Fun Questions to Ask an Interviewee
Twenty openers for the first few minutes of an interview. They stay job-relevant while giving a candidate room to show how they think, what they enjoy, and how they work with other people.
The questions
Open any question for the note
What does a good day at work look like for you, start to finish?
Why ask it
A safe opener that still produces usable signal, because it is easier to answer than a question about strengths. 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 would your teammates come to you for help with?
Why ask it
Asking through other people's eyes gets past rehearsed self-description. Strong answers are narrow and specific. A candidate who says anything, or lists five areas, either has not been on a team long or has not noticed what they are known for.
Teach me something in sixty seconds, anything at all.
Why ask it
Tests whether they can pick an audience-appropriate topic and hold a shape under time pressure, which is most of what explaining work to a colleague requires. 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'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's the best team ritual you've been part of?
Why ask it
Tells you what kind of team environment they will try to recreate, which matters more than whether they are a culture fit. Answers range from a Friday demo to a shared spreadsheet of mistakes, and the choice reveals what they think teams are for.
What kind of work do you enjoy even when it goes badly?
Why ask it
Separates people who like the outcome from people who like the activity, and the second group tends to last longer in a hard role. Answers that name a specific kind of problem are more credible than answers about loving a challenge.
What's a work habit you keep even when nobody would notice if you dropped it?
Why ask it
Aims squarely at self-set standards, which is the closest a warm-up question gets to conscientiousness. Documenting as they go, testing their own work, replying to the awkward message the same day. Watch for whether they can name a cost of keeping it.
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.
What's something you changed your mind about in the last year or so?
Why ask it
Tests whether they update on evidence or defend a position. The strong answer names what they used to think, what changed it, and what they do differently now. A vague answer about staying open-minded is a non-answer.
Who taught you the most at work, and what did they do differently?
Why ask it
The second half is where the signal is. Anyone can name a mentor, but describing the specific behavior they copied shows they were paying attention rather than just grateful.
What part of your work do you wish people outside it understood better?
Why ask it
Invites depth on their own terms and tends to expose real expertise, because people only get frustrated about things they know well. Also a useful check on whether they can explain their field without condescending.
What's a piece of your work you'd happily show a total stranger?
Why ask it
Combines two signals at once: what they are proud of, and whether they can describe it without inside jargon. If they cannot pick anything, ask what they would show a new teammate instead.
What kind of project would you volunteer for on a slow week?
Why ask it
Finds where their curiosity goes when nobody is directing it, which predicts what they will quietly get good at. Answers about tidying up something broken and answers about starting something new point to very different hires.
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.
What's a position you used to hold firmly and eventually let go of?
Why ask it
The mirror image of the previous question, and the pair together shows whether they can hold opinions loosely. A candidate who can only answer one of the two is telling you something either way.
What's the best question anyone has asked you in an interview?
Why ask it
Reveals what they think good judgment sounds like, since the question they admired is one they would use themselves. It also gives quieter candidates a chance to talk about ideas rather than themselves.
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. Listen for a real preference about timing, setting and directness rather than a claim that they welcome all feedback.
What would make you tell a friend to come work here?
Why ask it
Flips the interview quietly, because their answer describes what they actually need from a workplace. If the list is nothing you can offer, that is worth knowing before an offer goes out.
What have I not asked that you were hoping to talk about?
Why ask it
Closes by handing them the floor, which is only fair after twenty minutes of your agenda. Strong candidates use it to fill a gap they noticed; the answer often includes the experience your job description failed to ask about.
Using Warm-Up 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 three or four from this page, keep them fixed for the whole slate, and 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 questions at the top and one at the end 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.
What to Leave Out
- Anything that surfaces protected information: family, age, health, religion, immigration status, pregnancy plans.
- Hypotheticals about which animal or fictional character they would be, which correlate with confidence rather than competence.
- 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.