Questions to Ask Someone Who Wants to Work at a Startup
Written for the hiring side of a startup, whether that is a founder or the manager of a small team, and for a mentor or friend of someone who has decided a startup is where they want to work. The groups run in the order the conversation tends to go: motives first, then how the person handles a job that keeps changing and a company with nobody to hand things to, how they behaved when work went wrong, and what they expect on risk, salary and equity. The final group is for the mentor only, since it gets into savings and family, which an interviewer should leave for the candidate to raise.
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The questions
Each question, and why to ask it
Why a startup
Why do you want to work at a startup and not at an established company?
Why ask it
The weaker answers are about what the person is escaping: slow approvals, a boss, boredom. A stronger one names something a small company would make them do, such as owning a result from start to finish or sitting close to customers. Ask where they have already had a taste of it.
Why this startup, out of all the ones that are hiring?
Why ask it
Plenty of people want 'a startup'; fewer can say why yours. Listen for a detail they could only have from trying the product, reading what you have published or talking to one of your customers. If the reason would fit any company at your stage, ask what would make them take a competitor's offer over yours.
What do you picture a normal week here looking like?
Why ask it
You are comparing their picture with the real one before either of you commits. Correct it on the spot, dull parts included, such as chasing invoices or answering support email, and watch whether the interest holds. A candidate who pictures only strategy sessions and launches needs the correction most.
Have you worked at a small or early company before, and what surprised you about it?
Why ask it
Experience is not required, but the surprise is telling. People who have done it mention things like how much one resignation hurt or how often the plan was rewritten. With no small-company history, ask about the nearest thing: a new team inside a big firm, a family business, a club or project they ran themselves.
What do you expect to miss about a larger employer?
Why ask it
Someone who says 'nothing' has not thought about it yet. Honest answers include a training budget, colleagues in their own field, a known name on the resume, or a person to cover for them on vacation. Naming the loss and still wanting the job is the answer to trust.
What have you learned about our product, our customers and who we compete with?
Why ask it
How they prepared is a fair preview of how they will work when nobody hands them a brief. Give more credit for an opinion, even a mistaken one, than for your own home page recited back. Then ask what they could not find out and would like to know.
If our product were yours for a month, what would you change first?
Why ask it
A newcomer's criticism is some of the cheapest research you will get, so do not defend the product while they talk. A complaint that comes with a guess at why things are the way they are beats a wish list of features. Someone with nothing to change has either not used it or is being polite, and five minutes with the product open in front of you both settles which.
If you joined, what do you think you would end up doing that is not in the job description?
Why ask it
A candidate who has understood small companies will guess at the gaps: support tickets, hiring, ordering laptops, writing the first documentation. Tell them how close the guess is. A blank look means the posting was read as a complete list, and it is kinder to fix that now than in month two.
Where does a startup sit in your longer plan: a place to stay, a way to learn fast, or practice for starting your own?
Why ask it
All three can make a good hire, a future founder included. What you need is the true one, so you can judge whether two strong years would be enough for this role. Say that out loud before they answer and you will hear less of what they think you want.
Shifting roles
Tell me about a job that turned out to be different from the one you were hired for. What did you do?
Why ask it
Most people have one, and what they did about it sorts them: some renegotiated, some adapted quietly, some left within months. None of those is wrong in itself. What matters for you is how long it took them to notice the job had changed and who they raised it with.
When did you last start a piece of work with no brief, and how did you decide where to begin?
Why ask it
This is the ambiguity question with the abstraction taken out. Good accounts have a first move in them: a customer they called, a rough draft they showed someone, a number they went and found. Waiting for the brief to arrive is also an answer, and one to weigh against how much direction you can honestly give.
What work have you done that was well outside your title?
Why ask it
'Wearing many hats' is the phrase everyone brings, and this asks to see one of the hats. Look for work picked up without being asked, like a designer who took support calls or an engineer who sat in on sales meetings. Notice whether it is told with interest or as a grievance.
