Fun Questions to Ask an Interviewee
These are fun interview questions to ask potential employees, written for whoever sits on the hiring side and wants a candidate relaxed enough to sound like themselves. The 54 questions follow the hour: warm-ups for the first minutes, funny questions to ask once the nerves have gone, then craft, teamwork and curiosity, and a handful to close on. All of them stay on work and skill and leave home life alone, which is what keeps a light question from becoming an unfair one.
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The questions
Each question, and why to ask it
Warm-up
What was your very first job, and what did it teach you that you still use?
Why ask it
The paper route or the shop counter has no stakes left in it, so nearly everyone relaxes while telling this one. The lesson they name shows whether they learn from ordinary work or only from the impressive lines on a resume.
What does a good day at work look like for you, start to finish?
Why ask it
A gentler way in than asking about strengths, and no less useful. Listen for whether the good day is full of people or free of them, and whether it ends with something shipped or something figured out.
What made you laugh or smile at work recently?
Why ask it
Small and recent is the point, because few people can produce their funniest story on demand. For someone between jobs, add 'or at the last place you worked'. Whatever it was, a customer, a typo, a teammate's running joke, says a little about what they notice in a working day.
What's a recent small win you were pleased with that nobody else noticed?
Why ask it
Deliberately small, because asking for a big achievement invites the rehearsed story. Pride in something invisible points at internal standards rather than performance for a manager. Expect a cleaned-up process, a bug caught early, a hard email finally sent.
What part of your work could you happily talk about for an hour?
Why ask it
Enthusiasm is hard to keep up for longer than a sentence unless it is real, so let them run for a minute and watch where the detail gets thick. Ask one follow-up on whatever they pick, because the second answer is usually less polished than the first.
What first pulled you toward this kind of work?
Why ask it
An origin story is about the easiest thing a person can tell, which is why it belongs in the first five minutes. Notice whether the pull was a person, a problem or an accident, and whether any of it still holds for them.
What's a piece of your work you'd happily show a total stranger?
Why ask it
You hear what they are proud of and, in the same answer, whether they can describe it without inside jargon. If they cannot pick anything, ask what they would show a new teammate instead.
What are you oddly good at that has never made it onto a resume?
Why ask it
It needs no job history behind it, which makes it a kind one for a school leaver or someone coming back after a long gap. Untangling cables and remembering everyone's coffee order both count, and asking how they got good at it keeps the answer on skill.
Funny
What's the strangest job you've ever done, paid or not?
Why ask it
The story is the point here, and mascot suits, night shifts counting stock and a summer spent sorting screws all come out. Affection and detail in the telling are a better sign than embarrassment.
What's the worst piece of career advice anyone has ever given you?
Why ask it
Bad advice is funnier than good advice and far easier to remember. How they knew it was bad is the useful part, since it shows them weighing a confident voice against their own judgment.
Which piece of office jargon would you ban if you could?
Why ask it
Everyone has one, and naming it together is a quick way to end up on the same side of something. Offer yours first if the candidate hesitates, so it does not feel like a test of whether they will criticize a workplace.
What's a mistake from your early days at work that you can laugh about now?
Why ask it
Distance makes this safe: the person who replied to all, or labeled a whole shipment wrong, is years behind them. Laugh with them and keep it out of your notes on ability, since an honest story about a first-year slip is no evidence about the person across the table today.
What's a skill an old job gave you that is no use to anyone now?
Why ask it
Folding a fitted sheet to shop standard, reciting a product code from 2015, running a cash register nobody makes any more. It lets someone boast and joke in one breath, which is a comfortable register for the rest of the hour.
If your current or last job came with a warning label, what would it say?
Why ask it
Silly on the surface and oddly accurate underneath: the label is usually the part of the role that catches newcomers out. Compare it quietly with the warning label your own vacancy deserves.
What do people outside your job think you do all day?
Why ask it
Most jobs have a wrong version that other people carry around, and the gap between that and the real thing is reliably funny. You also get a plain-language description of their work without having to ask for one.
