How to be questioning

Published 10:03 pm Wednesday, July 31, 2019

By Patrick Belcher

In the fundraising world when we usually discuss ASKING, it is about the solicitation of funds. This column is to discuss asking in its truest form, inquiry.

Today, we are a world of telling. We tell about our foods, we tell about our daily activities, our celebrations. We tell so much these days digitally that people feel they do not need to ask when we are face to face. In fact, we tell the person in front of us about what we see on their social media.

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To ask, to inquire, is a skill. As children we are masters of it, constantly just asking “why?” It is not important if we are confident in the responses (magic fairies can’t explain everything), but just that we received an answer. With age, we learn about the magical wizards — Google, Alexa and Siri — and ask them. Yet, they do not provide conversation.

Asking thoughtful questions is a valuable skill in any profession. In fundraising, it helps us to understand the motivation of our donors to support our mission. In sales, it helps to understand why someone would be motivated to change from what they are currently doing, whether that be buying a car, uniforms or anything else. In courtship, it understands what would motivate someone towards a second date.

To question is not a form of disrespect but an indicator of desire for knowledge, insight and understanding of perspective. The way we question also has the ability to lengthen or shorten a conversation. Responding to a question with questions like “why would you ask that?” or “what do you mean?” can communicate discomfort and shorten a conversation. Short quips, such as “really?” or “You don’t say?” or repeating the last few words, like “He did what?” could keep a conversation moving forward.

As a sales trainer, we would give new reps a set of questions to ask prospects. As we started training, the new salesperson would ask a question, and not listen to the response, but be waiting to ask the next question, missing the important information the prospect was providing. We knew they were ready for the “field” when the questions we gave were just guidelines and they were asking questions to discover certain content such as what they liked or didn’t like about current services or their decision making process.

In fundraising, questions are often conducted as formalities that get you telling heartfelt stories or the statistics that support your mission, rather than understanding the donor and their connection to the organization. It can be more about using your value proposition to support a donation request, than it is about drawing a connection between your donor and programs or mission to reach a natural next step, their support.

As wonderful and moving as many of the stories of our charitable organizations are, the right story to an individual motivates them, and it takes some inquiry to identify the right story. Whether we are discussing the aged in Haiti, or the children impacted by poverty, or even allowing a veteran to enjoy the arts, the right story matters. We only discover which story is best through solid inquiry. It is similar to understanding whether a movie or a picnic in the park is best for a second date.

Like any skill, inquiry needs to be practiced and polished. There are games we can play like the “Questions Game” from “Whose Line is it Anyway?” where the first not to respond with a question loses. Try engaging a teenager and getting more than three words at once. Or simply pick one of those social media posts and inquire about it: what was the favorite part; what happened after the picture/post; why would you recommend that place or activity.

The greatest part of any inquiry, can be the response and recognition of someone when they know you are really listening. A wise person once said there was a reason why we were made with two ears and one mouth. Use them proportionately and appropriately. Let me ask, “what was the best part of this column?”

Patrick Belcher works with local non-profit organizations. He can be reached at