How Not to Ask for a Major Gift
By Claire Axelrad

Twice in the past month I’ve been asked for a major gift.

Pretty much out of the blue.

Without much preparation, relationship-building or making of an inspiring case for support.

It was clear to me what the charity would get out of it: my money. It was not so clear what I would get out of it. Should I not care?

 Perhaps not.
• Perhaps if I were the ideal, perfect donor I would give with no expectation of receiving anything in return.
Perhaps if I were less ego-centric, I’d just do it because it was the “right thing to do.”
• Perhaps if I were not on a quest for personal meaning, I’d give just because the person who asked is someone I know (though, not all that well); it would give them a feeling of success, and that would bring me some happiness.
• Perhaps if I were not searching for a community of folks who share my values, I’d give without quite understanding the depth and breadth of values enacted by these charities or without having met more of the people involved.
• Perhaps if I were not examining what it is that sparks joy in my life, I’d give whether or not this cause was currently at the top of my list or I’d been given opportunity for reflection and consideration.

But I’m not perfect.

I’m betting most of your donors aren’t either.

Donors have expectations… egos… personal meaning they’re seeking… communities they’d like to form… and cups of joy that need filling. Otherwise they wouldn’t be human.

And even if you could find a perfect donor prospect, in the instances where I was asked the case for why this was the right thing for me to do wasn’t even made all that well. The ask was about money, not impact.

There was simply an assumption that since I’d shown interest in the past, I would welcome this opportunity to demonstrate my interest even more passionately.

Okay. That’s not a bad starting place. But… you should never assume. You know what they say about the word “assume,” right.

Don’t Start on the Wrong Foot

If you ask for money right out of the gate, without first getting to know your donor a bit better, you won’t get their most passionate gift.

You may get a gift, but the donor won’t feel super good about it. Because they won’t be able to visualize what it’s making possible. They’ll only have a vague idea. At best, they’ll feel they did something “nice.” At worst they’ll feel coerced and won’t repeat their giving.

Major gifts are planned and thoughtful. Give the donor something to think about before you suggest an investment amount. MRI research shows people get a dopamine rush when they even consider making a gift. So your job is to give them something to consider!

That’s when they’ll feel a warm glow and experience the true joy of giving. Otherwise, they’ll feel they’re simply transferring money from their wallet to yours. You’ll check a task off your list as “done,” and they’ll be left poorer, not richer.

Steps to Asking Success

Rather than jumping the gun, instead, you should endeavor to:

• Ask for permission to talk about my philanthropic interests.
• Find out more by asking open-ended questions about what really floats my boat.
• Lead me gently toward greater interest in what you do, as it relates to my expressed personal values.
• Inspire me with what will happen if I become more invested.
• Paint a joyful picture for me of how this will light up my life.

Yep.  I said my life.

Of course I want to know how my gift will accrue to the betterment of the greater community and the world.  Of course I do!

But don’t forget you have to make me feel that’s truly what I’m doing!

Some Favorite Open-Ended Questions

“Getting to know you” and “relationship building” is a process. While you may be tempted (or pushed) to set up appointments to sell your proposal and ask for money, really the best way to do that is to set up visits (virtual or in-person) where you ask your prospects questions about themselves and listen to their answers.

These questions break down into six categories:

1. Questions about the donor.
People love to talk about themselves. Let them do this, and they’ll automatically like you better.

2. Questions asking for advice.
There’s an old fundraising adage: “If you want advice, ask for gifts. If you want gifts, ask for advice.”

3. Questions about philanthropic giving.
Most people weren’t born yesterday. They know why you want to meet with them. So it’s best to be upfront about it.

4. Questions to learn more.
People always have questions.  It’s your job to draw these out so you can provide the information your donor needs to fully consider your request.

5. Questions to build trust.
People almost always have a concern or two.  It’s your job to draw these out so you can address any niggling doubts your donor may have. For someone to make a passionate major gift, they must trust you completely.

6. Questions to get the donor more involved.
It’s nice to let donors know you value them for more than their money. This means asking questions about other ways they’d like to be involved.

It may take several visits to get to all your questions. That’s okay. Here, for each stage, is one of my favorite questions to ask:

1. About donor: Would you like to tell me a bit about your family? It’s easy for people to talk about what they know best, so it’s a great way to begin your conversation.
2. Advice: Are there others you would recommend we get together with to brainstorm this idea? Draw them in further; help them to see themselves as a leader and contributor at the ground level. This question also lets them know you’d like them and their network involved.
3. Philanthropy:What are your top three giving priorities? This is a great question, because sometimes you’ll find a passion your donor has that ties into one of your programs of which they might not even be aware. For example, while working for a social services agency I met with a donor who told me one of her causes was child bullying. I then let her know about a new anti-bullying program we were running out of our children’s services arm. She ended up funding it.
4. More info: Are there any questions I can answer for you? I always ask this question. You can also reframe it to ask if there’s ever been one thing they’ve always wondered about how your organization works.

5. Trust building: I hope you’d agree our campaign/project is important and that success would mean a lot to [population served]. What are your impressions thus far?
6. Involvement: How would you like to be involved in the coming year?Can I highlight a few ways others in the community have partnered with us?

7. BONUS: Ask at every stage — Can you tell me more about that? This is one of my favorite questions. It demonstrates you really care to hear their thoughts, plus you’ll often get your most valuable information when you ask something this open-ended.

A Major Gift Is Not an Impulse Purchase 

It takes time for donors to warm to the idea.  And they warm to it as they talk about it and bat ideas back and forth.

When asking for a major gift, think first about how the act for which you’re asking will enrich your donor’s life. Go BIG as you think this through.

Most people, donors included, are:
• Filled with expectations—mostly hopeful; often fueled by what’s going on in their world.
• Ego-centric—not in a bad way.
• Searching for personal meaning—as they ascend the Maslow Hierarchy of Needs.
• Looking for community—in a quest for belonging.
• Looking to spark joy in their lives—in a quest for healing and self-actualization.

David Brooks wrote an interesting opinion piece for The New York Times in which he spoke about the ways people develop different goals in life. He made an interesting distinction between happiness and joy.

• Happiness involves a victory for the self.
• Joy involves the transcendence of self.

How to Make your Ask about Potential for Greater Joy

Brooks notes those who find joy often put relationships at the center:
They ask us to measure our lives by the quality of our attachments, to see that life is a qualitative endeavor, not a quantitative one. They ask us to see others at their full depths, and not just as a stereotype, and to have the courage to lead with vulnerability.

When you meet with a donor to ask for a gift, lead with vulnerability.

Be open to their needs, not just yours.

Don’t overlook this critical step in the asking process.

I really might have made these gifts.

If the asker had lit my fire and opened my heart.

Sadly, I was left in my head. Simmering.

The most under-acknowledged major gift fundraising truism: It’s about the relationship, not the “ask.”

If you want your donor to dig deep, they must be inspired.


Claire Axelrad is a philanthropy consultant and fundraising coach who has been honored as an Outstanding Fundraising Professional of the Year by the Association of Fundraising Professionals. You can read more of her work at where she also offers an online fundraising school. She is currently offering a course in partnership with the Veritus Group: Making Effective Donor Asks