Positive Questions to Ask Someone
Positive questions to ask someone whose good news you'd like to hear: a friend you're catching up with, a coworker, a student, your own kids at dinner. They are grouped by where you are when you ask, from quick check-ins through friends, family and work or class, with a last group for a day that has gone badly. Most ask for something small and recent, such as what went right, who helped or what is coming up, because a small true answer is easier to give than a big polite one.
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The questions
Each question, and why to ask it
Check-in
What's gone right today, even if it was small?
Why ask it
'Gone right' is a lower bar than 'great', so a green light or a decent lunch counts. If they shrug, give one of your own first and the bar drops again.
What made you smile most recently?
Why ask it
The answer usually comes from the last hour or two: a dog, a text, something a kid said. Ask to see the photo or hear the joke, because the retelling is where they smile a second time.
What are you looking forward to in the next few days?
Why ask it
Small answers are the normal ones: Friday takeout, a new episode, a morning with no alarm. Remember what they said and ask how it went the next time you see them, which is what makes the question sound meant.
What are you thankful for today that you didn't expect to be?
Why ask it
The plain gratitude question gets 'my family, my health' by reflex. 'Didn't expect' pulls out something fresh, like the neighbor who took in the bins or the meeting that got canceled.
What's something you did this week that you're proud of?
Why ask it
Proud is a big word for a quick check-in, so show the size you mean with one of your own: 'I finally sent the email I'd been dodging.' If they wave it off with 'nothing special', ask what took the most effort this week, which is usually the same thing under a plainer name.
Who were you glad to see or hear from this week?
Why ask it
Asking for a person instead of an event tends to get a warmer answer, because the story comes with someone they like in it. A follow-up as plain as 'how do you two know each other' is all it needs.
What was the best thing you ate, saw or heard today?
Why ask it
Three doors, and nearly everyone has something behind one of them. It works by text as well as out loud, and a song or a sandwich recommendation often comes back with the answer.
What's one thing that's going better than it was a month ago?
Why ask it
A month is long enough to show progress that a single day hides. It suits someone who feels stuck, but if they can't find anything, don't supply one for them: move on and try again another week.
What did you finish lately that felt good to cross off?
Why ask it
Finishing is its own pleasure, and this lets in dull victories like a tax form or a cleared-out closet. 'That one's been hanging over you for a while' is the right size of reply.
What's a compliment you got recently that stuck with you?
Why ask it
People hold on to compliments and rarely get to repeat one without feeling boastful, so your asking gives them cover. Agree with it out loud.
Which part of today would you happily do again tomorrow?
Why ask it
It finds the good hour inside an ordinary day. When the same answer comes up a few times from the same person, you've learned what they would like more of.
Friends
What's the best thing that's happened to you since we last talked?
Why ask it
Naming the gap since you last spoke makes this a catch-up and not an interview, and shows you've kept track of it. Let them finish the whole story before you bring out your own news.
What are you proud of right now that you haven't told many people?
Why ask it
Friends often sit on good news for fear of bragging, and a direct question is the permission they were waiting for. React with as much enthusiasm as the news deserves, and don't add a 'but'.
Who do you admire at the moment, and what would you borrow from them?
Why ask it
The person someone names is often a clue to what they are working toward themselves. 'Borrow' keeps it practical: if they stop at a name, ask what that person does on an ordinary Tuesday that they'd like to be able to do.
What have you gotten better at this year?
Why ask it
Improvement is easier to claim than talent. Expect modest answers such as parallel parking or saying no, then ask what changed, since there is usually a decision behind it.
What do you have now that your younger self would be thrilled about?
Why ask it
The answers tend to be ordinary: a place of their own, a dog, staying up as late as they like. It makes a life they have grown used to look good again, and it's a fine one to trade answers on.
Who has made your life better lately, and do they know?
Why ask it
The second half is the part that does the work. If the answer is no, suggest sending the text right now while you're together; a friend sitting there is often the push it needed.
What are you excited about that I should be asking you about more often?
Why ask it
An honest way of admitting you may have missed something. Whatever they name, set yourself a reminder and bring it up again in a couple of weeks.
What's the kindest thing you've seen someone do recently?
Why ask it
Other people's goodness is easier to talk about than one's own, so this suits a friend who deflects praise. If they were on the receiving end, ask what they said back.
What's making you happy these days that has nothing to do with work?
Why ask it
Fencing off work gets you past the default answer and into the garden, the new friend, the band. Leave it for a calm stretch: asked of someone in the middle of a mess, it sounds as if you haven't been listening.
What small thing do you do that reliably improves your day?
Why ask it
You'll hear about the walk before breakfast, the good pen, the playlist for the commute. These are easy to copy, so try one and report back.
What's a memory of the two of us that still makes you laugh?
Why ask it
For old friends more than new ones. One story sets off another, so leave time, and argue about the details as loudly as you like, because that's half the fun.
What would you say you're good at if modesty weren't a thing?
Why ask it
Setting modesty aside as a joke is what stops this from sounding like a worksheet. Back up whatever they claim with a time you saw it yourself.