Tell me about a time you dealt with customers directly. What did you do with what you heard?
Why ask it
In a small company nearly anyone can end up on a customer call, whatever their title. The second half of the question separates people who passed a complaint along from people who changed something because of it. Never having done it rules nobody out, but tell them they might be on a call in their second week and see how that lands.
Which tasks would you consider beneath your level, or simply not your job?
Why ask it
Put this bluntly and it gets a truer answer than 'are you flexible?'. Most people have a line, and having one is fine; you need to know whether your week crosses it. If the job really does include packing boxes or cold calling, say so here and let them react.
Suppose the plan you were hired to carry out is dropped three months in. What would you need to hear from me?
Why ask it
Their questions back to you are the answer. Ones about the company, such as what was learned and what the new bet is, alongside ones about their own position, show someone thinking as part of the team. If your company has already changed direction once, tell that story and ask what they would have done in it.
Have you worked for a founder or an owner who changed direction often? How did you keep up?
Why ask it
A founder's change of mind is not always announced. Sometimes it arrives as a passing remark on a Thursday. People who coped well describe a habit, such as repeating the new priority back in writing or asking what comes off the list to make room. If the story is only about how maddening it was, describe your own habits truthfully and see whether they still want the seat.
How do you decide what to work on when everything looks urgent and nobody is ranking it for you?
Why ask it
A method is good and last month's example is better, so ask for both. Strong answers hang the choice on one thing: revenue, a customer's deadline, or whatever unblocks other people. 'I would ask my manager' is a sound habit that stops working when the manager is a founder who is traveling all week.
Tell me about a decision you made with less information than you wanted. How did it turn out?
Why ask it
Listen for how they sized the bet: what they checked, what they chose not to check, and whether the decision could be undone later. The result matters less than whether they could tell you, next time, when to wait and when to go.
If the company grows and I hire someone senior above you, how would that sit with you?
Why ask it
It happens to early hires at plenty of growing companies, and it is fairer raised now than sprung in the second year. Say honestly how likely it is in this role. Then listen for which they would mind more: losing the title, or the work becoming narrower.
No backup
What have you built or set up from nothing, with nobody to copy from?
Why ask it
This is the nearest thing to a startup work sample in a person's history. People who really did it remember the rough first version and can say what embarrasses them about it now, so that is the detail to go after. Side businesses, student projects and volunteer work all count.
If nobody gave you a plan for your first month here, how would you spend it?
Why ask it
There may be no onboarding to speak of, so this is close to a description of the job. The answers to hope for begin with finding out: sitting in on customer calls, reading the support inbox, asking each colleague what slows them down, then picking one small thing to finish. Be wary of a ninety-day strategy from someone who has not yet asked what you need most.
What do you do when you are stuck and nobody in the company knows the answer?
Why ask it
Useful answers are concrete: the documentation, a former colleague, a forum, an hour of a specialist's time, a cheap experiment. Ask how long they let themselves stay stuck before changing tack. Both extremes cost a small team, the person who asks at the first obstacle and the one who disappears for a week.
What did you last teach yourself because the work needed it and nobody else could do it?
Why ask it
Small teams are full of people doing something for the first time: the first contract, the first payroll run, the first data migration. The useful detail is how they knew they had learned enough to go ahead, and who they got to check the result. Reading everything first and learning by doing can both work. Which fits depends on what a mistake would cost in this role.
Tell me about a process you put in place because none existed. Who still follows it?
Why ask it
The second half is the test. Many people have written a checklist or a template, and far fewer got colleagues to adopt it. If it died when they moved on, ask why, and whether it was simply too heavy for a team that size.
How much checking of your work are you used to, and how do you catch your own mistakes without it?
Why ask it
In a larger company a reviewer, a test team or a legal department often stands between a person's work and the customer. Put a case to them: it is the evening before something goes out that no one else will read, so what do they do? A specific habit, such as leaving it overnight or going through it as a new user would, says more than 'I am detail-oriented'.
