How to Have a Great Conversation (Even If You’re Nervous or Feel Out of Practice)
Great conversations aren’t about being clever, impressive, or confident.
They’re about making the other person feel comfortable, heard, and genuinely engaged — and that’s a skill you can practice.
Here’s the good news:
You don’t need better lines.
You need better listening and a little structure.
Start With Curiosity, Not Pressure
If you feel stuck wondering what to say, try this reframe:
👉 You’re not there to impress.
👉 You’re there to be curious.
Simple, human openers work surprisingly well:
“What brought you here tonight?”
“What’s been taking up your time lately?”
“What’s something you’ve been enjoying recently?”
You don’t need a perfect question — just one that invites a real answer.
The Two Follow-Up Question Rule (This Changes Everything)
One of the simplest ways to instantly improve a conversation is this:
When someone shares something, ask at least two follow-up questions before changing the subject.
Not back-to-back interrogation — just genuine curiosity.
Example:
They say:
“I moved here last year.”
You might respond with:
“What brought you here?”
“How has the transition been for you?”
That’s it.
This keeps the conversation flowing, takes pressure off you, and helps the other person feel seen.
Why this works (the science, briefly)
Research published in the Journal of Personality and Social Psychology found that people who ask more questions — especially follow-up questions that directly build on what their partner just said — are consistently liked more in conversation.
In real face-to-face speed-dating interactions, participants who asked more follow-up questions were more likely to receive requests for second dates from their partners — a clear, behavioral marker of connection and interest.
👉 You can read the study here:
“It Doesn’t Hurt to Ask: Question-Asking Increases Liking”
https://pubmed.ncbi.nlm.nih.gov/28447835/
In other words:
Asking thoughtful follow-ups doesn’t just feel good — it actually increases how much people enjoy talking with you.
Listen to Understand, Not to Perform
You don’t need to plan your next line while someone else is talking.
Try this instead:
Listen fully
Let them finish
Reflect something back
Simple responses like:
“That sounds like a big change.”
“It seems like that really mattered to you.”
“I can see why you enjoyed that.”
You’re not trying to be interest-ing, you’re being interested.
Let Silence Do Some of the Work
A short pause isn’t a failure.
Silence:
gives people space to think
signals attention
often invites something more meaningful
If there’s a moment of quiet, breathe. Stay present. Let the conversation breathe too.
Keep It Light — Depth Comes Later
Good conversations don’t start deep.
They usually move like this:
light → curious → relaxed → meaningful
It’s okay to laugh.
It’s okay to keep things playful.
Connection builds faster when people feel at ease.
If This Feels Hard, You’re Not Doing It Wrong
Most people feel:
unsure what to say
worried about making the wrong impression
rusty after years of screen-based interaction
That doesn’t mean you’re bad at conversation.
It means you’re under-practiced.
And like any skill, conversation gets easier — and more enjoyable — with practice.
Practice Makes This Feel Natural
You don’t become better at conversation by thinking harder.
You get better by:
showing up
staying curious
asking follow-ups
practicing in real life
That’s exactly why guided, in-person experiences like The Connection Club exist — to give you a low-pressure place to practice the art of relating.
You don’t need to have it all figured out.
You just need space to practice.
Want to Learn More?
If you’re curious about the research behind great conversations, this episode is worth a listen:
🎧 The Diary of a CEO — Dr. Alison Wood Brooks
On why conversations go wrong — and how to make them better
