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

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 coveredWhy we still feel alone even with endless ways to connectJan’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 areThe difference between:connecting based on shared history (where you’re from), andconnecting based on shared direction (where you’re heading)Whether “belonging at work” is real, and why it’s harder when people didn’t opt inThe concept of challenge by choice (the pool metaphor) for vulnerability and participationHow Jan “holds space” by designing the right container and community agreements, so the group carries the space, not the facilitatorThe awkward truth about virtual events: the instant drop-off when you hit “Leave”, and why Jan now builds in an informal hangout after sessionsJan’s Campfire Formula for engagement: you don’t light a big log first, you build momentum with micro-actionsThe 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 perfectionismA line I’m stealing: Presence over perfectionPractical takeaways I’m sitting withIf 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 guestJan Keck Creator of Ask Deep Questions Mission: helping people feel less alone through meaningful conversations and experiences.LinksAsk Deep Questions: askdeepquestions.comJan’s site: jankeck.comPre-order my new book WORK FAME and get featured on the Wall of Work FameSign up for free for my best articles every week: Work Fame.Show notes for every episode at https://podcast.leannehughes.comLet's connect on all the channels:Leanne Hughes on LinkedInLeanne Hughes on InstagramVisit my website: leannehughes.comEmail me: [email protected] you like to deliver your own private podcast feed to your audience? Sign up for a free trial today at Hello Audio.