Mastering The Art Of Conversation With One Question

Anna Vander Stel
Anna Vander Stel

We hate it when other people do it to us at an event, but then we turn around and do the same thing to them:
“Hey, what’s your name?…Cool, so what brought you here today?…You know the host. Cool….So what do you do?…Oh okay…And where is that at?…That commute through the tunnel must be brutal”…

What the?!
Let me guess. You panicked didn’t you? You couldn’t think of anything else better to say…

It’s basically a ping pong match of arbitrary questions and unenthusiastic short answers, and all you’re trying to do is not crash and burn into awkward silence.
You failed.

So let’s break this vicious cycle and try something different. It’s astonishingly simple. I’m going to give you one question to ask colleagues, coworkers, or strangers at any social event, that will instantly engage them into conversation, and most likely, make you the most memorable person in the room.


Whether you are at a networking event or a bbq — you:

1) Walk up to the person or group. (Obvious right?)
2) Do the introductions and get settled in
3) Make eye contact with one person in the group (and I mean look into their optic stems!), and warmly ask them this question:

 So tell me, what made you happy this week?

Their reaction:
1) They’re taken aback by the question — their eyes will widen for a second.
2) They smile (uncontrollably) and try to think about the past week.

Good signs! And I can GUARANTEE you that everyone else in the group, is smiling and thinking about their past week searching for that “happy moment” as well.


You’ve dropped the bomb.
They’re getting over the pleasant shock.
They tell you about their happy moment that has a story behind it.

Note: There is ALWAYS a story behind it.

So now comes the other easy part — you LISTEN. And just so you know the ratio is about 90% listening/10% of you asking questions. You’ll notice that when they tell their story, if it’s something that TRULY made them happy, their body language is different.
They have a big smile on their face, they’re talking with their hands a lot, there’s fluctuations in their voice, their energy is amplified, and sometimes the phone gets pulled out so they can provide you with visuals.

They are fully engaged in telling their story — doing impressions and more. And it can be something small to you and the group, but it was a win for them.

With this one question, you were able to find out what excites them to the core — quickly! Now use that as your springboard.
They’re done telling you their story. You were LISTENING. Take a beat to make sure they’re done. Now ask questions about what you just heard.

Let’s use an example of someone who builds boats on the weekends:

  • How did you get into that?
  • How many have you built?
  • Where do you start?
  • Do you chop down a tree and then hollow it out?
  • Do you have to use specific type of wood?
  • I bet you know the good fishing spots. Do tell!

Give this Ron Swanson the third degree! Be excited, be curious to learn more. Most people mow their lawn on the weekend. This guy (or gal) builds boats!

The questions will segue way into other aspects of this boat builder’s outdoor life that will be relatable to others within the group — and candid conversation ensues. WINNING!

Most people don’t get a chance to talk about the events in their lives that they are really passionate about. Give them the platform to revel in this opportunity.


You might make it to one other person within the group with the question before they throw it back on you candidly, “So what made you happy”?
Because it’s your question, you will have 2–3 stories ready to roll. And you will be just as enthusiastic about the story and ready for your Q&A as your colleagues when they told their story. You got this ace!

Note: If nothing made you happy that day or week (bummer.), don’t be afraid to go back to last week, or the week before that. If you have to go back further than that  you might want to think about some lifestyle changes.

Whether you bump into that person later on in the night, or 6 months from now, even if they don’t remember your name, they’ll remember your story.

People can’t help but be drawn to the power of narrative and the positive association they had with you.


You’ve talked to everyone, had a few laughs, and are ready to move on. Some ways to politely leave the group:

“Oh, excuse me. I see some (food) that’s calling my name.”
“I see someone over there I haven’t spoken to in while. You folks enjoy yourself, excuse me.”
“Oh, I see someone I have to introduce you to. Come on.”


In the end, remember it’s about making a connection with other individuals. Step away from the small talk that is mundane, superficial, and overall awkward. This is your opportunity to meet new people, learn something new, make a fantastic first impression, and possibly make a new friend. With this in mind, keep it real, keep it authentic, and have some fun!


Who can you practice this technique on?

You walk into a room where you know nobody.
Your partner in conversation leaves to go find drinks.
(Blast, abandoned!)
As soon as they step away, that’s when you scan the room and look for the “low hanging fruit” — the person who looks the most uncomfortable in the room.
It could be that they’re an introvert, shy, they don’t know what to say when they walk up to a person or group beyond “Hey! So what do you do?”, or a plethora of other reasons.

Be nice. Go rescue them. They’ll be grateful.

For crying out loud, DO NOT hand them your business card – unless it’s serious business!
You’re on a roll with your question, let’s keep up the momentum.

If you are in a casual setting – most networking or social events happen at a bar/restaurant – and someone asks for your card or information, go Old School.
Grab a cocktail napkin and write your name and number on it. As you’re handing it to them, and they’re laughing out loud, say, “call me”.

As a woman, I would kiss the napkin – leaving my kiss imprint – and THEN put my name and number on it and give it to him or her.  They find this hilarious, but more importantly, they have always called or texted. Thought Catalog Logo Mark

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