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50 Questions to Ask a Coworker About the Future — the Work's, Not the CV's

50 questions to ask a coworker about the future: where the work is heading, what this team is becoming, and what you are each building toward.

By Endearist 50 questions

Ask a colleague where they see themselves in five years and you have not asked a question, you have run an interview. Ask whether they are thinking of leaving and you have started something you cannot take back — a rumour if it travels, and the end of the honesty between you if it does not. Which is a shame, because the future is the one subject two people who work together genuinely hold in common: the same tools going obsolete, the same team changing shape around them, the same trade turning into something neither of them trained for. These fifty questions are about that future, the one you are both already standing in, rather than the one on anybody's CV.

What the work itself is turning into

Everyone at work talks about where their career is going and almost nobody about where the job is going, even though the job is the part that visibly changes first. Tools get replaced, customers want something else, half of what used to take a Tuesday stops taking a Tuesday. These questions are about that change, which has the useful property of belonging to neither of you personally.

  1. Which part of your job here do you think will not exist in five years? Almost everyone has an answer and almost nobody has said it out loud. Whether they sound relieved or defensive about it tells you more than the part they named.
  2. Which of the tools we both use every day do you expect to be gone soonest? Ask what they would miss about it. People defend outdated tools for reasons that turn out to be about the work rather than about the tool.
  3. What is our industry going to be embarrassed about in ten years? It offers a way to criticise the trade without criticising anybody in it, which is why it gets a real answer. Whatever gets named is usually something they already quietly refuse to do.
  4. Which part of what we do will still need a person doing it — and why that part? The why carries the question; without it you get an opinion about technology. With it you get their definition of what this job is actually for.
  5. What did this job look like when you started, that someone hired last month would not recognise? Change is far easier to describe backwards. What gets listed is also the change they expect to keep happening, safely stated in the past tense.
  6. If our customers changed their minds about what they wanted, which change would we notice last? A question about blind spots that never names a colleague. Ask what the first warning sign would look like and it turns into something the team can use on Monday.
  7. What are we doing today only because it worked five years ago? Ask for one example, not a list. The list is a complaint; the example is something the two of you could actually change on a Thursday afternoon.
  8. Is there a change coming to this work that you are privately not looking forward to? The word privately is what makes it answerable, because it asks for a feeling instead of a position. Do not respond with reassurance about how it will probably be fine.
  9. What would have to change about this work for you to still find it interesting in five years? Be careful with this one in a dull stretch — it can land as an accusation of boredom. Asked in a decent week it produces a genuinely useful list.
  10. Which skill that everyone here has will stop being worth anything — and does that include yours? The second half is what stops it being a comfortable question about other people. Answer it about yourself first, or do not ask it.
  11. If you were designing this job from scratch today, what would you not put back in? Leaving out is where the honest answer sits, because adding costs nothing to imagine. What comes back is usually the thing they have been doing for years without believing in it.
  12. What is the newest thing you have had to learn here, and was it worth the trouble? A low-stakes way into the whole group, and it doubles as a recommendation you can use yourself. If the answer is no, ask who decided it was necessary.
  13. Do you think the work we do will matter more or less in ten years — and to whom? And to whom is what keeps it from becoming a mood. Anyone who answers less is not being cynical; they are usually describing a change in who the work is for.

The team you are both about to be in

A team never announces that it has changed. It gains three people, loses the one who ran the Friday thing, absorbs another team's work, and eighteen months later nobody can say when it stopped being what it was. These questions ask what this one is turning into while there is still somebody in the room who remembers the version before.

  1. What is the one thing about how this team works that you hope survives the next two years? Hope rather than expect keeps it out of complaint territory. What gets named is usually something fragile that a single departure would end.
  2. If someone joined us next month, what would they get that we did not? It gets a team's improvements listed by somebody who never otherwise gets to list them. Follow up with what that person would still have to survive.
  3. What is this team going to be bad at in two years that we are fine at now? Nobody has a rehearsed answer to this, so expect a long pause and let it run its length. It almost always turns out to be about a person nobody has replaced in their head.
  4. Which of our habits would you want written down before the people who invented them are gone? There is a task hidden in this one and it is worth doing. Agree on the first item before the conversation ends, or it will quietly not happen.
  5. Who on this team is doing something now that the rest of us will be doing in a year? Generous and specific, and unlike most predictions it can be checked in a year. Ask what that person does differently rather than what they are working on.
  6. When this team gets bigger, what stops working first? It sounds like a question about process and is really one about what they value. Ask what they would protect if they only got to keep a single thing.
  7. Is there something this team is heading toward that you have not said anything about? The reason for the silence is the real answer, and it is usually that saying it once already did not work. Ask when that was.
  8. What should the person who does your job here after you know on their first morning? After you rather than instead of you is what keeps this clear of the leaving question — it assumes an ordinary handover in an unspecified year. Write down whatever comes back; it is the handover nobody ever gets.
  9. Which meeting we currently have will still be here in five years, and should it be? Light and funny, and it still gets a real answer about what the team thinks is load-bearing. The should it be half is where the interesting disagreement lives.
  10. If this team lost three people at once, which three roles would we discover we had no plan for? Keep it on roles rather than names, or by Friday you have a ranking of colleagues. The gap it exposes is usually one nobody has ever been asked to close.
  11. What does this team believe about itself that stopped being true a while ago? Teams keep describing themselves with a sentence that expired two reorganisations back. Ask when they think it stopped being true, not whether.
  12. What would you want this team to be known for that it is not known for yet? A future question that sounds like an ambition, which is why it comes back without hedging. If the answer is very specific, they have been thinking about it for a long time.

