-after independent advancement professionals in the country, having worked with dozens of schools in every corner of the United States.
She has raised over $20 million for schools where she served as the Director of Development. Barbara is a New York Times bestselling author, speaker, and presenter who currently advises dozens of schools in various capacities. She is considered a thought leader in the world of advancement, with her writing widely shared by professionals in development offices worldwide.
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