1: Imagine we are at a neighborhood barbecue. Or perhaps a work event with people we don’t know. Or barely know at all.
Let’s say we want to connect. Get to know someone. Not just small talk.
Yesterday, we looked at questions we don’t want to ask. Questions that evaluate the other person. Or closed questions that limit the way they can respond. Or vague questions like “How’s it going?”
A better approach is to ask questions that look for commonalities.
“I’ve learned to sometimes ask, ‘Where did you grow up?'” David Brooks writes in How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen.
That question “gets people talking about their hometown,” David notes. “I travel a lot for work, so there’s a good chance I’ll know something about their place.”
Other easy introductory questions include: “That’s a lovely name. How did your parents choose it?”
Because that question encourages the person to share something about their cultural background or family history. “Those conversations often go off in good directions,” David observes.
2: Other situations call for different questions. Let’s say we are at dinner with people we know or want to know decently well.
In these situations, we want to ask big questions,” David recommends. “It’s easy to have a pleasant evening if only small questions are on the table, but it’s possible to have a truly memorable dinner if someone asks a big question.”
He shares the story of a dinner he attended where one of the attendees “put down his fork and said to the four of us: ‘I’m eighty. What should I do with the rest of my life?’
“That was a really humble but big question to ask,” David notes. “Essentially, he was asking, ‘What is the best way to grow old?'”
Which led to a discussion about what was important to him and how he wanted to spend the final years of his life.
“It was fantastic. Big questions interrupt the daily routines people fall into and prompt them to step back and see their life from a distance,” he writes.
Here are some of David’s favorite questions that do that:
“What crossroads are you at?” Because at any moment, “most of us are in the middle of some transition,” he notes. “The question helps people focus on theirs.”
Or “What would you do if you weren’t afraid?” Because most of us realize fear plays a role in our lives, but we often haven’t clearly defined it.
Or “If you died tonight, what would you regret not doing?”
Or “If we meet a year from now, what will we be celebrating?”
Or “If the next five years is a chapter in your life, what is that chapter about?”
Or “Can you be yourself where you are and still fit in?”
3: Author and consultant Peter Block “is a master at coming up with questions that lift us out of our ruts and invite fresh reevaluations,” David observes.
Here are some of the questions Peter likes to ask: “What is the no, or refusal, you keep postponing?…
“What have you said yes to that you no longer really believe in?”
“What forgiveness are you withholding?”
“How have you contributed to the problem you’re trying to solve?”
“What is the gift you currently hold in exile?”
The journalist Mónica Guzmán asks people, “Why you?”
As in: “Why was it you who started that business? Why was it you who felt a responsibility to run for the school board?”
All too often, we think deep conversations have to be painful. Or vulnerable.
Not so, David suggests. “I try to compensate for that by asking questions about the positive sides of life:
“Tell me about a time you adapted to change.”
“What’s working really well in your life?”
“What are you most self-confident about?”
“Which of your five senses is strongest?”
“Have you ever been solitary without feeling lonely?” or
“What has become clearer to you as you have aged?”
David’s observation? “I’ve found in almost all cases that people are too shy about asking questions, not too aggressive.
“People are a lot more eager to have a deep conversation than you think. People are longing to be asked questions about who they are.
“The human need to self-present is powerful,” says the psychologist Ethan Kross. One study conducted by Harvard neuroscientists showed that people often take greater pleasure from sharing information about themselves than from receiving money.
Journalist and author Studs Terkel collected many oral histories during his long career in Chicago. His approach? He’d ask people big questions and then sit back and listen.
“Listen, listen, listen, listen, and if you do, people will talk,” he once shared. “They always talk. Why? Because no one has ever listened to them before in all their lives. Perhaps they’ve not ever even listened to themselves.”
David’s final observation? “Each person is a mystery. And when you are surrounded by mysteries, as the saying goes, it’s best to live life in the form of a question.”
Indeed.
More tomorrow!
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Reflection: What can I learn or apply here from David Brooks, Peter Block, Mónica Guzmán, and Studs Terkel?
Action: Experiment with asking a “big” question at an upcoming dinner with friends.
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