Unusual Interview Questions to Ask Candidates
These are unique interview questions to ask a potential employee when the standard ones keep coming back with rehearsed answers, written for hiring managers, founders and anyone sitting on a panel. The 58 questions run in the order of the conversation: openers, track record, how the candidate thinks, a group of weird interview questions to ask once they have relaxed, how they see themselves, then the job itself. Even the oddest of them is about the work, so an unexpected question never has to be a trick.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Openers
What's something you taught yourself recently that has nothing to do with work?
Why ask it
A gentle opener that still tells you how someone learns when no manager is assigning it. Listen for whether they can describe how they got unstuck, since the people who only name the topic usually stopped in week one.
Pick an ordinary working day from the last month and walk me through it, hour by hour.
Why ask it
Nobody prepares a story about a Tuesday, so you hear what the job is really made of: how much is meetings, how much is their own work, and who they answer to. Hold it up against the day your role would give them, and if they are between jobs, ask for a typical day in the last one.
What's on your resume that nobody ever asks about, and you wish they would?
Why ask it
Interviewers all go to the same two lines, and this hands the candidate the rest of the page. What they pick shows what they are proud of, which is often different from what they were last hired for.
What job would you be terrible at, and why?
Why ask it
Light enough to get a smile in the first ten minutes, and the 'why' is a description of how they work, told backwards. A person who would be hopeless at anything repetitive, or anything involving cold calls, has given you something to check against the role.
What surprised you while you were getting ready for this interview?
Why ask it
'What do you know about us' has a ready answer in every candidate's notes, and this checks the same preparation from the side. A real surprise means they read past the home page, and no surprise at all usually means they did not look.
What have you had to explain lately that you thought was obvious?
Why ask it
It shows where their knowledge runs ahead of the people around them, and how patient they are about the gap. Tone matters more than content here: amused is fine, contemptuous is a preview of how they will treat your new starters.
What kind of work makes a whole afternoon disappear for you?
Why ask it
Asking what someone enjoys gets the prepared answer, and asking when they lose track of time gets a description of a real afternoon. Work out how much of that kind of work this role contains, and tell them honestly if the share is small.
Track record
Tell me about something you built or fixed that nobody asked you to.
Why ask it
Waiting for the ticket and noticing the problem first are different habits, and an unprompted fix is evidence of the second. The useful detail is how they got it adopted, because unsanctioned work that nobody else ever used says more about frustration than initiative.
What did you stop doing in your last job that turned out not to matter?
Why ask it
Most people only ever add tasks, so someone who has dropped one and confirmed nothing broke understands what their work is for. Ask how they found out it did not matter, since quietly stopping and hoping is a different habit from testing it.
What's the most expensive mistake you've made at work, in money or in time?
Why ask it
Putting a cost on it stops the answer shrinking into a harmless anecdote. You are listening for who they told and how quickly, and the size of the figure matters less than whether they know it.
Which of your past projects would you do completely differently now, and why?
Why ask it
Hindsight shows what they actually learned rather than what they can recite. Vague regret about timelines is common, while naming a specific choice and its cost tends to mark someone who ran a real post mortem.
Tell me about a project that went well for reasons that had little to do with you.
Why ask it
Luck, timing and other people's effort sit behind most successes, and candidates are almost never invited to say so. Someone who can separate what they did from what happened around them will give you a more reliable account of everything else on the resume.
What's a piece of work you finished that you'd rather not have your name on?
Why ask it
Everyone has shipped something under a deadline or a decision they argued against. The answer shows where their own standard sits and whether the blame lands on the constraint, the client or themselves.
Tell me about a time you were the wrong person for a task. How did you find out?
Why ask it
How they found out matters more than the task itself. Some people notice in the first week and say so, and some hear it in a review six months later, which tells you how much checking in they are going to need.
Whose job did you make easier in your last role, and would they say so?
Why ask it
Results on a resume are written from one side of the desk, and this asks for the view from the next one. A candidate who names a person and what changed for them has also given you something to verify at the reference stage.
What's a rule you broke at work, and would you break it again?
Why ask it
You are finding out where their line is, so keep your face still when you hear the rule. Skipping a slow approval to help a customer and skipping a safety or money control are very different answers, and the 'again' shows whether they thought about it afterward.
Tell me about a time you disagreed with your manager and lost.
Why ask it
Almost everyone has a story about being right, and few have a good story about being overruled. How they carried out a plan they argued against is the best preview you will get of the first time you make a call they dislike.
What's the most useful thing you took from a job you didn't like?
