Note: The brand new Future Focused We! Connect Cards featured in this video are free (and only available*) to attendees of the 2025 Connectors Summit.
In my humble opinion, this is one of the best team-building exercises for adults. And I say that after leading it with over 100,000 people around the world. Why does it work so well?
Because it does two powerful things:
- It primes people with the intent that they may have one of the best conversations they’ll ever have.
- It gives them autonomy and choice over how long they stay in a conversation.
If you hit the “conversational lottery” and you’re having an amazing connection—you can just stay there. There’s no forced swapping or artificial time limits.
Let’s unpack how it works and why it’s so effective for team building, group connection, and icebreaking for adults.
Note: The brand new Future Focused We! Connect Cards featured in this video are free (and only available*) to attendees of the 2025 Connectors Summit.
Thinking About Conversations Like the “Conversational Lottery”
How many of you have had phenomenal conversations in your life? The kind that left you inspired, energized, or with a completely new perspective?
And how many have had conversations that felt like a waste of time, or worse, that drained you?
Because that’s true for all of us, I like to think about conversations like the conversational lottery.
In this lottery, the prize isn’t money, it’s perspective. Sometimes, you walk away thinking:
“Wow, I never thought of it that way.”
Other times, that “first chat” turns into a lifelong friendship, a new client, or even a marriage! Conversations can shift the trajectory of your life.
The Story of Steve: A Lesson in Mindset
Let me introduce you to Steve, the janitor in my Pittsburgh office building.
One night, after leading a virtual workshop for a company in Australia, I stepped out of my office around midnight and accidentally scared the heck out of Steve. Once we caught our breath, we started chatting.
I asked, “How’s work going, Steve?”
He smiled and said, “Pretty good. I had a meeting.”
Now, I don’t know about you, but nobody in my world says they had a good day because they had a meeting.
Steve explained:
“My boss called me down and said, ‘Steve, I’d like you to clean half the floors you’re doing now.’ So he cut my work in half and gave me a raise! I walked out of that meeting thinking, ‘Man, I’ve got to have more meetings.’”
Unlike most of us, Steve walks into meetings thinking, “Something good could happen here.” That mindset is the foundation of the Conversational Lottery Exercise.
How to Facilitate the Conversational Lottery Exercise
Here’s how to run one of the most powerful icebreaker activities for adults or team-building exercises for work:
- Grab a Card
Use a deck of We! Connect Cards they’re perfect for this. Each person draws one at random. - Find a Partner
Pair up with someone you don’t know super well yet. - Ask and Answer
Take turns asking each other the question on your cards. Listen fully to their answer before sharing your own. - Swap and Repeat
After your chat, swap cards and raise your hand to find a new partner. Continue for several rounds.
What happens next? Magic. You’ll find yourself having conversations that feel surprisingly authentic, deep, and meaningful, even with total strangers.
You can keep this activity running for as little or as long as feels right. It’s self-facilitating, high-energy, and works beautifully as a no-prep icebreaker for adults or fun icebreaker for meetings.
The Debrief: What Struck You About Those Conversations?
After a few rounds, I like to bring the group back and ask one of my favorite reflection questions:
“What struck you or what did you notice about those conversations?”
It’s one of the best conversation starter questions for team building, because it allows everyone to respond from their own perspective, emotionally, logically, or reflectively.
People usually share things like:
- “They were surprisingly deep.”
- “I had to think more than usual.”
- “They felt authentic and introspective.”
This is where the science of the exercise shows up. When you’re asked a question you’ve never been asked before, your brain creates new neural pathways. You’re literally simulating a new experience in your mind and trying on new ideas for size.
The Power of Autonomy in Questions
Here’s one of my favorite reminders:
When you are asked any question, you have 100% choice and autonomy in how you answer it.
That means even deep or personal questions can feel safe because you control how surface-level or vulnerable your response is.
For example, if someone asked me:
“Chad, how would you like to be remembered?”
I could keep it light:
“As someone who made a positive splash wherever I went.”
Or go deeper:
“About six years ago, I went on a kayak camping trip in the middle of nowhere and got really clear on why I exist: to gently eradicate small talk and create conversations that matter.”
Same question. Two completely different depths. When people are reminded they have full autonomy, they tend to respond more authentically.
Why This Is One of the Best Team-Building Activities for Adults
By the end of this exercise, people usually raise their hands and say, “I just had a conversation I never would’ve had otherwise.”
And that’s the magic. Connection before content.
It’s a powerful, low-cost, high-impact way to build trust, spark meaningful dialogue, and strengthen teams, whether you’re working in person or virtually.
If you’re looking to create deeper connection in your next meeting, retreat, or classroom, try the Conversational Lottery with We! Connect Cards.
