This article is based on a lively discussion between our senior consultant, Chuck Davis, and me, as part of our Pain Points of Major Gift Fundraising video series.

Chuck and I dug into why fundraisers sometimes avoid making the ask, and how to turn that anxiety into confidence.

How to Turn Fundraiser Anxiety Into Confidence In High-Stakes Donor Conversations.

Even experienced fundraisers sometimes stall before asking for a major gift. 

You polish your notes again. You wait for “the perfect moment.” Even more, you convince yourself the donor isn’t ready. 

But what is the real truth? It may be that YOU are not ready.

The good news? You can fix this. The right preparation turns anxiety into confidence—and even joy—in asking for transformational gifts.

This post is part of our Pain Points of Major Gift Fundraising series, where we name the toughest challenges in securing big gifts – and give you practical, real-world ways to move past them. 

If this one resonates with you, you’ll love our new Major Gift Officer Bootcamp, built to help you move into major gift conversations with clarity and confidence.

Why Fundraisers Avoid the Major Gift Ask

Every major gift officer knows the feeling.

Your donor relationship is warm. You’ve had great conversations with the donor. Now, it’s time for a Gift Conversation. 

But instead of scheduling the meeting, you stall.

• “I’ll refine my proposal one more time.”
• “Next month might be better timing.”
• “I’m not sure they’re ready yet.”

“This hesitation often comes from fundraiser anxiety, not donor readiness.”

Chuck Davis, one of our top consultants, has been in that exact spot—sometimes with a chancellor or president watching. When the stakes feel high, the pressure is real.

And here’s the truth: whether you’ve been in fundraising for 2 years or 20, this can still happen. 

That’s why training, role play, and real-world coaching—like we do in the Major Gifts Bootcamp—make such a difference. They replace fear with muscle memory.

How Physical Comfort Impacts Fundraising Confidence

Before strategy, think about your own personal physical comfort.

If your chair is awkward or your feet don’t reach the floor, you can’t fully focus on the donor.

“Comfort frees up your mental space so you can pay full attention to your donor.”

That might sound trivial. But when you’re distracted, you’re not listening at your best. Physical ease helps you stay grounded, maintain eye contact, and project confidence- essentials in any high-stakes donor meeting.

We talk about this in the Bootcamp because your presence in the room is part of the ask. Comfort helps you be present, so your donor feels heard.

Three Donor Conversation Questions That Reduce Fundraising Anxiety

Most anxiety before asking for a major gift comes from uncertainty in three areas:

1. Is the timing right to ask for a major gift?
2. Is the gift amount realistic for this donor?
3. Is the project aligned with the donor’s interests?

“Most anxiety before asking for a major gift comes from three questions: timing, amount, and alignment.”

If you can answer these, your confidence soars. If you can’t, you’ll second-guess yourself.

1. How to Confirm the Timing for a Major Gift Ask

In major gift fundraising, timing is everything.
The donor knows when they’re ready—if you ask the right questions.

We use a permission-based approach:

• “Would this be a good time to talk about your support for the program you’ve been so interested in?”
• “When would you like to have a conversation about your gift?”

“It’s respectful. It keeps the relationship warm. And it gives you clarity before you walk in the room.”

2. How to Qualify the Right Gift Amount

Many fundraisers guess—and that’s where anxiety creeps in.
Instead, qualify.

“We’ve always imagined you would be a lead donor to this campaign. Could you share what range of gifts you might consider to make the biggest difference?”

Gail once used this approach with a prime naming prospect. She floated the idea of putting his father’s name on the building. His immediate reply—“What a great idea”—qualified him instantly.

In the Bootcamp, we go deep into qualification questions that feel natural and get you the answers you need before you sit down to make the ask.

3. How to Ensure Your Proposal Matches Donor Interests

Even if you think you know the donor’s passions, major donor cultivation requires regular check-ins. You’ll need to ask those discovery questions over and over, so you know where the donor stands!

“Donor priorities shift over time—your proposal should too.”

Ask open-ended questions to confirm alignment:

• “Why is this cause important to you right now?”
• “Has anything changed in your philanthropy plans? 
• “What impact would you like to see from your giving?”

And the sooner you learn about a shift, the sooner you can pivot.

How Scenario Planning Boosts Fundraiser Confidence

Preparation isn’t just knowing your ask—it’s knowing how to adapt. We always recommend thinking through various scenarios when planning an important ask. 

Donors can be like a box of chocolates – you never know what you’re going to get! 

What if:

• The donor says “not now”?
• They sidetrack to their European vacation?
• They look uncomfortable or distracted?

In major gift training, we teach scenario planning so you can pivot with ease. On some occasions, we even have our clients map out a “decision tree” for how they might respond in different situations.

“This isn’t about memorizing lines—it’s about being ready for anything.”  

Role Playing to Improve Major Gift Solicitation Skills

Role plays can feel awkward—but they also can be your best friend. 

Practicing asking for major gifts with a trusted colleague helps you:

• Find comfortable language for the ask
• Practice active listening
• Adjust naturally to donor cues

“Role play builds muscle memory so you’re ready when it’s real.”

In the Bootcamp, our group coaching calls include live role play. That way, when you’re in the real meeting, your brain already knows the moves.

Reading Donor Body Language in Gift Conversations

Donor body language can make or break a conversation. It’s important to keep your eye on your donor’s posture because it reflects their attitude.

If they shift uncomfortably, cross their arms, or glance at their watch, it’s best to slow down—or step back.

Sometimes naming what you see keeps the door open:

“I’m sensing I might have lost you – would it help if I clarified something?”

Your Role in the Major Gift Process

The best way to approach a major donor is to think of yourself as a bridge. You are connecting your donor and your organization’s impact.

“You’re not selling. You’re inviting.”

You’re connecting people with the vision that excites them. This mindset can take away the fear—and make the work joyful.

The Bottom Line: Preparedness Builds Confidence

The antidote to “ask anxiety” is full and complete preparation.

When you know:

• The timing is right
• The gift amount fits
• The project aligns

“Preparation is the antidote to fundraising anxiety.”

…you can walk into the meeting calm, grounded, and ready.

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We’re launching our series on the real pain points holding back major gift fundraising with the Major Gifts Officer Bootcamp. So stay tuned for our Pain Point series!

Introduction to the 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!

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

Pain Point #4: Admin Overload is Killing Your Major Gifts Program