In the reality TV show The Bachelor, the rose ceremony at the end of most episodes marks a clear moment of decision. A rose isn’t a proposal, but it is an unmistakable invitation to move the relationship forward. Both sides understand what is being asked and what it means to say “yes.”
As a planned giving professional, you probably don’t hand out roses, but you are responsible for creating moments of clarity where a donor understands that the next step isn’t just continued interest, but commitment.
One of your defining roles is helping donors move from connection to commitment. Whether the conversation is delicate or direct, the invitation to make a planned gift allows donors to turn intentions into impact. For those who want to create a heartfelt legacy, a thoughtful ask can be a true act of service when it’s approached with care, clarity, and follow-through.
From Interest to Commitment
If asked who your secret admirers are, you could probably think of supporters who care deeply about your organization but haven’t yet formalized that commitment. A clear ask invites them to take intentional, future-focused action to support your work as part of their financial or estate plans, such as:
• Updating estate documents to include your organization
• Designating your organization as the beneficiary of their life insurance, retirement accounts, or donor-advised funds
• Signing a letter of intent or bequest confirmation
When a donor commits, everyone benefits. The donor expresses their values with an enduring impact, while your organization gains greater financial stability and planning clarity.
Asking as a Promise, Not a Pitch
Often, the question is not whether to ask—but how.
In planned giving, words matter. The ask is not just informational; it’s relational.
A pitch goes in one direction. Someone delivers information, describes the impact, and makes the ask. No matter how well intentioned, this approach risks feeling transactional. It isn’t likely to deepen the relationship.
A promise is different. It’s a two-way conversation grounded in mutual respect. The donor commits to a future gift that will help sustain your work for decades to come. In return, your organization commits to honoring the donor’s values and intentions over time. That sense of mutual responsibility builds trust and reinforces that the relationship doesn’t end with the “yes.”
Reflecting on Your Approach
If you’ve been working in planned giving for a while, you likely do these things instinctively. Still, it can be useful to take a step back and reflect on whether your approach consistently reinforces commitment as a shared promise.
• Create space for genuine conversation. Building rapport is the start of a personal connection that sets a collaborative tone. This isn’t just small talk—it helps donors feel seen as individuals, not just as prospects.
• Listen for the donor’s true motivations. Ask open-ended questions about the donor’s values, priorities, and personal history with your organization (or with philanthropy in general). This often reveals much more than a purely technical discussion about gift options and financial goals.
• Connect their priorities to your mission’s future. As donors share what matters most to them, reflect those values back through the lens of your organization’s long-term work and impact.
• Close with clarity and mutual commitment. Invite the donor to take a concrete next step. Be explicit about your organization’s commitment to stewarding their gift as intended.
• Address hesitation with curiosity, not urgency. Hesitation often signals an unresolved question, not a lack of interest. More listening is usually the answer.
• Offer clear next steps and support. Once a donor is ready, guidance around options and implementation helps transform intention into action.
These conversations aren’t about planning for death. They’re about planning for continuity—carrying mission, values, and impact into the future. Done well, the ask is collaborative, forward looking, and affirming.
When a donor says “yes” to a planned gift, they’re expressing trust in your organization and belief in its value and its future. Even without a rose, that commitment can mark the beginning of a deeply rewarding partnership.
