The Big Question

Once you’ve passed the age of 11 or 12, it becomes difficult to ask someone for a gift.  And yet, for non-profits to be strong and well positioned for growth, getting charitable gifts is vitally important. Asking the question is part of the process; getting a yes is another.  For that, you must have a good reason—or case—to convince the prospect that a gift will be beneficial not only to your organization but also to the prospect.

Asking for an endowment or legacy gift is takes this to a whole different level.  In order to get a yes for this kind of gift you need to first discover who in your prospect pool is long-sighted, and what hopes and desires they have for the organization’s future.  You have to be able to dream with them and show them how an endowment or legacy gift can meet their aspirations.  Getting there doesn’t come easy, and it doesn’t come quick.

The time commitment is one reason why working in teams works best for gifts that require long-range cultivation and sophisticated solicitations.  Endowment gifts are often planned gifts—coming out of someone’s assets and not their current income.  That requires a level of knowledge and comfort about talking about ways of giving that is not often required with an annual gift.

Endowment gift teams are comprised of both volunteers and professional staff.  Typically, the development director acts as the glue that holds the process together.  He or she is the person who ensures that the process moves forward and that all other parties have the information they need

The most important member of the team is the person who can say to the prospect “Join with me in supporting this important initiative.” That means that this person must also be a donor, preferably having given a gift at the level you hope you will get from the prospect. From that start, you must discover the donor’s values and how those values can be extended beyond their lifetime through an endowment gift.  In all your visits, therefore, you must be listening more than you are talking.

Your first meeting will, of course, require that you tell the prospect about the endowment program.  The best way to start that is for the lay leader to describe his or her commitment to the program and why it is so important to the lay leader and the organization.  As you share this information make sure you are doing it in a way that will resonate with that prospect.  Why would he or she care?  Ask open-ended questions and really listen to the answers.

This first visit is meant for you to gauge the prospects true interest in supporting your organization with an endowment gift.  One way to ensure that there is real interest is to end the meeting by setting a date for the next visit.  At that next meeting—and the following ones—there are a number of questions you really want to get answered:

  • What are the prospect’s primary interests and values?
  • Is there additional information about the endowment or the organization the prospect wants or need?  If so, what would be most helpful?
  • Are there specific programs or recognition opportunities that are of special interest?
  • What are the prospect’s personal and family circumstances and ambitions?
  • Is endowment of interest?  If not, what else might be?
  • Are you already remembered in his or her will?  If not, would they consider that?
  • Is there a specific planned gift technique beyond a bequest that might be of interest?
  • Who else would the prospect need or want to meet with?

Once you know the answers to these questions, you are ready to move on to developing gift plan that speaks to the prospect’s basic motivations; motivations that will inspire your prospect to say yes when you ask that big question:  Will you join with me?

Janet Levine works with nonprofits and educational organizations, helping them to increase their fundraising capacity—and, through legacy and endowment gift programs, ensure their future.  Learn more at