The Best Questions Gift Officers Can Ask to Move Prospects Toward Solicitation

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Knowing how to turn a discussion with a prospect toward a specific gift commitment requires intuition and skill. It is a matter of timing that requires us to know where each prospect is in the philanthropic decision-making cycle.

This we know: From the time we begin the philanthropic dialogue with a prospect until she or he makes a significant commitment takes, on average, 21 months and involves nine interactions.

The following advice, therefore, assumes that the prospects you’ve selected have given previously to your institution for years or have given elsewhere for an extended period of time.  It further assumes that you have had at least three or four earlier interactions in which you have determined that your prospect:

  • Has genuine philanthropic intent,
  • Believes in the agency of your institution to convert philanthropic investment into tangible institutional and/or societal gain, and
  • Is either an institutional supporter (think long-term donor or very active donor) or a supporter of one part of the institution (arts, athletics, sciences, etc.).

Engaging the Prospect Early

If all of the above are true, you can begin to turn the dialogue toward investment by saying that you would like your prospect to become more deeply engaged in the direction-setting of the institution or in the realization of important goals.

Then, ask any of the following:

  • Would you take a look at a very early draft, perhaps a white paper, describing a new initiative (or describing the next stage goals for an ongoing program), and give us your very candid assessment?
  • Would you join in a small-group discussion (or focus group) to help us develop an idea that is just beginning to take shape?
  • Can I introduce you to X (a thought leader, project leader, campus official, student activity leader)?  I would like you to see and hear about what they’re trying to achieve.  You really have to see it to fully appreciate the potential, and we’d really benefit from your counsel.
  • Your experience would be so relevant to what we’re trying to achieve. Can I put you together with the project leaders so they can learn from it?

These questions are designed to prompt early-stage engagement and to give the prospect a voice in the development of the project, which demonstrates that you value their time and talent. This is a far more certain way of securing their treasure than springing on them a fully developed idea, perhaps described in a well-produced video or a four-color brochure. The latter is abrupt, gives the prospect much too little time to appreciate or take ownership of the initiative, and makes its clear that you are only interested in them for one purpose: securing their funds.


If you are enjoying this article, you might also find Jim Langley’s in-depth fundraising guides useful:

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The Soft Ask

If you have already introduced or engaged your prospect in a particular initiative, and you have seen them grow more enthusiastic, you could, depending on the prospect’s level of enthusiasm, try a “soft ask” such as:

  • I think you now see, and are helping us see, what is possible. Can we open up discussion about how we might earn your support? Is that something we can do soon?
  • Can I share the project budget with you? I’d like to make sure you think it’s reasonable. Can you see yourself getting behind it?
  • May I bring you a specific proposal? I’d like to see if it corresponds with your thinking and talk through how we can begin to realize these important objectives.

Prospects make big decisions by degrees and over time. If we work them, demonstrating the art of patient persistence, and ask the right questions at the right time, we allow our prospects to tell us when they are ready to move to the next step. There is no more certain way.