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January 7 - May 2, 2025
These three conversations—which correspond to practical decision-making conversations, emotional conversations, and conversations about identity—are best captured by three questions: What’s This Really About?, How Do We Feel?, and Who Are We?
“I learned that if you listen for someone’s truth, and you put your truth next to it, you might reach them.”
Asking about someone’s beliefs or values (“How’d you decide to become a teacher?”) Asking someone to make a judgment (“Are you glad you went to law school?”) Asking about someone’s experiences (“What was it like to visit Europe?”)
Do they become quiet, their expressions passive, their eyes fixed somewhere besides your face? Do they seem overly contemplative? Do they take in your comments without adding thoughts of their own? People often misperceive these responses as listening. But they usually aren’t. (In fact, as the next few chapters explain, listening is much more active.) These are signals that someone is declining our invitation and wants to talk about something else—in which case, you need to keep searching—and experimenting—to learn what everyone wants.
In particular, he believed people should talk about their emotions. When we discuss our feelings, something magical happens: Other people can’t help but listen to us. And then they start divulging emotions of their own, which causes us to
The data shows people feel “significantly more connected to their deep conversation partner” after asking and answering just a few questions. The sense of vulnerability that comes from “sharing personal information about one’s past experiences, preferences or beliefs,” and saying things aloud that “leave people feeling more vulnerable to others’ evaluations,”
Reframe your questions so they are deeper. Ask follow-ups. And as people expose their vulnerabilities, reveal something about yourself. It will be less uncomfortable than you imagine. It will be more fascinating than you think. And it might lead to a moment of true connection.
The goal is not to repeat what someone has said verbatim, but rather to distill the other person’s thoughts in your own words, prove you are working hard to understand and see their perspective—and then repeat the process, again and again, until everyone is satisfied.
side. This explains why looping for understanding is so powerful: When you prove to someone you are listening, you are, in effect, giving them some control over the conversation. This is also why the matching principle is so effective: When we follow someone else’s lead and become emotional when they are emotional, or practical when they have signaled a practical mindset, we are sharing control over how a dialogue flows.
Deep questions are particularly good at creating intimacy because they ask people to describe their beliefs, values, feelings, and experiences in ways that can reveal something vulnerable. And vulnerability sparks emotional contagion, which makes us more aligned. Deep questions can be as light as “What would be your perfect day?” or as heavy as “What do you regret most?” Deep questions don’t always seem deep at first: “Tell me about your family” or “Why do you look so happy today?”
A deep question asks about someone’s values, beliefs, judgments, or experiences—rather than just facts. Don’t ask “Where do you work?” Instead, draw out feelings or experiences: “What’s the best part of your job?” (One 2021 study found a simple approach to generating deep questions: Before speaking, imagine you’re talking to a close friend. What question would you ask?) A deep question asks people to talk about how they feel. Sometimes this is easy: “How do you feel about…?” Or, we can prompt people to describe specific emotions: “Did it make you happy when…?” Or ask someone to analyze a
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There’s a technique for this—looping for understanding. Here’s how it works: Ask questions, to make sure you understand what someone has said. Repeat back, in your own words, what you heard. Ask if you got it right. Continue until everyone agrees we understand.
Reciprocity is nuanced. If someone reveals they’ve gotten a cancer diagnosis, we shouldn’t reciprocate by talking about our own aches and pains. That’s not support—it’s an attempt to turn the spotlight on ourselves. But if we say, “I know how scary that is. Tell me what you’re feeling,” we show we empathize and are trying to understand.
Looping for understanding, until you understand what someone is feeling. Looking for what someone needs: Do they want comfort? Empathy? Advice? Tough love? (If you don’t know the answer, loop more.) Asking permission. “Would it be okay if I told you how your words affect me?” or “Would you mind if I shared something from my own life?” or “Can I share how I’ve seen others handle this?”
First, acknowledge understanding. We do this through looping and statements such as “Let me make sure I understand.” Second, find specific points of agreement. Look for places where you can say “I agree with you” or “I think you’re right that…” These remind everyone that, though we may have differences, we want to be aligned. Finally, temper your claims. Don’t make sweeping statements such as “Everyone knows that’s not true” or “Your side always gets this wrong.” Rather, use words like somewhat or “It might be…” and speak about specific experiences (“I want to talk about why you left dishes in
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