Thoughts

The Dying Art of Asking Questions

By nature, I am a curious person — annoyingly so. My parents never complained about it, though I was definitely the “why?” child. While I’m sure this can be outwardly irritating, as an adult this practice keeps me well-informed on things of immediate or peripheral importance; a valued skill in nonprofits.

In recent years, however, I have noticed a downward slope with regard to asking questions, and this comes on all sides. Board members who express little interest in knowing what’s happening; staff who miss opportunities to learn more about the organization’s direction; “leaders” who make decisions based on internal feelings rather than seeking input. While not attempting to break this down on a systematic or psychological level, from my direct experience I’ve surmised a few roads which lead to lack of questioning:

  1. Time. “There are only so many hours in the day; I don’t have time to seek feedback and input when things just need to get done.”
  2. Fear. “Gosh… what if I get an answer I don’t want, or don’t like?”
  3. Ignorance. “Oh, wait, was I supposed to ask someone about this?”
  4. Ego. “I know better than everyone, so why would I waste my time asking questions to which I already know the answer?”

Those things all read badly, though not all of them come from a bad place. How many of us enter a situation where — sorry for using this phrase, but — we don’t know what we don’t know. The people before us didn’t keep running records or manuals, the staff has 100% turnover so there’s no institutional knowledge, and the Board are nowhere to be found for inquiries.

For whatever reason, we are losing the drive to be curious. Lack of creativity and inquisition are an issue in schools with children, but gosh, it’s an atrophying skill in adulthood too. In organizations, some of this is a top-down issue. Years ago I worked in places where questions were frowned upon, because how dare you question the all-knowing executive director.

I am, however, finding pockets of hope. I very recently joined the Board of a scrappy (their word, not mine) creative nonprofit, which has been enlightening. At each meeting, I talk with the team about fundraising, future planning, etc., and to my surprise… they ask a lot of questions. There are things about which they don’t know, and they want to know. As a volunteer, it’s kind of amazing to see the lightbulbs go off, but that really only happens when people ask genuine questions, and genuinely want to know the answers.

AskAway

This is creepy but cute, right?

As a fundraiser, I believe there is an art to asking questions. Some of the best visits I’ve had with donors and prospects end with the people saying things like, “Gosh, it was so nice learning about you!” In reality, I’m simply asking questions about them (some guided, some open-ended), which get conversations moving. It’s not simply “What are you interested in supporting and can we have your money so we can do that?” Rather, it’s asking about their experiences, what interests them, what organizations they believe are doing great work, where they see philanthropy making a difference, and so forth. Little of that is about “me” or “my work,” yet at the end of a good conversation, you can paint a nice little picture, simply by asking questions.

So ask away, friends! Ask genuinely and honestly. People want to share, and sometimes it simply takes a little prompting. “The smart ones ask when they don’t know,” mused Malcolm Forbes, “…and sometimes when they do.”

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3 thoughts on “The Dying Art of Asking Questions

      • I’m a thinking coach, so I ask thought-provoking questions all the time. Today I asked a question related to the 1911 theft of the *Mona Lisa*, which is credited for bringing fame to the painting: “Can you think of other similar scenarios, in which something bad ended up being something good?” The title of my most recent blog post is a question: “What did Mr. Rogers think about?”

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