What are you hoping the next year brings?
Why ask it
A hope is softer than a goal, so nobody has to defend a plan or a deadline. Notice which part they say with the least certainty and ask about that one.
Family
What was the best part of your day, and what made it good?
Why ask it
The dinner-table standard, and it goes stale when it's asked the same way every night. The second half keeps it alive: 'recess' turns into a story about who was there.
What did you do today that deserves a high five?
Why ask it
A high five is pride at a size a six-year-old will ask for, and it works on adults too: 'I got through the whole inbox' earns one. Give the actual high five across the table, since the slap is the half the kids are answering for.
Who was kind to you today, or who were you kind to?
Why ask it
Either direction counts, which keeps a child from feeling quizzed about their own behavior. Over a few weeks the same names keep coming up, and you find out who their people are.
What did you try today that you weren't sure you could do?
Why ask it
It praises the attempt before anyone knows the result, so an answer ending in 'and it didn't work' still earns a 'good for you'. Parents should answer as well: a child who hears an adult say 'I wasn't sure I could' learns that not being sure is allowed.
What did someone at this table do this week that you appreciated?
Why ask it
Go around so that each person gives one and gets one. Small and concrete is better than grand: 'you saved me the last waffle' means more than 'you're always nice'.
What's your favorite memory of a time we were all together?
Why ask it
Good for a holiday table or a visit from grandparents. Everyone remembers the same trip differently, and nobody has to win the argument about what really happened.
What's one thing we should do together before the month is over?
Why ask it
Looking forward works better with a date on it. Write the answers where everyone can see them and do at least one, or the question stops being believed.
What did you learn today that you didn't know this morning?
Why ask it
A fact from class, a shortcut at work, how to whistle. When a teenager says 'nothing', try 'then tell me something I don't know' and see what you get.
What's something our family does that you hope we never stop doing?
Why ask it
Expect the odd traditions: the made-up song, pancakes for dinner, everybody talking at once. Whatever gets named has just been voted in, so keep doing it on purpose.
What's the best thing about being the age you are?
Why ask it
Ask it across the generations at one table. The seven-year-old and the seventy-year-old both have an answer, and each tends to be surprised by the other's.
Work or class
What went well this week that we should do again?
Why ask it
It opens a team meeting or a class review on evidence instead of cheerfulness. Put the answers where people can see them, because a good thing that goes unrecorded is seldom repeated.
What work of yours from this month deserves more attention than it got?
Why ask it
A lot of good work is invisible: the cleanup, the careful handoff, the error nobody will ever meet. A one-to-one is the place for it, and you can pass the credit along afterward if they're happy for you to.
Who helped you this week, and what exactly did they do?
Why ask it
'Exactly' is the point. 'She caught the mistake in my slides before the client did' shows the room what help looks like here, and 'everyone's been great' shows it nothing.
What did you figure out recently that would save someone else time?
Why ask it
It treats what they know as worth passing on, which is a compliment in itself. In a class, let the student show it at the board; at work, ask whether they'd write it up in three lines.
Which task this week did you enjoy more than you expected to?
Why ask it
Nobody has to pretend to love the whole job or the whole subject to answer, only to admit that one task beat its reputation. Keep the answer in mind the next time you hand out work.
What's one strength of the person next to you that the rest of us should know about?
Why ask it
Give a minute's warning so nobody has to improvise praise, and go around in order so no one is skipped. In a group that has only just met, change it to a strength they've noticed in anyone in the room.
What feedback have you been given that turned out to be useful?
Why ask it
A reminder that criticism can help, with no speech required. It also tells you which kind of feedback this person can take in, which is worth knowing before the next review or report card.
What do you understand now that confused you a month ago?
Why ask it
A progress report written by the student. Save the answers and read a few back in the last week of term: they show how far a class has come in a way a grade doesn't.
Which upcoming project or topic are you most curious about?
Why ask it
An answer with energy in it tells a manager or a teacher where to point this person. A flat 'whatever comes up' is information too, so ask what they'd pick if the choice were theirs.
What does this team do well that we take for granted?
Why ask it
Groups list their problems easily and their competent habits hardly ever. Name one yourself so the question doesn't hang in silence, and keep it for another week if bad news is in the air.
What's a win from this week, of any size, that you'd like the group to hear?
Why ask it
'Of any size' has to be true. If only the big wins get a reaction, people stop offering the small ones, so give the fixed printer the same nod as the signed contract.
Hard day
What's one thing that helped a little today?
Why ask it
On a bad day the honest scale is 'a little', and asking at that size doesn't require anyone to pretend things are fine. Whatever they name, a walk or a phone call or a nap, see if you can make more of it possible.
Who has been in your corner through this?
Why ask it
Saying a name out loud reminds them they aren't alone, and it lands better than hearing 'you're not alone' from you. If the answer is 'nobody, really', don't contradict it: say you'd like to be, and then turn up.
What did you handle today that you can give yourself credit for?
Why ask it
On a rough day the list is short: got out of bed, made the call, showed up. Accept it at the size it's offered, because 'that's huge!' for a small thing sounds like a pat on the head.