Why ask it
It lets a bad job into the conversation without inviting a complaint about a former employer. What they took away might be a skill, a rule for themselves or only a list of things other people did wrong, and the last of those is the one to worry about.
Thinking
What's a widely accepted idea in your field that you think is wrong?
Why ask it
An opinion that came from their own experience arrives with a story about where the standard advice let them down, and one borrowed from a conference talk does not. If nothing comes, ask which piece of common advice they follow without quite believing in it.
What's the last thing you changed your mind about at work, and what changed it?
Why ask it
People are moved by evidence, by someone they respect or by being outvoted, and the story tells you which it was this time. Strong answers name the figure, the conversation or the failure that turned them, while a vague one about growing usually means nothing shifted.
If you were hiring your own replacement, what would you ask them?
Why ask it
Their question is a statement of what the job really demands, as opposed to what the posting said. It also shows whether they can tell the hard part of their work from the visible part.
Walk me through a decision you made when you knew you were missing information.
Why ask it
Plenty of real work is done on partial information, so this sits closer to the job than a tidy success story. A full answer covers what they did to shrink the unknown, what they chose to live with, and whether they told anyone which was which.
When did you last say 'I don't know' at work, and what happened next?
Why ask it
Admitting it in front of colleagues is harder than it sounds, and a person who never does leaves you to discover the gap yourself. If no occasion comes to mind, ask what they do when they are unsure in the middle of a meeting.
What's a problem you decided was not worth solving?
Why ask it
Prioritising is mostly a matter of what gets left alone, and hardly anyone is asked for an example of it. A good one includes what the problem cost to live with and why the fix would have cost more.
When a project starts going wrong, what do you do in the first hour?
Why ask it
The first hour is where you see instinct rather than method: some people gather facts, some tell stakeholders, some quietly try to fix it alone. The last group is the one to probe further.
What number do you keep an eye on that nobody asked you to track?
Why ask it
People who understand their work usually have a private gauge: the length of a queue, the refund count, how long a build takes. Having none is not fatal, but follow up by asking how they would spot a bad month before their manager did.
What's a shortcut you take that you would not teach a beginner?
Why ask it
Experienced people know which steps can be skipped safely, and that knowledge is hard to fake. The judgment is in the reason a beginner should not copy it, so make sure you get that part.
If I handed you a week with no assignment, what would you work on?
Why ask it
Whatever they pick is the thing they think is broken or neglected in their corner of the work. The best answers are unglamorous and specific, and a candidate who names a fashionable project may just be reading the same news you are.
Oddball
What's the strangest thing an employer has ever asked you to do?
Why ask it
This is a weird question with an easy start, since most people have a story ready and most of the stories are funny. Pay attention to what they did about it, whether that was going along, asking why or saying no, and to how they talk about the person who asked.
How many unread emails are in your inbox right now, and what does that say about how you work?
Why ask it
Neither zero nor four thousand is the right answer. What you want is someone who can describe their own system and its weak point without getting defensive about the number.
If you wrote the instruction manual for working with you, what would the first page say?
Why ask it
It sounds like a party game and is really a request for their working preferences in their own words. Keep the answer, because if you hire them it is the most useful thing their new manager could read.
If you could delete one meeting, report or tool from your working life, which goes first?
Why ask it
The choice tells you what they count as overhead, and the reasoning tells you whether they understand why the thing exists. Be wary only if what they would delete is the main way your own team keeps in touch.
If you had to do your job with half your tools, which ones would you keep?
Why ask it
Stripping the kit back shows which skills are theirs and which belong to the software. Strong candidates answer quickly and can say what they would then do by hand.
What's the title of a talk you could give tomorrow with no preparation?
Why ask it
This finds the subject they know cold, which is not always the one in their job title. If the title is interesting and you have time, ask for the first two minutes of it.
Pick something you told me earlier and argue the other side of it.
Why ask it
Odd to be asked, and a fair test of whether they hold a view because they have weighed the alternative. Give them a moment to choose, and treat a decent case for the other side as a strength, not as proof they did not mean the first one.
If a colleague had to cover your job for a week, what would confuse them first?
Why ask it
Holiday cover is where the undocumented parts of a job show up, which makes it a gentle way to ask how much of theirs lives only in their head. Honest answers name a spreadsheet, a workaround or an unwritten agreement, and the candidates worth having sound a little embarrassed about it.
Would you take a great boss with dull work, or great work with a dull boss?
Why ask it
A forced choice with no safe option, so there is no script for it. Either pick is fine, because the reasons describe what they will put up with, and you can set that beside what the role honestly offers.
What boring task do you secretly enjoy?
