How to ask better questions in conversation
Open-ended questions are supposed to be the generous move. Usually they're the opposite. "So what's nursing like?" hands the other person a blank page: they have to pick an angle, guess what you're after and build an answer on the spot. Most people give you something flat, and the conversation stalls. A specific question does that work for them.
What it trains
- —Noticing one detail about someone and aiming your question at it
- —Asking questions that are easy to answer well, not just easy to answer
- —Spotting the interview question: polite, specific and dead on arrival
Why it works
Open questions put the work on the other person
A broad question feels like an invitation, but it's really a task. The other person has to decide what part of their life you mean and how much to say. Under that load most people pick the safest, shortest answer. A narrower question removes the decision, so the good answer is the easy one.
Specific shows you were listening
A question about one detail proves you heard it, and it hands them a starting line. "What's the thing about night shifts nobody warns you about?" is easier to answer than "What's your job like?", and far more interesting to hear the answer to.
Some specific questions are still dead ends
"What year did you graduate?" is specific and easy, and it gets you a year. Anything you could answer from someone's résumé asks for a record, not a person. The drill calls these interview questions and flags them every time.
An example
ICU nurse in Miami, a year out of UCF.
- works night shifts in the ICU
- plays pickleball most weekends
- has a small Bichon named Pepper
So what's nursing like?
What's the thing about ICU nights nobody warns you about?
It aims at one detail and hands her an angle, so the first line of her answer is already there.
Is pickleball what keeps you sane after a run of nights, or is that giving it too much credit?
It carries a guess she'll want to confirm or correct, which is the easiest kind of question to answer at length.
How the drill works
- 1.You get a short card about someone you've just met: a name, an age, one line about them and a few details.
- 2.You ask them one question, typed the way you'd actually ask it.
- 3.It's scored on specificity, ease and opening (does it invite a story?), with one adjustment for next time.
- 4.You see two other questions aimed at different details: a safe one anyone could ask, and one that takes a small risk.
- 5.As you get better, the card gives you less: fewer details, one marked as already covered, and a clock.
How it's scored
- Specificity
- Low: Generic; could be asked of anyone. High: Aims at one detail and implies a guess they'll want to confirm or correct.
- Ease
- Low: They'd have to organize a lot, or guess what you meant. High: Instant to answer, and the obvious first answer leads somewhere.
- Opening
- Low: Closed and factual: asks for a record, not a person. High: Invites a story and makes it easy to be a little revealing.
Try it every morning
Whetstone is in private testing. Join the waitlist.
The other drills: How to keep a conversation going · How to be quicker with comebacks · How to tell a story in conversation · What to say instead of "I agree" · How to think faster in conversation