The Art of the Question

Ever notice that the person in the room who is often most revered is he/she who asks really good questions?  It’s true.  Observe very carefully the next time you sit in on a Q&A session following a lecture or in a meeting.  All eyes turn to the first person who asks a great question – all minds think, “What a great question.  Why didn’t I ask that?”

The best questioner I can think of is WHYY’s Terry Gross.  I listen to her on NPR’s “Fresh Air.”  She is a highly skilled interviewer and I am always amazed at how she gets her guests to open up.  I love how she probes and urges her visitors to go a layer deeper… then another layer deeper… then another.  And, none of it sounds scripted.  Oh, like any good interviewer, I’m sure she goes in prepared – at least knowing a bit about her guest’s interests, expertise, background, but the interviews themselves are so authentic, so real, so raw.  She seems to start the interview with one key question – usually about their latest project – but the rest of the conversation flows so organically.  The listener usually learns something about the guest’s upbringing, early career, passions.  I suppose the best explanation for why all of her interviews sound so natural is that, simply put, they are.  She listens – really listens – to the guest’s initial response, then asks the next obvious question.    Even those guests who seem reticent to respond come back with personal, thoughtful, thorough answers – when they don’t, Terry asks another question to get them talking.  And, hey, she’s Terry Gross, so it stands to reason that perhaps she has some license to ask the more probing, more personal questions – we might not all have that type of authority – but paying careful attention to her style can be very instructive and I believe we all could learn a thing or two by listening to some of her interviews.  [Here are a few relatively recent interviews that I particularly enjoyed:  Alice Waters; Brad Pitt; Gillian Welch & David Rawlings]

I continue to be intrigued by this notion that it is critically important to be a great questioner.  While visiting last week with my friend and mentor, Eric Morgenstern from Morningstar Communications, he mentioned a quotation meaningful to him in his own networking efforts, “Questions are the creative acts of intelligence.”1  In fact, Eric prides himself on asking meaningful, probing (but not invasive!) questions.  Like Terry Gross, Eric goes into networking situations well prepared in terms of knowing who he is meeting with or hearing from.  He always asks a few opening questions like, “What does success look like coming out of this session?”  He then allows the session to evolve naturally, asking iterative questions to enable a comfortable, conversational flow to the discussion.  And, he is more concerned with listening than with the questions themselves.  He tells me that he doesn’t formulate his next question until he has the answer to his last question. 

Synthesizing what I have gathered from Terry Gross and Eric Morgenstern, here are a few tips for asking great questions:

  1. Listen.  Really listen.
  2. Be genuinely curious.
  3. Don’t have a pre-determined list of questions that you feel you must get through.
  4. Even if you have a pre-determined list of questions, allow the answers to come organically and out of order.
  5. More specifically, allow your questions to be iterative and organic based on the answer to the prior question.

As ever, I am interested in what you have to say.  Do you have a useful formula for formulating great questions?  Who do you know who always seems to have the right question at the right time?  What tips can you share with the rest of us?  Inquiring minds want to know.

1    Origin of this quotation is questionable (no pun intended).  Some sources attribute it to Einstein.  Others (I Googled it) cite Dr. Frank Kingdon; yet others say, “Anonymous.”  With special thanks to whoever said it, I think it still holds great relevance and meaning when it comes to networking!

4 thoughts on “The Art of the Question

  1. Thanks again, Alana, for helping to share some of my suggestions. Its amazing how much we all can learn if we listen to great answers, rather than just keep talking. Hmmm, perhaps that’s why we have two ears, and one mouth 😉

  2. Luv-ly, Alana, as usual! I tried to do this as a board member for a NFP over a three year period. It proved challenging – not because I couldn’t sit back and wait for answers – but because of the organizational dynamics involved. Terry Gross has a willing and often eager partner in her conversational dance. In our work or volunteer lives that may not always be the case!

    1. Such a good point, Leslie. Indeed, the interviewee must be complicit in the discussion. After trying and trying… and trying, one may reach a point of frustration in that the interest and inquiry is met with stony silence. But, alas, we should not give up on asking solid, iterative questions as a means for developing relationships!

  3. Alana, I love questions. I always say, “Your questions dictate your answers”. And I think getting the question right is more than halfway to coming up to a great business innovation, idea or solution to a problem. I love asking questions that really get our team to think to. i.e. “How do we create 10x – 100x in value for this product?” or “If we had no legacy in this business and were starting all over is the type of product we’d put out?” This question got us moving in a revised direction that is going to have a greater impact than anything we’ve ever done. (btw – love what Kauffman FastTrac is up to – let’s connect at some point.)

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