How to Confidently Ask for Big Gifts: The Power of Practice and Alignment

The following is guest post by executive coach and fundraising consultant Mallory Erickson. If you’ve ever felt anxious or unsure before a big ask, you’ll find Mallory’s insights super-helpful.

If asking for major donations makes your palms sweaty and your heart race, you’re not alone. When I first started fundraising, I remember sitting anxiously in my car before meetings, rehearsing my pitch and fearing rejection. Big asks can feel intimidating, but they don’t have to.

After years as a frontline fundraiser, coach, and researcher, I’ve discovered how to shift the conversation from awkward solicitations to empowering, authentic exchanges. The secret?

Practice, alignment, and understanding the real value of your ask.

Here’s how you can confidently ask for big gifts, feel great doing it, and build lasting, meaningful partnerships.

Why Asking for Big Gifts Feels Hard

Fundraising is vulnerable, especially when large sums of money are involved. Whether it’s fear of rejection, worry about coming across as pushy, or anxiety about making someone uncomfortable, these feelings are normal but challenging.

In my book, What the Fundraising, I share how our thoughts, beliefs, and energy directly shape our fundraising experience. Negative thoughts about our capabilities, feelings of self-doubt, and assumptions about how donors might react all create resistance and anxiety, holding us back from effective fundraising.

But here’s the good news: it doesn’t have to stay that way.

Shift Your Perspective: Alignment Fundraising

Alignment Fundraising is a powerful method that transforms fundraising into a mutually beneficial partnership. Instead of feeling like you’re trying to persuade someone, Alignment Fundraising focuses on genuine connection between the donor’s interests and your organization’s mission.

When you approach fundraising with alignment in mind, the conversation naturally changes from transactional to relational. You begin to build a true partnership, focusing on shared vision and goals rather than just financial contributions.

Quick Tip: Ask Yourself…

Before reaching out to potential major donors, ask yourself:

• What are their values and interests?
• How do those values align with our organization’s mission and impact?
• What kind of partnership would benefit both of us?

How Practice Changes the Game

Practice is about honing your ability to respond authentically and confidently under pressure. Like athletes who train to perform under the spotlight, fundraisers can dramatically improve their effectiveness through deliberate practice. This intentional practice helps you:

• Overcome the fear of rejection — The more comfortable you become with “no,” the less power it has over you.
• Clarify your message — Practicing helps refine your narrative, making your ask clear, concise, and compelling.
• Build empathy and connection — Role-playing different scenarios enhances your capacity to genuinely connect with funders, understanding and aligning with their interests.

3 Practical Strategies to Prepare for High-Stakes Donor Conversations

Here’s how you can structure your practice for maximum impact:

1. Role-play donor conversations — Simulate real scenarios with colleagues, focusing on various donor motivations and concerns.
2. Record and review — Watching yourself back can be uncomfortable but incredibly revealing and constructive.
3. Practice strategic alignment — Identify your organization’s core values and assets, and clearly connect these to potential funder interests.

Introducing Practivated: Your Personal Donor Conversation Simulator

Imagine having a tool that enables you to rehearse high-stakes donor meetings in a safe, supportive environment. That’s exactly why I created Practivated, an innovative, AI-powered platform designed specifically to help fundraisers refine their approach and build genuine confidence before critical conversations.

Practivated Allows You To:

• Practice personalized, campaign-specific scenarios.
• Receive targeted, real-time feedback to sharpen your messaging.
• Build fluency, confidence, and strategic clarity that translate directly into fundraising success.

This platform complements your existing fundraising strategies by ensuring that when you walk into donor meetings, you’re prepared, authentic, and aligned with your values.

Special Offer: Exclusive Discount for Capital Campaign Pro Community

To help you maximize your impact, we’re offering an exclusive discount for the Capital Campaign Pro community. Experience firsthand how practice can transform your fundraising outcomes.

Click here to explore Practivated and request a demo »

Practice might not make perfect (perfection is an illusion anyway!), but it certainly makes progress, confidence, and alignment. And in fundraising, that’s everything.

Let’s change the fundraising narrative together, one ask at a time.