Every New Year, instead of making resolutions, I’ve begun setting intentions for different areas of my life. These aren’t hard goals, but more like gentle reminders to guide how I want to show up—in work, relationships, health, and beyond. Under the “relationships” category this year, I wrote: Ask better questions, and practice deeper listening.
Because let’s be honest—knowing how to keep a conversation going isn’t always as natural as it seems. We've all experienced awkward silences or moments where we wished we'd asked a better question or truly listened instead of planning our response.
Over time, I’ve realized that the heart of meaningful connection is not just talking—it’s how we talk. It’s about creating moments where people feel valued, heard, and truly seen. And that starts with presence, curiosity, and empathy.
So, if you’ve ever struggled to maintain a flowing, engaging dialogue—whether it’s with a new acquaintance or a longtime friend—this guide is for you.
Let’s dive into five powerful strategies that can transform your conversations from surface-level to truly soulful.
1. Start by Actually Listening
We’ve all had those moments: you’re halfway through telling a story and realize the other person isn’t really paying attention. Or maybe you’ve been that distracted listener, already thinking about what to say next while they’re still talking.
Here’s the truth: the best conversations start with listening—really listening.
When you’re fully tuned in, you’ll naturally pick up on details that invite further exploration. The interaction begins to feel less like an exchange of information and more like a shared experience.
Listening shows that you care. It’s how you signal to someone, “You matter. I’m here with you.”
And the best part? People remember how you made them feel—not how clever or articulate you were. Being present is powerful.
2. Ask More Questions
If you’ve ever walked away from a conversation feeling like it was all about the other person, you’re not alone. In fact, a study from Harvard Business Review found that people who ask more questions are generally better liked and perceived as more empathetic.
But being a great conversationalist doesn’t mean having all the answers—it means being curious.
Start with simple, sincere questions. Ask about their city, their routines, their past, or their passions. You don’t need to sound like a journalist—just be genuinely interested.
Here are a few to try:
How did you end up living in [their city]? What do you love about it?
What’s a hobby you picked up recently that stuck?
What’s the best vacation you’ve ever taken—and why?
Who was your first celebrity crush? (Bonus points if it still holds!)
What was the first book you remember loving? Do you still think about it?
These types of questions open the door to unexpected stories and shared memories, often leading to richer, more meaningful conversations.
3. Lean Into Follow-Up Questions
If you want to know the secret to keeping a conversation going effortlessly, here it is: follow-up questions.
They show you’re really listening—and they take things a layer deeper. It’s the difference between someone feeling like they’re being interviewed versus feeling truly seen.
Try:
What makes you say that?
How did that make you feel?
Can you tell me more about that.
Even kids pick up on the difference when you ask thoughtful follow-ups. My son, Henry, lights up when I prompt him to elaborate—it’s how he knows I’m genuinely engaged. The same applies to adults: it builds trust and emotional intimacy.
Here’s how to upgrade everyday small talk into something more substantial:
How was your day? → What was the best part of your day?
How’s your mom? → What’s been keeping her busy lately?
Why’d you choose that? → What motivated you to do/say that?
How’s work? → What’s something interesting you’re working on?
These small shifts can dramatically elevate your conversations.
4. Ask Open-Ended Questions
Closed-ended questions—those that can be answered with a quick “yes” or “no”—often stall a conversation. Open-ended ones, on the other hand, encourage people to reflect, share, and open up.
I’ve seen this firsthand while interviewing guests for work. The most powerful stories come when you give people room to expand on their thoughts.
Keep these in your conversational toolkit:
What’s something that’s brought you joy recently?
What’s your take on [a recent book, film, or event]?
What’s a memorable encounter you’ve had with a stranger?
Tell me about your last great meal—what made it so special?
What’s something you’ve learned about yourself lately?
Open-ended questions invite vulnerability, humor, and depth—all ingredients for a meaningful connection.
5. Resist the Urge to Interrupt
I get it. You hear something that resonates and feel the impulse to jump in with your own story. But when we interrupt, even with good intentions, we can unintentionally cut off the flow of someone else’s thought.
One of the most underrated conversation skills is patience.
Let the other person finish. Pause before responding. Sit in a moment of silence without rushing to fill it. Sometimes the best response is simply: “Tell me more.”
As the old saying goes: Seek to understand, more than to be understood.
The Power of Good Questions
If you’re still not convinced that better questions lead to deeper connection, look no further than the famous 36 Questions That Lead to Love. Popularized by a New York Times Modern Love essay, the study demonstrated how structured, meaningful dialogue can create intimacy—even between complete strangers.
The study's authors emphasized “sustained, escalating, reciprocal, personal self-disclosure” as the secret sauce of human connection. In other words: ask more, share more, feel more.
Good questions—and the space to answer them—can change everything.
Final Thoughts
The most memorable conversations aren’t the ones where everything goes perfectly. They’re the ones where both people felt present. Where curiosity led the way. Where silence was okay and stories were shared freely.
So next time you're worried about what to say, remember:
- Listen deeply.
- Ask thoughtfully.
- Follow up intentionally.
- Be patient.
- Stay curious.
The goal isn’t to be impressive—it’s to be interested.