Where big bequests really begin

By Diana Coyle, CICF Director of Nonprofit Services and Sustainability 

Every organization has heard the story of the gift nobody saw coming. A longtime supporter leaves a major endowment gift through a will, trust, IRA beneficiary designation, or other legacy plan, and the staff learns about it after the fact. It’s natural to wonder, “When is our big gift coming?”

Sometimes the surprise is real. Most of the time, though, the seeds were planted years earlier. The donor gave modestly but consistently, the organization stayed in touch, and a staff member learned why the mission mattered. The relationship deepened over time, and eventually the donor included an endowment gift in an estate plan.

Don’t underestimate the donor who gives $100.

It’s easy to focus on donors who can make large gifts today. But today’s $100 donor could be tomorrow’s loyal annual donor, and someday could leave your organization a significant portion of an estate.

2026 gives you a timely reason to engage donors at all levels. Beginning this year, taxpayers who do not itemize deductions may deduct up to $1,000 in qualifying cash charitable contributions, or $2,000 for married couples filing jointly. Taxes shouldn’t become the centerpiece of your message, and your mission should always lead. Still, it’s one more reason to reach out to people who give at modest levels or haven’t yet become donors. Consider a simple message:

New for 2026! Taxpayers who don’t itemize deductions may be able to deduct up to $1,000 in qualifying cash charitable contributions, or $2,000 for married couples filing jointly. If you’re considering gifts to charity this year, [ABC Charity] would be honored to be included. Thank you!

Keep in touch. The person making a $100 gift today may matter to your organization for decades.

Make endowment giving feel accessible, not exclusive.

If every message about your endowment features six- and seven-figure gifts, donors may conclude that endowment giving isn’t for them. Help them see that an endowment is something everyone can help build. A $250 gift, a $2,500 gift, a gift of appreciated stock, and a future gift through a will, trust, or IRA beneficiary designation can all strengthen your organization’s long-term future. You might say:

We invite you to support [ABC Charity]’s endowment fund at whatever level fits your charitable giving plans. Every gift, from a $250 online donation to appreciated stock to a future gift through your will, trust, or IRA beneficiary designation, helps strengthen our organization for the future, and we are grateful!

Not every donor needs to give to the endowment today. Every donor should understand that supporting it isn’t reserved for someone else.

Plant more than one legacy seed, and a lot more.

Communicating endowment and legacy opportunities isn’t a one-and-done effort. Repeat it in different ways and through different channels. A donor may hear you mention a legacy gift today and barely notice. Six months later, that donor reads a story about what your endowment makes possible. Two years from now, the donor is updating an estate plan and passes your website URL to an estate planning attorney.

You don’t need an endowment or legacy ask in every communication. Mention legacy and planned giving often enough that plenty of seeds get planted, so donors know your organization is focused on today’s needs and tomorrow’s mission.

We’d be glad to talk with you about planned giving, legacy giving, and ways we can help administer and manage your endowment or reserve fund. Use the form below to get in touch.

About the author

Diana Coyle, director of nonprofit services and sustainability, is dedicated to helping Central Indiana nonprofits access the tools, knowledge, and relationships they need to thrive. In collaboration with her CICF colleagues, she supports CICF’s nonprofit partners by offering professional development, resources, and technical assistance that strengthen organizations and their leaders. With more than 15 years of experience in leadership and community engagement, she is committed to fostering connections that amplify the missions of nonprofits and create lasting impact across the region.