When people imagine a “good conversationalist,” they often picture someone who can produce entertaining stories forever.
In practice, the skill can be broken into smaller parts.
Pick up a hook from what the other person just said. Ask one follow-up. Offer a short story of your own. If the energy is low, switch topics. If the other person suddenly lights up, stay there and go deeper.
And in a group, remember one more thing: you are not automatically the host.
Forget that, and a casual meal somehow turns into a project where you manage airtime, distribute topics, rescue silence, and make sure everyone gets a turn.
Nobody assigned you that job.
1. People who keep conversations moving do not invent every topic from scratch
If someone says they traveled recently, the sentence already contains branches: where, why there, food, mistakes, surprises, whether they would go again.
If they say work has been busy, there are branches too: busy season, the actual task, days off, what has gotten easier, what is still annoying.
A 2017 study of live dyadic conversations found that people who asked more questions, especially follow-up questions tied to what their partner had just said, tended to be liked more by their conversation partners.[1]
The next line of a conversation is often already hiding inside the previous line.
2. But questions alone can accidentally create an interviewer
There is a trap.
“Where did you go?” “What did you do?” “What was best?” “Would you go again?”
Keep that up and you have not built a conversation. You have opened a low-budget interview panel.
That is why your own short episodes matter.
A tiny story is enough: “I once wandered into an event about water infrastructure, found it unexpectedly interesting, and then a few days later heavy rain made everything I had just learned feel absurdly real.”
Ask about them. Return twenty or thirty seconds of your own experience. Hand the ball back.
That prevents the roles from freezing into “questioner” and “respondent.”
3. Reflection quietly becomes an episode inventory
You do not need to manufacture stories specifically for conversation.
If you regularly talk through what happened during the day, write about it, or use AI to reflect on it, ordinary events start getting stored in a more retrievable form.
Not just “I went somewhere,” but:
what was weird, what was funny, what surprised you, what connected to something else, where the punch line landed.
Later, when someone talks about travel, work, food, hobbies, strange facilities, weather, or anything nearby, your brain has something indexed to retrieve.
It is less like memorizing conversation material and more like turning everyday life into a searchable episode database.
4. One-on-one conversation and group conversation are not the same activity with extra chairs
In a dyad, going deeper can feel natural.
In a group, the speaker may also be tracking who is listening, who will speak next, who might repeat the story later, and how the disclosure will look to everyone else.
A review on dyadic versus group conversation described a “many minds problem”: as group size increases, airtime, turn-taking, and listener feedback change, with consequences for what people disclose and how they feel about disclosing it.[2]
So when someone becomes quiet in a group, it is too simple to conclude that they are “bad at conversation.”
The same person may talk freely one-on-one and brake hard when the audience expands.
5. If you enjoy digging, small talk can become a career interview before anyone notices
Career, values, future plans, family, and relationships are especially easy to over-dig.
Someone casually mentions work and suddenly the questions become:
“Why did you choose that career?” “What matters most to you?” “Where do you want to go next?” “What does that say about your priorities in life?”
Congratulations. The free career consultation is now open.
One-on-one, with an enthusiastic partner, that can be great.
In a group, however, the question is not only whether the person can answer. It is whether they want this whole audience to hear the answer.
6. A useful group strategy is: move sideways, watch the energy, then go one level deeper
Start shallow.
Travel. Food. A recent outing. A light work story. Hobbies. Weekends. Something funny you saw.
If the answer is short, move on.
If the answer gets longer, more specific, more animated, or comes with a question back, that is a better signal to stay.
A 2025 Harvard Business School piece distinguishes introductory, mirror, topic-switching, and follow-up questions. Topic-switching questions move the conversation somewhere new; follow-ups deepen a topic once both people have found something worth staying with.[3]
That is the operating system:
In groups, scan sideways. When a topic catches, dig a little.
When the conversation becomes one-on-one, you can go much deeper.
7. Being excited in the moment does not guarantee being happy about the disclosure later
There is another complication.
Someone can be genuinely animated while speaking and still go home thinking, “Why did I tell that whole group all of that?”
Values, family, relationships, and real career feelings are easy to overshare when the room is warm and the momentum is good.
The speaker ultimately decides what to reveal. The listener does not have to become a privacy officer for another adult.
But it helps to read two signals, not one:
How much energy is there? How public is this setting?
That alone prevents a lot of accidental over-digging.
8. Most importantly, you do not have to run the room
In a group, conscientious people sometimes start doing unpaid facilitation.
Silence appeared. Someone needs a question. That person has not spoken yet. We need a new topic.
No.
If nobody asked you to host, you can simply participate.
Eat. Look at your phone. Rest. Let other people carry a thread that they are already enjoying.
“I must keep this room alive” is often a project you assigned to yourself.
9. It is also fine to be silent and suddenly jump in with “Wait, what is that?”
Participation does not have to be continuous.
You can be quiet for ten minutes, hear one interesting thing, and suddenly ask:
“Wait, what is that?” “That part sounds interesting.” “Hold on, tell me more about that.”
People may be briefly surprised because the quiet person just entered at full speed.
That is okay.
Conversation does not require a subscription plan. Pay-per-use is allowed.
Join the parts you care about. Leave the rest alone. When the topic ends, go back to your food.
Conclusion
Conversation becomes exhausting when “being good at it” means talking constantly.
A more practical model is simpler.
Go vertical one-on-one. Do not let questions turn into an interview; return short stories of your own. In groups, move horizontally across light topics. Go deeper only where the other person clearly engages. When the audience is broad, do not treat enthusiasm as unlimited permission to probe. And do not become the moderator unless that is actually your role.
If you do not want to talk, you do not have to.
When something interesting finally appears, you can simply look up and say, “Wait, what is that?”
That is enough conversation.
And you still get to eat.
References (3)
- Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It Doesn’t Hurt to Ask: Question-Asking Increases Liking. Journal of Personality and Social Psychology, 113(3), 430–452 doi.org
- Cooney, G., Mastroianni, A. M., Abi-Esber, N., & Brooks, A. W. (2020). The many minds problem: disclosure in dyadic versus group conversation. Current Opinion in Psychology, 31, 22–27 doi.org
- Brooks, A. W. (2025). The Elements of Meaningful Conversation: Fewer Mirror Questions, More Follow-Ups. Harvard Business School Working Knowledge library.hbs.edu
