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Depth2 min read · Depth · The Art of Being Interested
Skip the Weather
The default questions get default answers. One slightly unusual question can rescue a whole conversation.
"How was your weekend?" "Busy, you?" "Yeah, busy." You've had this exact exchange a hundred times, and you can't remember a single one of them.
Predictable questions run on autopilot. To wake a conversation up, you have to ask something the other person hasn't already answered five times today.
A fresh question interrupts the script
When you ask "what's been the best part of your week?" instead of "how are you?", the other person has to actually think. That small pause — the one where they stop reciting and start considering — is where a real conversation begins.
Ordinary questions get answers people have already given. Ask the one they haven't.
Swap the autopilot question
AUTOPILOT
How was your weekend?
WAKES THEM UP
What's something good that happened this week?
THE TAKEAWAY
Replace one default question with a slightly unexpected one.
You don't need to be clever — just curious enough to break the script.
PRACTICE THIS · DEPTH
- Ask for the story, not the summary.
- Trade "What do you do?" for "What are you proud of lately?"
- Share something real first — it gives them permission to.
- Follow your curiosity, not the script.
- Before asking someone to open up, share one true thing yourself first.
- When someone states a fact, ask why it matters to them.
- Trade "how are you?" for "what's the best part of your week?"
- Ask about firsts and turning points — they always come with a story.
SOURCES & FURTHER READING
- Debra Fine. The Fine Art of Small Talk — Hachette Books (2005; on open-ended questions that move past scripted exchanges)