As nonprofit leaders enter the final and often most pivotal stretch of Giving Season, the conversations you have with donors can shape your entire year-end. This moment is about more than fundraising goals; it’s about helping people make decisions tied to identity, impact, legacy, and stewardship.

Recently, we had the privilege of hosting a webinar with someone who has transformed how our entire sector understands generosity: Dr. Russell James, J.D., Ph.D., CFP®, professor at Texas Tech University and the nation’s leading researcher on charitable giving and principal at EncourageGenerosity.com. His work has given nonprofits something we’ve long needed: evidence-based clarity on why donors give, how they think, and what inspires transformational generosity.

Together, we explored the psychology behind wealth conversations, practical fundraising questions that unlock generosity, and the specific moments when donors are most open to giving, especially non-cash gifts such as stock, crypto, and donor-advised funds (DAFs).

Replay our webinar on how to encourage generosity this giving season and beyond with transformational gifts.

Why Traditional Fundraising Asks Often Fall Flat

Most nonprofit leaders have felt the frustration of making an ask that “should” work… but doesn’t. According to Dr. James, the problem isn’t the mission or the donor—it’s the conversation itself.

Traditional asks often rely on logic:
Here’s the need. Here’s the cost. Can you help?

But high-capacity donors don’t respond to logic first. They respond to identity and story.

Dr. James explained that when donors enter a giving conversation, their brains begin organizing information around who they are and what narrative they want to live out. Generosity becomes an expression of meaning instead of just math.

This is why transformational gifts are almost never triggered by budget gaps or urgency alone. They’re sparked by moments when donors see themselves as the kind of person who gives boldly.

Why Non-Cash Gifts Are So Much Larger

One of the insights we often share at Infinite Giving (and one of our favorite parts of Russell’s research) is this:

Non-cash gifts are 60–100x larger than cash gifts, on average.

This isn’t just about tax efficiency (though that matters). It’s behavioral.

People feel differently about giving assets they’ve never mentally categorized as “spendable.” Stock, crypto, and other investments exist in a psychological bucket that makes generosity feel easier and less risky. When donors give from assets, they often give with greater joy, freedom, and scale.

Understanding this shift opens the door to far bigger impact.
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The Questions That Unlock Donor Values

Many nonprofit leaders tell me they freeze in the moment because they don’t know what to ask. Russell shared that great fundraising questions do one thing above all:

They surface values.

Here are examples of values-based questions that work:

• “When you think about the impact you most want to make, what rises to the top?”
  
• “What legacy do you hope your giving creates?”
  
• “Which parts of our mission resonate most deeply with your story?”
  

These questions lead donors inward toward meaning.

Just as important are the questions to avoid. Anything that feels transactional, presumptive, or overly tactical tends to shut generosity down. Questions like “How much can you give?” or “What’s your annual commitment?” shift the conversation away from identity and back into the logical, limited part of giving.

In contrast, one well-timed values question can open the door to transformational gifts which is something Russell has observed repeatedly in his research.
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Starting Wealth Conversations Without the Awkwardness

A lot of nonprofit leaders worry about bringing up wealth or assets. But donors are often far more open to these conversations than we assume, especially when it’s done respectfully and at the right moment.

Great openings sound like:

• “Many of our donors have been asking about giving from stock or their DAF. Is that something you’ve ever considered?”
  
• “With year-end planning coming up, this is often when people think about the most tax-efficient ways to give. How can we help support those conversations for you?”
  

These scripts feel natural, generous, and donor-first. And they work because they remove pressure while increasing possibility.

When donors mention their advisor, their investments, or tax planning, that’s usually a green light vs. a red flag. It means they’re already thinking about giving strategically.
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Why Year-End Is the Best Time to Inspire Transformational Gifts

There is no moment in the year where donor psychology shifts quite like the holiday Giving Season.

People are:

• Making tax decisions
• Reviewing investment performance
• Considering legacy and meaning
• Feeling heightened emotional connection to causes they care about
  

This combination creates a perfect window for discussing stock and DAF gifts.

At Infinite Giving, we’ve seen again and again that simply adding a “More Ways to Give” section on a nonprofit’s website increases the size of gifts. Why? Because visibility creates confidence. It signals that your organization is prepared to steward more sophisticated (and generous) forms of giving.

One of our favorite examples: Washington’s National Park Fund received a surprise $170,000 stock gift because a donor saw the stock giving button on their website. No ask. No phone call. Just clarity and confidence.

It’s a powerful reminder that donors often want to give more, and they’re just waiting for permission plus a clear path.
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The Heart of Generosity

After more than a decade studying donor behavior, Dr. James has shown that generosity grows in the presence of three things:

1. Identity – Donors give when it aligns with who they want to be.
   
2. Story – They give when they see themselves inside your mission.
   
3. Ease – They give more when the path is simple, strategic, and visible.
   

This is where modern stewardship matters. When nonprofits embrace non-cash gifts, communicate confidently, and create donor-centered conversations, generosity grows and often beyond what leaders imagined possible.
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A Final Invitation

If you’d like help strengthening your year-end giving strategy or streamlining your non-cash gift process, our team at Infinite Giving would love to connect with you.

Here’s to a powerful Giving Season, and to the generosity that fuels every mission we serve.

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