Questions to Ask a Startup Founder
Questions to ask a startup founder when you get time with one: over coffee, on a podcast, for a class or an article, or across the table when a job at their company is on offer. Most suit the founder of a company at any age, and a handful are written for one whose firm is long past its first years: how their own job has changed, what they fought to keep, whether anyone has offered to buy it. The list opens with the questions nearly every such conversation starts with, then works through the product, growth and competition, money and the team before turning to the founder's own life and the advice they would pass on.
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The questions
Each question, and why to ask it
Start here
What problem does your company solve, and how did you first run into it?
Why ask it
Most founders have a polished version of the first half, so the conversation really starts with the second. A problem they lived with at a job or at home comes with detail no market report supplies. If they found it by going looking for a business to start, ask who they spoke to first to check it was real.
What were you doing right before you started this, and what made you leave it?
Why ask it
The job they walked away from tells you what they gave up: a salary, a title, a team they liked. Ask whether they resigned first or built at night until the numbers allowed it, because those are two different appetites for risk. Someone who was laid off and started from there has a story worth hearing too.
What has been the hardest part of building the company so far?
Why ask it
Leave it this open and see whether they go to money, to people, to the product or to their own head. The first thing named is usually whatever is hard this month, so ask whether the answer would have been the same a year ago. That comparison shows how the job changes as a company grows.
Who was your first paying customer, and how did you find them?
Why ask it
The first sale tends to come from somewhere unglamorous: a former colleague, a cold email, a reply on a forum. Public tellings often skip it, so ask what that customer paid and whether they are still a customer today.
What is the biggest mistake you have made so far, and what do you do differently because of it?
Why ask it
Every founder has been asked for a lesson, so ask for the change in behaviour instead. A hire made too fast, a contract signed unread or six months on the wrong feature only counts as learning if something is done another way now. 'I worked too hard' is a dodge, and the polite follow-up is to ask for the one that cost money.
When did this stop being an idea or a side project and become a real company?
Why ask it
The turning point is often small and oddly specific: a stranger paying, a resignation letter, a first invoice with tax on it. Whatever they name is what they needed to see before taking the risk.
What did the people closest to you say when you told them you were doing this?
Why ask it
Good for a podcast or a relaxed coffee, because it produces a story with other people in it. You hear whether there was backing at home, a sceptical parent or a partner covering the bills. Leave it out of a formal interview, where family is not your business.
What do you know now that you wish you had known on day one?
Why ask it
It comes up at nearly every founder talk, so narrow it to get past the stock reply: something about money, something about people, or something about their own limits. The most useful versions are plain facts, such as how long a large customer takes to sign or how much of the week goes on hiring. Ask whether knowing it would have changed a decision or only spared them some worry.
Where do you want this to be in five years, and are you still running it in that picture?
Why ask it
The first half invites the vision speech, and the second half is where it gets interesting. Some founders are building a company to keep and some are building one to sell, and the two lead to different choices about hiring, debt and how fast to grow. If there is a long pause before the second answer, ask what they would want to be doing instead.
Product
What did the first version look like, and how different is it from what you sell now?
Why ask it
Ask to see it if a screenshot or an old prototype survives, because founders usually enjoy showing how rough it was. The distance between that and the current product is a fair measure of what customers taught them.
Before you built anything, what did you do to find out whether anyone wanted it?
Why ask it
The strong versions involve someone who could have said no: a deposit taken, a signed letter, a waiting list of strangers. Friends who liked the idea are weaker proof, and plenty of founders will admit they built first and asked afterwards. That admission is useful in itself, so ask what the delay cost them.
How does the business make money, and has that changed since you started?
Why ask it
A plain question that plenty of company websites leave unanswered. Subscriptions, a cut of each transaction, advertising and one-off projects all behave differently when times get tight. The second half often brings out an earlier model that failed, and that story is worth having.
Who turned out to be your real customer, and is it who you expected?
Why ask it
Products are often bought by someone other than the person they were designed for. Software meant for teachers gets ordered by the school office, or a tool built for large firms sells to freelancers. A founder who can describe that shift has been watching who pays, so ask what had to change once they noticed.
How close are you to product-market fit, and what would tell you that you had it?
Why ask it
The phrase gets used loosely, so the second half pins it down. Signs worth hearing are customers who renew without being chased, who complain loudly when something breaks, or who bring a colleague along. 'Not yet, and here is what is missing' is a more useful answer than a confident yes.
What do customers do with the product that you never planned for?
Why ask it
Founders tend to enjoy this one, and the surprise uses are where a next product can come from. Find out whether they followed the surprise or steered people back to the original plan, and why.
What is the complaint you hear most, and why is it not fixed yet?
Why ask it
A founder who can recite it is reading the support inbox. The reason it remains is usually a trade-off: the fix would take the whole team a quarter, or it would break something the larger customers rely on. Treat 'we do not get many complaints' as a sign that nobody is asking.
