Open-Ended Questions to Ask
For anyone who wants examples of open-ended questions to ask someone, the kind that cannot be answered with a yes or a no. The first ten work on almost anyone (three ways to start, six short follow-ups and one to finish on), and the rest are grouped by who you are asking: a date, a friend, a child after school, a colleague, and a customer or client, with each group in the order the conversation tends to go. Every question has a note on the kind of answer it draws out, and many name the closed question it replaces.
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The questions
Each question, and why to ask it
Anyone
What's keeping you busy these days?
Why ask it
The open form of 'Been busy?', which leaves room for one word and a nod. Expect two or three things in a row, a deadline, a kid's tournament, a kitchen being redone, and ask about the one they sounded least tired of. If the reply is just 'work', ask which part of work.
What was the best part of your weekend?
Why ask it
Asking for the best part makes the person choose something, where 'Good weekend?' lets them say 'fine' and move on. A good answer is a small scene: who was there, what they ate, what went wrong. Use it on a Monday with someone you only half know.
How do you like to spend a day with nothing planned?
Why ask it
The open cousin of 'Do you have any hobbies?', which a lot of people answer with 'not really' and then feel dull. A free day is easier to describe: the long breakfast, the hardware store, the nap nobody admits to. Ask about whichever detail they lingered on, since that is the part they enjoy.
How did you get into that?
Why ask it
Have it ready for the moment someone mentions a job, a hobby or a team they follow. 'Have you done that long?' gets a number of years; this gets the uncle with the darkroom or the summer job that never ended. If they say they just fell into it, 'fell into it how?' tends to bring out the longer version.
What did you make of it?
Why ask it
For anything you have both just sat through: a film, a match, a meeting, the best man's speech. 'Did you like it?' asks for a verdict, and people tend to give whichever one seems polite. Hold your own opinion until you have heard theirs, and treat a careful 'it was interesting' as a view worth one more question.
What was that like for you?
Why ask it
The feelings question, with no feeling suggested. 'Were you scared?' and 'You must be thrilled' both tell the person what to say, and this leaves the word to them. If they only repeat the facts, they have answered as far as they want to, so move on.
What's the story behind that?
Why ask it
For something you can both see: a mug with a faded logo, a tattoo, a framed photo, a bike helmet on a desk. 'Is that new?' ends in one word, where this lets the owner decide how much to tell. If you hear 'long story', it is private, and the kind thing is to leave it there.
What happened next?
Why ask it
Three words, and the most useful follow-up on this page. It tells the speaker you are still with them and hands the story back without steering it. Reach for it whenever you are tempted to jump in with a story of your own.
What was the hardest part of that?
Why ask it
After someone describes a move, a race, a launch or a first year of parenting, this gets beneath the summary. The answer is rarely the obvious thing, and people tend to be glad to be asked. Do not rush to say you know how it feels.
What should I have asked you that I haven't?
Why ask it
The open version of 'Anything else?', which tends to get a no. It hands the other person the choice of subject, so it is the one to reach for when the talk has stalled or is winding up. Whatever they name, ask it straight away; a laugh and 'nothing' is a fair answer from a private person.
A date
What made you choose this place?
Why ask it
Only for when they picked the venue. You hear whether it is an old favorite, a recommendation or a guess, which is a gentler way in than 'Have you been here before?'. If you chose it, flip it and ask what kind of place they would have picked.
What does a normal week look like for you these days?
Why ask it
The answer sketches a whole life in a minute: work, friends, the gym, the dog, the Sunday phone call home. It beats 'Do you work a lot?' because they decide what to put in. Notice what the week is built around and what gets squeezed.
How did you come to live here?
Why ask it
'Are you from here?' is a yes or a no. The 'how' asks for the chain of decisions, and people show a lot in the telling: a job followed, a person followed, a plan made or an accident stayed with. Trade your own version afterward so it does not feel like an interview.
What do you and your friends get up to when you're all together?
Why ask it
People describe their friends more freely than they describe themselves, and the description tells you what their social life feels like from the inside. A specific habit, like a standing trivia night, is a good sign. Someone who struggles to answer may simply be new in town, so ask about that.
What do you like about your work, and what would you happily hand to someone else?
Why ask it
The two halves keep it from becoming a job description. Most people light up on one half and you will hear which. If work is a sore subject they will answer the second half only, and that is your cue to move to something else.
How does your family tend to celebrate things?
Why ask it
A sideways route into family that avoids 'Are you close with them?', which can corner someone on a first date. Loud birthdays, quiet cards in the mail, nothing at all: each is easy to say and tells you something real. Let a short answer stay short.
What have the last few years taught you about what you want?
