Blog

Sharing insights, strategies and inspiration you can use right now.

This is where I share strategies, action steps, and ideas for scaling major gifts, and answers to questions that matter most right now. 

137. Crafting Offers for Transformational Giving
Trent Thompson Trent Thompson

137. Crafting Offers for Transformational Giving

In this week's episode of The Intentional Fundraiser, I walk through the anatomy of a truly transformational gift offer. The five elements that belong on one page. The multi-year and blended structures that feel doable to your donor. And the co-creation conversation that turns a good offer into a great partnership.

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135. A Modern Tech Stack for Major Gift Success
Trent Thompson Trent Thompson

135. A Modern Tech Stack for Major Gift Success

Today, we're talking about your tech stack, what belongs in it, how to evaluate what you've already got, where AI actually fits in major gifts work, and how to do a ninety-day tune-up that genuinely frees your team to focus on what matters most: donors.

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134. Writing Donor Messages with AI, Not by AI
Trent Thompson Trent Thompson

134. Writing Donor Messages with AI, Not by AI

On this week’s Intentional Fundraiser Podcast, I’m sharing how I use AI to draft and refine messages that still sound like me, while saving precious time for deeper donor connections.

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133. Take Back Your Week, Grow Your Major Gifts
Trent Thompson Trent Thompson

133. Take Back Your Week, Grow Your Major Gifts

Some weeks, your calendar looks full of “important” meetings, but your top donors barely hear from you. In my experience, your calendar will tell the truth about your priorities long before your strategic plan does. The good news is, you can change that story. Here’s a new way to look at your week.

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130. Next-Gen Major Donors and the New Rules of Engagement
Trent Thompson Trent Thompson

130. Next-Gen Major Donors and the New Rules of Engagement

We’re unpacking the new rules of engagement with next‑gen donors in greater depth. You’ll hear stories of fundraisers who’ve built trust faster, simplified reporting, and created shared experiences with donors who lead with their values. If you’ve wondered how to shorten cultivation cycles without feeling transactional, this episode is for you.

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129. Your 2026 Case for Transformational Gifts
Trent Thompson Trent Thompson

129. Your 2026 Case for Transformational Gifts

In a 2026 world, with AI on everyone’s radar, economic uncertainty, and donors asking sharper questions about impact and equity, an outdated case for support is a real liability.

In my experience, updating your case is one of the most leveraged things you can do to inspire six and seven-figure gifts.

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128. Making Your Major Gift Portfolio Shock-Resistant
Trent Thompson Trent Thompson

128. Making Your Major Gift Portfolio Shock-Resistant

In my experience, many nonprofits are one donor decision away from a serious budget problem. The good news is, you can make your portfolio far more shock‑resistant with a few intentional shifts.

Here’s how I think about it.

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127. Discovery That Builds Trust, Not Pressure
Trent Thompson Trent Thompson

127. Discovery That Builds Trust, Not Pressure

In my experience, when discovery feels like a test, donors feel it too. I want to share a simpler, more human way to approach discovery calls so they build trust instead of pressure. This is the focus of this week’s Intentional Fundraiser podcast episode, “Discovery That Builds Trust, Not Pressure.”

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126. Turning Leaders into Effective Major Gift Partners
Trent Thompson Trent Thompson

126. Turning Leaders into Effective Major Gift Partners

In my experience, pressure shows up most intensely when a CEO or board member joins a major donor visit at the last minute with little or no briefing. You’ve done the relational groundwork. Then someone “swoops in” and the conversation drifts, the message gets fuzzy, and you walk out wondering what just happened.

Here’s the shift I want to invite you into: instead of treating leaders as last‑minute heroes, start treating them as intentional partners in your major gift work.

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125. Making Stewardship Personal, Scalable, Sustainable
Trent Thompson Trent Thompson

125. Making Stewardship Personal, Scalable, Sustainable

You’re working so hard to love on your donors. You want stewardship to feel personal and heartfelt. At the same time, you feel pressure to scale, meet goals, and protect your team from burnout.

In 2026, donor expectations are higher, AI tools are everywhere, and many nonprofit teams feel stretched thin. You’re not imagining the tension between personalization and volume.

