How Can We Earn the Opportunity to Make That Big Ask?

by Barbara Barron | Posted September 21st, 2022 | Subscribe to this newsletter

The time it takes to ask the following question is minimal:

“Could you consider an Annual Fund gift of $20,000?”

Or, perhaps more likely, something like:

“We very much hope you will consider being an anchor donor for our campaign with a commitment of $1,000,000. Is that something you can consider?”

Mere seconds. Of course, they may well be the scariest 5-10 seconds anyone can imagine. But it’s quick. Once it’s over, it’s over.

But, in a way, the question itself is the culmination of days, weeks, months, and years of cultivation. It is a moment we have earned. Earned through trust, transparency, and the permission we’ve been granted to sit with this individual or family to ask for their support for our outstanding school or program or project.

So how did we earn this question? And how do we earn the answer we want, a resounding “Yes!”

Start with an Intention

Anyone who has read a single article of mine knows that we must start with intentionality. And after intentionality, planning. And then, the benefit of practice.

Think of your closest friends. How did you get to know and build trust with them? I suspect that it happened over time, by talking about the things that really matter. From sharing what is most important to you. What you deeply value. Why would it be all that different with a family you are entrusted to engage in your community? Someone from whom you are asking for their support?

The intention is essential. This is not about prying into their lives. Or casting around for the right angle that will hook them. No. Yuck. What’s required is a respectful, grateful attitude. And a curious mindset.

This conversation will only be comfortable for both parties if you have asked for the meeting and been clear that one of your hopes is to get to know more about their values around philanthropy and volunteerism. Otherwise, it might feel a little intrusive. And you also need to be prepared to share what you personally value. What you care about and how you make your own philanthropic choices.

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Ask the Right Questions

With those caveats, let’s move to the questions. Good questions lead to good conversations. So, I have crafted a few here to help you get started. These are intended to begin a discussion about what really matters to us. Obviously, this is one side of a two-sided endeavor. It’s a conversation. You will need to be prepared to share information about your organization – its history and its current priorities. What are some of the pain points and also some of the inspiring opportunities you are exploring? Let them see inside so they feel invested. And trusted.

Back to the good questions. Here are two:

1. What has been the most meaningful volunteer and/or philanthropic experience of your life? Why?

2. How do you and your family make decisions about what and where your give support?

Can you see where this conversation could lead? As you listen deeply, you’ll discover important things about this family that will be invaluable as you decide what and how you bring ideas for them to consider. And as my brilliant colleague, Andrea Kihlstedt reminds us, “People don’t remember what you said. They remember what they said.”

Being asked a really good question feels great. Sharing something personally meaningful engenders intimacy. Being heard fosters trust.

Good luck and enjoy the moment!

Be well,

Barbara Barron

[email protected] // @BBAdvancement

About the Author

My name is Barbara Barron, and I’m writing this blog to share advice on a profession that I adore.

I’ve been working in the field of Independent School Advancement for over 20 years. In that time, I’ve had the pleasure of creating and implementing successful fundraising plans and programs for so many incredible schools. I’ve had the privilege of seeing real growth at The Carey School, Marin Primary & Middle School, Woodside Priory, Crystal Springs, Presidio Knolls, Sage Ridge, and San Diego French American, and others. (Maybe we’ve met!)

Nothing makes me happier than seeing a struggling school start to thrive. My hope is that you’re here to make a positive change as well. I hope my advice can be a part of that change.

Shoot me an e-mail if you want to swap tips, or share your voice here.

Let’s do this, together.

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