Some people can make a story about waiting in line at the DMV hilariously entertaining, while others manage to lose you halfway through describing their incredible backpacking trip through the Himalayas. According to Dr. Alison Wood Brooks, Harvard Business School professor and MasterClass instructor, that gap is less about charisma, and more about how we engage the other person. Conversation, she says, is a skill, not a personality trait, and it can be taught.
In fact, great conversation is built on a handful of specific, learnable habits. Here’s how to put them into practice in your next conversation.
Levity as conversational CPR
Boredom, rather than conflict, is what actually kills most conversations, according to Dr. Alison. “Conversations rarely explode, they slowly fizzle out.” That’s where levity comes in, something she jokingly calls “conversational CPR.” The goal isn’t to be funny. “Ask yourself, how can I make this interaction more enjoyable? How can I help my partner feel comfortable, cared for, and engaged?”
Sometimes that’s a joke. More often it’s warmth, playfulness, or simply naming the moment out loud, like saying “whew, that got intense.” The test she shares is to ask yourself, “am I using humor to acknowledge what’s happening, or to avoid it?”
What to do when someone starts to check out
Dr. Alison’s research found that minds wander during conversation roughly 25% of the time, and she suspects that might even be under-counted. “That’s not a personal failing,” she says. “It’s simply how conversation works.” What matters more is catching the moment someone starts to check out. Look for longer pauses, wandering eyes, a topic that has overstayed its welcome, or fewer of those small verbal nods like “yeah” and “uh-huh.”
When you notice it, “treat it as feedback,” not rejection. After all, this is a conversation, not a one-person show. A topic switch, a bit of levity, or a well-timed question can pull someone back in.
Active listening isn't the same as being understood
Nodding, eye contact and leaning in are the basics of active listening, and Dr. Alison says they still matter. But they’re also easy to fake. “I can nod and smile while thinking about my grocery list.” What she calls responsive listening goes deeper. Instead of showing someone you’re paying attention, you show them you understood. That means affirming and paraphrasing what they said, following up on something they mentioned earlier, or naming an emotion or value underneath their words.
If you overdo it though, it backfires. “If you’re paraphrasing every sentence or reflecting every emotion, it starts to feel less like a conversation and more like you’re following a script.” Her fix is to listen for the golden nugget, the one idea, feeling or moment that genuinely caught your attention, and respond to that instead of everything at once.
Stop trying to tell a great story
Dr. Alison’s first piece of advice upends the instinct most people lead with. “I actually don’t think you should go into a conversation hoping to tell great stories,” she says. “You should go into a conversation hoping to help the other person tell theirs.”
Most people want to feel heard and understood. Help create that feeling, and they are more likely to enjoy the conversation and seek you out again.
When it is your turn to share, the goal isn’t a polished narrative. “Good conversational stories aren’t miniature autobiographies, they’re invitations,” she says. Skip ahead to the interesting part, give just enough context to follow along, and leave openings for the other person to jump in with a question or a reaction. Those small interjections are what linguists call backchannels. Think: “Ooh!” “Really?” “No way!” They are signs the story is being built together instead of performed at someone.
What to do when your mind goes blank
Going blank mid-conversation is a pressure problem, not a knowledge problem, according to Dr. Alison. Stress narrows attention and working memory, which makes it harder to retrieve the thoughts you already have. Her fix is to buy yourself a beat with a line like “let me think about that for a second,” reframe anxiety as excitement (both are high-arousal states, and research shows this shift can actually improve performance), or ask a clarifying question, which buys your brain time while the other person talks.
Once you’ve bought yourself that beat, Dr. Alison suggests leaning on a simple structure instead of searching for the perfect sentence. Whatever the question, big or small, give your answer first, then your reasoning, then what comes next. Or, lead with your main point, back it up with two or three supporting details, then note any caveats.
Either format works for almost anything: what you think of a friend’s outfit, whether you’re on board with a plan, or how you’d handle a work problem. The goal is to give your brain a template to fill in rather than a blank page. “A brief pause feels much more confident than rambling, apologizing, or talking in circles.”
When sharing your own story becomes hijacking
Relating to someone’s story can build closeness, or it can steal the spotlight. Dr. Alison frames the difference as a matter of sequencing. Stay with the other person for another turn (or two!) before bringing in your own experience. “Self-disclosure is incredibly valuable, and it builds trust, reciprocity, and closeness, but only after the other person feels heard.”
One habit to keep an eye out for is something researchers call boomerasking, or asking a question, letting someone answer, then immediately answering it yourself at length. “It looks like curiosity, but it often feels like you were just waiting for your turn to talk.”
The CALM method for hard conversations
For higher-stakes moments, Dr. Alison teaches a method called CALM:
- Confirm understanding
- Admit uncertainty
- Learn
- Make it human.
Confirming means checking that you’ve actually understood before responding. Admitting uncertainty can make people more persuasive, not less. Learning means entering the conversation curious about the other person’s experience rather than focused on making your point. And making it human means remembering there’s a real person on the other side, someone whose feelings can be validated even if you disagree with their conclusions.
The thing that kills conversations before they start
According to Dr. Alison, the biggest conversation killer is treating conversation like a performance. “We’re worried about how we sound, whether we’re interesting enough, what we’ll say next.” That self-focus shows up as interrupting, oversharing, jumping to advice, or simply not asking enough questions. “The best conversationalists aren’t the most entertaining people in the room. They’re the best collaborators.”
Does asking more questions increase likeability?
“Yes. And the evidence is surprisingly strong,” says Dr. Alison. In a study she co-authored analyzing roughly a thousand speed dates, people who asked more questions were significantly more likely to land a second date. “If you went on twenty dates and asked just one additional question on each one, you’d turn about one first date into a second date.”
The mechanism is simple. A good follow-up question communicates, “I’m listening. I care. Tell me more,” and that alone tends to make people more likeable, not because they seem more interesting, but because they make the other person feel more interesting.
If there’s a single way to improve your next conversation, Dr. Alison suggests this: ask one more follow-up question than you normally would.
Great conversation isn’t about having all the right things to say, and the coolest way to say them. It’s about staying curious enough to build something with the person across from you.
Check out Dr. Alison’s new class, The Conversation Advantage, exclusively on MasterClass.
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