In my experience, the answer is not doing more, it’s doing the right things, for the right donors, at the right level.

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124. AI-Powered Prep: Human-Centered Conversations
Trent Thompson Trent Thompson

124. AI-Powered Prep: Human-Centered Conversations

If you feel pressure to “keep up” with AI and still stay true to your values, you are not alone.

Donors are living in an on-demand world, and they notice when your outreach feels generic or underprepared.

In my experience, the answer is not to avoid AI, but to use it carefully so your work becomes more thoughtful, not less human.

Listen to “AI-Powered Prep, Human-Centered Conversations,” then share this episode with a colleague or board member who is asking big questions about AI and major gifts.

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123. Finding Your Real Top 25 Donor Prospects
Trent Thompson Trent Thompson

123. Finding Your Real Top 25 Donor Prospects

Drowning in “prospect” names?

If your major gift list looks impressive on paper but doesn’t translate into actual conversations or gifts, you’re not alone.

I’ve sat with teams staring at hundreds of “top prospects” and quietly thinking, “Where do we even start?”

In my latest episode of The Intentional Fundraiser podcast, I share how I helped one nonprofit narrow 600+ “major gift prospects” down to a focused Top 25 using simple donor signals, capacity, affinity, and engagement, not just wealth.

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122. Your 2026 Major Gifts Plan: Aspirational but Realistic
Trent Thompson Trent Thompson

122. Your 2026 Major Gifts Plan: Aspirational but Realistic

Creating a major gifts plan that’s both aspirational and realistic is more challenging than ever in 2026.

If you’ve ever felt that pull between wanting to say yes to your leadership’s ambition and knowing your current portfolio can’t stretch that far yet, you have plenty of company.

Today, I want to walk you through a practical framework that helps you set aspirational goals that are grounded in data, strengthened by alignment, and fueled by possibility.

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121. How ‘Calling All Heroes’ Elevates Fundraising and Community Impact
Trent Thompson Trent Thompson

121. How ‘Calling All Heroes’ Elevates Fundraising and Community Impact

If there’s one thing my nearly three decades as a major gifts professional have taught me, it’s that our work is never just about dollars. It’s about people, purpose, and possibility. This week is especially meaningful for me as I celebrate the official release of my new book, Calling All Heroes: Combining the Best of Donor-Centered and Community-Centered Fundraising for Greater Impact. I wrote this book for you: the major gift officers, development directors, executive directors, and board leaders who show up each day with passion for your mission and a commitment to making real, lasting change.

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117. Why “Tips and Tricks” Are Failing Fundraisers
Trent Thompson Trent Thompson

117. Why “Tips and Tricks” Are Failing Fundraisers

This one has been simmering inside me for months.

It’s about the language we use in the nonprofit sector—and why we need to be more mindful of it.

Specifically, I’m making a plea to eliminate phrases like “tips and tricks” when we talk about engaging donors.

Because giving is not a “trick.” Donors are not targets. And we are not magicians trying to perform sleight of hand to win gifts.

Listen in and let’s transform our language (and our sector!) together.

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116. Strategies for Major Donor Retention
Trent Thompson Trent Thompson

116. Strategies for Major Donor Retention

In my 30 years working in major gifts, I’ve learned that retention isn’t just a metric—it’s the engine behind your mission’s sustainability and growth. Stick with me in this post, and I’ll share a handful of personal stories, proven strategies, and actionable advice that can help you—and your team—turn one-time generosity into lifelong, game-changing partnership.

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115. Breaking Down Silos: Why the Future of Fundraising is Human-Centered
Trent Thompson Trent Thompson

115. Breaking Down Silos: Why the Future of Fundraising is Human-Centered

Have you ever felt torn between honoring your donors and staying true to your community? If you work in the nonprofit sector—whether you’re a major gift officer, development director, executive director, or board member—I’m guessing the answer is yes. Lately, I've seen this divide growing, and I know just how exhausting and lonely it can feel to stand at this crossroads, being told you must choose either donor-centered or community-centered fundraising. But what if I told you there’s a way forward that doesn’t force us to pick sides? In this episode, I’m going to share what human-centered fundraising really looks like—and promise you’ll leave with clear, practical strategies for connecting people and unlocking more meaningful, sustainable giving.

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