Why ask it
Somebody on most teams likes reconciling the spreadsheet or tidying the shared drive, and it is worth knowing when you are talking to them. The answer also shows what kind of order they bring without being asked, which counts for more on a small team where nobody else will.
Self-view
Which item on your resume are you weakest at?
Why ask it
A resume lists every skill at the same volume, so you are asking them to turn one down. If everything on the page is still a strength afterward, lean harder on the work sample than on the document.
How would someone who found you difficult to work with describe you?
Why ask it
Putting the criticism in someone else's mouth makes it easier to say than the standard weakness question allows. A boast dressed as a flaw, such as caring too much about quality, suggests the real complaint never reached them.
What advice do you give other people and not follow yourself?
Why ask it
The gap between what someone knows and what they do is often where their real development area sits. It tends to get a laugh first and an honest answer second, so wait for the second.
What's the most useful piece of feedback you've been given, and who gave it?
Why ask it
Naming the person makes the story checkable and specific rather than a tidy parable. The feedback worth hearing about stung at the time, so ask what they did differently the week after.
What compliment about your work do you not quite believe?
Why ask it
Nobody rehearses this one, which is how it gets past the prepared list of three strengths. The compliment they doubt often marks a skill they have and undervalue, or a reputation they suspect they have outgrown.
What are you consistently bad at that you've decided to stop trying to fix?
Why ask it
Grown professionals have made peace with a few limits and route around them, and hearing which ones tells you what support they will need. Check the limit against the role: a designer who has given up on spreadsheets is fine, a team lead who has given up on hard conversations is not.
How do you know when you've had a productive week?
Why ask it
Some people count what they shipped, some count hours, and some count the colleagues they unblocked. If the only measure on offer is a pleased manager, think about how much supervision this role really comes with.
If you left your team tomorrow, what would get harder for them and what would get easier?
Why ask it
The first half is the usual account of their value, and the second half is the unusual one. Someone who can name what would get easier, such as quicker decisions or fewer rewrites, knows what their own style costs the people around them.
What kind of manager brings out your worst work?
Why ask it
Fit failures are often management style mismatches that neither side names until it is too late. Compare their answer honestly against how the actual hiring manager runs a team instead of hearing it as a complaint about the past.
What's a question you're hoping I won't ask?
Why ask it
Asked with a smile late in the conversation, it often brings out the gap in dates, the short job or the missing skill they have been steering around. Thank them and ask about it plainly, because pouncing teaches a candidate to stop being candid for the rest of the hour. If it turns out to be about health or family, say you do not need to know and move on.
This job
What part of your last job would you be happy never to do again?
Why ask it
Candidates rarely volunteer their dealbreakers, and this gets them stated out loud early. If the thing they never want to touch again is the daily core of the role you are filling, you have saved yourself six months.
Now that you've read the job description, what do you think we left out of it?
Why ask it
Postings are written to attract, and an experienced candidate knows roughly what a role like this one hides. Their guess shows how well they understand the work, and it gives you a fair opening to tell them the truth.
What would you need from us in your first ninety days to do this job well?
Why ask it
For a few minutes the interview becomes a preview of onboarding, and you see whether they have pictured the role in practical terms. Concrete asks for access, context or a named counterpart are a good sign, while wanting the whole plan handed over is not.
A year from now, how would we both know that hiring you was the right call?
Why ask it
Candidates are often asked where they see themselves and seldom asked what the proof would look like. An answer you could measure gives you a first-year goal to agree on, and it is fair to tell them what yours would be.
If the pay were identical, what other job would you take instead of this one?
Why ask it
With money taken out of the answer, what is left is the pull of the work itself. A candidate whose alternative sits far from what you do may still be fine, but you now know what will tempt them away in year two.
If you were hiring for this role, what would worry you about a candidate like you?
Why ask it
The concern you have been circling gets said out loud, by them, with a chance to answer it. Candidates who name the real gap and what they would do about it in the first months are easier to work with than those who cannot find one.
What have you noticed about us today that we probably don't see ourselves?
Why ask it
A candidate has watched your scheduling, your emails and the way the panel talks to each other, and nobody asks what they made of it. You get a free outside view, plus a sense of how they deliver an observation to people who have power over them.
What would make you turn this job down if we offered it?
Why ask it
Better to hear the condition now than to learn it from a declined offer. Commute, pay band, the on-call rota or the reporting line are all things you can speak to today, even if all you can say is that they will not change.
If you take this job and it doesn't work out, what will most likely have gone wrong?