What happened the last time you raised your prices?
Why ask it
Pricing stories are short and full of facts: who objected, who did not notice, how many left. The telling detail is how long they hesitated beforehand and whether the fear turned out to be justified. If the price has never moved, ask how it was picked in the first place.
Have you had to pivot, and what told you it was time?
Why ask it
A pivot is a decision to stop, and the hard part is telling a slow start from a dead end. Find out whether it was a number that would not move, something a customer said plainly, or simply the cash running down. With a founder who has never changed course, ask what would have to happen before they did.
What have you built that nobody used?
Why ask it
An abandoned feature is a gentle way into the subject of failure, and most founders can laugh about one. Where the idea came from matters, because a feature copied from a competitor fails for different reasons than one a single loud customer demanded. Then ask how they test demand now before any work starts.
How do you decide what not to work on?
Why ask it
A small team can afford to build very little, so the rule for saying no shapes the product more than any roadmap does. Ask for the last request they turned down and who was disappointed by it. If no example comes, the real rule may be that the loudest customer wins that week.
What are you working on right now that you are most excited about?
Why ask it
This belongs in the last third of a conversation, once the hard questions are done and you want them talking freely. The answer is often something not yet announced, so say up front whether you plan to repeat it.
Growth and competition
Where is your growth coming from right now, and can you repeat it on purpose?
Why ask it
You are asking how new customers arrive: search, referrals, a sales team, one large partner. The second half matters because a channel that worked once is different from one they can turn up when they choose. Word of mouth is a fine answer, and the follow-up is what they do to encourage it.
What number do you actually look at first on a Monday?
Why ask it
Whatever they open first is what the company runs on this year: cash in the bank, active users, deals in progress, cancellations. Ask what that number was six months ago and what moved it. Some will not share the figure itself, and the choice of number still tells you plenty.
What did you try in order to grow that went nowhere?
Why ask it
Failed experiments are cheaper to learn from secondhand. Adverts that never paid back, a conference stand, a partnership that produced meetings and no sales: each saves you from trying the same thing blind. Ask how long it ran before they called it, since giving up on a channel too early is a mistake of its own.
When you lose a deal, who do you lose it to?
Why ask it
The reply is not always a rival company: buyers often stay with a spreadsheet, hand the job to their own staff or decide to do nothing this year. Ask how they find out why a prospect said no, because that takes a deliberate phone call and a small team may never have made it.
Which competitor do you respect most, and why?
Why ask it
Asking about respect gets a calmer read on the market than asking who the rivals are. Praise for something specific in another company's product means they study it closely. If every rival is waved away as slow, ask what that rival's customers would say.
If a well-funded team started on the same idea tomorrow, what would take them longest to catch up on?
Why ask it
This asks for the real advantage without using the word moat. The answers that hold up are things that take time: relationships with a hard-to-reach kind of buyer, data gathered over years, a licence, a name in a small field. When the answer is the code or the head start, ask how many months that lead is worth.
What did you know about this industry going in that an outsider would not have?
Why ask it
This is the polite way of asking why they are the one to build it. Years inside a trade give a founder contacts, vocabulary and a feel for what buyers will not put up with. Someone who came in cold can still answer well by describing how they learned the field and who taught them.
What change in your industry are you betting on?
Why ask it
Many startups exist because something shifted, whether a new rule, a cheaper technology or a change in habit. Naming the bet tells you what has to stay true for the company to work. Ask whether they have seen any sign of the shift slowing, and what they would do if it did.
What keeps you up at night about the business?
Why ask it
The phrase is worn, but founders tend to answer it more candidly than a formal question about risk. When the reply is a list, narrow it by asking what the likeliest cause would be if the company closed a year from now. A named worry with a plan beside it is a good sign, and you can ask what that plan has cost so far.
Money
How is the company funded, and what did you give up to get that money?
Why ask it
Savings, revenue, a loan, angel investors and venture capital each put a different kind of pressure on a company. The second half brings out what the money cost: a share of ownership, a seat on the board, a growth target or a personal guarantee.
Does the business cover its own costs yet, and if not, what has to happen before it does?
Why ask it
This is the profit question without the accounting terms, and a founder can answer at whatever level of detail suits them. Not yet is a normal reply for a young company, which is why the second half is there. If costs are already covered, ask when that began and what they changed to get there.
How did you meet your first investor?
Why ask it
Fundraising advice tends to be abstract, and this gets you one real route in, perhaps an introduction from a former boss, a pitch night or a cold message that finally got a reply. Ask how long it took from the first meeting to money in the bank. A founder who never raised can tell you what they would have needed to believe before doing it.
What did investors or lenders push back on hardest?
