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Question set · Coworker

50 Hypothetical Questions to Ask a Coworker

50 light, workplace-safe hypothetical questions for a coworker — what-ifs that break the ice without crossing a single professional line.

By Endearist 50 questions

You can sit two desks from someone for years and know their email signature better than anything else about them. A good what-if is the shortcut: light enough to ask over coffee, revealing enough that you both leave knowing each other slightly better. These fifty stay firmly on the professional side of the line — fun, not nosy, never the kind of question that follows someone home.

If the office ran your way

The safest what-ifs change the room rather than the person. Nobody has to give anything away to redesign a kitchen, a calendar or the temperature — and yet the answers show you exactly which part of the shared day someone has been quietly putting up with. Start here with anyone you barely know.

  1. If the office could only keep one snack in the kitchen forever, what should it be? Harmless and instantly opinionated. A safe read on whether they'll play along.
  2. If you could swap your commute for any other way of getting here, what would it be? Let it stay about the journey. And where exactly do you live, then? is the follow-up that turns a light question into a personal one.
  3. If our team had a theme song that played when we walked in, what is it? A team-level question that's fun out loud and never singles anyone out.
  4. If the company gave everyone a surprise extra day off next week, how do you spend it? The answers split cleanly into rest, catching up, and something they never get round to. Only the third one is worth a follow-up.
  5. If you could work from anywhere in the world for one month, where's the laptop going? Travel dreams are safe territory and tell you what they're drawn to.
  6. If meetings could only happen in one format forever, what's your pick? Sounds like small talk and is not. This is how you find out whether someone has been suffering quietly through a format for a year.
  7. If our office could add one perfectly useless but delightful thing, what is it? Useless is the operative word. If the answers turn practical, the team is tired, and that is worth noticing rather than laughing off.
  8. If this building got one more room and you decided what it was for, what would you put in it? Half the answers are a room to nap in and the other half are a room with a door that closes. Both are the same request.
  9. If the office went completely silent for two hours a day, when would you put them? The placement is the answer. Morning people are protecting their best hours; afternoon people are protecting their worst ones.
  10. If you could set the temperature, the light and the noise level here yourself, what would it be like? The oldest argument in any office, defused by keeping it imaginary. Nobody has to be the person who touched the thermostat.
  11. If the kitchen had one rule that everybody actually followed, what would you write on the sign? Funny until two people name the same rule, at which point you have accidentally run a survey. Act on it, or do not ask it.
  12. If this whole team could move into any building in the city, where are we going? Nobody names a better office; they name a better neighbourhood. What they actually want is the lunch break, not the desk.
  13. If everyone here wore a badge showing one true thing about their day, what would yours say? Answer first yourself and keep it mundane. Start too honest and you have turned a game into a check-in nobody agreed to.

Swap the seat, swap the skill

These what-ifs move work around: a task handed over, a role borrowed for a day, a title rewritten, a skill granted for free. Because the trade is imaginary, people admit things they would never volunteer in a review — what drains them, what they envy, and which half of their own job they would keep if it were cut in two.

  1. If you could instantly master one boring work skill, which would save you the most pain? Reveals their daily friction without prying into performance.
  2. If you could rename your job title to something honest, what would it say? Usually gets a laugh and a surprisingly accurate self-portrait.
  3. If you could automate one part of your day, which would you never touch again? A gentle window into what drains them, framed as a perk not a complaint.
  4. If you could have any other job in this company for a week, whose chair do you steal? Curiosity about another role, kept playful — never about replacing anyone.
  5. If you had to teach a class on anything you've learned here, what's the subject? Quietly flags the expertise they have that the team may be underusing.
  6. If you ran this team for a day with no consequences, what's the first thing you change? Invites honest opinion safely. Keep it about systems, not specific people.
  7. If you could swap one of your daily tasks for a colleague's, no questions asked, which? Keep it about the task and not the colleague. The interesting half is which of their own tasks they were willing to hand over.
  8. If you had a totally free Friday to learn something new for work, what would you dive into? Reveals their curiosity and growth edge without sounding like an appraisal.
  9. If you had one week to train someone to replace you, what would you spend the week on? What they teach first is what they believe the job actually is, and that is rarely what the job description says.
  10. If you spent a day in the role here you understand the least, what do you think would surprise you? Note that it asks about a role, not a person. Keep it there and the answer stays curiosity instead of commentary.
  11. If you could borrow one strength from this team for a month — a strength, not a person — which one? The clarification is doing real work. Without it this becomes a popularity vote, and somebody goes home counting.
  12. If your role were split into two jobs tomorrow, where's the line — and which half do you keep? Remember the half they give away. They will never say more clearly what they would rather not be doing.
  13. If you had to do this job entirely in writing or entirely by talking, which do you pick? Useful well beyond the game: someone who picks writing has just told you how to give them bad news.

Rewind and replay

What-ifs that run the clock backwards are gentler than they look. Asking what someone would do again, or what this place used to do better, invites a story rather than a confession. It also hands the longest-serving person in the room something only they can answer, which is a kindness worth building on purpose.

