An idea (great conversation)

Last year, I found myself at a school party for my daughter.

It was one of those events I was genuinely excited to attend—but also quietly anxious about.

The venue was filled with parents who had established friendships over years in the community, while as a military family who's moved frequently, I often feel like the newcomer trying to find my place.

These events are full of unknowns.

The small talk.

The awkward pauses.

The search for common ground with strangers.

But I've discovered something about myself: I'm genuinely curious about people's stories. (This is why I love doing podcasts).

So rather than worrying about what to say about myself, I lean into asking questions.

Strangely, that often feels more natural to me than sharing my own journey.

Maybe you can relate?

Looking back, I've realized that the moments I treasure most at gatherings like these aren't the networking opportunities or the catered food—they're the conversations that transcend small talk and create genuine connection.

Today, I want to share what I've learned about having those kinds of conversations.

The Illuminator's Advantage

I've been diving into two transformative books—How to Know a Person by David Brooks and TALK by Alison Wood Brooks—that have fundamentally changed how I approach conversations, both in daily life and leadership.

(By the way, my recent conversation with Alison Wood Brooks has over 96,000 views on YouTube—clearly her insights are resonating with people!)

At the heart of it all is this powerful truth:

Great conversations aren't about impressing people.

They're about seeing people.

David Brooks calls this being an "illuminator"—someone who shines the spotlight on others and helps them feel seen, heard, and valued.

In a world where distraction is the norm and deep attention is rare, this kind of presence is remarkable.

Here are three practices to transform your conversations and become that kind of person:

1. Practice Genuine Curiosity with "Empathetic Attention"

Curiosity isn't just a skill—it's the doorway to connection.

David Brooks introduces the concept of "empathetic attention" in his book—a way of listening that goes beyond hearing words to understanding the emotions, values, and meaning beneath them.

What this looks like in practice:

Make eye contact and put away your phone completely
Nod and provide small verbal affirmations like "I see" or "That makes sense"
Notice emotional shifts in their tone or body language
Resist the urge to immediately relate their experience back to your own

Try asking these curiosity-driven questions:

"What's something you've been thinking deeply about lately?"
"What's energizing you in this season of life?"
"What are you excited about right now?" (My new favorite question)
"What would you be creating or pursuing if time and money weren't factors?"
"What's been surprising you recently?"

Then—pause.

Don't rush to respond or share your own story.

Let the silence work for you.

As Brooks notes, "The most important moments in conversation are often when no one is talking."

Pro tip from Alison: When someone gives a brief answer, try counting silently to three before responding.

This tiny pause often encourages them to continue with something deeper.

2. Use "Spark Questions" to Ignite Meaningful Exchange

Alison Wood Brooks studied thousands of conversations and discovered something fascinating: people often default to safe, surface-level questions, yet most of us are actually hungry to go deeper.

We want to be known.

We just need an invitation.

In her book TALK, she introduces "spark questions"—emotionally rich prompts that build trust, invite vulnerability, and encourage meaningful storytelling.

Standard questions get standard answers.

Spark questions create memorable conversations.

Spark questions to try in different contexts:

For work settings:

"What's been the most unexpected challenge in your role?"
"What part of your work gives you the most satisfaction?"
"What's one thing about your professional journey that most people wouldn't guess?"

For social gatherings:

"What's something you're learning right now that's exciting you?"
"What's a small habit that's made a big difference in your life?"
"When was the last time you changed your mind about something important?"

For deeper relationships:

"What's something you wish more people understood about you?"
"What's a belief you hold that's been shaped by a specific experience?"
"What's one value you're not willing to compromise on?"

Both Brooks and Brooks (David and Alison!) emphasize an important truth: If you want others to be more open, start with a little more openness yourself.

Share something real (though appropriate to the setting) from your own experience.

This signals psychological safety and invites deeper connection.

3. Master the Art of the Follow-Up

Both authors emphasize that great conversations aren't about checking off questions from a mental list—they're about following the trail of what matters.

When someone shares something meaningful, resist the urge to move on to your next prepared question.

Instead, lean in.

The follow-up question is often more important than your initial question.

David Brooks calls this "going to the second question," while Alison Wood Brooks refers to it as "responsive questioning."

Both agree: this is where the magic happens.

I've found this to be true in podcasting, too.

Effective follow-up techniques:

The Simple Extension: "Can you tell me more about that?"
The Emotion Probe: "How did that make you feel?" or "What was that experience like for you?"
The Values Clarifier: "What about that matters most to you?"
The Storytelling Invitation: "What led up to that?" or "How did that unfold?"
The Reflection Prompt: "Looking back, how do you think that shaped you?"

According to Alison Wood Brooks' research, the most successful conversationalists aren't those who ask the most questions—they're those who ask the right follow-up questions that show they're truly listening.

Pro tip from David Brooks: Pay attention to "gleams"—those moments when someone's energy shifts, their eyes light up, or their voice changes.

These are clues to what truly matters to them.

When you spot a gleam, follow it with a question.

Putting It All Together: The Conversation Blueprint

Based on both authors' research, here's a simple framework for your next conversation:

Begin with presence: Put away distractions and offer your full attention
Open with a spark question: Start with something that invites a meaningful response
Listen for gleams: Notice what energizes them or carries emotional weight
Follow the gleam: Ask follow-up questions about what seems to matter most
Share thoughtfully: Offer your own relevant experience, but return the focus to them
Express appreciation: Thank them for sharing, especially if they've been vulnerable

This rhythm—curious question, attentive listening, thoughtful follow-up, brief sharing, return to curiosity—creates the conditions for genuine connection.

The Conversation Revolution

Whether you're at a school event where you know few people, leading a team meeting, or having dinner with old friends, every conversation is an opportunity—either to connect meaningfully or merely pass time.

These practices from Brooks and Brooks can transform ordinary exchanges into moments of genuine connection.

You don't need to be the most charismatic person in the room.

You just need to show up with attention and care.

The reward is immeasurable: deeper connections, richer relationships, and the profound joy of truly knowing others—and being known yourself.

A question

What’s one relationship you would like to deepen—and how might asking better questions help?

A quote and resource

“Being heard is so close to being loved that for the average person, they are almost indistinguishable.”

— David Augsburger

The Mission

I am on a mission to help thousands of leaders gain clarity, courage, community, and consistency in their lives. Thank you for joining me on this journey!

I'm rooting for you,

Cal

➡️ When you're ready, I can help you gain more joy and deep clarity with my Core Values Mini Course. It has helped over 150 leaders live a truly intentional life. Join here 🎯

Intentional Letter: Beyond Small Talk