Questions That Ask Tend to Offer the Richest
Twenty general-purpose questions that reliably get past small talk, useful in interviews, one-to-ones, first meetings and long car journeys. Each entry says what the question tends to surface and what a thin answer to it looks like.
The questions
Open any question for the note
What's the story behind that?
Why ask it
Works on an object, a job, a scar or a decision, and it asks for a narrative rather than a fact, so it cannot be answered in one word. If you get a one-line answer, the story exists and the trust does not yet.
How did you end up doing this?
Why ask it
Almost nobody's path was planned, and this question gives permission to say so. The interesting material is in the accidents, and people rarely volunteer them until asked how rather than what.
What's it actually like, day to day?
Why ask it
The word actually does the work: it invites the unglamorous version rather than the job description. Expect answers about admin, waiting and small indignities, which is where the truth of most work lives.
What surprised you most?
Why ask it
Surprise marks the gap between what someone expected and what happened, so the answer tells you what they believed going in. A blank here often means they have told the story so many times it has gone smooth.
What was the turning point?
Why ask it
Asks for one moment, and the single-answer constraint is why it works. Whatever they name is what they consider the cause, which may not be what an outsider would have picked.
What nearly stopped you?
Why ask it
Better than asking about obstacles in general, because it asks about the one that came closest. People are usually more candid about a near miss than about a failure.
What kept you going when it was bad?
Why ask it
Answers split into people, money, stubbornness and having nothing else, and each says something different about the person. Watch for the rehearsed version, which tends to be a slogan rather than a name.
What did you get wrong at the start?
Why ask it
Easier to answer than a general question about mistakes, because early errors are safely in the past. Someone who cannot name one either has not reflected or is managing you.
What do most people misunderstand about this?
Why ask it
Invites the correction they have been waiting years to make, so it usually produces the most fluent answer of any question here. It also hands you the shape of the field from the inside.
What's the part nobody sees?
Why ask it
Points at the hidden cost or the hidden labour rather than the highlight. Useful with anyone whose work looks glamorous from outside, and it often surfaces something they are quietly proud of.
What would you tell someone starting this week?
Why ask it
The tight time frame makes the advice concrete instead of inspirational. General wisdom in reply usually means they are talking about themselves rather than the beginner.
What did you have to give up for it?
Why ask it
A question people are rarely asked, and the pause before the answer is worth noticing. Answers involve money, health, a city, or a relationship, and they tell you what the achievement actually cost.
Who taught you the most, and what did they do?
Why ask it
The second half stops it becoming a name-drop. What the person did is usually small and specific, and it reveals what the speaker considers good practice.
What's a decision you'd make differently now?
Why ask it
More answerable than a question about regrets because it is framed as information rather than fault. If they revise nothing, they may be defending a story rather than describing one.
What are you still not sure about?
Why ask it
Live uncertainty is more interesting than settled conclusions, and admitting it takes a degree of confidence. This is the question that separates people who are thinking from people who are presenting.
What are you working on that isn't going well yet?
Why ask it
The word yet gives them somewhere to stand while being honest. Answers here are usually current, unpolished and the closest thing to real news you will get.
What would you do with a year and no obligations?
Why ask it
Removes constraints to find out which of them are actually the problem. If the answer is close to their current life, that is worth knowing too, and it is usually said with some surprise.
What have you changed your mind about recently?
Why ask it
Tests whether new information reaches them at all. Recently matters: a conversion from twenty years ago is a story, while a shift last month is a habit of thinking.
What does a good version of the next five years look like?
Why ask it
Asking for good rather than best gets a realistic answer rather than a fantasy. Vagueness is not failure here; it tells you they are in an open stretch rather than a planned one.
What should I have asked that I didn't?
Why ask it
Hands over the direction at the end, and it routinely produces the best material of the conversation. If the answer is nothing, ask what they were expecting you to ask instead.
How to Ask Questions That Open People Up
Practical guidance for the conversation itself
What makes a question open up
- It asks for one instance rather than a general rule. "What happened the last time" gets a story; "how do you usually handle that" gets a policy.
- It carries no answer inside it. As soon as a question implies what you think, you get agreement instead of information.
- It is short. Anything over about fifteen words invites the other person to answer the easiest clause and ignore the rest.
- It is about them, not about the subject. People are generous about their own experience and cautious about their opinions.
- It can be answered without self-flattery. Questions that only have a boastful answer get a boastful answer.
Follow-ups that do the real work
- 1"What happened next?" Keeps a story moving without you steering it.
- 2"What was that like?" Moves from events to experience, which is where the useful detail is.
- 3Repeat one of their own words back as a question. If they said "chaotic," say "chaotic?" and stop.
- 4Wait. Four or five seconds of silence produces the second, truer sentence more reliably than any prompt.
- 5"You mentioned two things. Say more about the second." People bury the interesting item in the middle of a list.
Common pitfalls
Stacking two questions together
Ask about the turning point and what they learned in one breath, and you will get the second half only. Ask one, wait, then ask the other.
Leading with your own theory
"It must have been exhausting, was it?" hands them a script. Say the neutral half only, and let the adjective be theirs.
The counsellor voice
"How did that make you feel" makes some people withdraw, especially at work or across generations. "What was that like" asks the same thing without the appointment.
Filling the silence you created
A big question needs thinking time, and rushing in to rephrase resets the clock. Count to five before you say anything at all.
Interviewing instead of talking
Six questions in a row with nothing offered back makes the other person the subject. Answer one of your own every few minutes, briefly, then return the floor.
Asking for wisdom before you have the facts
Reflection questions land badly before you know what happened. Get the story first, then ask what they would do differently.
Reading what comes back
- The polished anecdote is the one they always tell. Ask a detail question inside it, and you leave the script for the first time.
- Hesitation usually means thinking, not reluctance. Immediate, fluent answers to hard questions are the ones to probe.
- "I don't know" is often a pause rather than a full stop. Say nothing, and roughly half the time they carry on.
- Notice which subject they return to unprompted. That is what the conversation was really about, regardless of what you asked.
- If a question lands badly, say so plainly and move on. Acknowledging the misfire costs you nothing and salvages the rest.
Where these fit
- One-to-ones at work: the uncertainty and not-going-well questions get you further than any status update.
- Interviews and reference calls: ask what they got wrong at the start, and what nobody sees.
- First meetings and dinners: begin with the story-behind and how-they-ended-up questions, and stay there.
- Family, especially older relatives: turning points, who taught them most, and what they gave up. Record it if they will let you.