  1. If you could give your past self one piece of advice about your first day here, what is it? Light nostalgia that often surfaces a genuinely useful tip for newcomers.
  2. If you could keep one habit from this job for the rest of your career, what makes the cut? Whatever they name, they picked it up here from somebody. Ask who — it is usually a colleague who never heard the credit.
  3. If you started your own version of this company, what's the one rule you'd carry over? What they'd keep tells you what they actually value about the work here.
  4. If you could give every new hire one honest sentence on their first morning, what is it? Their one sentence is usually the hard-won lesson this place taught them.
  5. If you could watch a recording of one meeting from before you joined, which would you pick? Newer people pick the meeting where a decision they inherited got made. That is a request for context, not gossip, so answer it.
  6. If this company could un-make one decision, which one do you think it would be? Stay at the level of the decision, never the people who made it. If a name comes up, steer back to the choice itself.
  7. If you had to explain how we ended up working the way we do, where does the story start? Ask the person who has been here longest, in front of the person who arrived last. Half of the answer is written down nowhere.
  8. If someone had told you on day one exactly what this job would be, would you still have taken it? A hesitation here is not a complaint and should not be treated as one. Let the pause go by without filling it.
  9. If you could bring back one thing this place used to do, what returns? Usually a lapsed ritual that stopped for no reason anyone can remember. Several of these can simply be restarted the same week.
  10. If the version of you that interviewed for this job saw your week now, what would surprise them most? Works on anyone past their first year and gets better the longer they have been here. The surprise is usually about pace, not content.
  11. If you could ask the person who had your job before you one question, what would it be? If there was no predecessor, turn it around: what would they ask whoever invented the role? Same answer, different door.
  12. If a photograph existed of this team on its best day so far, which day is it? Rarely a launch day. It is usually the afternoon something nearly went wrong and did not, which tells you what the team is proud of.

The long view

Save these for the end, and only for someone who has already been playing along. They ask what a working life is for, which is a real question — but every one of them stays on the professional side of the line: no household, no health, no politics, nothing a colleague could not turn down with a shrug.

  1. If you woke up tomorrow and could do any career with zero risk, would you still do this one? A yes is not a boring answer, it is a rare one. Ask what makes it a yes before you move on to the next question.
  2. If you could fast-forward five years in your career, would you want to see it? A yes or no here hints at whether they feel excited or anxious about where they're headed.
  3. If money were no object, would you still want to work at all — and at what? The deepest this set goes, but still safely about work, not private life.
  4. If you could be remembered for one thing at the end of your career, what would it be? Give them the silence. This is the first question in the set that people genuinely have to think about, and rushing it wastes it.
  5. If you had to choose between work you love and work that pays double, where do you lean? A real values question kept abstract enough to be comfortable at a desk.
  6. If you could change one thing about how the working world is set up, what's first? The one question here that can drift into politics. If it starts heading that way, narrow it back to how work is organised, not who governs it.
  7. If you knew you'd switch careers entirely in ten years, what would you want it to be? Lets them dream out loud without committing to anything about their real plans.
  8. If you had to define a good day at work without mentioning money or praise, what's in it? Surfaces what genuinely motivates them, which is gold for working well together.
  9. If your work had to leave one mark on the people you do it for, what would you want it to be? Best asked of someone whose work has no obvious end user. Often the answer is the first time they have had to name one at all.
  10. If you could trade certainty about your career path for total freedom in it, would you? How they weigh security against freedom is the most telling answer here.
  11. If the next twenty years had to be spent getting very good at one thing, or a little better at twenty, which do you pick? The generalists always answer faster. Ask the specialists what they would give up for it, because they have already worked that part out.
  12. If we looked back on this job years from now, what do you hope we'd say it gave us? End here. It turns a colleague into a fellow traveller without overstepping.

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What to do with the answers

The most honest answer you'll get tonight is gone in three months unless you write it down. Endearist keeps it — per person, end-to-end encrypted, with a cadence reminder so you can pick the thread back up next time without scrolling through your messages.

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Frequently asked

How do I make sure these don't get too personal for work?

The whole list is built to stay on the professional side — nothing asks about relationships, money in their pocket, health, or politics. The simplest test before you ask anything is whether they'd be comfortable answering it in front of the team. If yes, it's fine. If they'd want to lower their voice, skip it. Comfort in the open is the line, and these stay on the right side of it.

When's a good moment to actually ask these?

The soft edges of the day work best: a coffee run, the slow minutes before a meeting fills up, a team lunch, the walk back from the printer. Never mid-deadline, never one-on-one in a way that feels staged. Float one lightly and let them decide whether to bite — a what-if offered as an aside lands far better than one announced as an activity.

What if my coworker clearly isn't interested in chatting?

Take the hint gracefully and drop it — these are opt-in, and forcing them sours the very rapport you're trying to build. A short or flat answer is a no for today, not forever. Laugh, pivot back to work, and try again another time with a lighter one. The goal is an easier working relationship, and respecting a boundary builds that faster than any clever question.

Can these actually help a team, or are they just small talk?

They're better than small talk because a forced choice reveals how someone thinks, not just what they did this weekend. Knowing a colleague would pick meaningful work over double pay, or that they'd automate the exact task you assumed they enjoyed, makes you collaborate better the next morning. The fun is the cover; the quiet result is a team that understands each other a little more.

I want to remember what colleagues tell me. Is that overstepping?

Not at all — remembering that a coworker dreams of teaching, or wants their work to leave a particular mark, is simply paying attention, and people notice when you do. Endearist's private, end-to-end encrypted notebook is built for low-key relational memory: a light note per person, just enough to follow up warmly next quarter, kept entirely to yourself and never anything you'd be uneasy them seeing.