Have you ever noticed how most live online sessions start the exact same way?
“Drop your name and where you’re calling in from in the chat.”
And that’s OK. It’s familiar and safe.
The problem is that it doesn’t spark connection.
A few years ago, I joined an online course that opened with a very different question:
👉 “What’s one thing you’re bad at?”
The only instruction: share something “you wouldn’t normally say out loud.” One sentence. No explanation.
Every bone in my body resisted it at first.
My inner positive psychology voice wanted to reframe it: “What’s something you want to be better at?”
But I trusted the facilitator (🙌 Kevon Cheung). So I stuck with it.
And then suddenly it came to me:
“I’m really bad at finding a first small step to implement a big idea.”
I’d never expressed that before. And something shifted.
I felt… relieved.
The chat filled with responses like:
💬 “Being consistent.”
💬 “Keeping track of my coffee intake.”
💬 “Following through on small habits.”
We nodded as we read the responses. The chat lit up with comments and reactions. And instantly—we were a group.
The Power of a Great Prompt
That’s the magic of what I call a Power Prompt—a short question that you drop in the chat at the start of your session that invites people to share something a little deeper.
It goes a step beyond name and location.
And when you get it right, it immediately answers the unspoken question every participant is asking at the start of your session:
👉 Do I belong here?
Why does it work?
Because when people feel that they can relate to the other members of the group, they’re more likely to stay engaged, take risks, and contribute meaningfully.
✅ How to Craft a Power Prompt
Want to try one in your next session? Here are the 6 elements I use for formulating power prompts for fast-tracking connection:
1️⃣ Connect it to your purpose
Use it to warm people up for the session’s theme or goal.
2️⃣ Tailor it to your audience
What feels fun for one group might feel awkward to another.
3️⃣ Find the right level of risk
Gently nudge people into their stretch zone—never the panic zone.
4️⃣ Make it universally answerable
Avoid niche or insider questions.
5️⃣ Spark curiosity
Ask something people want to answer—and are eager to hear others respond to.
6️⃣ Keep it focused
Use phrasing like “One thing…” or “Something that…” to encourage quick, thoughtful responses.
🔥 5 Power Prompts You Can Steal
(Feel free to adapt them for your purpose and audience by adding “…when it comes to X topic”)
1/ One thing you’re celebrating right now
Great for starting on a positive note
2/ One superpower you wish you had
Useful for surfacing challenges in a playful way
3/ One thing you’ve been curious about lately
Opens creative thinking for idea-generating sessions
4/ One work win you’ve had recently
Perfect for teams working toward common goals
5/ One piece of advice you’ve found helpful lately
Encourages peer learning and invites people to share wisdom (without being preachy)
💡 Facilitation Tips for Leading Power Prompts
✨ Warm up first: Set an inviting tone before dropping the question
✨ Model your answer: Share your answer to build trust
✨ Narrate responses: Highlight patterns, celebrate surprises
If you see eyes rolling, take a second to give your group some context and let them know why you are asking the question.
🎤 Over to you
What’s a Power Prompt you could use (or already love using) to fast-track connection in your groups?
Hit reply—I’d love to hear it!
This week’s Facilitator Finds 💪
In this section, you’ll find curated events, resources, tips, and tools that I’ve found super valuable — and I think you will too!
⚒️ Check In Magic. A brilliant prompt generator by expert facilitator (and my long-time mentor!) Nadia Chaney. It helps you find the perfect check-in question for any group. I’ve tested it—it’s amazing.
⚒️ Daresay. A simple, swipe-friendly prompt generator packed with inspiration for crafting fresh check-in questions. Quick. Playful. Surprisingly useful.
✍️ Six Questions for 2026. From Tiny Experiments author Anne-Laure Le Cunff. These reflective questions are designed for journaling—but they also make great session prompts if you’re guiding a group into future thinking.
💌 Thanks for reading The Quest
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Creatively yours,
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