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. 

Trent Thompson Trent Thompson

How to Secure and Steward Major Gifts of Stock, DAFs, and Other Non-Cash Assets

This is for major gift officers, development directors, and nonprofit CEOs who want to grow major gift revenue without leaning harder on cash donors who are already stretched. After reading this, you'll be able to spot the donors most likely to give a non-cash asset, open the conversation in a way that respects them and their advisors, and steward the gift so well they want to do it again.

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Trent Thompson Trent Thompson

How Do I Align With My ED or CEO on Major Gifts Strategy?

Managing up is one of the most underrated skills in major gifts. The fastest way to align with your ED or CEO is to translate your front-line donor experience into the language they use with the board: shared goals, realistic timelines, and a steady rhythm of briefings that mix data with story. If you lead major gifts, this is how you earn room to do the work the way it needs to be done.

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Trent Thompson Trent Thompson

Storytelling for Sophisticated Major Donors

In this week's edition of Scaling Major Gifts, I share: The Story Spine framework I use with major donors (5 simple beats); How to weave data inside the story, not bolt it on after; How to tune the same story for an investor vs. an educator donor; and Why dignity-first storytelling is non-negotiable in 2026.

Read this week's edition and share it with your team and leadership. The donors are waiting for both the heart and the proof.

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Trent Thompson Trent Thompson

Major Gift Metrics that Actually Drive Behavior

In this week's edition of the Scaling Major Gifts newsletter, I'm walking through the metrics quietly demoralizing your best fundraisers, the small set of leading indicators worth tracking, how to use AI inside your CRM to surface patterns, not punishments, and a simple "metrics reset" you can run with your team this month.

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Trent Thompson Trent Thompson

Portfolio Optimization: When and How to Let Go of Prospects

In this week's edition of Scaling Major Gifts, I share the four lenses I use to decide who stays active, who graduates, who pauses, and who needs another look. I also walk through how to bring your leadership along so quality, not quantity, becomes the story you tell.

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Trent Thompson Trent Thompson

The New Nonprofit Tech Stack for Major Gifts

This week's Scaling Major Gifts newsletter is all about cutting through the noise. I walk you through the four core tech categories that actually matter for major gifts work (hint: it's not that many), a simple five-criteria check to evaluate anything in your stack, where AI genuinely fits (and where it honestly doesn't), and a 90-day "stack tune-up" plan to help you retire what's not working and feel good about what is.

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Trent Thompson Trent Thompson

Time Blocking for High-Value Major Gift Work

In this week’s Scaling Major Gifts, I share how I finally took back my week using time blocking, clear communication, and a few smart AI helpers to protect high-value donor time and grow major gifts.

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Trent Thompson Trent Thompson

Generational Giving: Engaging Next-Gen and Values-Driven Donors

Have you noticed how different donor conversations feel these days? I’m hearing it everywhere. The donors leading with values, especially women and next‑gen wealth holders, are changing what generosity looks like in 2026. They ask sharper questions. They expect quicker answers. And they want their giving to align with their worldview and social circles, not just their wallets.

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Trent Thompson Trent Thompson

Make Your Discovery Calls Feel Natural Again

You feel the pressure to qualify donors fast in 2026.

Budgets are tight, boards want forecasts, and donors expect personalization every time.

Scripted discovery calls can start to feel like an interrogation, for you and for them.

This week, I want to help you redesign those conversations so they feel more like mutual exploration and less like a checklist.

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Trent Thompson Trent Thompson

Coaching Leaders and Boards to Show Up Well with Major Donors

Every nonprofit is feeling this tension as donor expectations rise and teams run lean. Personalized stewardship still matters most, yet doing it for dozens or hundreds of donors feels impossible. Especially when every new automation tool promises ease, but adds setup and management time.

Let’s simplify.

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Trent Thompson Trent Thompson

Hyper-Personal Stewardship at Scale Without Burning Out Your Team

Every nonprofit is feeling this tension as donor expectations rise and teams run lean. Personalized stewardship still matters most, yet doing it for dozens or hundreds of donors feels impossible. Especially when every new automation tool promises ease, but adds setup and management time.

Let’s simplify.

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Trent Thompson Trent Thompson

Responsible AI for Donor Research and Call Prep

If you feel both curious and cautious about using AI for donor research, you’re not alone. Many fundraisers are testing tools that promise speed and intelligence. Yet, the fear of misusing data or losing authenticity keeps us on edge.

The truth is, AI can help without taking over. Your human presence still matters most. The key is learning where AI belongs in your prep process, and where it doesn’t.

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