Why ask it
Thoughtful candidates name something real about the team, the scope or themselves, which amounts to a risk review of your own role. An answer of 'nothing' is less a sign of confidence than of a job they have not looked at closely.
What question were you hoping I would ask?
Why ask it
Your list was written before you met them, so some part of their experience has probably gone unasked, and career changers feel that most. Put the question they give you straight back to them and let the answer run, since it is often their best material.
Using These Without Turning the Interview into a Stunt
Practical guidance for the conversation itself
How to Run Them Well
Ask Every Candidate the Same Ones
Unusual questions are only useful if you can compare answers. Pick three or four for the whole slate, ask them in the same order, and write the replies down before you discuss anyone with the panel.
Decide in Advance What a Good Answer Contains
Before the first interview, write one sentence per question describing the substance you want, for example a named decision and its cost. Without that, these questions become a personality test and you will just prefer whoever interviews like you.
Give Them Time to Think
Several of these take a moment to answer honestly. Say that you are happy to wait, and offer to come back to it later in the conversation rather than filling the silence with a hint.
Follow the Specifics, Not the Category
The value is in the second and third question: which project, who gave the feedback, what happened afterward. If you move on as soon as you get a general answer, you have learned nothing an ordinary interview would not have given you.
Put the Weird Ones in the Middle
Open with an odd question and the candidate spends the hour braced for the next one. The Oddball group works best after twenty minutes or so, once you have shown that the interview is a fair one, and one or two from it is the whole dose. Ten in a row is a quiz show.
Say Why You Are Asking
A line such as 'this one is a bit unusual, and there is no right answer' stops a nervous candidate hunting for the trick. If you cannot tell them what you hope to learn from an unusual question, that is the sign to drop it from your list.
Which to Ask for Which Role
- Individual contributors: the built-or-fixed question in Track record, with the missing-information and first-hour questions in Thinking, tells you the most about how they work when the plan breaks.
- First time managers: the difficult-to-work-with and worst-manager questions in Self-view, and the disagreement they lost in Track record, surface how they handle authority in both directions.
- Senior hires: the accepted idea they think is wrong, the shortcut they would not teach a beginner and the question about what will have gone wrong if the job does not work out are where experienced candidates either show real judgment or reveal they have been coasting.
- Career changers: the self-taught opener, the resume line nobody asks about and "What question were you hoping I would ask?" let them bring evidence your standard questions do not ask for.
- Roles with little supervision: the productive-week question in Self-view and the first-ninety-days question in This job are the two you should not skip.
- High turnover roles: the part of the last job they never want to do again and the identical-pay question are worth asking plainly, because both point at why someone might leave early.
Common Pitfalls
Skip the Brainteasers
Puzzles about golf balls and windows measure exposure to puzzles. If you want to see thinking, use a problem from the actual job and let them ask you questions about it.
Keep Out of Protected Territory
Questions that drift toward age, family plans, health, religion or national origin are a legal risk in many places, not a quirky one. Anything phrased as getting to know the real you should be checked against that line first, and since the rules differ by country and state, ask HR or an employment adviser how they work where you hire.
Don't Read Answers as Diagnosis
Choosing a particular animal, sandwich or superpower says nothing reliable about how someone will do the work, which is why the Oddball questions on this page ask about inboxes, tools, meetings and old jobs. If a question would not change your hiring decision, cut it and give the time back.
Don't Let These Replace the Work Sample
A good answer to an unusual question is pleasant to hear and is still only talk about work. Keep the bulk of your assessment on the actual task, whether that is a writing sample, a code review or a mock sales call, and use these questions to understand fit, motivation and self awareness.
Ready Made Sequences
The Thirty Minute Screen
- 1Open with: "What's something you taught yourself recently that has nothing to do with work?"
- 2Move to: "What part of your last job would you be happy never to do again?"
- 3Then ask: "When a project starts going wrong, what do you do in the first hour?"
- 4Close with: "What question were you hoping I would ask?"
The Self Awareness Pass
- 1Start with: "Which item on your resume are you weakest at?"
- 2Follow with: "How would someone who found you difficult to work with describe you?"
- 3Go deeper with: "What's the most useful piece of feedback you've been given, and who gave it?"
- 4End with: "What are you consistently bad at that you've decided to stop trying to fix?"
The Final Round Fit Check
- 1Begin with: "What kind of manager brings out your worst work?"
- 2Continue with: "What would you need from us in your first ninety days to do this job well?"
- 3Then ask: "If the pay were identical, what other job would you take instead of this one?"
- 4Land on: "If you take this job and it doesn't work out, what will most likely have gone wrong?"