Deep Questions Elicit Authentic and Vulnerable Conversations

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Deep questions are simple yet effective ways to prompt individuals to share their values, beliefs, or experiences in an authentic and potentially vulnerable manner. By asking questions like 'What made you decide to go to law school?' or 'What's the best part of being a lawyer?' we can encourage others to open up. These questions not only help us understand where someone's emotions lie but also guide the conversation towards a more meaningful and personal direction. By actively listening to the responses and paying attention to the emotional content of their answers, we can delve deeper into authentic and emotionally rich conversations.

According to Merriam-Webster, the word “conversation” has 36 synonyms, ranging from the alliterative (”confabulation”) to the arcane (”persiflage”). Why the linguistic profusion? Because conversing is a fundamental part — maybe the fundamental part — of being human.

We chat with our families, friends, strangers, and co-workers, and we communicate in phone calls, text messages, emails, and, occasionally, postcards. When these tête-à-têtes go well, it is oddly thrilling; we become better versions of ourselves — warmer and wiser, funnier, and consistently insightful. Best of all, a good dialogue is a direct route to connection. “The bond of all companionship,” wrote Oscar Wilde, “whether in marriage or in friendship, is conversation.”

But when a conversation goes poorly, when it stays on the surface (”what do you do for a living?”) or devolves into a sputtering mess of misunderstanding (”you’re overreacting!”), we don’t feel the invigorating pulse of connection. What we feel, instead, is the emotional equivalent of a busy signal.

So, this hour, we’re asking: how can we have better conversations? And to help answer that question, we’re joined by Charles Duhigg, a Pulitzer Prize–winning journalist and the bestselling author of “The Power of Habit” and now “Supercommunicators: How to Unlock the Secret Language of Connection.” Charles, as you’ll hear, is something of supercommunicator himself, a lithe storyteller who’s as well-versed in evolutionary biology as he is in the latest psychology, and after studying the art and science of communication for the last few years, he’s concluded that anyone can become a great conversationalist. You just have to master a few simple skills. Tune in to find out what they are.

Host: Rufus Griscom

Guest: Charles Duhigg

Book: “Supercommunicators: How to Unlock the Secret Language of Connection”

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