A few weeks ago I tossed a simple prompt on LinkedIn: “You only get 1 discovery question to use for the next six months—what are you asking?”

Sixty-seven donors, fundraisers, and coworkers jumped in. (Thank you!) Their answers were funny, wise, and deeply practical. If you’re heading into Q4—calendar invites stacking up, year-end goals staring back—this crowd-sourced wisdom can sharpen your next conversation and your results.

Here’s what rose to the top, with the best examples you can use verbatim in your donor meetings.

Five Patterns from the Pros

1) Start with the heart (JOY & WHY).
Questions that target identity and values unlock trust—fast.

• “What gives you joy?” (Mark DeWitt)
• “Why do you give, even when you don’t have to?”
  These invite donors to talk about who they are, not just what they fund.

2) Invite a story (ORIGIN & MEMORY).
Stories reveal priorities, mentors, and defining moments.

• “What’s your earliest memory of generosity?” (J. Paul Fridenmaker)
• “What is your testimony/story?”
  If you hear a story, you’ll also hear how to serve.

3) Aim time-forward (VISION & OUTCOMES).
Give the conversation a horizon so you can work backward.

• “Five years from now, what story would you love to tell about your impact here?” (Katelyn Baughan)
• “What do you hope to accomplish with your giving?”
  These turn vague goodwill into measurable, shared goals.

4) Widen the frame (NO LIMITS).
Removing constraints surfaces true priorities.

• “If you had a magic wand for your philanthropic capital, what would you do—and why?” (Tyler Murphy)
  You’ll walk away with a roadmap instead of a guess.

5) Keep the door open (PROBE & PAUSE).
The Swiss-army knife of discovery:

• “Tell me more.” (credited multiple times)
  Ask it, then wait. Silence is your ally—answers get richer on the second beat.

Ten High-Utility Lines You Can Use Tomorrow

Mix and match one of these with “tell me more” and a long pause:

1. What gives you joy?
2. Why do you give, even when you don’t have to?
3. Five years from now, what story would you love to tell about your impact here?
4. What’s your earliest memory of generosity?
5. If you could change one thing in the world, what would it be?
6. Looking back on what you’ve supported, what impact made you most proud?
7. What excites you about our work?
8. What prompts your heart to give generously?
9. You have many places to give—why us?
10. If nothing were off-limits, what would you want to accomplish with your giving—and why?

Pro tip: For organizations with multiple initiatives, #7 (“what excites you about our work?”) quickly reveals program fit. For legacy conversations, #6 and #8 move you to values, family, and time horizons that matter.

A Simple Q4 Discovery Playbook

When your calendar is packed and attention is scarce, simplicity wins. Try this:

1. Open with gratitude—specific, not generic.
   “Thank you for your monthly gift and the note you sent about ___.” Specific praise earns the right to ask a deeper question.
2. Ask one question from the list and stop talking.
   Let silence work for you. Count to five slowly if you need to.
3. Use the probe.
   “Tell me more.” or “Why is that important to you?” Once. Maybe twice. Then listen.
4. Name the outcome you heard.
   “So if five years from now you’re telling that impact story, the big milestone this year is ______.”
5. Offer the next right step.
   “Would you like to see a plan for how we could make that happen together by June 30?”

Why this matters now

Year-end generosity is real, but dollars follow clarity. The clearer you are on a donor’s why, the easier it is to co-create a plan that respects their story and advances your mission. Remember: fundraising is an act of service—an invitation to transformation for donors and beneficiaries alike.

I’m grateful for the 67 voices that sharpened this conversation. We’re better together.

Your turn: What’s your single best donor discovery question? Hit reply and share it with me. I’ll compile the most helpful ones, and I might feature yours (with credit) in a future post so the whole community can benefit.

Email

Subject: {First Name}, what’s your one go-to discovery question?
Preheader: 67 practitioners weighed in—now I want yours (hit reply and tell me).

Hi {First Name},

Quick one for you.

I published a short Linkedin Post crowd-sourcing the one donor discovery question you’d use for the next six months. Sixty-seven fundraisers, donors, and coworkers chimed in. There’s decades of fundraising experience represented there for Q4 touchpoints and year-end visits.

Here’s why this matters: when we ask better questions, we hear real stories, surface values, and co-create plans that actually get funded. That’s the difference between a “nice visit” and a meaningful next step.

Would you hit reply and send me your single best discovery question?
Bonus points if you add one line on why it works.

Then skim the roundup for fresh language you can use this week:
👉 [Read: The One Discovery Question Roundup] (link)

If you’re crunched for time, borrow one from the post, add “Tell me more,” and let the silence do the heavy lifting.

Grateful for you, {First Name}. Let’s make Q4 conversations count.

—Jon

P.S. If your question made a donor light up recently, tell me the setup you used (where, when, and how you asked). I may feature it—with credit—in a follow-up.