What's something comforting you could do for yourself tonight?
Why ask it
This moves from the day that's gone to the evening that's left. Practical answers are the best ones, soup or a bath or an early night, and if you can supply part of it, do.
Is there anything coming up that you're still glad about?
Why ask it
Hold this until they have said their piece and gone quiet; in the first minutes of someone's upset it sounds like a hurry-up. The yes-or-no shape makes 'not really' easy to say, and if that is the answer, leave it there.
What has gotten you through days like this before?
Why ask it
Their own track record is more convincing than any reassurance from outside. If the answer is a person, ask whether they'd like to call them tonight.
Did anything good, however tiny, happen in the middle of all this?
Why ask it
Ask only after they've had the chance to complain in full, and take 'no' as a complete answer. Pushing for a silver lining is how a kind question becomes an irritating one.
What would make tomorrow a bit easier than today?
Why ask it
Steer it toward something small and movable: an earlier night, a ride, one task taken off the list. If it's a thing you can do, say 'I'll do that' and not 'let me know if you need anything'.
What would you say to a friend who'd had the day you just had?
Why ask it
People are often gentler with a friend than with themselves, and this lets them hear their own kind answer. Don't spring the trap with 'so take your own advice': say 'that sounds right to me' and let them join the dots.
How to ask a positive question without it sounding staged
Practical guidance for the conversation itself
Making it sound like you
Put one true detail in it
A bare question about gratitude or pride can sound like a form being filled in. Tie it to something you know about them: the move, Tuesday's exam, the dog, the new manager. 'What went right with the move?' is the same question as 'what went well this week', and only one of them sounds as if a friend wrote it.
Change the wording until you would say it
Nobody is checking your sentence against this page. If 'what are you proud of' feels stiff in your mouth, 'what are you pleased with yourself about' may not. A question in your own voice gets a real answer where a recited one gets a polite one.
Go first, and keep yours small
Offering your own answer before you ask shows the size of answer you are after and makes it clear this isn't an exercise. 'Best thing about my day was a parking spot right outside. What was yours?' sets an easy bar. Keep yours short and ordinary, then hand over.
Ask one, then stay on the answer
Three upbeat questions in a row turn a chat into a gratitude workshop. Ask one and follow where it goes with plain follow-ups: what happened then, who else was there, what did you say. Moving on the second they finish is what makes a good question feel like decoration.
Let a short answer be enough
Some people answer 'the coffee was good' and stop. That is a full answer. Say 'where from?' or simply 'glad to hear it', and resist asking for something bigger.
Fitting the question to where you are
In passing or by text
The Check-in group is built for a hallway, a car ride or a message sent at lunch. One line back is all these ask for. By text, send the question on its own and without a string of emojis propping it up, and answer it yourself in the next message if the reply is slow.
With a friend
The Friends questions need more room than a check-in: a walk, a long coffee, the drive home. Pick the one you are honestly curious about for this particular person and leave the rest. Several of them ask the friend to say something good about themselves, so be ready to agree with it and add an example.
At the family table
Go around the table with the adults answering too, and let anyone pass. Change the question from night to night, because the same one at every dinner becomes a chore to get through before dessert. If a child clams up at the table, try again in the car or at bedtime, where nobody is watching them answer.
In a meeting or a classroom
Say how long the round will take and that a pass is fine. In a class, having students write the answer on a slip gets the quiet ones in. One caution for both rooms: if there is a real problem everybody is waiting to talk about, deal with that first. A cheerful round laid over it looks like avoidance.
On a day that has gone badly
Hear the bad part first
The Hard day questions come second in the conversation, never first. Let the person say what happened, all of it, without steering. The questions work once they have run out of things to say and the silence is the tired kind.
Ask before you ask
'Can I ask you something on the brighter side, or is this not the moment?' gives them the choice. If they say not now, drop it completely and do something practical instead: make the tea, walk the dog, sit there.
Keep the scale small
Words like 'a little', 'a bit' and 'however tiny' are in those questions on purpose. On a bad day nobody can find a highlight, but most people can find a sandwich that was all right. Take the small answer as it comes and don't try to grow it.
What a question cannot do
These are for an ordinary rotten day. If someone has seemed low for weeks, or says something that frightens you, a list of questions is the wrong tool. Tell them plainly that you are worried and help them reach someone qualified to help.
How a positive question goes wrong
Using it to change the subject
Asking 'but what went well?' the moment someone starts complaining tells them their complaint is unwelcome. If they need to grumble, let them. The question keeps until afterward, or until tomorrow.
Fishing
'What was your favorite part of the party I threw?' is a request for a compliment dressed up as curiosity, and people can tell. Ask about their good things, not about your part in them.
Grading the answer
Whatever someone is proud of or thankful for is theirs to choose. 'Is that all?' and 'you should be prouder of the promotion' both teach them to stop answering. So does overpraising a small thing until it sounds like sarcasm.
The same one every day
A question asked on a schedule gets a scheduled answer. Rotate through a group, skip days, and now and then ask nothing and just tell them something good about your own day. They will often answer the question you didn't ask.