Pain Point #3: Major Gift Fundraising Gone Wrong – When You Ask Too Early

At Gail Perry Group, we’re hearing this over and over again: Fundraisers are feeling pressure to “make the ask”—whether or not the donor is truly ready. 

It’s one of the most frustrating pain points in major gift fundraising today.

Our senior consultant Chuck Davis recently sat down with EVP Kathryn Gamble to unpack this issue. 

Together, they shared their own real world stories from capital campaigns and current GPG clients. Hopefully these stories will help you navigate what can be very tricky terrain.

Let’s talk about what’s really going on here—and what you can do about it.

Major Gift Fundraising Gone Wrong: When You Ask Too Early

Kathryn opened with a story every major gift officer can relate to.

Years ago, she was out to lunch with a high-potential donor and a veteran board member. She and her volunteer were excited and prepared with a strong ask.

At the beginning of lunch, the donor leaned in and asked,

“What do you all want?” 

Talk about jumping the gun!! They were so excited, thinking that the donor was opening a door, that they leapt into the ask. A scripted, full-fledged ask with a strong pitch.

Except… the donor meant: What do you want for lunch?

Oops. Dead silence! No gift.

That moment of misplaced urgency cost them the relationship. Why? Because their eagerness overrode their instincts. The pressure to secure the gift overshadowed the donor’s readiness.

This wasn’t a rookie mistake. It was a symptom of a deeper problem: feeling rushed by internal goals and the urgency to show results.

Why Fundraisers Feel Pressured to Make the Ask Too Soon

Let’s name it: This pressure often comes from inside the organization.

• Leadership wants fast results.
• CFOs want cash in the door.
• Boards want to announce big wins.
• Development teams are held to metrics that prioritize speed over strategy.

It’s not that these goals are wrong – they’re actually really important. However, when goals start driving fundraising timelines, that’s when your strategy may just slip into a transactional mode.

Here’s the truth: The donor drives the timing. Not us. Not your capital campaign calendar. Not the quarterly board meeting.

As Chuck put it, 

“The donor always controls the amount and the timing. We forget this at our peril.”

Managing Leadership Pressure in Major Gift Fundraising

Chuck shared a powerful story about a big moment when he brought an institutional leader to meet a major donor prospect. 

It was an exciting opportunity. They were aware that the donor had what we would call “serious capacity.” 

The donor had already stepped up with a generous annual gift, so they felt the time was right to move the donor relationship forward. They were especially optimistic because the chemistry was strong.

But . . .  the leader insisted they make an ask – at the very first dinner.

Chuck knew it wasn’t the right time. But his advice was ignored. The leader was the person in charge and was calling the shots, no matter how much Chuck tried to slow him down. 

As Chuck put it,

“I even warned the donor at the dinner table: ‘I couldn’t stop it. He’s going to ask you for money.”

They got a gift. But not a large one.

And, they always wondered if that early ask really cost them a much larger one down the road.

Just imagine the outcome if they’d waited for the right moment. With the right timing, that one gift could’ve become a multi-year commitment – or even a transformational investment.

Two Essentials for Major Gift Officers Under Pressure

How can you protect your donor relationships while still meeting institutional expectations?

1. Create a shared cultivation plan – on paper.

Before bringing leadership into donor conversations, make sure you have a clear, agreed-upon cultivation and solicitation plan in writing. This keeps everyone aligned and helps avoid last-minute ambushes.

That plan should reflect the donor’s pace – not your fiscal year!

And most importantly? Everyone involved needs to commit to it and agree to abide by it. No going rogue. 

2. Ensure better communication with your CFO and senior leadership.

If the pressure is coming from the CFO and finances, step into the role of educator. Help your colleagues understand how major gifts really work:

• Gifts are often pledged over time.
• Campaign cash flow isn’t front-loaded.
• Major gifts don’t solve immediate budget shortfalls.

The more informed your internal partners are, the more effective you’ll be as a fundraiser.

Why Educating Your CFO Matters in Capital Campaigns

Kathryn recalled a campaign where the CFO declared – in a board meeting of all places –  that the campaign was failing! 

Kathryn was horrified. But, she turned it into a teaching moment and worked with the CFO to help her understand the major gift process.

When the CFO understood how gift timelines and pledges actually work, she became one of the campaign’s strongest champions.

As Chuck put it, “

Your CFO should be your best friend on the Campaign Cabinet.”

Once your CFO understands gift timing, pledge schedules, and the long arc of campaign fundraising, you can gain a powerful internal ally who supports your donor strategy – not fights against it.

Internal Pressure: When Fundraisers Get Ahead of Their Donors

Sometimes the pressure doesn’t come from leadership. It comes from us.

You’re excited. And, you’re passionate. Even more, you see a clear line from this donor to a transformational gift.

But if the donor isn’t ready – if the relationship hasn’t matured – you could actually blow the whole opportunity.

Yes, you might get a gift. But . . . you might be leaving a significantly larger gift on the table.

The best major gift officers learn to manage their own urgency. They stay present with the donor. And, above all, they focus on a trusting relationship first.

That’s how you move from transactional asks to transformational relationships.

Bottom Line: How to Avoid Asking Too Early in Major Gift Conversations

Never forget: when you align your ask with the donor’s readiness, everything changes. 

Conversations deepen. Trust builds. And transformational gifts start to flow! 

• Donor readiness matters more than your internal calendar. Respect it.
• Create a written plan with leadership before you engage a donor together.
• Educate your CFO and executive team – again and again – about how major gift fundraising really works.
• Don’t let your own excitement override your instincts. Take a breath. Lead with curiosity.
• Stay grounded in the donor’s timeline. You’ll build stronger, longer-lasting support.

This is your moment to go bold – but not too soon. Want more smart strategies like this one?

Major Gift Officer Bootcamp

Are you and your team ready to close bigger gifts with less stress—and more confidence?

You’ll build the skills to qualify top donors, lead natural gift conversations, and ask for major gifts without the pressure. our new Major Gift Officer Bootcamp is a live, expert-led training that gives you real-world tools, coaching, and a clear strategy you can use right away.

The Bootcamp begins September 11, 2025, so join us if you want to bring in transformational major gifts to support your nonprofit organization!

We’re running our series on the real pain points holding back major gift fundraising – to launch the new Major Gifts Bootcamp. So stay tuned for our full Pain Point Series!

Pain Point #1: Finding the Hidden Major Gift Potential Hidden In Your Database

Pain Point #2: – What to Do When Donors Ghost You!

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