What's the strangest thing a customer or colleague has ever asked you for?
Why ask it
Anyone who has worked a counter, a help desk or a shared inbox has one ready. A candidate who can tell it without sneering at the person who asked is showing you how they talk about customers when none are in the room.
What would a book about your career so far be called?
Why ask it
Give them a moment, since a title takes longer to invent than an anecdote. Whether it comes out as a comedy, a thriller or a repair manual, you learn how they see the road that led to this interview.
What's the oddest rule a workplace of yours has ever had?
Why ask it
Somewhere there is always a rule nobody can explain any more, like a form to borrow the stapler. Do not ask which employer it was. The bonus comes when the candidate starts guessing what once went wrong to get it written.
What's a meeting you sat through that could have been an email, and what gave it away?
Why ask it
A shared groan warms a room up fast. Their tell, whether it was no agenda, twelve attendees or one person reading slides aloud, shows what they think a group's time is for.
What did you think you'd be doing for a living when you were ten?
Why ask it
The fun is in the distance between the astronaut or vet they had planned on and the resume on the table. Now and then a thread survives, the would-be vet who ended up looking after customers, and candidates enjoy spotting it themselves.
Craft
Teach me something in sixty seconds, anything at all.
Why ask it
Choosing a topic the listener can follow and giving it a shape against the clock is most of what explaining work to a colleague takes. Say up front that the subject does not have to be work-related, or nervous candidates freeze.
What's a tool or trick you use that most people in your role don't?
Why ask it
Craft shows up in small habits: a keyboard shortcut, a checklist, a naming convention, a spreadsheet they rebuilt. The answer tells you whether they have opinions about their own workflow or just inherit whatever they were handed.
What does your desk or screen look like in the middle of a busy day?
Why ask it
People describe this with real relish: forty tabs, one sticky note, a notebook nobody else can read. Neither tidy nor chaotic is the better answer. You are checking that they know their own system and can say why it works.
What kind of work do you enjoy even when it goes badly?
Why ask it
Some people like the result and some like the doing, and this is a quick way to hear which. An answer that names a specific kind of problem is more believable than one about loving a challenge.
What's a task other people find dull that you quietly enjoy?
Why ask it
Reconciling a spreadsheet, renaming files, proofreading the footnotes. Every team needs somebody who likes an unglamorous part, and it helps to know whether that part exists in the job you are filling.
What's a work habit you keep even when nobody would notice if you dropped it?
Why ask it
Whatever they name, whether it is documenting as they go or answering the awkward message the same day, is a standard they set for themselves. See whether they can also say what keeping it costs them.
What's the first thing you do when you're handed something you've never done before?
Why ask it
There is no wrong answer, only different ones: some read everything, some call a person, some start and see what breaks. Picture each approach inside your team during their first month.
What's the most satisfying thing you've ever finished?
Why ask it
The word 'satisfying' invites a different story from 'biggest' or 'most important', and often a smaller one. Hear whether the pleasure came from the result, the tidiness of it, or simply being done.
What time of day do you do your best thinking, and what usually gets in the way?
Why ask it
There is a practical edge under the small talk: whatever gets in the way is the interruption they find hardest to work around. Good to know before you seat them beside the busiest phone in the building.
If you could hand off one part of your current job forever, what would it be?
Why ask it
Easier to answer honestly than a weakness question, and it surfaces a real preference rather than a polished flaw. It also tells you whether the role you are hiring for is full of the thing they are trying to escape.
If you had a free afternoon to fix one small annoyance in your work, what would you fix?
Why ask it
Small is the important word: you are after the wobbly template or the form with one field too many, not a reorganization. People who notice these things and already have a fix in mind are a pleasure to hand a messy process to.
Teamwork
What would your teammates come to you for help with?
Why ask it
Asking through other people's eyes gets past rehearsed self-description, and the best answers are narrow. If you hear 'anything, really', ask about the last time somebody actually came to them and what it was for.
