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. 

159. Today’s Gifts, Tomorrow’s Legacy
Trent Thompson Trent Thompson

159. Today’s Gifts, Tomorrow’s Legacy

This is for major gift officers, development directors, executive directors, and board members at small and mid-sized nonprofits. You'll walk away knowing which donors to talk with about legacy, what to say, and who to bring to the table.

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158. Calming the Waters: Supporting Anxious Donors
Trent Thompson Trent Thompson

158. Calming the Waters: Supporting Anxious Donors

This is for major gift officers, development directors, and nonprofit CEOs who are watching good donors slow down. After reading, you will be able to spot the behavioral signals of donor anxiety, use four conversational moves that lower the emotional temperature, and offer five gift structures that make a large commitment feel safer.

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157. Growing the Next Wave of Major Gift Talent
Trent Thompson Trent Thompson

157. Growing the Next Wave of Major Gift Talent

This is for development directors, chief development officers, and senior major gift officers who want to grow the people on their team instead of replacing them every eighteen months. By the end, you'll be able to name what the fundraisers coming up now need, coach inside work you're already doing, and build a development plan in about thirty minutes.

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Trent Thompson Trent Thompson

Major Gifts and Digital Giving Experiences

This is for major gift officers, development directors, and executive directors who want their digital presence to support high-touch relationships instead of quietly undermining them.

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Trent Thompson Trent Thompson

Scenario Planning for Campaigns in a Shifting Landscape

This is for major gift officers, development directors, and executive directors who are running or preparing a campaign in an unsettled year. After reading this, you'll be able to:

  • Set one working goal and build three response scenarios around it

  • Name the assumptions your plan is quietly resting on

  • Talk to your board about uncertainty without losing their confidence

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155. Campaign Planning when the Future is Fuzzy
Trent Thompson Trent Thompson

155. Campaign Planning when the Future is Fuzzy

This is for development directors, major gift officers, and executive directors who are running or preparing a campaign and feel stuck waiting for conditions to settle. By the end, you'll be able to set a working goal and build three response scenarios around it, name the assumption your plan is quietly resting on, and talk to your board about uncertainty in a way that increases their confidence.

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Trent Thompson Trent Thompson

Reimagining Recognition and Naming in 2026

This is for major gift officers, development directors, and executive directors who want their thank-yous to match how values-driven and next-gen donors really want to be seen. After reading this, you'll be able to audit your current recognition practices, retire what's fading, and design one or two updates that center the mission instead of the donor's ego.

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154. Recognition That Feels Right Today
Trent Thompson Trent Thompson

154. Recognition That Feels Right Today

This is for major gift officers, development directors, and executive directors who want their recognition to match how values-driven and next-generation donors want to be seen. By the end, you’ll have a practical recognition audit to run, a way to distinguish meaningful recognition from vanity recognition, and a clearer framework for navigating sensitive naming questions.

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153. Building for What’s Next
Trent Thompson Trent Thompson

153. Building for What’s Next

In my recent conversation with Mark Stuart, President and CEO of the San Diego Foundation, one idea kept coming back to me:

Fundraising is not a department.

It is a team sport. Listen in to learn what that means in practice.

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Trent Thompson Trent Thompson

Listening Sessions and Donor Advisory Councils

This is for major gift officers, development directors, and executive directors who want to move from reporting at donors to genuinely listening with them. After reading this, you'll be able to design a simple listening touchpoint, decide whether a session or a council fits your situation, and capture donor input in a way that actually shapes decisions.

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152. Listening Sessions and Donor Advisory Councils
Trent Thompson Trent Thompson

152. Listening Sessions and Donor Advisory Councils

This is for major gift officers, development directors, and executive directors who want to deepen trust with their closest donors and move beyond one-directional reporting. By the end of this post, you'll be able to design a listening touchpoint, tell a listening session apart from an advisory council, and turn what you hear into decisions donors can actually see.

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Trent Thompson Trent Thompson

Building a Culture of Philanthropy Around Major Gifts

This is for major gift officers, development directors, and executive directors who are carrying the weight of donor relationships alone inside their own building. After reading this, you'll be able to describe what a culture of philanthropy looks like in practice, name everyday behaviors that build or erode it, and start one simple internal habit that spreads donor-centered thinking beyond the development office.

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151. Culture as Your Ultimate Major Gifts Strategy
Trent Thompson Trent Thompson

151. Culture as Your Ultimate Major Gifts Strategy

This is for major gift officers, development directors, and executive directors who feel like the only person in the building who thinks about donor relationships. By the end of this post, you'll be able to describe what a culture of philanthropy looks like in practice, name the small steps that shift it, and understand why your internal communication channels matter more than you'd expect.

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Trent Thompson Trent Thompson

Navigating Donor Power Dynamics and Boundaries

This is for major gift officers, development directors, and executive directors who want to honor generous donors without absorbing behavior that crosses a line. After reading this, you'll be able to name the power dynamics that show up in major gift work, spot the early signs a relationship is drifting out of balance, and use language that resets expectations while keeping the donor's dignity and your own intact.

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150. Healthy Boundaries with Major Donors
Trent Thompson Trent Thompson

150. Healthy Boundaries with Major Donors

This is for major gift officers, development directors, and executive directors who want to honor generous donors without absorbing behavior that crosses a line. By the end of this episode, you'll understand the power dynamics that show up in major gift work, you'll know the red flags that a relationship has drifted out of balance, and you'll have language you can use this week to reset expectations while protecting everyone's dignity.

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Trent Thompson Trent Thompson

Building Cross-Functional Major Gift Teams

This newsletter is for major gift officers, development directors, and executive directors who want to stop chasing information from other departments and start building it into the way your organization works. After reading, you will know who belongs on your internal coalition, how to run a meeting that respects everyone's time, and where to start if you have never tried this before.

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149. It Takes a Village: Internal Partners in Major Gifts
Trent Thompson Trent Thompson

149. It Takes a Village: Internal Partners in Major Gifts

This article is for major gift officers, development directors, and executive directors who want a practical way to bring the right internal partners into their biggest donor relationships. After reading, you will know why this kind of collaboration matters more in 2026 than it used to, exactly who belongs at your table and why, and how to run a coalition meeting that produces real next steps instead of another calendar entry.

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