Dec. 26, 2025

🌴361. Ask Deep Questions feat. Jan Keck (Weekend Rewind)

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Show Notes

Today I sat down with Jan Keck (a self-proclaimed “community addict”) whose tagline is “Let’s have conversations that matter.” Jan created Ask Deep Questions, which started as a deck of cards to help friends connect on a camping trip and has since grown into a global tool for facilitating meaningful conversations.

We talked about the real stuff: loneliness in a hyper-connected world, how to build belonging without forcing it, and how to hold space when things get awkward or emotional, especially online.

What we covered

Why we still feel alone even with endless ways to connect
Jan’s definition of a close friend: who could you show up to at midnight with a bottle of wine and they’d let you in?
The moment a personal goal-setting retreat changed Jan’s path, and why belonging hits different when you feel accepted as you are
The difference between:
connecting based on shared history (where you’re from), and
connecting based on shared direction (where you’re heading)
Whether “belonging at work” is real, and why it’s harder when people didn’t opt in
The concept of challenge by choice (the pool metaphor) for vulnerability and participation
How Jan “holds space” by designing the right container and community agreements, so the group carries the space, not the facilitator
The awkward truth about virtual events: the instant drop-off when you hit “Leave”, and why Jan now builds in an informal hangout after sessions
Jan’s Campfire Formula for engagement: you don’t light a big log first, you build momentum with micro-actions
The three levels of Ask Deep Questions cards:
Curious: “What are you most grateful for in your life?”
Brave: “If you could relive a moment of your life, which one would you pick?”
Vulnerable: “How do you want to be remembered?”
Scaling connection in large groups using breakout rooms, structure, and clear instructions (plus the link to the bystander effect)
Confidence on camera: why Jan credits improv (and repeating discomfort) for killing perfectionism
A line I’m stealing: Presence over perfection

Practical takeaways I’m sitting with

If you want depth, design for depth. It doesn’t “happen naturally” on Zoom.
The “closing” matters. Virtual events need a deliberate debrief runway.
For groups bigger than about 6–7, you need structure or you’ll get silence.
Don’t ask for vulnerability first. Earn it.

About today’s guest

Jan Keck

Creator of Ask Deep Questions

Mission: helping people feel less alone through meaningful conversations and experiences.

🌴361. Ask Deep Questions feat. Jan Keck (Weekend Rewind)

What we covered

Practical takeaways I’m sitting with

About today’s guest

Links

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