What's the best team ritual you've been part of?
Why ask it
The ritual they pick is one they may well try to start on your team, so treat it as a preview. A Friday demo and a shared spreadsheet of mistakes are both good answers, and they describe very different ideas of what a team is for.
What's the nicest thing a colleague has ever done for you?
Why ask it
Kindness stories are short, specific and very hard to rehearse. What counted as kind, a covered shift, a quiet word before a presentation, credit given in front of the boss, is a fair guide to how they will treat the people beside them.
Who taught you the most at work, and what did they do differently?
Why ask it
Anyone can name a mentor. Describing the specific thing that person did, and that the candidate went on to copy, shows they were paying attention and not only grateful.
What would a new teammate find out about working with you in the first week?
Why ask it
Framed as a discovery, this gets a lighter and more honest reply than 'describe your working style'. The good ones include a quirk: answers messages at odd hours, thinks out loud, needs the agenda in advance.
When you're stuck, who do you go to first, and what makes them the right person?
Why ask it
The answer is a small map of how they use the people around them. Someone who names a peer, a junior colleague or a person in another department is describing a wider net than someone who only ever asks the boss.
What's the best welcome you've ever had on the first day of a job?
Why ask it
A good first day stays with people, down to the desk that was ready or the lunch somebody had planned. Write the answer down: if you hire them, it is the brief for their own first morning.
What kind of colleague makes you better at your job?
Why ask it
Asking for the good version keeps the tone warm where 'who do you struggle with' would not. The description is a wish list, and you can hold it honestly against the people they would sit next to.
How do you like to get feedback when something you made isn't working?
Why ask it
Practical and job-relevant, and the answer saves a manager weeks of guessing later. A real preference about timing, setting and directness is worth more than a claim that they welcome all feedback.
What's a small thing you argue for at work that others find odd?
Why ask it
Values show up more clearly in minor stubbornness than in stated principles. Meeting notes, plain language, no acronyms, a real changelog. Judge the reasoning, not the position, and note whether they can drop it gracefully.
Curiosity
What are you learning at the moment, however slowly or badly?
Why ask it
Permission to be bad at it is what makes this fun, and it removes the pressure to sound impressive. A new piece of software and a sourdough starter are equally good answers, because what you are hearing is how they talk about not being good at something yet.
What's something you changed your mind about in the last year or so?
Why ask it
A full answer has three parts: what they used to think, what changed it and what they do differently now. If you get a general remark about staying open-minded, ask for one example and wait.
What question about your field would you love to know the answer to?
Why ask it
Veterans and beginners both have one, though they sound different. A sharp question shows where the edge of their knowledge sits, which no list of achievements will.
What job completely unlike yours would you like to shadow for a day?
Why ask it
Follow with what they would hope to steal from it, because the reason is where the curiosity shows. Air traffic control, a bakery at four in the morning and a courtroom all come up.
What good advice did you ignore for far too long?
Why ask it
A cheerful way to talk about learning things slowly. Expect a pause before the answer, and a story with a moment in it when the advice finally landed.
What kind of project would you volunteer for on a slow week?
Why ask it
With nobody directing them, where does their attention go? Tidying up something broken and starting something new are both fine answers, and they point to very different hires.
What surprised you most when you started in this line of work?
Why ask it
First impressions of a trade are often funny in hindsight. For a career changer, turn it around and ask what they expect to be surprised by in this one.
Closing
What part of this job sounds like the most fun to you?
Why ask it
Ask it straight, near the end, once they have heard enough about the role to answer. If the part they name is a tenth of the real week, say so now, which is a kindness to both of you.
What's the first thing you'd want to find out in your first week here?
Why ask it
A forward-looking question that lets them picture the job as theirs for a moment. Whether they reach for the people, the product or the coffee machine, you hear how they settle into somewhere new.
What's the best question anyone has asked you in an interview?
