When people think of icebreakers for adults, they often imagine a list of pre-made questions designed to help strangers get to know each other. But what if I told you there’s a better way—one that allows you to create the perfect question in under 10 seconds, tailored to any environment?
Instead of giving you a simple list of icebreaker questions, I’m going to teach you a skill that will help you spark meaningful conversations anytime, anywhere.
Forget Icebreakers—Think “Connection Before Content”
I have to destroy the word “icebreaker”—shatter it, delete it, make it disappear—and replace it with something much more intentional: connection before content.
The goal of icebreakers for meetings, teams, or any adult gathering isn’t just to get through a scripted question. It’s about making people feel comfortable, helping them gel, and creating a space where they can connect before diving into content.
This approach comes from Ask Powerful Questions, a book I co-wrote with Will Wise. One of the key ideas we introduce is what I call the awkward elevator trick—a simple but powerful method to generate meaningful questions on the spot.
The Awkward Elevator Trick: How to Ask the Perfect Question Anytime
Imagine you step into an elevator with a stranger. You have no shared history, no common ground—except for the physical environment around you. Now, if you had to start a conversation in that moment, what would you ask?
Here’s the trick:
- Tap into your natural curiosity.
- Observe something they are wearing, carrying, or presenting.
- Ask a question rooted in that curiosity.
For example, if you’re on Zoom and meeting someone for the first time, you might ask:
- “What’s the story behind that map on your wall?”
- “That’s an interesting ring—what’s the meaning behind it?”
Why does this work? Because when people choose what to wear, carry, or display, they are already communicating something about themselves. By asking about those choices, you create a safe, non-threatening way to start a meaningful conversation.
How to Start Meaningful Conversations Without Making People Uncomfortable
A lot of traditional icebreaker questions throw people into the deep end too quickly. For example:
- “What’s one thing life is teaching you right now?”
It’s a great question, but if you just met someone, it can feel like too much, too soon. Instead, the best icebreakers are:
✅ Safe (They don’t put people on the spot.)
✅ Contextual (They make sense in the moment.)
✅ Inviting (They encourage open-ended responses.)
That’s why the awkward elevator trick works so well—because it naturally leads into deeper conversations without forcing them.
3 Simple Tricks for Asking Powerful Icebreaker Questions
Now that you know how to generate great questions in the moment, here are three quick techniques to make your questions even stronger.
1. Cut Out Superlatives
Instead of asking:
- “What was the best part of your trip?”
- “What’s your favorite book?”
Try:
- “What is one of your favorite memories from your trip?”
- “What’s one book that really impacted you?”
Why? Because superlative questions (best, favorite, greatest) force people to rank their experiences, which can be tough. But when you ask for “one of,” it’s easier and more inviting to answer.
2. Flip the Curiosity Switch
Some say curiosity is like a muscle, but I think of it more like a light switch—you can turn it on at any time.
For example, if I handed you a blank piece of paper and asked you to come up with 20 questions about it, you could do it.
- Where was it made?
- Who used it last?
- What could it be used for?
If you can generate endless questions about a blank sheet of paper, imagine how many interesting questions you can ask about a person—who has a lifetime of unique, ungooglable experiences.
3. Start Your Questions with “What” or “How”
The way you phrase a question determines the kind of answer you’ll get.
For example:
- “Did you like your trip?” → Yes or No (not much to work with)
- “What was one of your favorite moments from your trip?” → A rich, detailed response
Avoid “Why” questions.
- If I ask, “Why are you watching this video?”, you immediately have to rationalize and justify. That can put people in defensive mode.
- Instead, try “What made you interested in this topic?”—which invites curiosity instead of pressure.
Mastering the Art of Meaningful Icebreakers
If you really want to master the art of breaking the ice—especially with adults—you should check out my video on Connection Before Content. It’s packed with strategies for facilitating engaging, trust-building conversations in groups.
And if you’re still looking for a list of icebreaker questions, I’ve got you covered! Download our FREE printable question cards, book excerpts, and more right here.
Go out and spark some great conversations!
Chad