How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations

How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations

A couple of weeks ago, I was hosting an in-depth workshop about getting comfortable asking for money. The attendees were engaged and enthusiastic until the topic shifted to planned giving. “How do you even touch on that topic? What a downer, talking about death!” That’s when I realized that planned giving is all about death and taxes – two topics almost guaranteed to make Americans squirm in their seats.
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Yet if you’re looking to secure a sustainable future for your nonprofit, these conversations are essential. By addressing them with grace, you can help donors plan for their future, maximize tax benefits, and leave an enduring impact. Let’s explore strategies to make these conversations feel natural – and even inspiring – by knowing who your planned giving prospects are, leveraging real-life testimonials, and using content to pull donors in who are already interested in these giving options.

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The Great Wealth TransfeR

The "Great Wealth Transfer" refers to the projected shift of substantial assets from the baby boomer generation to younger generations over the coming decades. Estimates suggest that approximately $84 trillion will be transferred in the United States by 2045, with $72.6 trillion going directly to heirs and $11.9 trillion allocated to charitable causes. 
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Planned giving isn’t just another giving option – it’s a missed opportunity if left unaddressed. 

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Who are Your Planned Giving Prospects?

When it comes to planned giving, the biggest mistake nonprofits make is assuming that only the wealthy are viable prospects. The truth is, the best predictor of a planned gift isn’t the size of someone’s bank account – it’s their loyalty. Research consistently shows that donors who make bequests aren’t necessarily the ones writing big checks during their lifetime. Instead, they’re the steady, long-term supporters who have been giving consistently for years (James, 2013).  If someone has been giving $25 or $50 every year for the last 20 years, they might not look like a major donor, but they could be one of your most important legacy prospects.

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Age and Timing MatteR

People tend to create or update their wills during significant life transitions – getting married, having children, retiring, or facing a health scare. While the median age for making a first will hovers around the 50s or 60s, that doesn’t mean you should wait to talk to your donors about legacy giving (Caring.com, 2023). 

If you’re only marketing planned giving to seniors, you’re missing the opportunity to reach people when they’re making their very first estate plans. A donor might include your organization in their will at 35 and revise it multiple times over the years – but once a nonprofit is in, it’s much more likely to stay.

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Engagement, Not Wealth, Drives Legacy GivinG

​The best planned giving prospects are those who feel deeply connected to your organization – volunteers, board members, monthly donors, and those who show up at events year after year. They may not see themselves as philanthropists, but they already view your nonprofit as part of their story. Engagement builds the kind of emotional investment that leads to legacy gifts. Fundraisers who focus only on wealth indicators will miss some of the most committed, mission-driven donors out there.

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Shift the Focus: It’s All About LegacY

Instead of letting the conversation dwell on death, reframe it around the idea of legacy. (Cue that clip from Hamilton “A legacy is planting seeds in a garden you never get to see.”) Planned giving is less about what happens when we’re gone and more about how we can continue to support the causes we care about in perpetuity: a planned gift is a way to ensure that one’s values and passions live on.

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The Annual Donor Endowment ConcepT

What if your most loyal donors could turn their yearly gifts into a source of funding that lasts for generations?
Explain it like this for donors who give year after year,: "Imagine converting your annual support into a lasting endowment. By designating [your nonprofit] as a beneficiary in your estate plan or including a bequest in your will, your commitment can live on, providing stability and growth for our mission indefinitely."

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Attracting Leads Through Content CreatioN

​Rather than waiting for donors to approach you about planned giving, take a proactive role by creating engaging, informative content.

• Write Educational Blog Posts: Cover topics like the benefits of planned giving, how to set up a bequest, and donor success stories.
• Host Engaging Webinars: Invite estate planning experts to break down the process in easy-to-understand language and answer common questions.
• Offer Downloadable Resources: Provide guides, checklists, and templates that donors can reference when planning their gifts.
• Celebrate National Estate Planning Awareness Week: See this blog post about the power of rolling out concentrated planned giving content via email, social media, and video once or twice a year. ​Utilize testimonials: Nothing is quite as powerful as a peer recommendation, and that’s true even in planned giving. Highlighting donors who have already set up planned gifts for your cause is a winning strategy.

These content pieces not only educate your audience but also position your nonprofit as a trusted resource in an often-complex area of giving. All of this content should drive interested prospects to a web form where they can contact you if they want more information or guidance or if they have already set up a planned gift to benefit your nonprofit but haven’t let you know yet. Conversations are a lot less awkward when the prospect has already expressed interest in discussing planned giving opportunities.

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Practical Tips for Successful ConversationS

1. Keep It Simple: Use plain language and avoid jargon. Explain terms like “bequest” and “beneficiary designation” in everyday language.
   • Example: "A bequest is simply a gift you include in your will. It’s a way to ensure that even after you’re gone, your values and support for our cause continue to make an impact."
2. Use Consistent Messaging: Develop conversation scripts or guidelines that incorporate testimonials and the endowment concept. Having a consistent approach helps build confidence – for you and your donors.
3. Create a Resource Hub: Dedicate a section of your website to planned giving. Include FAQs, step-by-step guides, and downloadable resources.
4. Follow Up Thoughtfully: After your initial conversation, send a personalized thank-you note or follow-up email summarizing key points and offering additional resources. This reinforces that you’re there to support them throughout the process.

Planned giving isn’t about difficult conversations – it’s about meaningful ones. When you shift the focus from death and taxes to legacy and impact, you create opportunities for donors to shape the future of the causes they care about. By fostering engagement, sharing inspiring stories, and providing clear, accessible resources, you make it easy for supporters to take the next step. Start normalizing these discussions today, and you’ll find that donors are not only willing to talk about planned giving – they’ll be grateful you opened the door.
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Cheers!

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