Why deeper connection starts with asking better questions—and actually listening
The Supermarket Aisle Audit
Picture this: I’m driving my 13-year-old daughter home from circus camp, and like a well-programmed dad-bot, I fire off my signature question: “How was your day?”
“Fine,” she says, staring out the window.
I nod, mentally checking the connection box, and start thinking about dinner prep. Another successful father-daughter interaction in the books, right?
Plot twist: I just drove past a buried treasure worth my entire emotional 401k.
Here’s what happened when I tried again yesterday. Instead of my autopilot question, I got specific: “How did your silks routine go today? Were you able to nail that move you’ve been working on?”
Suddenly, my quiet teenager transformed. She lit up, hands gesturing wildly as she described her breakthrough with a particularly tricky sequence. For the next ten minutes, I got a front-row seat to her world—her struggles, her victories, even her fears about the upcoming show.
Same kid. Same car. Same dad. But this time, I actually struck gold.
The Emotional Goldmine: What You’re Leaving Buried
Here’s the hard truth I’m learning: Our relationships, with our kids, our wives, our friends, are sitting on emotional goldmines. But instead of mining for the good stuff, we skim for fool’s gold on the surface.
Research shows that the average person has only three meaningful conversations per week. Three. That means we’re spending most of our time in emotional shallow water, splashing around in safe, surface-level questions—while the deep end sits untouched.
I know this because I’m the king of surface-level dialogue. My greatest hits include:
- “How was your day?” (the classic)
- “How did you sleep?” (morning edition)
- “What was the best part of your day?” (dinner table special)
These aren’t bad questions, but they’re like using a plastic shovel when you need a pickaxe. They keep us safely in the topsoil while the real treasure lies deeper.
Gold Diggers Use Better Tools: Ask Questions That Break the Script
The problem with our default questions is that they trigger default answers. “How was your day?” gets “fine” because it’s the conversational equivalent of asking someone to summarize a movie in one word.
What if we upgraded our tools? What if instead of surface-scraping, we started with questions that were already two or three layers deep?
Instead of “How was your day?” try:
- “What made you laugh today?”
- “When did you feel most like yourself this week?”
- “Was there a moment today you wished you could re-do?”
- “What was the last thing you thought about before falling asleep?”
- “Did you dream about anything interesting?”
- “What surprised you today?”
- “When did you feel proud of yourself?”
- “What made you curious today?”
These questions work because they bypass the autopilot brain and require actual thought. They’re specific enough to spark memory but open enough to let the conversation go where it wants to go.
Shut Up and Dig: Listening Is the Actual Mining
Here’s where I really struggle: Once I ask a better question, I have to shut up and actually listen. Not listen-while-planning-my-response. Not listen-while-thinking-about-the-dishwasher-that-needs-fixing. Actually listen.
This is harder than it sounds because silence makes us squirm. When our kid pauses to think, we jump in with follow-up questions or pivot to advice mode. It’s like doing a plank…uncomfortable, but that’s where the growth happens.
I’m trying to practice what I call the Pause-Repeat-Reflect method:
- Pause before replying. Count to three. Let the silence do its work.
- Repeat a key part of what was said. “So you felt nervous about the presentation…”
- Reflect with curiosity. “That sounds tough; what made it feel that way?”
This isn’t about becoming a therapist; it’s about becoming interested. There’s a difference between hearing your kid’s words and actually receiving them.
The Dad (or Partner) Practice: Connection in the Margins
The beauty is that you don’t need to carve out special family meeting time to practice this. The goldmine is hiding in the margins of ordinary life:
- In the car: “What’s something that happened today that I probably wouldn’t guess?”
- At breakfast: “What are you most curious about today?”
- During dinner: “What made you feel understood today?”
- At bedtime: “What are you grateful for right now?”
I’m also realizing this applies beyond kids. My wife and I have been defaulting to logistics conversations—who’s picking up whom, what’s for dinner, did you pay the water bill? By the time we collapse on the couch at night, we’re too fried for anything deeper. Our Saturday morning coffee talks are literally the only time we dig below surface level, and even those get interrupted by someone needing help finding socks or asking if they can have a snack.
Mini-challenge: I’m giving myself 48 hours without asking “How was your day?” Instead, I’m trying three upgraded questions and seeing what happens.
The Payoff: What Happens When You Actually Mine the Gold
When you start asking questions that matter and actually listening to the answers, something shifts. Your kids start trusting you with the real stuff, not just the sanitized highlights reel. Your conversations get deeper. You start seeing your children as the complex, fascinating humans they actually are instead of just the responsibilities they represent.
That breakthrough with my daughter’s circus routine? It wasn’t just about silks and aerial moves. In that ten-minute conversation, I learned about her perfectionism, her fear of looking silly in front of others, and her pride in pushing through something difficult. I got a glimpse of who she’s becoming.
And here’s the thing: She didn’t offer this information when I asked “How was your day?” She needed a question that matched the specificity of her experience.
This isn’t about raising obedient robots who report their daily metrics. We’re raising whole humans with rich inner lives, and if we want access to those lives, we need to ask questions worthy of the invitation.
The Cost of Skimming the Surface
Look, I’m not pretending I’ve figured this out. I still default to autopilot questions more often than I care to admit. I still jump in with advice when I should be listening. I still let logistics conversations crowd out real connection with my wife.
But here’s what I’m learning: You don’t get connection by being the perfect dad with perfect questions. You get it by being present enough to notice when you’re skimming the surface and humble enough to try again.
Our kids are walking around with rich inner worlds, complex emotions, and fascinating thoughts. Our partners have depths we haven’t explored in years. The emotional gold is sitting right under our feet; in car rides, at dinner tables, during bedtime routines.
Maybe it’s time to stop walking and start digging.
Focused Action This Week:
✅ Try The Question Upgrade: Ask one meaningful question each day, and practice sitting with the silence that follows.
📥 Bonus: Jot down one surprising thing you learn.
P.S. If you discover any question gold of your own, hit reply and let me know. We’re all learning to dig deeper together.
The Focused Fool Newsletter. Growing As Men. Leading As Fathers.
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