Women Heads of School: Finding Your Voice

by Barbara Barron | Posted December 4th, 2024 | Subscribe to this newsletter

I recently have begun to get to know the Executive Director of The Heads’ Network, Jen Evers.

I learned about this cool organization through my association with the School Leaders Connect. Jen was a recent guest speaker.

Afterward, I referred a former colleague of mine, a fairly new Head of a great school in San Francisco, to them. I believed the leadership growth opportunities they offer would be a great fit for her.

T.H.N., or The Heads Network, “brings schools together to elevate women leaders”. Many of their members are aspiring Heads, and new Heads, but also other school leaders seeking to advance their skills.

What Jen and I talked about recently is the need we both see for women who are aspiring to greater leadership to gain the essential skills of donor cultivation and solicitation. While T.H.N. offers some important grounding in this work through their programs, we agree that there’s a need for more. This issue can be amplified when the woman leader follows a man in the role.

How can she find her voice?

Her style?

Her comfort and confidence in the work?

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We’re naturals

What’s ironic is that—and I am generalizing here—women often, but not always, naturally possess the skills needed to be really good at cultivating and asking for support from donors. At the heart of any good relationship is trust and the knowledge that we are seen and heard, right? Listening deeply, we learn what a person or a family cares about, what about our school’s mission resonates with them, and what they hope to achieve through their philanthropy.

This is all central to effective donor relations.

It is in those moments when we are really hearing someone share what matters to them that we have the opportunity to establish a real connection. It is from that place that we can begin to build a partnership in the work. And I see women doing that every day. But from my experience training people in the “art of the ask”, I know that we tend to skip over this part, thinking we need to know and memorize a “script”. Not so.

I was training a group of school trustees recently in helping solicit gifts for their capital campaign. I assured them that no one is an expert in this work right away. I asked them to remember the first time they served a tennis ball, or made an omelet, or executed a three-point turn. They were likely rather awkward, and if not, most certainly unsure. We know that to master a skill, we need to do it repeatedly.

Remember the 10,000 hours notion? Well, maybe we don’t need 10,000 hours here, but we do need plenty of opportunities to practice this set of important skills.

We’ve heard the adage that “practice makes perfect”. Maybe for a tennis serve but I’d like to rewrite that for our donor work: practice make proficient. And out of competency rises confidence. That order matters.

More useful phrases

Now, there are some useful phrases we can learn that help us navigate the conversion. But it is never going to be a script. Why not? Because we’re having a live, authentic conversation with real human beings.

I’ve written on the value we can gain from improv. A great concept from that world is “yes, and”. So, too, is the notion that maximum practice allows for ultimate flexibility. The more fluent and comfortable we get talking about our giving programs and how gifts bring our schools closer to delivering on the promise in our inspiring missions, the easier it will become.

When we can be clear about where we are in the conversation, we won’t get lost, distracted, or confused about the purpose of the meeting. We’ll be able to navigate the conversation and ask for the support we are seeking gracefully and with respect. Our effectiveness will rise, and we’ll raise those vital dollars we need for our worthwhile people and programs.

But perfect is not the goal: authentic is. So, too, is passion for your school and your program. And the good news is that both of those qualities are readily available to you.

Make it your own

You may need some help honing your own style, finding your unique voice. It’s natural that you might compare yourself to those who came before you. But do not attempt to emulate them. Your families want to know you. They want to hear your perspective and your vision. You are the leader. 

Finding your voice and style and gaining fluency and confidence does take practice. You’ll be well served to have a partner in this work, either in your DoD or someone on your Board. Or an outside consultant who can coach you, like me.  And once you do find your voice and your style, you’ll still want to run through the plan before an important meeting. There’s a reason that athletes practice drills between games or matches, musicians spend hours playing scales, and actors run lines. If the meeting is important — so, too, is the preparation for it.

I recently heard a good re-definition of the word “responsible”. It means that we can respond (not react) from a frame of mind and heart to fully, deeply, and calmly handle what’s ours to do. It is about doing what we need in order to put ourselves into that place. As we do, I believe our impact is enhanced. Let’s work and speak and listen from that frame.

Wishing you well. And thank you for all you are doing. 

Barbara Barron
[email protected]


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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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