In 2025, successful fundraising is all about building genuine relationships, sparking meaningful dialogue, and offering donors opportunities to create long-term impact. One powerful yet underutilized strategy is integrating planned giving into major donor conversations. Planned giving refers to charitable contributions arranged in advance—often through a donor’s will, trust, retirement accounts, life insurance policies, or appreciated assets like real estate and stocks—to support an organization’s future. This article outlines how to do just that—naturally, effectively, and with confidence.
1. Lay the Groundwork: Be Strategically Prepared
Before you bring up planned giving with any donor, build a solid foundation by deeply understanding your organization. Know your mission, vision, strategic goals, and what you're raising money for and why. This ensures that you speak with clarity and purpose.
Key Tools for Preparation:
- A clear strategic plan
- A well-maintained donor database (CRM)
- Planned giving policy and procedures
You also need to understand the donor's goals:
- What do they want to achieve with their philanthropy?
- What types of assets are best suited to their giving?
- What are the basics of tax benefits and giving mechanisms?
You don’t have to be a tax attorney, but having a working understanding of capital gains, estate tax implications, and giving vehicles like bequests, donor advised funds, and charitable gift annuities can help create meaningful conversations.
2. Set the Framework for Meaningful Conversations
Nearly 90% of all donations are influenced by personal relationships. Wealth in the U.S. is highly concentrated, and the top 10% hold nearly 70% of the nation’s capital. This presents a clear opportunity for deeper, more meaningful conversations that spark generosity.
The secret? Ask great questions.
Use open-ended questions to invite donors into a thoughtful, reflective conversation:
- "Tell me about your journey as a philanthropist."
- "What do you hope to accomplish with your giving?"
- "What causes are closest to your heart, and why?"
- "Has anyone from our organization ever talked to you about planned giving?"
These types of questions create space for stories, reflections, and genuine connection. Listening is the most important thing a fundraiser can do. It’s what makes the work dynamic, interesting, and impactful.
3. Keep Conversations Donor-Centered
To build trust and understanding, guide conversations across three broad categories:
1. About Them
- Major life changes
- Family updates (births, marriages, retirements)
- Career milestones
2. About You (Your Organization)
- Strategic priorities
- Special initiatives
- Milestone campaigns
3. About the World Around You
- Current events
- Shared interests
- Hobbies, travel, mutual connections
These topics help create the relational glue that connects a donor’s life with your organization’s mission. Ask questions like:
- "What inspired your past philanthropic gifts?"
- "What legacy would you like to leave behind?"
- "What are your hopes and fears for the future?"
Yes, donors can be friends. Authenticity is essential. Let your mission lead, but know that real connection makes a lasting difference.
4. Embrace the Art and Science of Fundraising
You don’t have to be a fundraising expert to succeed. You just need to:
- Know your organization deeply
- Care about your donors
- Be genuinely curious
Fundraising is part science (data, strategy, planning) and part art (listening, adapting, inspiring). The best fundraisers blend both seamlessly.
5. Recognize the Right Moments for Planned Giving
Life changes often signal an ideal opportunity to introduce planned giving. Key moments include:
- A new grandchild
- The sale of a family business or real estate
- Job changes or retirement
- The passing of a loved one
- Establishing a family foundation or DAF
- Tax law changes
Helpful prompts to use in these moments:
- "How do you think this new job might shape your retirement goals?"
- "Have you considered including our organization as a beneficiary in your estate plans?"
- "I’d love to learn more about your family’s values and legacy."
- "Have we ever discussed the benefits of giving real estate or appreciated assets?"
Bonus Tip: As you get to know your donor, ask:
- "Who do you know that might share your passion for this mission?"
- "Have you ever thought about how your giving could inspire others to follow suit?"
6. Never Forget a Strong Follow-Up
A successful planned giving conversation isn’t about closing the gift on the spot—it’s about moving the conversation forward. Strong outcomes require preparation, research, and intentionality.
Here’s how to do it well:
- Go into the meeting with clear goals and questions.
- Be authentic, be interesting, and be interested.
- Take notes and record donor preferences in your CRM.
- Send a thoughtful and timely follow-up
- Offer to connect the donor with a financial advisor or estate planning resource.
Remember, these are long-term conversations. Building trust and planting seeds now leads to fruitful gifts later.
Final Thoughts
Your mission is worth it. Your donors are ready. And you’re the perfect person to bring these opportunities together.
Always lead with care. Never assume. Be brave enough to ask meaningful questions. Our organizations need the support, and our donors deserve the opportunity to make an impact that outlives them.
Legacy is about meaning. So go ahead and start that conversation.
Need help getting started?
Mighty Penguin offers hands-on coaching, strategy development, and storytelling support to help you lead confident, mission-aligned donor conversations—including planned giving. Whether you're creating a new program or strengthening what you already have, we're here to help. Reach out anytime at
