How Can We Get Better at Asking Parents for Gifts?

by Barbara Barron | Posted September 12th, 2018

Let me start this by asking you a question: how many big asks have you made today?

“Well, Barbara, I asked my favorite barista Chloe for a little less foam on my latte, and then I asked Jason to re-send that e-mail he sent yesterday because it didn’t show up…”

I’m being silly here. Clearly, I mean big, as in, important asks. How many times today have you picked up the phone and asked a parent to give?

I imagine that most of us would answer with a big fat goose egg. Which is okay, honestly. There are likely a dozen reasons why. I’m not here to judge. Really. Rather, I’d like to pose a question to you:

Why, even though it’s our job to raise money for our schools, do we spend much of our time not actually asking for donations?

The answer?

Because asking is hard.

That’s right. Asking is hard. It’s tough to put yourself out there. I love it, personally, but that doesn’t mean I think it’s easy.

Here’s the thing: we naturally avoid hard things in our day-to-day. It’s very easy to stack our agendas with everything but asking.

But asking is what we should be doing. You and I both know that.

So how do we make what is always going to be hard to do, a little less painful?

I believe the solution is always in approaching it with confidence.

“Okay, Barbara. I’ll agree that confidence would help, but I can’t just magically become more confident…”

Sure you can! And there’s only one way to do it.

Do it regularly.

The reason we feel unsure is that we are out of practice.

So start by resolving to make a call with an ask every morning.

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First thing you do after you’ve had your coffee and have your wits about you. Can’t be an email. Has to be a call.

Can you agree to that? Write it down on a post it. Slap it on the monitor.

One ask every morning

I’m going to double down here: Make the most important call first. Just do it. I bet you’ll ride the wave of energy from that for hours!

See, it’s not just the best part of the job, it’s the most effective part – even if you aren’t feeling it. In every profession, whether you’re a cop or an attorney or a dentist or an airline pilot – there are parts of the job that are routine and easy, and aspects of them that no layperson can really do. That’s what makes them professions. Right? Right.

So, for us development professionals, the hardest part of the job is the ask. The fear of rejection exists in all of us – even those who don’t outwardly show it.

But it’s also the job.

Sometimes it takes extraordinary circumstances to see where you really thrive. Several years ago I worked at a school and for about six months solid, we worked to complete a major capital campaign. During that period, I routinely had as many as three big asks a day. My Head of School felt like he was about to collapse, but I was buzzing – even during my off hours.

I discovered that that was my happy place. Which means that my sad place is a week with no solicitations scheduled. When I see the calendar with open terrain, my energy sinks.

The ask is the most honest and real moment we have in this work. It’s the moment we get to (hopefully) look into the eyes of people who already care about our school and connect.

Connect, not sell. We’re not salespeople. We don’t have to sell our schools and their programs to these fine folks. We meet with people who are already believers. The hard work of touching their hearts has already been done. By our teachers. Coaches. Advisors.

Our job, in advancement, is to translate the feelings our supporters have into action. We give believers the opportunity to express their support in the form of a money gift.

We don’t create the feelings. We simply help others put them into fruitful action.


“Hmm. That’s beautiful, Barbara. But that doesn’t make the morning ask any easier…”

Sure it does!

Because in those breathless moments before your donor arrives, or as the phone rings, you can tell yourself: “I’m about to have a conversation with someone who believes in my school as much as I do.”

That’s all you’re doing: having a conversation with an intent to collaborate.

That sounds like a fun bit of ego-less problem-solving! A way to connect with someone right after breakfast!

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I’ve written previously about how some of the lessons they teach in improv comedy are helpful for our profession. And you’ve no doubt read (or heard of) Malcolm Gladwell’s Outliers: The Story of Success and heard of the 10,000-hour rule. What’s the overlap, here?

You have to do the hard thing a lot to become a master at it, to harness your fear of it and turn it into power.

Think Stephen Curry shooting 3 pointers until his arms feel like lead.

Or Yoyo Ma, going over the same arpeggios for hours every day.

If you’re feeling really out of practice, which can happen after a day or two of not making any big asks, practice with your team. They might find the request strange – but they shouldn’t. Practice in a no-fail environment first, then take your act on the road.

Take 15 minutes at a Development Committee meeting or (even better) Trustee meeting and lead a practice session for them. Have them ask the person next to them for $5,000 for the Annual Fund.

Need a script or some talking points? Here you go:

1. Tell the person next to you about the specific program/initiative at your school that excites you most.

2. Explain why. (This should be easy.)

3. Follow up with: “So many people feel like you do about [that program/initiative.] Would you consider joining us with a gift of $5,000 to support its successful launch?”

4. Now, wait. In silence.

From that point on, instinct will take over.

Do that a couple of times. Do it in pairs. Then switch partners.

Heck, I’ll do you one better. If you, your Head, or one of your trustees, is feeling less than confident, maybe even a bit intimidated to ask for a gift for your school, I volunteer to practice with you over the phone.

I write this because I love my professional community, and I’m always happy to talk to a member of it. Even a total stranger!

Here’s how it’ll work: you have my e-mail and phone number and Twitter handle. Reach out via whichever method you like, and we’ll set up a 15-minute call in the next few days. (Obviously not if it’s a major holiday, yada yada, etc.)

We’ll shoot the stuff for a few minutes, then roleplay your big ask a few times.

Sounds like fun, doesn’t it? I can’t wait.

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 nearly 20 years. In that time, I’ve had the pleasure of creating and implementing successful Strategic Fundraising Plans 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 SpringsSage Ridge and others. (Maybe we’ve met!)

Nothing makes me happier than seeing a struggling school start to thrive. I’m sure 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.