If you’ve ever asked a question that landed flat or one that suddenly opened up a deep, meaningful conversation you know there’s an art to asking powerful questions.
In this exercise, inspired by my book Ask Powerful Questions, you’ll learn a simple but profound trick: contextualize your questions. When you personalize a question and put it in someone’s real-world context, it becomes significantly more engaging, relevant, and trust-building.
This is a simple, flexible icebreaker for meetings, a thoughtful conversation starter for groups, and one of the best team building activities for adults who want to deepen relationships fast.
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.
The Secret Behind Powerful Questions
I begin with a simple observation:
“Most powerful questions are powerful because they’re personalized and put in the context of someone’s life.”
Take a question like, “What brings you joy?”
If you walk up to a stranger at a bus stop and ask that out of nowhere, it’s…well, awkward. That question on its own is meaningful but abstract. It doesn’t build trust because it’s missing context.
But if you say:
“I think this is my 12th time taking the same bus route this week. I’m curious, during your commute, which probably isn’t the most enjoyable time what brings you joy about traveling to and from work?”
Now, you’ve created a bridge. You’ve made the question relevant to that person’s moment.
That’s the key. When a question is anchored in someone’s lived experience, it becomes powerful, not probing.
Step 1: Contextualize Your Questions
Almost every question in the We! Connect Cards or We! Engage Cards deck can be made more powerful just by adding context to the end.
Try these variations:
- What brings you joy at work?
- What brings you joy as a parent?
- What brings you joy in this season of life?
- What brings you joy in your community?
Each small tweak makes the question more relevant, more personal, and more likely to open up a genuine conversation.
Step 2: Choose a Question That Serves the People You Serve
Invite participants to flip through the deck and find one question they like, something that resonates with them and could serve the people they serve.
For example, if you work in education, healthcare, or leadership, think about questions that might help your students, clients, or team reflect more deeply.
Then, add context to the end of your chosen question to tailor it specifically for them.
Example:
“What helps you feel connected?” becomes “What helps you feel connected to your students?”
These slight adjustments can completely change the quality of the dialogue that follows.
Step 3: Mix It Up—Musical Chairs Style
Because we’re all creatures of habit, it’s easy to stay seated next to the same people. This exercise shakes that up!
Once everyone has chosen and personalized their question, have them stand up and find a new seat next to someone they haven’t connected with yet.
Ask your question, listen to their answer, and share your own. You might only get through one exchange, but even one intentional question can spark surprising insight.
This version of “musical chairs” isn’t just fun, it creates new connections across the room. It’s an excellent icebreaker for small groups or a conversation starter for team meetings.
Step 4: Extend the Conversation
Even though time might be limited, Chad encourages participants to carry these conversations forward throughout the day at lunch, during breaks, or in future client interactions.
“The conversations we start here become little anchors and seeds to start future conversations.”
When you know a bit more about someone’s story, it changes how you engage with them later. You might find yourself asking:
“Hey, last time we talked about what brings you joy at work, how’s that going lately?”
That’s how small talk becomes meaningful talk.
Why Personalized Questions Build Trust
Personalized questions show presence, curiosity, and care. They:
- Demonstrate that you’re listening to someone’s reality
- Invite authentic stories and insights
- Create shared meaning and trust faster than generic questions ever could
And the best part? You can do this anytime, no fancy setup required.
Try It with Your Team
Next time you meet, grab a deck of We! Connect Cards or print a few from our DIY Printable Cards Pack.
Invite your group to:
- Choose one question that resonates with them
- Add context to personalize it
- Share it with someone new
Then, watch how quickly “icebreakers” become real, energizing, and memorable.
For even more techniques like this, check out the Engage to Educate Masterclass it’s packed with strategies to make every interaction more meaningful.
And don’t miss your free connection tools, printable cards, and exclusive book excerpts at weand.me/tools.
