How asking the right questions leads to more meaningful conversations

Every story has a beginning, a middle and an end. We have a tendency to focus more on the end, while we should be focusing on the middle. “It’s the middle that makes the story worth it; the middle is what compels us,” New York Times bestselling author and Pulitzer Prize-winning columnist Charles Duhigg told attendees at the recent BenefitsPRO Broker Expo.

Duhigg started off by telling attendees how the session would end: “I’m going to ask you to turn to the person next to you and ask you to ask and answer one question: When was the last time you cried in front of another person?”

And then, he spent the middle of his keynote talk explaining what attendees would gain by asking (and answering) this question.

Drawing from his latest book, “Supercommunicators: How to Unlock the Secret Language of Connection,” Duhigg explored the science of what goes on when we have conversations with each other.

“We tend to think of a discussion as just one conversation,” he said, explaining that conversations actually fall into one of three “buckets.” Each discussion contains many different kinds of conversations. They tend to fall into one of three buckets: practical, emotional or social.

Each of these types of conversation serves a different purpose, whether it’s problem-solving or empathizing. ”If two people are having different kinds of conversations at the same moment, it’s very hard for them to hear each other,” Duhigg said. “When you can connect, have the same kind of conversation at the same moment, it’s easier.”

But how to start building that connection? By asking what is known as “deep questions.” Instead of asking questions that invite a factual response, ask about feelings. “Instead of, ‘where do you work?’ ask, “What do you like about your job?” he suggested. “Instead of, “Where did you go to high school?” ask, ‘What was high school like for you?’ It invites them to say something deep but doesn’t mandate it.

“When someone shares something authentic and meaningful with you, reciprocate,” he added, acknowledging that this can be intimidating. “Sharing something about ourselves does not diminish who we are. It only makes us stronger in talking to someone else.”

This skill is especially important to the benefits industry. “People are turning to you during the most challenging moments in their lives,” Duhigg said. “These are the moments that are the most deeply human moments. It makes such a huge difference to know that when someone is going through something hard, someone else wants to understand them.”

Near the end of the keynote, Duhigg invited attendees to posit his initial question to the person sitting next to them, saving time at the end to go over some key themes that emerge whenever this experiment is done.

“People say consistent things,” he said. “They felt more connected to the other person than they anticipated, or how unusual that they had this thing in common. People say the other person is more caring, they listened more intently than they expected.”

But, he added, there’s nothing special about the people in the room or the situation; we could (and should) be opening ourselves up to these types of conversations. “You’re actually doing this for yourself,” he said. “When we overcome our own hesitancy to ask deep questions, we are actually giving a gift to the other person, the gift of a real conversation.”