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The Art of Asking Questions

An under-considered key to successful relationships, professional and personal.

Jose Miguels, Pixabay, Public Domain
Source: Jose Miguels, Pixabay, Public Domain

The art of questioning is an under-considered key to professional and personal success. It makes people feel cared about and you get to learn, especially if you ask good questions.

And we have more opportunities to ask questions that we may realize: At meetings even if just on Zoom, creating a family history or slideshow for a major birthday, interviewing someone for a job, or on a date, interviewing someone for your employer’s newsletter, or in your podcast. I have clients who set up podcasts specifically to improve their employability — they interview people they’d like to hire them.

Becoming a better questioner

Of course, it helps if you’re curious, but even if you’re not, recognizing the importance of questioning, pretend you are: “What questions would a curious person ask?”

Also key is to listen: Your best questions may be follow-ups to what the person said. When they’re talking, rather than mainly thinking about what you’re going to say, listen for a possible follow-up to ask. For example, “Can you give me an example? Or even just, “Tell me more.” But politely raising a counterpoint can also work: “I’m not sure how that would work because of X. What do you think?”

Start easy. No one wants to feel put on the spot. That’s why on quiz shows, for example, NPR’s Wait, Wait Don’t Tell Me, the host’s first question of a caller is, “Where are you from? “ And then, “Tell me something about the area.” Those are questions nearly anyone can comfortably answer. There’s time later to be more probing.

I’ll never forget interviewing Los Angeles Dodger legend Maury Wills. I started with easy questions like, “So what have you been doing since you retired?” But after he felt comfortable, I asked, “The Dodgers had a reputation of doctoring the baseball so that pitches dipsy-do. Was that true, and if so, any idea how they did it?" Wills admitted that he was responsible: After a strikeout, the catcher throws the ball around the infield, and when it came to Wills, he rubbed it against an emery cloth that he had hidden in his glove. If I had asked that question first, I doubt if he would have been so forthcoming.

Be disclosing. If you mainly ask questions, you risk coming off like an interrogator. Balance asking with telling, asking probing questions with making disclosures.

A few questions to keep in your quiver

As mentioned, the best questions often come in response to listening to what the person said, but these questions are good to keep in reserve:

  • What are you thinking about these days?
  • What are you looking forward to?
  • What might surprise me about (insert a topic s/he knows a lot about)?
  • What’s something not obvious about (insert a topic s/he knows a lot about)?
  • What’s the best and worst thing about X?

I’d be hypocritical if I didn’t leave you with a question. So, is there anything in the foregoing that you’d like to incorporate into your interactions?

I expand on this, including unrehearsed role plays on YouTube.

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