“How many of your donors have made a planned gift?” A question like this, or really anything related to “planned giving,” strikes terror into your heart and the hearts of every other fundraiser I know, especially those who are not planned giving officers.

The concept of discussing something with your donor that will happen upon their death is a skill that many fundraisers have difficulty visualizing themselves doing. But here’s the problem: if you’re not having these conversations with your donor, you can be sure that some other charity is.

And my experience in working with donors for the past 40 years is that this conversation is natural for them. Many donors, especially older ones, have already dealt with issues of mortality, and we know from studies somewhere between 50 and 70% of individuals have some sort of plan that will take effect when they die. These are typically wills and living trusts, but they also include beneficiary designations, retirement plans, life insurance, and various charitable vehicles.

Studies have also shown that people who have done something in their estate plans for charity are often reluctant to tell that charity what they’ve done. Something on the order of two-thirds of people who’ve made a testamentary gift say they will not tell the charity. However, those people who want to tell the charity what they’ve done generally won’t do so unless the charity actually asks them. When I taught a planned giving course at a university in Chicago, I would bring planned gift donors to talk to the students. The students always asked why the donors told the charity about their plans. The answer was “because they asked.”

Have you asked your donor? If not, make a plan to do so. You will find that it is not as scary as you think it is.

And the simplest possible testamentary gifts are the ones you should be talking about to your donors. Contributing through a legacy society, making a gift through a will, or making a gift through a beneficiary designation in a retirement plan or other account are the most common ways for people to make planned gifts.

In order to make an appropriate and useful planned giving proposal to a donor, you also need to learn, in an authentic way, some information about that person’s family, business, investments, and tax situations. These conversations need to take place in a very natural way that doesn’t feel manipulative. Approach these conversations by continually asking permission to ask more questions and by focusing on remaining aligned with the donor throughout.

Your first step in these conversations is to talk to the donor about what they hope their gifts will accomplish at your charity. This does two things: It elevates their own view of themselves as philanthropists of their assets, not just donors of their income. And it often allows the fundraiser a chance to get information about what type of gift the donor has made (or plans to make).

Here are some conversation starters to help your donors talk to you about estate plans, financial information, and other relevant matters:

  1. “Many of our supporters have joined The Legacy Society as a way to show their commitment to our org. Could I ask you some questions about your legacy giving plans?” An alternative might be: “Many of our donors have found that there are low- or no-cost ways of making a legacy commitment. Commitments like this help to create sustaining support for our mission to continue to thrive. Could I share more about these opportunities with you?”
  2. “I’d love to learn more about what inspired you to create your business. Would you mind if I asked you some more questions about it? What does your business primarily do?”
  3. “I’m curious to know more about your investment approach. Would you mind sharing how you got started and what you hope to accomplish?”
  4. “Did you know there are ways you can use your retirement funds to make a charitable gift? Would you be interested in more information about that?”

As you listen for key indicators around planned giving potential, you may decide it’s time to introduce your planned giving officer, if you have one. For instance, “Mary is our Legacy and Gift Planning expert, and she knows a lot more about these things than I do. I know we’ve talked about your will / estate plan / our Legacy Society… may I ask Mary to share some ideas about wills and the Society with you?”

The goal is to learn specific indicators of planned giving potential, such as past experience making a planned gift; broader philanthropic activity including gifts of stock, gifts through IRA, or other non-case assets; business interests; investments; and concerns about income and/or taxes, as you build an authentic relationship with that donor.

It’s critical that these conversations come from a place of building trust and a focus on the donor relationship, not the money. As you continue to learn more about the donor’s charitable plans and their passions and interests, you can bring a proposal for how they can continue their legacy by making a charitable gift to your organization, such as a will bequest or making your charity a beneficiary in a retirement plan.

So, make a commitment to do two things with each of your qualified caseload donors: start a conversation with them where you’re asking permission to learn more about their charitable plans, such as if they have a will, and plan to present a proposal to donors who indicate that they have potential to make a planned gift. Taking these actions will help you get over any fears about planned giving, AND it will take the relationship with your donor to a whole new level.


Bob Shafis is the Director of Planned Giving Services at Veritus Group. He has been a successful fundraiser, speaker, and attorney for over 30 years, and programs under his direction have accounted for over $750 Million in major and planned gifts. As Director of Major Gift Planning at Chicago’s Museum of Science and Industry, and Director of Major and Planned Giving for The Field Museum, he participated in campaigns of over $200 Million each. Bob is a board member of the National Association of Charitable Gift Planners and speaks to national and local groups about planned giving, estate planning, charitable tax issues, and the process of fundraising.