Why ask it
This covers the ground of 'Why did your last relationship end?' without asking for the story of an ex. A thoughtful answer is about the person giving it; a worrying one is a list of other people's faults. Save it for when the conversation has warmed up.
What are you hoping for from dating right now?
Why ask it
The closed version, 'Are you looking for something serious?', pushes people toward the answer they think you want. Asked openly, you get their own words, and vagueness is information too. Be ready to answer it yourself, because it will come straight back.
What would you like to do if we did this again?
Why ask it
It is lighter than 'Do you want to see me again?' and lets both of you off easily. An idea with a detail in it, a particular taco truck or a trail, is encouraging. A polite 'oh, anything' tells you something as well.
A friend
What's the funniest thing that's happened to you since I last saw you?
Why ask it
A warm-up for a catch-up, when 'How have you been?' would only get 'good, busy'. Asking for one funny thing gives your friend a job they can do. It also sets a tone in which the heavier news can come out later without ceremony.
What's the latest with the thing you were telling me about last time?
Why ask it
Name the thing, whatever it was: the landlord, the application, the sister. It shows you remembered, which matters more to a friend than any clever wording. If you cannot remember, 'what was on your mind last time, and where did it land?' is honest and works.
How are you doing with all of it, the long version?
Why ask it
Adding 'the long version' is what opens it, since 'How are you?' is treated as a greeting. Then stay quiet and let them start wherever they start. If they give the short version anyway, they have heard the offer, and it sometimes gets taken up a day later by text.
What have you been thinking about that you haven't said out loud yet?
Why ask it
For a friend you know well, on a walk or a drive, not across a noisy table. It draws out half-formed plans: a move, a career change, a doubt. Treat what you hear as a draft and resist giving a verdict on it.
How is the new job turning out, compared with what you pictured?
Why ask it
Swap in the new city, the baby, the marriage or the retirement. The comparison is what makes it open, because 'Do you like it?' pulls a yes out of almost anyone who chose the change. Listen for the gap between the picture and the reality, and ask about that.
What would help most right now?
Why ask it
Use it when a friend is having a hard time and you are tempted to start fixing. Some people will name a practical thing, a ride or a meal or a second pair of eyes on a form. If they cannot say, offer a short menu: advice, company, or just listening.
What are you proud of lately that you haven't had a chance to mention?
Why ask it
Friends undersell their good news because nobody wants to brag. This gives permission. The right response is to make a fuss, and to ask how they pulled it off.
What should the two of us be doing more of?
Why ask it
A friendship question that stays easy, unlike 'Are we okay?', which sounds like trouble. The answer is usually simple and fixable: more walks, fewer rescheduled dinners, an actual phone call. Put a date on whatever they say before you part.
What are you hoping is different for you by this time next year?
Why ask it
Bigger than a resolution and smaller than a five-year plan. A friend who answers with something concrete has usually been turning it over for a while, so ask what the first step is. If the answer is 'nothing, I like where I am', believe them and say you are glad.
A child
What was the silliest thing that happened at school today?
Why ask it
'How was school?' has a stock answer, and it is 'fine'. This one asks for a single moment they can replay, and the retelling tends to bring more of the day with it. Ask it at snack time or in the car, once they have had a few minutes to land.
Who did you sit with at lunch, and what did you all talk about?
Why ask it
Lunch is where the social part of school happens, so the answer tells you who matters this month. A new name is worth a gentle follow-up. If the answer is 'nobody' more than once, do not fix it on the spot: ask what lunch is like, and mention it to the teacher if it keeps coming back.
What was the trickiest thing you had to do today?
Why ask it
'Trickiest' is easier for a child to answer than 'Was anything hard?', which invites a quick no. You might hear about long division, or about asking to join a game. Praise the trying before you offer any help.
What did you learn today that you could teach me?
Why ask it
Putting the child in the teacher's seat changes the answer from 'nothing' to a small lecture on volcanoes. Play the slow student and ask questions. It suits the walk home or the dinner table, where there is time for a demonstration.
What's happening in your picture?
Why ask it
Use it in place of 'Is that a dog?', which is awkward for everyone when it is a horse. The child tells you the story of the drawing, and it is usually longer than the drawing suggests. The same wording works for a block tower or a made-up game.
How did you figure that out?
Why ask it
Ask it when a child solves something, right or wrong. You hear the thinking, which is more useful than the answer, and it shows that the working out interests you as much as the result. Keep your voice curious, because in the wrong tone it sounds like doubt.
What happened right before that?
Why ask it
For the aftermath of a squabble or a meltdown, once everyone is calm. 'Did you push her?' invites a flat no; this asks for the order of events, and the order usually shows where things turned. Ask each child separately and expect two different films of the same event.
Who was kind today, and what did they do?
