Ask this. Get that. Why questions matter.

When I was fresh out of college, I had a conversation with my sister’s academic advisor, a Ph.D. in in immunology. He was giving me advice on how to get academics to explain their work in more detail. His advice, challenge them by saying, You don’t really believe that, do you? A great question to get people, not just academics, to talk.

The Case for Support and good questions

Are you asking long-lever questions?

Albert Einstein said, If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes.

Frances Peavey, an early leader in the use of strategic questions said, Questions can be like a lever you use to pry open the stuck lid on a paint can. . . . If we have a short lever, we can only just crack open the lid on the can. But if we have a longer

lever, or a more dynamic question, we can open that can up much wider and really stir things up. . . . If the right question is applied, and it digs deep enough, then we can stir up all the creative solutions.

The soul of the case comes from the interview and the strongest argument for a cause generally comes into view through long-lever questions. Short-lever questions provide for an–at best–average case. When you make your case, invest your best thinking into producing dynamic questions.

Things to keep in mind when preparing the interview.

1. Ask open-ended questions. You don’t want one-word answers, rather you want to pan for nuggets of information. Instead of asking if the charity has a good reputation in the community, ask the interviewees to describe the charity’s reputation. Or better yet, ask them how they think their neighbours would describe the charity’s reputation and role in the community.

2. Ask how, what and why questions. Think of a journalist’s go-to questions, the 5W+H: What, why where, when, who and how. What, why and how generally make  the most powerful questions. Explore on these them. For example: How do you think the new equipment will make a difference? in your opinion, what impact has this organization and its cause made over the past X years? With so many good causes in the community, why is it important to you to support this organization?

3. Ride the why. Why is a question that can never be fully satisfied. There is always another why waiting to be answered. A parent knows this well. [Why can’t I have a chocolate bar? // because we’re having dinner in 10 minutes // why are we having dinner in 10 minutes? // because we invited Grandma and Grandpa for dinner at 6:30 // why, why, why.] But there is a time and place for why questions. In fact, it can be most helpful to ask a series of why questions. Try it and you’ll find that eventually you will hit bedrock, that core reason or idea that makes you say, aha…go it.

4. Look for the relationship between the why and the how. Your case will be clear when you align the why of the cause with the how of how the funds will be used. This is elementary and obvious for some cases, but not for all.

5. Give yourself time. Prepare your questions a day or two in advance of the interview. When you review the questions, look, with fresh eyes, for ways to lengthen the lever.

6. Be curious. Go in to the interview with a lineup of good questions, and give yourself freedom to explore. It’s okay to detour from your plan, if you think it will provide you with good content.

One last thing. I attended a coaching workshop last year. The facilitator placed a rubber ducky on each of the session packages. She said this is to remind you to shut the duck up. When you meet with a donor or a volunteer (your partner or parent) listen, listen, listen. You don’t gather information when you are talking.

My question for you: If you had 45 minutes with a donor or a volunteer, what would you ask him or her?

For more on the art of powerful questions, visit

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