What tools, budget or help did you have in your last role that you could not have done the job without?
Why ask it
Set their list beside what you can offer. If they name an analyst, an agency or a large software budget and you have a spreadsheet, tell them, then ask how they would do the work with what is here. That second answer is the one to write down.
When did you last do a job the scrappy way because the proper way cost too much or took too long?
Why ask it
You are after proof that they can tell good enough from sloppy. Two details matter: what they deliberately left rough, and where they refused to cut a corner. A person with nothing in the second group is as much a worry as one with nothing in the first.
When have you seen a problem that was nobody's job and dealt with it yourself?
Why ask it
Check whether they told anyone afterwards, because problems fixed in silence can hide a pattern the founders need to see. Be careful with a story that is mostly about colleagues failing to do their work. That is a complaint, and you asked for an example of ownership.
Bad stretches
Tell me about the last time something you were responsible for went badly. What did you do on the first day?
Why ask it
The first day shows instinct: who they told, what they fixed first, whether they went quiet. Keep steering back to what they personally did, since a story told entirely in 'we' can hide a bystander. If they have to reach back many years for an example, ask about something smaller and more recent.
Have you been through a layoff, a failed project or a company that closed? What did you take from it?
Why ask it
Ask gently and accept a short answer. Someone who has lived through one knows what a bad quarter feels like from the inside, which no interview exercise can reproduce. A person who has not can answer with the worst month their team ever had.
What is the longest you have worked on something that did not pay off, and how did you know when to stop?
Why ask it
A startup needs persistence and the ability to abandon a dead end, often from the same person in the same month. Listen for the signal they used: a date, a number, a customer's reaction. Having had no stopping rule at all is the thing to note.
Tell me about a time you had to give bad news to a boss or a customer.
Why ask it
Find out how soon they said it and what they brought with it. The pattern to hope for is early, plain and with a proposal attached. If they held on until it could no longer be avoided, ask what they were hoping would happen in the meantime.
What does a hard month do to you, and what would the people around you notice first?
Why ask it
This asks for self-knowledge, which counts for more in a team of eight than in one of eight hundred, because everyone sits within range. The believable answers are specific and slightly unflattering: shorter messages, skipped lunches, going silent. Find out what helps, and tell them what you are like under the same strain.
Tell me about a time you disagreed with a decision, lost the argument and had to carry it out anyway.
Why ask it
Founders decide quickly and are sometimes wrong, so this situation will come. You are looking for a person who argued the case and then did the work properly, without sulking or quietly doing it their own way. The ending is worth hearing too: whether they turned out to be right, and what they did with that.
Say we lose our biggest customer and freeze spending for a quarter. What would you do differently in your own job?
Why ask it
Save it for late in the interview, once they know something about the business. Some people start listing where they could help bring money in or cut a cost. Others ask how safe their own pay would be, which is a fair thing to want to know. If the company has already had a quarter like that, say what was cut and what was protected.
Risk and pay
How do you think about the risk that this company might not exist in two years?
Why ask it
Hope for a considered answer, neither bravado nor alarm. A person who knows what they would do next, and what they would have gained by then, is taking the risk with open eyes. In a hiring interview stop there: savings, a partner's income and dependents are not yours to ask about.
What is the lowest salary that would make this job workable for you?
Why ask it
Asking for the floor instead of the hope saves both sides a wasted process. If your range sits below it, say so now. Rules on asking about past pay, and on when an employer has to state its own range, differ from place to place, so keep the question on what they need from here on and check how it works where you hire.
How would you weigh a lower salary with equity against a higher salary without it?
Why ask it
The answer shows whether they treat equity as a lottery ticket, as part of their pay or as worth nothing. Someone who counts it at zero will feel underpaid on a salary you set with the grant in mind. If there is room to trade one for the other, lay out the choices.
What do you already understand about startup equity, and what would you like explained?
