Today I sat down with Jan Keck (a self-proclaimed âcommunity addictâ) whose tagline is âLetâs have conversations that matter.â 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
⢠Janâs definition of a close friend: who could you show up to at midnight with a bottle of wine and theyâd let you in?
⢠The moment a personal goal-setting retreat changed Janâs path, and why belonging hits different when you feel accepted as you are
⢠The difference between:
⢠connecting based on shared history (where youâre from), and
⢠connecting based on shared direction (where youâre heading)
⢠Whether âbelonging at workâ is real, and why itâs harder when people didnât opt in
⢠The concept of challenge by choice (the pool metaphor) for vulnerability and participation
⢠How Jan âholds spaceâ 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 âLeaveâ, and why Jan now builds in an informal hangout after sessions
⢠Janâs Campfire Formula for engagement: you donât light a big log first, you build momentum with micro-actions
⢠The three levels of Ask Deep Questions cards:
⢠Curious: âWhat are you most grateful for in your life?â
⢠Brave: âIf you could relive a moment of your life, which one would you pick?â
⢠Vulnerable: âHow do you want to be remembered?â
⢠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 Iâm stealing: Presence over perfectionPractical takeaways Iâm sitting with
⢠If you want depth, design for depth. It doesnât âhappen naturallyâ on Zoom.
⢠The âclosingâ matters. Virtual events need a deliberate debrief runway.
⢠For groups bigger than about 6â7, you need structure or youâll get silence.
⢠Donât ask for vulnerability first. Earn it.About todayâs 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
⢠Janâs site: jankeck.com
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