Is there anything more impactful to a meaningful philanthropic solicitation than truly understanding your prospect’s motivations, feelings, and values – not just about our organization, but about their lives?

These factors are the very foundation of helping our donors achieve their fullest giving potential, and in turn create the greatest impact.

The use of probing questions is one of the best tools in a fundraiser’s kit to make such solicitations. These questions are critical to the three keys to bringing allies on board for our organization: Assume less. Accept more. Listen well.

What are probing questions? They are follow-up questions that ask for additional information on what your prospect has said, or ask your prospect to give even deeper insights into her thoughts. By “going deeper,” you demonstrate your interest and desire to understand your prospect, and you are able to:

  • Set the stage for a successful strategy by obtaining information that will lead to better decisions and outcomes
  • Assess situations from a variety of vantage points
  • Move a relationship from conversational to transformative, built on creating trust with your prospect
  • Ensure you see issues from your prospect’s perspective, including anticipating objections to a solicitation
  • Open a dialogue where your prospect asks you questions, allowing you to best match her passions with institutional priorities

Probing questions are transformational. Imagine if we all accomplished each of the items listed above in our prospect meetings – our giving conversations would increase in both efficacy and frequency! So ask yourself in your next meeting, “Am I truly seeking to understand? Did I ask How did you decide…, Tell me more about…, Why do you think…?”

We should remember that when we authentically ask and listen,

  • We are fully attentive to the other person
  • We ask questions that are not leading, diagnostic, or confrontational
  • We listen to comprehend
  • We expand our ability to match the passion and mission of our donors to the passions and missions of our organization

The more we ask thoughtful questions, the more thoughtful our donor relationships become … and the more effective we become in raising the critical funds that our institutions rely upon to do their good work.

I will be sharing more about probing questions in my book, Productive Conversations with Donors: A Handbook for Frontline Fundraisers. It shares specific questions that I’ve seen used to great success, discuss how these questions can help overcome objections, and more.

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