Why ask it
Use this to find out what to explain, not to mark them down. Cover vesting, what exercising would cost and what happens to the grant if they leave, and hand over the plan documents. How a grant is taxed depends on the country and the type of grant, so tell them to ask a qualified adviser how it works for them.
If the equity ended up worth nothing, would the job still have been worth taking?
Why ask it
A yes with reasons attached, such as the skills, the people or the work itself, comes from someone who will not resent you over a modest outcome. A long pause is honest too, and a cue to go back to salary. Do not fill the pause by predicting what the shares will be worth.
How do the hours and pace I have described compare with what you are used to?
Why ask it
Describe a real recent week before asking, evenings and weekends included if they happen. Then let them say what they can keep up, and take it at face value. Leave the reasons alone: family, health and outside commitments are theirs to raise, and what an interviewer may ask about them depends on where you are.
What other offers or options are you weighing, and how does this one compare?
Why ask it
You find out what you are competing with: a bigger salary at a large company, another startup, or staying put. If the alternative is far safer and better paid, ask what would tip the decision your way, then resist the urge to oversell. A person talked into the risk is the first to regret it in a bad month.
What would make you leave in the first year?
Why ask it
Asked without defensiveness, it brings the deal-breakers out early: a missed payroll, a move away from the work they came for, a founder who shouts. Some of these you can truthfully rule out and some you cannot. Tell them which is which.
Which of our numbers would you want to see before accepting an offer?
Why ask it
Somebody choosing startup work with care will want to know how long the money lasts, what revenue is doing and how many people have left, and a lack of curiosity about them is an answer in itself. Decide before the interview how much you will share at each stage. Then share it straight, because a figure that later proves rosy costs you the hire's trust.
For a mentor
Are you choosing a startup, or mainly leaving your current job?
Why ask it
Both can be true at once. If it is mostly the second, a different team or another large employer might fix the problem at far less risk. Ask what would have to change where they are for them to stay, and if nothing would, the startup question is at least a real one.
Which stage suits you: five people and no customers yet, or a hundred people and a sales team?
Why ask it
'A startup' covers very different jobs. Early means more chaos, more say and less certainty, while later means more structure and a narrower role. Have them describe a good day at work and see which end of the range it resembles.
Who do you know who has worked at a startup, and what have they told you about it?
Why ask it
What reaches most people about startups is the highlights: funding news, founder interviews, the occasional big exit. One conversation with someone who stayed through a rough year, and one with someone who left, fills in the rest. If they know nobody, an introduction may be the most useful thing you can give them.
If the paychecks stopped with no warning, how long could you manage?
Why ask it
This one belongs to a mentor, a friend or a parent, never to an interviewer. No number is the correct one, but having a number turns the decision from a feeling into a plan. If the honest answer is none, talk about what the salary and the company's funding would need to look like for the move to make sense.
Who else is affected if this goes wrong, and have you talked it through with them?
Why ask it
A partner, someone who shares a lease, or family relying on the income should hear about the risk before the offer is signed. You are not asking on their behalf or seeking anyone's permission. You are checking that the conversation has taken place, and offering to help plan it if it has not.
What will you ask the founders before saying yes, and which answer would make you walk away?
Why ask it
Help them write the list: how long the money lasts, who has left, what the equity terms are, what the first three months of work would be. Settling the walk-away answer in advance matters, because after a flattering interview nearly any reply sounds acceptable.
If it does not work out, what is your plan for the six months after?
Why ask it
A person with a fallback takes the risk more calmly and negotiates from a steadier place. It need not be elaborate: a field that is hiring, a few people to call, a skill the job will have added. If thinking it through makes them want to withdraw, that was worth learning over a coffee and not after resigning.
