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The Art of Inquiry


My friend Dan recently suggested I write a bit on how I ask questions and delve into things. He said, “perhaps you should title it, 'The Art of Inquiry’”. Dan, here are a few of my thoughts on the subject.

I. Mindset

I believe an important part of inquiry and discovery begins before the questioning with a mindset. Curiosity has cultivated itself in me over the years and often am intrigued to hear a person’s story, how something works or the history behind a place or building. When I devote myself to a topic or conversation, I almost always find out it is more complex, interesting or surprising than I would’ve guessed. With a word like curious being so common, I think it’s valuable to state its definition: "eager to learn or know; inquisitive.” If someone desires to be more curious, I find a valuable way to do so is spot when I am doing the opposite of a thing. A couple of antonyms for curious are: disinterested or unconcerned.

Part of what can keep us from being curious and willing to ask questions is a fear of vulnerability. When we are asking questions, we are seeking to understand something, which means we do not know it well. As Brené Brown’s research has shown, some of the opposites of vulnerability are perfection and certainty. If we feel a pressure to appear overly self-assured, we may be afraid that questioning will make us look uninformed. Therefore, a first step I might suggest is finding confidence in your curiosity.

II. Role

If it helps to think of this through occupations, it is time to decide if you wish to play the role of detective or judge. Will you investigate the situation with openness or move to conclusions? The judge takes in what is before them and makes a ruling. The detective turns over rocks and asks questions. From the crime dramas we have all watched (which I’m sure mirror real life exactly), we know that when a detective is with a witness or suspect they probe. Even after being given an answer, they’ll work to go deeper. I’ve been taking an online writing class by Malcolm Gladwell and remember him saying at one point, “Most people don’t realize they are interesting. It’s your job to slow them down as they’re telling you something and ask them to take you in deeper.” When someone is telling you about their business or life they may glaze over something they view as ordinary and it’s your job to say, “Wait a second… would you mind going back and explaining that part to me in more detail?"

Another example I see as analogous to this (and frankly just enjoy telling) comes from Jamie Foxx who said at one point while he was on "In Living Color" that during a particular cast discussion he said to the director, “these jokes the writers gave us aren’t funny!” The director turned to him and said, “you have to find the funny”. What he meant is it was Foxx’s job to investigate how to make the joke funny (aka “interesting”) in that scenario. If you are interested enough to dig into the person’s story sitting across from you, I bet you’ll find something interesting and the questions will flow naturally.

III. Practice

Since our lives are largely made up by a series of habits and routines (h/t Atomic Habits), we have to work on how we practice inquiry and curiosity. In this vein, we have to look at how we approach our daily lives in the roles of detective vs. judge. Are you allowing social media and the news to transform you from detective to judge? Have you found a way for rancor to reinforce your commitment to stay with something longer and investigate? Remember, !!BREAKING NEWS!! means, "we don't have the whole story yet". When we regularly practice being self-assured and closed off, it may make it harder to switch over to open and curious at another point.

"It's not that I'm so smart, it's just that I stay with problems longer”

Albert Einstein

One of the best questions I’ve heard that demands curiosity, especially in today’s fractured social and political climate is, “what would have to be true in order for you to change your mind?”

IV. No right way

I do not have a "5 questions I always ask” list. Rather I just attempt to dig in when something seems interesting to me. Rather than asking great questions, another great place to start is to be a generous listener. We should all practice listening to others with the same intensity which we want to be heard when we speak (e.g. electronic devices down, resist the urge to formulate thoughts or butt in).

“During an interview, I want to be as quiet as I can and take in as much of your energy as possible”

Cal Fussman

The above-listed Cal Fussman may be unknown to you. He started out his career as a sports writer, then traveled the globe for almost a decade without a home and later became the author of Esquire’s “What I’ve Learned” column. During his time at Esquire he interviewed countless heavy-hitters and is considered by some to be one of the best interviewers of our time (sample interview with Kobe Bryant). Cal once had the opportunity to interview Mikhail Gorbachev but as the date of the interview approached, Gorbachev’s assistant kept reducing the time they’d have together. When they finally sat down, Fussman knew if he was going to learn something interesting for his column, he didn't have the time to ask about the topics everyone typically did: the fall of the Berlin Wall, Perestroika or the collapse of the Soviet Union, instead he made an unexpected request, “tell me about your father”, he said. Fussman counted that Gorbachev suddenly perked up in his chair and went on to give him an incredible interview and multiple times dismissed his assistant who was attempting to end the interview saying he wanted to continue talking with Fussman. Cal said he took an important lesson away from that interview, “First aim for the heart, then the head, from there that's your gateway to the soul.”

V. On aiming for the soul

Fussman’s statement on finding the "gateway to the soul" may be deeper than some of you intend to or would ever-want to go. If that’s the case, I would challenge you to stop and think on it this way. Having just wrapped up 3.5 years in banking, the coveted industry term that our sales people wanted to embody to their clients is “trusted advisor”. If you want to be different than other advisors, your discussions with them can and should go beyond what they’re having with others. They don't just want to talk about their business but why they are and how they got started. The Harvard Business Review article “End of Expertise” says when working to build "trustworthiness" in today's professional services world, only two states of mind remain that are not under threat from technology or your competition, “I feel comfortable discussing [this] with my advisor” and “I trust he/she cares about my [business / life]”. The way you can move into this space is by being willing to be vulnerable, curious and human rather than self-assured and reserved.

Restaurateur Danny Meyer says of restaurant regulars, “The number one reason guests cite for wanting to return to a restaurant is that when they go there, they feel seen and recognized.” I would draw this out even further as understood and cared about.

The real secret to asking great questions is about being willing to go where others will not.

Go Forth Boldly


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