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. 

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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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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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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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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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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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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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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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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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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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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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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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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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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