3 Questions to Ask
Questions that work almost anywhere, with a stranger at a table or someone you have known for years: what they are into at the moment, what a good day looks like for them, what they have changed their mind about, and what is coming up next. Light ones first, so you can stop after three if that is all the time there is.
The questions
Open any question for the note
What have you spent an unreasonable amount of time on lately?
Why ask it
The word unreasonable does the work: it gives people licence to admit to the hobby, game or rabbit hole they would normally play down. Those are the subjects they can talk about without effort, which is exactly what you want in the first two minutes.
What is the best thing you have read, watched or listened to recently?
Why ask it
Almost impossible to get wrong, and it reveals taste without asking anyone to be interesting on demand. If they say they have not had time for anything, that is worth following, because it usually means they are in the middle of something demanding.
Which part of your week do you actually look forward to?
Why ask it
The answer is nearly always small and specific: a Thursday swim, the drive home, one particular colleague. Those details tell you more about a life than a job title does, and they are easy to remember and ask about next time.
What is a small thing that reliably puts you in a better mood?
Why ask it
Cheerful, easy, and quietly useful: you learn how to be thoughtful toward this person later. Notice whether the answer involves other people or solitude, because that is a decent early read on how they recover from a hard day.
What were you like as a kid?
Why ask it
One of the few questions almost everyone answers immediately and at length, because the material is already sorted in their head. It also gives you a version of them with no professional armour, and the shy child inside the confident adult often explains a lot.
What does a genuinely good day look like for you?
Why ask it
Ask for an ordinary day rather than a holiday and you get their real values instead of their stated ones. Vague answers about relaxing usually mean they have not had many lately. Concrete ones, hour by hour, tell you what they are currently short of.
What are you into at the moment that you could talk about for an hour?
Why ask it
Better than asking about passions, which makes people feel they need something impressive. The invitation to talk at length is the permission most people are waiting for, and enthusiasm is the most reliable way to make a conversation stop feeling like small talk.
Where do you feel most like yourself?
Why ask it
Places carry stories, so this rarely gets a one-word answer. The answer is often somewhere they no longer go, which opens a much more interesting conversation about what changed than a direct question about their life would.
What are you better at than most people realise?
Why ask it
People are rarely given a socially acceptable way to mention a skill, and they enjoy it when they are. Expect something practical and unglamorous: mending things, remembering names, calming a room. It is a good question for someone who has been quiet so far.
Who has shaped how you work more than anyone else?
Why ask it
You learn the standards they hold themselves to, and who they measure themselves against. Watch whether the answer is an admired mentor or someone they are still reacting against, since a boss they are determined not to resemble is just as formative.
What would you do with a free month and nothing you had to do?
Why ask it
The answer separates rest from ambition. Some people describe sleeping and doing nothing, which tells you how depleted they are; others immediately name a project, which tells you what they would be doing if the rest of life allowed it.
What skill would you like to have by this time next year?
Why ask it
Specific enough to be answerable and forward-looking enough to feel hopeful. If they have already started, you get the real story of how it is going. If it is the same skill they named last year, that is a gentle opening rather than something to point out.
What are you working on at the moment that you actually care about?
Why ask it
The word actually lets them skip the parts of their job or week they are indifferent to, which is most of it. Expect a side project, something at home, or one strand of their work; the enthusiasm gap between this and their usual answer is informative.
What is the kindest thing someone has done for you?
Why ask it
Warmer than it looks. Answers tend to arrive with a whole scene attached, and they are often about a small act during a bad stretch rather than anything large. It changes the temperature of a conversation quickly, so it works well when things have stayed on the surface.
What is something you used to want and no longer do?
Why ask it
This finds the turning points without asking about regret. Some answers are relief at an escape, some are quiet grief about something set aside. Either way you learn what they chose deliberately, which is a more revealing thing than a list of goals.
What have you changed your mind about in the last year or two?
Why ask it
How someone updates their thinking tells you more than what they currently believe. A real answer includes what changed it: a person, an experience, being wrong in public. Someone who cannot think of anything at all has told you something too.
What is something you got through that you are proud of?
Why ask it
Pride is the safer frame; asking about hardship directly can feel like a request to perform pain. Let them choose the size of what they share, and follow the part they linger on rather than the part that sounds most dramatic.
What do you believe that most people around you do not?
Why ask it
Save this until the conversation has some ballast, since it asks for exposure. The interesting part is not the belief but how comfortably they hold it: whether they have argued it before, whether they expect you to disagree, whether they are testing you.
What question do you wish people asked you?
Why ask it
Hands the conversation over. It usually goes straight to the thing they most want to talk about and never get asked: an illness, a new baby, a project, a loss. Ask it, then actually ask their question and let them answer it properly.
What is coming up for you that you are looking forward to?
Why ask it
A good place to finish, because it leaves the conversation pointing forward and gives you a specific reason to get in touch afterwards. If nothing is coming up, that is worth hearing gently rather than filling with suggestions.
Using three questions well
Practical guidance for the conversation itself
Choosing which three
Match the question to the time you have
At a five-minute introduction, stay with the first four or five on this list: recent enthusiasms, the good part of the week, what they are into. The searching ones need enough time for the answer plus the follow-up, and cutting someone off mid-answer is worse than never asking.
Ask one thing, not two
Double-barrelled questions get half answers, because people respond to whichever part is easier and quietly drop the rest. Ask the first half, wait, and let the second half become your follow-up if it is still needed.
Earn the deeper question
Beliefs, regrets and what someone got through land well after twenty minutes and badly after two. If you want to go there sooner, answer it yourself first, briefly, so the risk is shared rather than requested.
With people you already know, ask about now
The failure with a long-standing friend or relative is assuming you know the answers. What they are into this month, what they have changed their mind about, what they are looking forward to: all of it moves, and none of it comes up in the usual exchange about work and weather.
The follow-up is where it happens
- 1Leave a gap after the answer. Most people stop at the tidy version and add the real one about four seconds later, if nobody fills the silence.
- 2Ask how rather than what: how did that start, how did you get into it, how did you decide. It moves the conversation from category to story.
- 3Follow the detail they gave you, not the topic you had planned. If they mention a place, a person or a year, ask about that specific thing.
- 4Reflect one phrase back in their own words. It shows you were listening more convincingly than any amount of nodding.
- 5Take your turn briefly. Thirty seconds of your own answer keeps it a conversation; three minutes turns it into your interview of yourself.
- 6Say what you liked about the answer before moving on, then move on. Interrogating one subject to exhaustion is as awkward as skipping between four.
What makes these fall flat
Firing them off in sequence
Three questions asked back to back with no follow-up feels like a form being completed. Two questions and real interest in the answers beats all twenty on this page.
Reaching for the profound too early
A stranger asked what they most regret will retreat rather than open up. The rule of thumb: never ask for more exposure than you have offered.
Answering your own question first, at length
It sets the length and the subject and quietly takes the turn away. Ask, listen, then match roughly the length of what they gave you.
Treating a short answer as a failure
Sometimes someone is tired, or the question missed. Take the short answer graciously, offer something of your own, and try a different angle later rather than pressing the same one.
Forgetting it all by next time
The whole value of a good answer is that you can return to it. Remember one concrete thing, the swim, the brother in Lisbon, the deadline in March, and ask about it when you next speak.