Why ask it
A bedtime question that closes the day on something good. Younger children tend to name a teacher or a best friend; older ones may need a minute. Turn it around now and then and ask who they were kind to.
What are you thinking about for tomorrow?
Why ask it
The closed version is 'Are you nervous?', which plants the idea. Left open, the child might mention a test, a swim lesson or nothing at all. If a worry comes out, ask what would make it a little easier before you offer reassurance.
A colleague
What do you wish you had known in your first month here?
Why ask it
One for the new person to ask, over lunch or at the end of an onboarding chat. 'Any tips?' gets 'you'll be fine'; this gets the shared drive nobody explains, the meeting that matters and the person to check with before ordering anything. Ask two or three colleagues, because the advice they have in common is the real induction.
What are you working on right now that you find most interesting?
Why ask it
A way into a one-on-one or a coffee that skips the status report. People talk longest about work they would have chosen, so you find out where their energy is going. If you manage the person, a long pause before the answer is worth noticing.
What's getting in your way this week?
Why ask it
'Is everything on track?' invites a yes, because nobody wants to be the one who is behind. This assumes something is in the way, which makes it safe to name. Write the answer down and say what you will do about it, or do not ask.
What's your read on the plan so far?
Why ask it
Ask it before you give your own view, especially if you are senior, since a room tends to line up behind whoever spoke first. A useful answer includes a reservation. If everyone says it looks fine, ask what would have to go wrong for it to fail.
What questions does this raise for you?
Why ask it
The replacement for 'Any questions?' at the end of a presentation, which mostly produces silence. It presumes there are some, so asking one no longer looks like a failure to keep up. Then wait a slow five seconds before you take the next slide.
How did you arrive at that estimate?
Why ask it
This draws out assumptions, and those are where estimates usually go wrong. Ask it of numbers you like as well as numbers you doubt, or people will learn that the question means trouble. A strong answer names what was left out.
What would you do differently if this project were yours to run?
Why ask it
People closest to the work often have a view they have not been asked for. You will hear either a real improvement or a constraint you did not know about. Thank them even if you cannot act on it, and say why you cannot.
What kind of feedback is most useful to you, and when do you want it?
Why ask it
Some people want it in the moment and in writing; others want a day's notice and a closed door. Asking beats guessing, and this conversation is easier than the one that follows feedback landing badly. Then say how you like to get yours.
What part of your job would you like more of?
Why ask it
A manager's substitute for 'Are you happy here?', which few people answer honestly to their boss. The answer points at what to delegate their way, and its mirror, 'and less of?', tells you what is wearing them down. Ask it well ahead of a review, while there is still time to act.
What could I do differently that would make your week easier?
Why ask it
It turns the feedback around and makes it concrete, which 'Any feedback for me?' never manages. Expect something small the first time: shorter messages, earlier notice, fewer meetings. Do the small thing, because that is what earns a bigger answer next time.
A client
What prompted you to look into this now?
Why ask it
A natural first question for a sales or discovery call. 'Now' is the important word: something changed, a deadline or a complaint or a new boss, and that event tells you how urgent this is. An answer of 'just browsing' is honest and saves you both an hour.
How are you handling this at the moment?
Why ask it
Before you describe anything you offer, find out what it would replace. That might be a spreadsheet, a competitor, a cousin, or nothing. Listen without correcting, because the current way of doing things has reasons behind it.
What have you already tried?
Why ask it
It stops you from proposing the thing that failed last year. The detail to listen for is why each attempt was dropped: cost, effort, a person who left. Those reasons are the objections you will meet later, stated early and without heat.
What would a great result look like for you six months from now?
Why ask it
'Would you like to save time?' gets a yes that means nothing. This makes the customer describe success in their own terms, and those terms are what your proposal should repeat back. If the picture is hazy, ask how they would know it had worked.
What happens if you leave things as they are?
Why ask it
A calm question, not a scare tactic, and it should be asked that way. Sometimes the answer is 'not much', in which case this is not a priority and you should not pretend otherwise. When there is a real cost, the customer has just named it without your help.
How does a decision like this usually get made on your side?
Why ask it
The blunt version, 'Are you the decision maker?', can put people on the defensive, and tends to get a yes whoever really decides. Asked this way you hear about the partner, the board, the spouse or the budget cycle. Then ask what each of those people will want to see.
How are you thinking about budget for this?
Why ask it
Softer than 'What's your budget?', and it lets people answer with a range, a comparison or a worry. A customer who has not thought about it yet will say so, which is good to know before you write a quote. If they ask for your usual range, give it plainly.
What concerns do you have about going ahead?
Why ask it
'Does that all sound good?' collects a polite yes and a silence afterward. Presuming there are concerns brings them out while you can still answer them. If the reply is 'none', ask what the person they report to is likely to raise.
What has it been like working with us so far?
