How to have a real conversation (and get out of small-talk jail)
- Elle Beecher Hogan
- Jun 15
- 5 min read
You know the conversation I mean.
You're at the thing. Someone asks what you do. You tell them. You ask it back. They tell you. A comment about the weather. A laugh about how it's already June somehow.
And then you both just… stand there. Smiling. Quietly calculating how soon you can go refill a drink you don't even want.
That's small-talk jail.
The conversation is technically happening and absolutely nothing is being said. You leave a whole evening of it feeling like you ate a meal made of air.
So here's how you get out.
The short version, before we go deeper:
To have a real conversation, stop trying to be interesting and get genuinely curious instead. Bring one real question. Swap "what do you do?" for "what are you into lately?" Ask "tell me more" before you offer any advice. And be willing to go first... to say one true thing and let the half-second of silence be a little awkward.
Depth isn't a personality trait you were born without.
It's a handful of small, repeatable moves. Anyone can learn them.
Small talk isn't the enemy. The doorway is.
First, let's be fair to small talk. It has a job. "How's your weekend?" is a handshake: a low-stakes way to check whether someone's open before you walk through the door.
The problem is that most of us stop at the door. We handshake back and forth forever, because going further feels risky. What if I'm too much? What if they don't actually want to go there? What if it gets weird?
So we stay safe. And safe, it turns out, is exhausting... because performing a pleasant, frictionless version of yourself for an hour takes real energy and hands you nothing back. It's not the talking that drains you. It's the not-quite-connecting.
Good news: the door is right there.
You just have to be the one willing to walk through it first.
The method (we use it every Saturday)
We've now run this experiment more than 20,000 times, across 16+ cities, with total strangers, for four years straight.
The walk runs on a few simple rules that reliably turn surface chatter into the kind of conversation you're still chewing on days later. None of them require charisma.
Here they are, stripped down so you can use them at any dinner table on earth.
1. Be the one who brings a real question. We treat conversation like a potluck: everyone shows up with one thing worth chewing on. Most people wait around hoping someone else makes it interesting. Be the one who doesn't. Walk in with a real question in your back pocket — something like "what's the last thing that brought you full-body joy?" — and set it down. The whole room changes.
2. Trade "what do you do?" for "what do you think?" "What do you do?" sorts a person into a job title and a tax bracket and quietly ends the conversation it pretends to start. Our crew's go-to is the opposite: what do you think? What are you into lately? What's a rabbit hole you've fallen down? You learn ten times more about someone from what lights them up than from what's on their business card.
3. Treat it like jazz, not a monologue. The best conversations have a rhythm two people build together: a share, a question, a share back. If you notice you've been talking a while without asking anything, pause and hand over the mic. "Okay, enough about me... what about you?" is a complete sentence.
4. "Tell me more" beats advice every time. When someone shares something real, the instinct is to fix it, match it, or quietly one-up it. Resist all three. The most magnetic thing you can say is "tell me more." Curiosity, not solutions. You're not there to solve them. You're there to see them.
5. Go first, and let it be a little awkward. Depth needs one person to take a small risk before it feels "allowed." Be that person. Say the slightly-too-honest thing. The half-second of awkward quiet afterward isn't failure... it's the sound of a door opening. People tend to match the depth you offer. Almost every time.
6. Float without guilt. Here's the secret that makes all of the above feel safe: you're allowed to leave. On the walk we call it floating: "I loved this, I'm going to float over and say hi to someone new." Knowing you can exit kindly is exactly what lets you dive in bravely. When no one's trapped, everyone can be real.
Steal our questions (real ones, from real walks)
People always ask what kind of question actually cracks a conversation open.
So here's a bank of them. Every single one brought by a real walker, on a real Saturday, on an actual trail. Screenshot it. Bring one to your next dinner.
Light openers that still go somewhere:
What's the last thing that brought you full-body joy?
What's a bad habit you actually managed to kick?
What are you weirdly into right now?
Waffles or pancakes, and defend your answer. (Yes, really. A silly question melts the ice faster than a deep one.)
For going a layer deeper:
Where does your sense of self-worth come from?
How has your past shaped who you are today?
What does self-love actually look like in your life right now?
When in your life did you look most like yourself?
What's the most enlightening question anyone's ever asked you?
The ones that make people stop walking:
What's something you haven't said out loud that you want to?
How do you know when it's time to uproot your life and start over?
What are the three things that most shaped who you are?
If you could go anywhere (any place, any moment in history) where would you go, and why?
If you had a ridiculous amount of money to give away, what cause would you throw it all at?
That last one came up on a recent walk in Columbus, Ohio, and it turned into one of those mornings nobody wanted to end.
One woman said she'd fund support for young single fathers because her own son became a dad at 16, and the only group he could find to join was one for people coming out of jail. Someone actually pulled out their phone to write down what people were saying.
That's the thing about a good question.
It doesn't just fill the air. It hands you the whole person.
Wait... what's a walk?
If you've never heard of us:
The Board Walks is a free, 5-mile walk every Saturday morning in cities all over. No phones. No pitching. No agenda. Just a long walk and a real conversation with people who showed up for the same reason you did.
The whole event is basically this conversation method, set loose outdoors for five miles. Everyone brings a topic. Nobody asks what you do. You float between people, follow your curiosity, and somewhere around mile three a stranger asks you something that quietly rearranges your week.
It started with eight people in Austin in 2022.
It's now more than 20,000 people across 16+ cities, and it grew entirely by word of mouth, because a real conversation is the kind of thing people can't help telling their friends about.
The Board Walks in Aveiro, Portugal. Established May 2026.
Come practice with us
The fastest way to get good at real conversation is to spend two hours doing nothing else. So come.
Find your city and RSVP for this Saturday → here
Bring one good question and a decent pair of shoes. We'll handle the rest. (And if, after a few walks, you meet someone you want to keep talking to off the trail... here's How to Ask Someone to Hang Out Without Making It Weird.)
If you're looking for something more intimate, there's a quieter door inside this one called The Board. You'll find it when you're ready.
See you on the trail.
Elle Beecher Hogan is the founder of The Board Walks — a free, phone-free, 5-mile Saturday morning walk happening in 16+ cities around the world. Her mission is to make real connection a weekly habit again.
