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Depth2 min read · Depth · The Art of Being Interested

Ask About the Turning Points

People don't remember their averages. They remember the moments things changed — and those are the stories worth asking for.

"What do you do?" gets you a title. "How's work?" gets you a shrug. These questions ask people to summarize their lives, and summaries are boring to give and boring to hear.

There's a better target: the turning points. The firsts, the pivots, the moment something clicked or fell apart.

Memory lives in the moments that changed things

Ask someone about the first time they knew they loved their work, or the moment they decided to leave a city, and you get a story with a beginning and a stake. Turning points come pre-loaded with emotion, because they're the moments that mattered enough to remember.

Don't ask people to summarize their lives. Ask about the moment everything turned.

Questions that find the pivot

1
Ask about firsts

"What first got you into that?" or "When did you first know?" Firsts always have a scene attached.

2
Ask about the decision

"What made you finally decide to leave?" People love to revisit the moment they chose.

3
Ask what changed them

"Was there a moment that shifted how you saw it?" This invites the story, not the summary.

THE TAKEAWAY
Ask about beginnings and turning points, not general summaries.
Every turning point is a story waiting for someone to ask about it.
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
  1. Elizabeth Stokoe. Talk: The Science of Conversation — Little, Brown (2018; on how question design shapes the answers people give)
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