The Questions That Shape a Legacy | Sharpe Group
Posted February 2nd, 2026

The Questions That Shape a Legacy

question words- legacy

When donors share their desire to support your charity in their long-term plans and leave a legacy, the conversation can often get stuck on details—wills, beneficiary designations, percentages, timelines—or become too transactional, potentially turning off some of your donors.  

Though details are obviously essential to the estate planning process, guiding donors through their gift planning doesn’t start and end with choosing the right vehicle or securing short-term donations with a Shark Tank-style pitch (whether or not your organization has a quota to meet). Donors are the people who ensure your organization can fulfill its mission today, tomorrow and fifty years from now—they are not potential investors.

Stewarding your donors should begin with two questions: Who are you, and what legacy do you want to create for yourself and your loved ones? 

The answers to these questions demonstrate values and the impact a donor wants to achieve now and in the future.

Many donors find that thinking about their giving philosophy clarifies their vision. Instead of asking, “How should I give?” the focus shifts to “What matters most to me?”

In one of our recent Sharpe Insights: Conversations With Your Planned Giving Experts podcast episodes, we spoke with Dr. Russell James about “Socratic Fundraising”—helping your donors articulate their own legacy goals by asking leading questions. He gave us some great examples, and I highly recommend listening.

Ultimately, we’re not selling a planned giving product to donors—we’re building relationships based on their values. A good starting point is to consider what you should avoid asking a donor:

  • We really need some funding. How much can you leave us?
  • Have you included us in your will yet?
  • Don’t you think you’d feel better about yourself if you supported our mission?
  • What assets do you have?

These types of questions are suitable for a car salesperson—social pressure, the bandwagon approach, the illusion of scarcity—but they can undermine trust and seem too transactional. The aim is not to pressure donors but to build relationships with them. 

Planned giving can be very personal, and donors have many different reasons for including your organization in their plans—such as lived experience, faith, gratitude for help received along the way, or a desire to make an impact on the world in ways that matter to them. Here are some open-ended questions that might serve as a helpful starting point: 

  • What kind of impact do you want to make on the world?
  • What values do you want your generosity to reflect?
  • What are your hopes for the future?
  • What is your connection to our organization, and why does our mission mean so much to you?

These questions aren’t about getting things “right.” They’re about making room for reflection. Planned giving stewardship is an ongoing conversation shaped by the values, hopes and priorities that form a donor’s vision of the legacy they want to leave behind. 

By understanding your donors’ motivations—and ultimately helping them understand their own—we help them leave a strong legacy that reflects not just their goals, but the values that matter most to them and their families.

Grant Miller, Sharpe Senior Editor, planned givingGrant Miller is an award-winning writer and editor for Sharpe Group, Sharpe Insights newsletter and blog contributor and host of the Sharpe Insights Podcast. Connect with Grant via email or LinkedIn.

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