Let me share a story from a few years ago that changed how I approach social situations.
As an introvert, I've never found initiating deep conversations easy. That's what makes this story surprising...
I was co-hosting a dinner party with guests who were astrangers to each other. Before everyone arrived, I grabbed our Icebreaker Deck on my way out—just in case we needed conversation starters.
As we sat down to eat, I randomly pulled a card from the "Deep" category, asking about a time I failed at something important. Instead of shuffling it back for something lighter, I decided to jump into the deep end and shared a vulnerable story.
What happened next amazed me. One by one, each person followed my lead, sharing meaningful experiences from their own lives. Despite lighter question categories, everyone kept saying, "Let's stick with the deep ones." By the end of our two-hour dinner, we'd formed connections that typically take months to develop.
This taught me something powerful: whoever goes first sets the tone.
What "One Level Deeper" Sounds Like
Going deeper doesn't mean sharing your darkest secrets. It means offering something more authentic than expected:
With a colleague: "What was the best part of your weekend?" or "Do anything fun I should know about?"
With a new acquaintance: "What are you obsessed with right now?" or "Working on anything exciting?"
With a friend you haven't seen in a while: "I was just thinking about our Chicago trip—remember that ridiculous pizza place? I've missed our adventures. What's been eely?"
With a service provider: "Love that pin on your apron—where'd you get it?" or "Your car is immaculate! How long have you been driving for Uber?"
🗓️ Weekly Challenge:
The 3-Minute Connection Challenge
Today, try revolutionizing one interaction by going first:
1️⃣ Choose Your Moment (30 seconds)
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Pick one conversation where you'd normally stay surface-level.
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Decide what level you're willing to share.
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Commit to "going first" within the first minute.
2️⃣ Break the Pattern (2 minutes)
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Share a genuine challenge you're facing.
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Give a specific and thoughtful compliment.
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Ask a deeper question.
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Admit something you're learning or don't know yet.
3️⃣ Notice What Shifts (30 seconds)
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Pay attention to the energy changes.
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Watch the other person's response. They'll likely match your depth.
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Notice how differently you feel in this more authentic exchange.
🥇 Quick Win
Next time someone asks "How are you?", pause before answering. Instead of "fine," share something specific: "I'm feeling energized about a project I started this morning" or "I'm juggling a few challenges this week, but learning a lot." Watch how quickly the conversation transforms.
Reading the Room
While vulnerability builds connection, there's wisdom in matching the context:
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The setting: Go deeper in casual settings; stay professionally relevant in formal ones.
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Your relationship: Share more with established connections.
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Their energy: Notice if they seem rushed or distracted.
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Cultural context: Be mindful of different disclosure norms.
The key is being one step deeper than the expected conversation—not three steps. If everyone's talking about the weather, sharing your passion project is perfect. If they're discussing work challenges, sharing how you navigated a similar hurdle works well.
🛠️ Weekly Top Picks:
📚 Reading Corner
"The Power of Moments" by Chip & Dan Heath
This book transformed my thinking about creating meaningful connections. The Heath brothers show our most significant relationships are built not on time spent but on key moments of authenticity, elevation, and shared vulnerability.
🔍 Resource
21 Connection Prompts for Going First
Unsure what to say when "going first"? I've created a free resource with 21 conversation starters organized by vulnerability level—from gently opening the door to creating deeper connection. Perfect for skeptics wanting to try this approach but aren’t sure where to start!
Here's to being brave enough to go first,
Cheers,
Cathryn
