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Success in Planned Giving: A Move Away from the Transaction and towards the Relationship

Writer's picture: andyragoneandyragone

Updated: Nov 21, 2024

By Andy Ragone


Planned giving isn’t just a line item in a fundraising campaign. It’s something far deeper, richer—a relational journey. While most fundraising hinges on transactions, planned giving invites us into a shared story. A story of curiosity sparked, trust built, and visions aligned.


But let’s not sugarcoat it: planned giving is also about solving problems—specifically, the thorny ones tied to taxes. Through thoughtful education, authentic connection, and patient stewardship, this complex challenge transforms into a profound opportunity. Donors discover a path to turn their abundance into something lasting. Something unforgettable.


At Pleiades, we work alongside organizations of all stripes—large and small, sophisticated and scrappy. Each has its unique culture and mission, but they share a universal truth: passionate people make the magic happen. These are the individuals drawn to leaving a legacy. They’re not just donors; they’re co-creators of impact.


Simplicity: The Secret Sauce of Marketing Interest


Planned giving starts with marketing, but not the kind that overwhelms. Too often, we bury donors under layers of legalese, jargon, and complexity. A menu of four or five giving options? Analytics will show you the result: crickets.


Instead, keep it simple. One idea at a time. Drip those messages consistently—once or twice a month. Planned giving messaging isn’t a flash sale; it’s a slow burn. Let the

ember of curiosity catch.


When you speak about planned gifts, don’t just talk about the why—talk about the how. Show donors the specific possibilities. A gift that avoids capital gains tax while funding a cherished cause? A retirement plan beneficiary designation that saves heirs from a tax burden while driving transformative impact? An IRA donation that satisfies a Required Minimum Distribution for the year? Along with the why, these can be compelling motivators.


Tax Solutions with a Mission-Driven Twist


Here’s the reality: donors may give because they care, but they also care about their tax bill. And that’s not a bad thing. A well-crafted planned giving program turns tax problems into possibilities.


Frame your messaging to highlight both the heart and the head. Yes, your mission matters deeply. But when you show donors how they can give and receive income for life or redirect IRA assets to charity instead of the IRS, you’re speaking their language. They’ll see not just the impact, but the logic of generosity.


Community: The Fertile Soil of Generosity


Generosity isn’t just a transaction; it’s a culture. And cultures are built in community. Seth Godin says it best: “People like us do things like this.” Planned giving thrives when donors feel they belong—not just to a cause, but to a movement.


Legacy events and educational seminars become catalysts for connection. Imagine donors sitting around a table, swapping stories:


“Wait, you can give from your IRA? I didn’t know that!”

“I’ve been thinking about leaving an estate gift in my trust—how did you get started?”


That’s the magic. These shared moments don’t just educate; they inspire. Host events that bring together donors and professional advisors. Keep them welcoming, not high-pressure. Your goal isn’t a hard sell; it’s creating a space where donors feel seen, heard, and part of something bigger.


From Event to Relationship


An event is just the beginning. The real magic happens after the last handshake. Follow up. A coffee, a phone call, a Zoom chat—these are where connections deepen.


Here’s the secret: listen more than you talk. Ask questions about their goals, their challenges, their dreams. People give when they feel understood. And they give more when they see how giving benefits not just your organization but also their own family, finances, and legacy.


Use the spark of an event to ignite the flame of a relationship.


Stewardship: The Long Game


The biggest gifts aren’t made in a moment. They’re made in the context of trust, built brick by brick over time. Stewardship isn’t about pressuring for a quick yes. It’s about consistent, meaningful touchpoints—stories of impact, shared victories, and quiet moments of possibility.


“Imagine what could be…” Those words invite donors into a vision, not a pitch. They open the door to a journey, not a transaction. And when the time is right, those seeds of possibility bloom into something extraordinary.


The Big Picture: Vision and Discovery


Planned giving isn’t about closing deals; it’s about opening doors. When a donor’s values align with your vision—and when the numbers make sense—they’ll take the step not because they were convinced, but because they were inspired.


This is how legacies are built: not with urgency, but with intention. By showing donors how their impact can last far beyond their lifetime, you’re not just securing gifts. You’re inviting them to co-create a future that matters.


Make It Happen


Planned giving isn’t just a fundraising strategy; it’s an art. The art of listening, of inspiring, of walking alongside donors as they discover their capacity for impact.


So, keep it simple. Keep it human. Plant seeds of possibility, nurture them with patience, and watch as generosity blossoms into a legacy that transforms lives—for generations to come.


Let’s get to work.



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