by Barbara Barron | Posted September 24th, 2025 | Subscribe to this newsletter
At the heart of my work as an advancement consultant is helping schools get better at creating the environment that makes it possible to raise more money to support their inspiring mission.
Whether that’s for the annual fundraising or special moments like a major gift opportunity or the high-stakes capital campaign, having the skills that give us the confidence to sit with a family and ask them to support the hopes and dreams of the school is imperative to creating that environment.
But there’s a teeny, little barrier there.
When asked, most people say they’d rather do just about anything else than ask someone for money. I’ve worked with dozens of school Boards as well as hundreds of development professionals themselves. That’s a very common feeling. Or let’s call it what it is, fear. Who likes being scared? Anyone out there love the idea of trying something you have no experience with and doing it in front of others, and at a moment that’s very important?
Didn’t think so.
But here’s the good news: these are not terribly difficult skills to gain. Do they take a bit of practice? Well sure. But like most skill-based activities (making the perfect omelet, giving a great speech, executing a slick parallel parking job), all can be learned.
What gets in the way are those awkward and vulnerable moments before that skill is landed. It’s those moments we avoid.
And that’s where training helps.
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Training time
The very best musicians, actors, dancers, athletes – they get coached. And they welcome it. They listen and then follow the coach’s instructions and advice because they know it works. Same for learning how to skillfully and compassionately ask for support.
I’ve had the truly joyful experience recently of helping some terrific volunteers and staff gain those skills so they can be the leaders they want to be in the areas of advancement as well as governance and the running of a school. And it starts a little gingerly, for sure. But once we actually get to practicing, those fears begin to fade, and what emerges is excitement.
Because what is always, always revealed is the why behind the ask.
These volunteers feel anew why they love and care for the school. They remember that they are asking not for themselves, ever, but for the teachers and the program that they have seen have a huge positive impact of the students it serves. They get right on over themselves in the most beautiful ways when they center the mission in their asks.
Mission. It’s all about the mission.
The first time I ever asked an alum for $1000, I was afraid a frog was going to leap out of my mouth. I’m sure I was awkward and weird. Sweet, guy, he still said yes. I’ve never forgotten him. So, I get it. But I’ve also had the pure delight of asking for a transformative gift from a family and hearing them say yes. And not just “well, ok” but “YES!.” They felt the joy of being able to do something significant and meaningful with their resources that changed lives.
That’s what we have the possibility of doing here, friends. That’s why we do it.
So if you – or those you work with – could benefit from coaching in this critical area, call me. If you know you could use a boost of skills and confidence yourself, let’s talk. In the end, the impact of this work can create huge ripples of good.
As always, thanks for everything you’re doing.
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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