How to find out whether someone suits startup work
Practical guidance for the conversation itself
Setting up the conversation
Decide what your startup demands
A company of six with no revenue yet and one of two hundred with a finance department are both called startups, and they ask different things of a new hire. Write down the three conditions of this job that a newcomer would find hardest, perhaps no senior person in their field, a plan that changes monthly or pay below what larger firms offer. Choose the questions that test those three, and leave out any group that does not apply at your stage.
Pick eight to ten, not the whole page
Once follow-ups are counted, an hour rarely has room for more than eight to ten questions. Two from each of the first five groups is a workable spread, starting each group near its top. Put the same ones to every candidate for the role, so that afterwards you are comparing answers and not interviews.
Describe the job before you test for it
Several of these questions only work after you have told the truth about the company: the runway in broad terms, the hours of a recent week, what is still missing. A candidate can tell you how they would cope only with conditions they have heard about. Being frank early also lets the people who would dislike the job withdraw before either side has spent more time.
If you are the mentor and not the employer
Your job is to help someone see the decision clearly, not to judge them. Start with Why a startup, move to Risk and pay, and finish with the For a mentor group, which holds the questions about savings and family that an interviewer has no business asking. Ask, then wait: the useful part is often what the person works out while answering.
What to listen for
An occasion behind every claim
Nearly every candidate will say they are comfortable with uncertainty, because saying so is free. Each claim needs an occasion: which job, what was unclear, what they did on the Monday. Where no occasion exists yet, as with a new graduate, use something outside paid work, or describe a real situation from your company and ask for their first three moves.
A big-company resume is not a mark against anyone
A person from a large employer may never have been given the chance to show these traits at work. Look for where they went around the structure: a side project, a team they started, a tool they built without asking. The reverse holds as well, since years spent at startups do not show that someone was good at it.
Notice what they ask you
People suited to this work tend to ask about cash, customers and what they would own. Someone whose questions are all about title, perks and promotion timing may be picturing a different kind of company. Take it as a prompt to describe the job again, more bluntly, and see what they ask next.
Enthusiasm is not evidence
Startups attract people who like the idea of one. Excitement helps in the first week and says little about the ninth month. When the notes from an interview pull in two directions, give the Bad stretches and No backup answers more weight than the Why a startup ones.
Where an interviewer should stop
Ask about the job, not the person's life
Savings, debts, a partner's work, children, health, age and plans for a family are for the candidate to bring up, not for you to ask about. What an employer may ask differs by country and state, so check the rules where you hire or ask whoever handles your employment matters. The safer form is to state the requirement, such as the salary, the hours or the travel, and ask whether it works for them.
Explain the equity without selling it
Say what the grant is, how it vests, and hand over the documents. Do not put a future value on it, and do not set it against the salary someone is giving up as if the two were the same kind of money. Tax and exercise costs depend on the country and the type of grant, so the candidate should ask a qualified adviser how it works in their case.
No tricks and no staged crises
A surprise deadline or a deliberately hostile interviewer shows how someone handles an interview stunt, which is not the same as handling a bad quarter. If you want a work sample, keep it short and close to the real job, say how long it should take, and find out what your local rules say about paying for trial work.
After the conversation
Write down what was said that day
Note the occasions each candidate gave, in their words, before the impression of how likeable they were takes over. For every group you covered, one line is enough: the story, and what the person did in it. A group with no story against it is a gap to fill in the next round.
Take one story to a reference
With the candidate's agreement on who you call, pick the strongest account from No backup or Bad stretches and ask a former manager or colleague about that event by name. 'I gather the launch slipped in the spring; what did she do that week?' gets a fuller reply than a general request for strengths and weaknesses.
Repeat the hard parts with the offer
Whatever you said about runway, hours and how the role may change, say it once more when you make the offer, in writing if you can. A hire who accepted with the hard parts in front of them stays steadier when those parts arrive.
When the answer is not yet
A strong person can be wrong for a company at ten people and right for the same company once it has a few teams and some process. If that is your reading, tell them so plainly and keep in touch. A mentor who reaches the same conclusion can suggest a later-stage company as a first step in place of dropping the idea.