Becoming a Question Artist

I have a confession to make: I am not a reader. Meaning, when I want to learn something, I don’t usually read a book or article on the subject. And when I do borrow a book or print an article, it tends to sit on my dresser for months (there is a stack sitting there right now, in fact). I much prefer experiential learning, which is not always practical. So—what easy learning opportunities are out there that are more dynamic than reading?

I thought about this question in terms of my interest in working on the skill—or art, as many call it—of asking questions. The art of asking questions is fundamental to work in human-centered innovation. When we are doing field research, artful questions help us build empathy. When we are generating ideas, artful questions help us stimulate an expansive mindset. When we are experimenting, artful questions help us obtain critical input. When we are providing feedback, artful questions help us advance discussions in a non-judgmental, forward-looking way.

When I’m not practicing the art, my antennae are tuning to find artful questions during Q&As at conferences and while listening to podcasts, watching media interviews, or observing a professional coach or consultant do their magic. I’ve started to realize that people deliver questions with a variety of intentions, and lots of them are just—bad. So, how do I train myself to ask better ones?

Here are some ways that could help folks like me work on this muscle:

• Have coffee with your mentors. You probably call them mentors because they know how to bring out the best in you and help you grow by asking good questions.
• Check out Brandon Stanton’s work on Humans of New York, which you can find on many social media platforms, including Facebook. Stanton captures exquisite stories about everyday people in their own environments, using their own words.
• Watch episodes of Inside the Actor’s Studio with James Lipton. The show is 22 years old, so he must be doing something right.
• Watch some reruns of The Oprah Winfrey Show. She gets her guests to open up on her show in ways they wouldn’t otherwise by cultivating a persona of trust and safety.
• I unfortunately don’t have any news journalists or specific podcasts to recommend, as most of the ones I’ve heard recently have been asking rather biased or loaded questions. These are some recommendations I found.
• Be a fly on the wall: Listen to the questions people around you are asking. Are they judgmental, self-serving, narrow, broad, open, closed? Are they using questions to obtain information or to implicitly guide a discussion in a new direction? Which tactics do you want to adopt or avoid? So much to learn here!

For those who like to read, here are a few resources that have been recommended to me. Let me know how they are if you get to them first!

• “Relearning the Art of Asking Questions,” by Tom Pohlmann and Neethi Mary Thomas, Harvard Business Review
• Humble Inquiry: The Gentle Art of Asking Instead of Telling, by Edgar H. Schein
• A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas, by Warren Berger