The skill, not the title

Ambition is unsayable at work in its usual form, because a title is somebody else's chair and naming it makes you a rival to whoever is sitting in it. Stated as a skill it costs nothing — nobody loses a thing when a colleague gets better at estimating. These questions ask what your colleague is building, in the one grammar that makes it safe to build out loud.

  1. What are you slowly getting better at here that you were bad at when you arrived? Slowly and bad at when you arrived both do work: together they give permission to name something still unfinished. The brisk version of this question only ever collects achievements.
  2. What do you want to be good enough at by next year that someone here would come to you for it? The come to you for it clause turns a vague intention into something with a visible finish line. Ask again in the spring — being asked a second time is what makes it real.
  3. Which skill have you been meaning to build since you got here, and keep not building? Ask what gets in the way and you will usually hear a scheduling problem that is actually a permission problem. That second kind a colleague can do something about.
  4. Which of your skills is going rusty here, and do you mind? The and do you mind is the half that matters: some decay is a choice and some is drift, and people can tell you which within a sentence. If it is drift, ask what would have to change this year.
  5. If this place gave you one uninterrupted month to get better at one thing, what would it be? The constraint stops it becoming a wish list. If the answer arrives instantly, they have been carrying it around for a while.
  6. Is there a part of this job you have quietly decided you will never be the best person here at? It is as personal as this page gets and it never once leaves the job. Do not argue anyone out of theirs — name yours instead.
  7. Who here do you learn the most from, and what exactly do you take? The exactly is what turns a compliment into something transferable. Most people have never once put into words what they are copying.
  8. What would you have to stop doing here to get properly good at something new? Everybody wants the new skill and nobody has costed it. The list of what would have to go is usually the reason nothing has happened yet.
  9. What have you learned here that you will still be using in twenty years? Quietly a compliment to the place and easy to answer, which is what makes it a good opener. What gets named is almost never on any training plan.
  10. Is there something you are good at here that you have started to resent being the one who does it? Competence turns into a cage the same way every time: you get good at it, you get given more of it, and nobody asks you about anything else again. Nobody has ever asked them this one.
  11. What kind of problem do you want to be handed in five years — not what job, what problem? The clarification is the entire question; without it you get a job title and the conversation stops there. With it you get something you can genuinely put their name beside.
  12. What would you need to learn before you could do the work you actually want to do? It lets somebody describe an ambition entirely as a gap, which is why the answer comes back honest. Whatever they name, ask whether anyone here could teach it.
  13. Which of the things you are learning is for this job, and which is for whatever comes after it? This goes close to the line and stays behind it, because the after is left entirely unspecified. If only the first half gets answered, take the first half and move on.

What you would want anywhere at all

Every honest answer about the future turns dangerous the moment it can be read as a plan about this company. So these questions take the company out of the sentence entirely. What somebody wants to be doing at sixty, what they would refuse to do again anywhere, what work would have to give them to be worth a decade — none of it says a word about whether they will be at their desk in April, and that is exactly why it can be said at all.

  1. What would you want to still be doing at sixty, wherever you happen to be doing it? Wherever you happen to be doing it is what makes it safe, so keep the clause in when you ask. Answers come back far more specific than anything about a career does.
  2. What would you never do again, at any company? At any company is the permission slip: it aims the complaint at a kind of work rather than at this place. Do not ask which job it was.
  3. What does work have to give you for it to be worth ten years? Ten years makes it a piece of accounting rather than a preference. Listen for whether the answer is money, people or the work itself — those three behave completely differently over time.
  4. What is the best thing about your working life right now that you would want to keep whatever changes? One of the few future questions that reliably gets a warm answer, so it helps when the mood has gone heavy. Whatever gets named is worth defending on their behalf.
  5. Is there something you want your working life to have been for? Nobody answers this quickly, so ask it somewhere with no next appointment waiting. The answer will not sound like a mission statement, and that is how you know it is real.
  6. What do you want less of in your working week in ten years, regardless of who you are working for? Hardly anyone asks about less, and the answer comes back much more concrete than any answer about more. Ask what would have to be true for it to start shrinking.
  7. If you woke up doing the same job somewhere else, what would you want to be different about the day? A neat way to separate the work from the conditions, and most dissatisfaction turns out to live in the conditions. Nothing in the answer identifies this employer.
  8. When the ambition wears off, what do you think will still make the work worth doing? It presumes the wearing off, which is what makes it answerable — nobody has to admit to being tired in order to reply. Put the same question to an older colleague and you get the version that has already happened.
  9. What would you want a colleague ten years from now to be able to count on you for? It asks for a commitment with no employer attached, which is the only kind anyone can make honestly. What comes back usually describes who they are trying to become.
  10. What do you think you will believe about work in twenty years that you would argue with today? It asks somebody to predict their own change of mind, which is genuinely hard and genuinely enjoyable. No answer to it can be held against them later, and that is the point.
  11. Is there a kind of working life you have already ruled out — and are you still sure? Decisions like that get made once, early, and never reviewed again. Ask when it was made rather than whether it was right, and leave the reviewing to them.
  12. In five years, what would you want to be able to say the two of us built here — not the company, us? End on this one. It is the only question on the page that puts the two of you inside the same future, and it is the one people remember having been asked.