Why ask it
The question they admired is one they would likely ask themselves, so you hear what a good conversation sounds like to them. It also gives quieter candidates a chance to talk about ideas instead of themselves.
What would make you tell a friend to come work here?
Why ask it
Their answer describes what they need from a workplace without your having to ask for it outright. If nothing on the list is something you can offer, better to know before an offer goes out.
What would you like me to remember about this conversation tomorrow?
Why ask it
By tomorrow several candidates will have blurred together in your head, and this lets each one choose their own headline. Write the answer at the top of your notes in their words.
What have I not asked that you were hoping to talk about?
Why ask it
After an hour of your agenda, the floor is theirs. Candidates often use it for the experience your job description never asked about, so leave real time for the answer instead of asking on the way to the door.
Using Fun Questions Without Undermining a Fair Interview
Practical guidance for the conversation itself
Keeping It Fair
Ask every candidate the same warm-ups
Improvising different openers for different people is how interviews start measuring familiarity instead of ability. Pick four or five from this page and keep them fixed for the whole slate. For any you mean to weigh, write down what a good answer would sound like before the first interview.
Do not score them as culture fit
These questions are for warming someone up and hearing how they explain things, not for judging whether you would enjoy a drink with them. If an answer feels off, ask yourself whether it is about the work or about resemblance to you.
Time-box the warm-up to five minutes
Twenty minutes of fun questions leaves no room for the ones the decision actually rests on. Two from Warm-up or Funny at the top, one or two from Craft, Teamwork or Curiosity in the middle and one from Closing is usually the right shape.
Offer an alternative to anything performative
The sixty-second teaching question is hard for people who are nervous, or who process by writing. Say they can skip it, or answer in writing afterwards, and mean it.
Using the Funny Questions
Say that the tone has changed
A funny question that arrives without warning sounds like a trap. Say something like 'a couple of lighter ones before we get into the role', so the candidate knows nothing rides on being witty.
Go first when it helps
For the jargon question or the early mistake, give your own answer before asking for theirs. It shows the level you mean, and it makes plain that the laugh is shared and not at their expense.
Never score the laugh
Some people are funny under pressure and some only on a quiet afternoon with colleagues they trust. Humor in an interview depends on nerves, culture and first language as much as on character, so use the Funny group to relax the room and take your evidence from the other groups.
Keep every joke pointed at the work
The Funny questions are all about jobs, meetings, rules and mistakes for a reason: they are unlikely to wander into family, age, health or beliefs. If an answer heads that way anyway, smile, move on and do not follow up.
Match the dose to the interview
One funny question is plenty in a thirty-minute phone screen, and two sit comfortably in an hour. On a panel, give them to one interviewer, since three people each trying a joke turns the hour into a performance.
What to Leave Out
- Anything that draws out personal details a hiring decision should not rest on: family, age, health, religion, immigration status, pregnancy plans. Which of these the law protects depends on the country and state, so check the rules where you hire.
- Hypotheticals about which animal or fictional character they would be, which reward confidence rather than competence. The made-up questions in the Funny group, the warning label and the book title, are about the candidate's real work.
- Puzzles and brainteasers with a single trick answer. They test whether someone has seen the puzzle before.
- Questions about their weekend, hobbies or home life that only exist to check whether they are like you.
- Asking a candidate to solve a live problem you are currently stuck on. That is unpaid work.
- Follow-ups that pressure someone to elaborate on a personal detail they mentioned in passing.
What to Listen For
Specificity over polish
A slightly awkward answer with a real project, date and name in it is worth more than a smooth one built from adjectives. Ask what happened next until you hit something concrete.
Whether credit gets shared
Warm-up answers are where people forget to manage this. Notice who else appears in their stories, and whether teammates are described as helpers or as people with their own judgment.
How they handle a question they cannot answer
Some of these have no obvious right response, so you will see how they behave when stuck. Saying they need a moment, or asking a clarifying question, is a better sign than filling the silence with generalities.