How to Engage High-Net-Worth Donors: A Guide for Nonprofits

By Jeremey Cramer

Need to Raise Major Gifts? Don’t Rush the Ask

If you’re thinking about implementing or expanding your major gifts strategy, you’re already ahead of the curve. So many nonprofits focus time on small gifts, rather than growing exponentially with fewer, more impactful donors. 

But even if you are in the know, we’ve all been guilty of skipping a few steps when having initial conversations with donors.

When you need to raise money ASAP, it’s tempting to move quickly into the ask. 

But major gifts aren’t made in one conversation. They’re built through curiosity, alignment, and trust.

In this post we’ll dive deep into donor psychology, as well as the key questions you should be asking (and, in our next post, the mindset shifts you must make as a fundraiser) to be most successful in receiving transformational gifts.

 

Understanding Donor Psychology: What Truly Drives Giving

I’ll never forget a conversation I had with my former mentor. He has been a guiding force in my life, both personally and professionally, and we often talk about everything from raising sons to leadership and legacy.

One day, he broke down what he called “the social science of wealth.” He explained that there’s a significant psychological difference between people worth $1–10 million, $10–100 million, and $100 million and above, and understanding those differences can completely change how you fundraise.

At the $1–10 million level, donors are still in the building phase of their careers. They want to make an impact, they care about their personal brand, and they crave connection to peers and causes that make them feel part of something bigger.

Between $10–100 million, the psychology shifts. These donors aren’t just seeking community…they want to lead it. Their philanthropy becomes a tool to influence their peers and colleagues. That’s why challenge grants and matching campaigns work so well: they let donors inspire and mobilize others to give.

At $100 million and above, donors are seeking a concierge-level philanthropic experience with customized impact, transformational scale, and legacy. They’re less interested in public recognition of their values and more interested in measurable, systemic change.

And according to the 2025 Bank of America Study of Philanthropy, wealth and generosity exist across every dimension of age, race, gender, and sexual orientation. High-net-worth donors are not a monolith; their motivations are as diverse as their lived experiences.

 

The Common Thread: Meaning, Not Money

Every wealthy donor, regardless of tier, shares one universal truth. 

Money doesn’t buy happiness… Relationships do. 

The longest-running Harvard study on human happiness found that people with strong connections live longer, healthier lives. No matter how much wealth someone has, what they’re really searching for is belonging, meaning, and community.

That’s why great fundraisers act less like salespeople and more like guides.
They align giving opportunities with what the donor finds most meaningful. 

 

Exploratory Conversations: The Key to Major Gifts Fundraising

Once you understand what drives donors, the next step is learning how to connect with them.

Engaging high-net-worth donors begins by slowing down and getting curious.
Transformational giving is about connecting mission to meaning.

This happens through exploratory conversations, a framework that helps development leaders ask the right questions instead of rushing to the ask.

Exploratory conversations are really about four things:

1. Understanding a donor’s motivations
2. Exploring their aspirations
3. Learning their impressions of your organization
4. Discovering their philanthropic interests

The greatest gift of an exploratory conversation is that if there isn’t alignment, you can—with love and without judgment—kiss that prospect goodbye and move on.

Because the best fundraisers say no to what doesn’t matter, and lean into the opportunities that have the highest potential for impact.

So, let’s walk through what that looks like in practice.

 

1. Motivations

Motivation is the “why” behind a donor’s giving, including their values, lived experiences, and personal sense of purpose. Understanding this helps you connect your mission to what matters most in their life.

Try asking:

• “What gives your life meaning and purpose?”
• “When you think about your philanthropy, what do you most hope to achieve?”
• “At the end of the day, what problems in the world do you want to help solve?”

 

2. Aspirations

Aspirations are about the future: what they want to build, contribute to, or be remembered for. These questions help you understand their long-term vision and how your organization might fit within it.

Try asking:

• “What legacy do you want to leave?”
• “What do you want to be remembered for?”
• “What would you love to accomplish for the next generation—your children, grandchildren, or the young people we serve?”

 

3. Impressions

Every donor carries perceptions about your organization. Asking about impressions allows you to understand how they see your work and gives you the opportunity to gently clarify misconceptions.

Try asking:

• “How familiar are you with our work?”
• “What are your impressions of our mission and impact?”
• “In what ways do you think we could make a bigger difference?”

 

4. Philanthropic Interests

This is where you discover where they’re currently giving, what lights them up, and how they define meaningful engagement. It helps you align your invitation with their existing commitments and passions.

Try asking:

• “Where are you currently involved philanthropically?”
• “What brings you the most joy or fulfillment through your giving?”
• “Could you see yourself becoming involved with our work in the future?”

When you ask with curiosity instead of agenda, you’ll uncover alignment naturally and set the stage for transformational partnership.

 

Most Importantly, Remember: Every Donor Is Different

If you’ve met one high-net-worth individual, you have not met them all.

Serious major gifts philanthropy requires nuance, patience, and curiosity. You cannot treat donors as a group. 

They are all different, and they deserve the TGP process: one that meets them where they are, honors their humanity, and builds a partnership rooted in shared purpose.

When you take that approach, you don’t just raise more money.
You change the way people give and the way your organization grows.

 

Take the next step in your major donor strategy:

If your team is ready to replace transactional fundraising with a transformational system that consistently secures six- and seven-figure gifts, explore The Transformational Giving Playbook™.

It’s the proven framework we’ve used to help organizations double their $10K+ donors and grow $100K+ gifts from a handful to dozens. 

We’re here to help!