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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.

More questions for your coworker

More questions about the future

Related tools

Frequently asked

Why is “are you thinking of leaving?” not on this list?

Because a colleague cannot answer it safely, and a question nobody can answer safely is not a question, it is a risk you have handed them. A yes is only theirs until it travels, and the day it reaches a manager they had not chosen to tell, they have lost control of the timing of their own exit — which in practice can cost them the reference, the handover they wanted, or the offer they were still negotiating. A no is a promise about a future nobody controls. And the pause people use instead reads as an answer to anyone within earshot. There is no wording that fixes this, so the question is simply absent, along with the softer versions people reach for: how long do you see yourself staying, are you happy here, would you take a call from a recruiter. Everything on this page is designed so that the honest answer costs nothing, which is also why the honest answer is what you get.

Isn't “where do you see yourself in five years” the obvious question here?

It is the obvious one and it is the reason most of these conversations produce nothing. That sentence has been an interview question for forty years, so it comes pre-loaded with an interviewer, and people answer it in the register they learned for interviews: a title, a scope, a plausible upward line. None of that is a lie and none of it is information. Swap the frame and the same curiosity gets you something real. Instead of a title, ask what kind of problem they want to be handed. Instead of a five-year plan, ask what they want to be good at by next spring. Instead of where, ask what they would want to still be doing at sixty wherever they end up. Same subject — the shape of somebody's next decade — but nothing in the answer commits them to a destination, so nothing in it has to be defended.

What if they turn one of these back on me and I am thinking about leaving?

Answer the question that was asked, which will not be that one. None of these require you to disclose a plan: what you want to be good at next year, what you would never do again anywhere, what you want less of in a decade — all of those are true whether you stay or go, and you can answer them fully without a word about your own timing. That is not evasion, it is the same protection you extended to them by not asking. If they ask you outright anyway, a plain “I would tell you before I told anyone else here” is honest, keeps the friendship, and holds. What does damage is a false no: it gets remembered on the day you resign, and it is the reason so many workplace friendships do not survive somebody's notice period.

Can I ask these of someone I manage?

More of them than you could from the values set, because these are largely about the work rather than about the person — where the trade is heading, what the team is becoming, what somebody wants to be good at. Those are close to the best conversation a manager can have, and they are more useful than any development form. Two groups still belong to peers only. Anything about what somebody would want anywhere at all reads, from a manager, as a test of whether they are staying, and gets a staying-safe answer. And anything about a skill they resent or fear they will never have will be filed by the person answering as evidence about their next review, whatever you say. If you do ask, answer first and at length, name one thing you are visibly bad at, and say once that none of this goes into a review. Then make that true, because it will be checked.

When is a good moment to ask a coworker about the future?

Not in the fortnight after a reorganisation, a round of layoffs or a resignation, when every future question is heard as a question about jobs — including yours. Not in review season either, in either direction. What works is an ordinary week with nothing pending, sideways, one question at a time: the walk back from lunch, a long drive to a customer, the flat stretch after a launch when everyone is tired and slightly honest. Planning weeks are unexpectedly good too, because the whole company is already talking about next year and a personal version of that question does not stand out. And ask one. A colleague who answers a real question and is not immediately handed four more will bring you the rest unprompted over the following months.

What do I do with the answers?

Keep them and act on the small ones. Future answers are unusually actionable — a skill somebody wants a month for, a strength nobody here has ever used, a habit they want written down before its inventor leaves. Any of those is a thing you can move in a week, and moving one is what proves the question was not just conversation. What must not happen is that the answer travels: what a colleague hopes to be doing in ten years is not context for a promotion discussion, and it is not a line at lunch. The other risk is simply forgetting. This is exactly the material working memory sheds first — the skill they wanted, the month they were promised, the question you agreed to ask again in the spring. Endearist is a private, end-to-end encrypted notebook with a page per person, which is a quiet place to keep the three sentences that let the spring conversation start where this one stopped.