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.

Links

• Ask Deep Questions: askdeepquestions.com
• Jan’s site: jankeck.com

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