Why ask it
For an existing client, in place of 'Is everything okay?'. A warm, vague answer deserves one more question: what one thing would they change? A specific complaint is a gift at this stage, so thank them and say what happens next.
Could you walk me through what happened?
Why ask it
For a complaint or a support call. On paper it is a yes-or-no question, but nobody answers it that way: it works like 'tell me about it' with better manners. Let the customer reach the end before you ask anything, then say the sequence back, because the step they skipped is often where the fault is.
How to ask open-ended questions
Practical guidance for the conversation itself
Open and closed questions
The one-word test
A closed question can be answered with yes, no or a single fact: 'Did you have a good trip?' An open-ended question cannot: 'What was the best part of the trip?' If you can imagine a one-word reply that fully answers it, the question is closed.
The words that open a question
Most open questions start with what or how, or with an invitation such as 'tell me about' or 'walk me through'. Questions that start with did, do, is, are, was, have, can or will are nearly always closed. Why is open too, but it can sound like an accusation ('Why did you do that?'), so 'What led to that?' is often the safer wording.
Closed questions still have a job
Use a closed question to confirm a fact, settle a decision or wrap up: 'Does Thursday work?' 'So the deadline is the tenth?' Trouble only starts when closed questions are all you ask, because the other person never gets to choose what to tell you.
Open is not the same as vague
'How's life?' is open and still gets 'fine', because it is too big to answer. A good open question gives a frame: a time ('this week'), a superlative ('the hardest part') or a specific thing ('the new job', or the 'that' you are both looking at). Most of the questions on this page have one.
Turning a closed question into an open one
Swap the first word
Take the closed question and restart it with what or how. 'Did you enjoy the wedding?' becomes 'What was the wedding like?' 'Is the new system working?' becomes 'How is the new system working for you?' The subject stays the same; only the first word changes, and with it the size of the answer you are asking for.
Ask for the best, the worst or the hardest
A superlative forces a choice, and a choice needs explaining. 'Was the conference good?' becomes 'What was the most useful session?' 'Did you have fun at camp?' becomes 'What was the best thing you did at camp?'
Take your guess out of it
A leading question carries your answer inside it: 'Is it the price that's putting you off?' 'Are you upset about the game?' Remove the guess and ask what is there: 'What is holding you back?' 'What is on your mind?' Sometimes you will find the guess was wrong.
Assume there is something to say
'Any questions?' and 'Any concerns?' make silence the easy answer. 'What questions do you have?' and 'What concerns you about this?' assume there is something, and that makes it easier to speak up.
More pairs to copy
Closed: 'Did you have a good day?' Open: 'What was the best part of your day?' Closed: 'Do you like your new teacher?' Open: 'What is your new teacher like?' Closed: 'Are you close to your brother?' Open: 'How do you and your brother get along?' Closed: 'Can I help?' Open: 'What can I do?' Closed: 'Was the service okay?' Open: 'How did the visit go for you?'
What to do with the answer
Wait
An open question takes longer to answer than a closed one, and the pause tends to feel longer to the person who asked than to the one who is thinking. Do not fill it by rephrasing or by offering options. Rephrasing in the gap usually turns the question back into a closed one.
Ask one question at a time
'How was the trip, did you get to the coast, was the weather okay?' gets an answer to the last and easiest part only. Ask the open one and stop.
Follow their words
The best second question comes from the answer and not from a list. Pick up a word the person used ('you said it was chaotic, chaotic how?') or use one of the six short follow-ups in the Anyone group. Two or three follow-ups on one answer do more than ten new questions.
When you still get one word
Some people, and most tired children, will answer 'fine' to anything. Go narrower instead of repeating yourself, offer your own answer first, or try again later while you are doing something side by side, like driving or washing dishes. Then let it go: an open question is an invitation, and people are allowed to decline.
Who you are asking changes how you ask
On a date
Trade answers. After they reply, give your own before asking the next one, or the evening turns into an interview. Hold the questions about the last few years and what they are looking for until you have both laughed at least once.
With a friend
Memory does more than wording. Bring up what they told you last time before you ask anything new, and let a silence run longer than you would with a stranger. A friend who wants advice will ask for it; until then, 'What happened next?' is enough.
With a child
Timing matters more than wording. Right at pickup is often the hardest moment to get an answer; after a snack, in the car or at bedtime tends to go better. Ask about one specific part of the day, and take an answer about recess as gladly as one about math.
At work
Ask only if the answer can change something. An open question about a decision you have already made is worse than no question, and people notice. If you are the senior person in the room, ask first and speak last.
With a customer or client
Ask, then stay quiet and take notes in their words. Resist pitching into the first pause: the second half of an answer is often where the real reason is. Read back what you heard before you propose anything.