Why ask it
An objection heard in meeting after meeting usually points at something real, such as a small market, a missing co-founder or one customer making up most of the revenue. Ask what they did about it and whether the next pitch went differently.
What would you do differently about fundraising if you were starting again?
Why ask it
Regrets gather around a few themes: raising too early, taking money from someone who proved hard to work with, months spent pitching while the product stood still. The particulars are worth more than any general rule. Terms and customs differ by country and by stage, so hear it as one person's experience.
What did you live on before the company could pay you?
Why ask it
Savings, a partner's salary, consulting on the side and a severance payment are all common answers, and each one sets a different clock. For anyone weighing the same leap it is the most practical question on the page. It is also personal finance, so ask gently and take a short answer as the whole answer.
How long will the money you have now last, and what is the plan if it runs short?
Why ask it
Founders call this runway, and it sits behind decisions on hiring, pricing and which customers to take. You may get a number of months, a vague reassurance or a polite refusal, and all three are fair at a first meeting. Stay on the second half: cutting costs, raising prices and raising another round are different plans, so ask which comes first.
Was there a month when you were not sure you could pay everyone?
Why ask it
Near misses are seldom discussed while they are happening, which is why this is asked in the past tense. Listen for the order of events, starting with whose pay stopped first and when the team was told. Do not press a founder who goes quiet here, because the month in question may be this one.
If the bank balance doubled tomorrow, what would you spend it on first?
Why ask it
You find out where they think the bottleneck is, and now and then the reply is nothing at all, because the limit is something money cannot buy. Then turn it around and ask what would go if the balance halved. Put together, the two answers are their priorities in order.
What does the company pay for that an outsider would not expect?
Why ask it
Compliance, insurance, payment fees, a lawyer for one awkward contract: the unglamorous costs of a young company rarely make it into talks or posts. Someone planning a budget of their own gets more from this than from a headline funding figure.
Has anyone offered to buy the company, and how did you weigh it up?
Why ask it
A company that has lasted a few years has usually had at least one approach, serious or otherwise. The figure is likely to be confidential, so ask about the thinking: who they talked it over with and what would have made them say yes. If part of it was sold, ask what was different about the job a month later.
Team
How did you meet your co-founder, or why did you decide to build this alone?
Why ask it
Co-founder stories run from a ten-year friendship to an introduction three weeks before the paperwork. The part to ask about is how well each knew the other's working habits beforehand. With a solo founder, ask who they argue ideas out with.
How do you and your co-founder settle it when you disagree?
Why ask it
You are asking for the mechanism, not the gossip. Some pairs give each person the last word in their own area, some bring in an adviser, some argue until one gives way. A claim that they never disagree usually means no decision has yet mattered to both of them.
Who was your first hire, and why that role before any other?
Why ask it
The first salary a founder agrees to pay shows what they could not do themselves, or could not stand doing. An engineer, a salesperson and an operations generalist each point to a different gap. Ask whether that person is still there.
Which hire was hardest to get right, and what did it teach you?
Why ask it
The story might be a role that sat open for half a year or a person who looked ideal and left within months. Either way you hear what the founder checks for now that they did not check for then. If the lesson is only that good people are hard to find, ask what they changed in how they interview.
Have you had to let someone go, and looking back, how long did you wait?
Why ask it
Waited too long is the usual reply, so ask what held them back: loyalty to an early colleague, dread of the gap it would leave, or plain reluctance to have the conversation. Keep it to what the founder learned and do not ask who it was. At a company of three or four people the honest reply may simply be not yet.
What do you look for in an early employee that a big company would not care about?
Why ask it
Worth hearing if you want to work at a startup, theirs included. Common answers are comfort with unclear instructions, a willingness to do work below the job title and a habit of finishing things. Ask for a person who had it, which turns a list of adjectives into someone you can measure yourself against.
How would your team describe working for you?
Why ask it
Seeing it through the team's eyes makes a founder step outside the official line on culture. The believable answers include a flaw, such as too many changes of direction, messages late at night or slow decisions on pay. If you might work there, put the same question to an employee and compare the two versions.
When did someone on your team last tell you that you were wrong, and what happened next?
Why ask it
A recent example with a name in it suggests people feel safe disagreeing with the boss. If the founder has to reach back a year, the team may have stopped trying. What followed counts just as much, whether that was a changed decision, a clear explanation of why not, or a grudge.
How do you tell the team bad news?
Why ask it
A lost customer, a missed target and shrinking cash all have to be shared at some point, and founders differ on when. Some say it the same day in a group message, and some hold it until the problem can be paired with a plan. Ask for the last piece of bad news and how long it took to reach the newest employee.
At what size did the company start to feel like a different place?
Why ask it
Founders who have grown a team can often name the headcount: the point where they no longer knew everyone, or where a decision was first made without them. Ask what they put in place then, whether managers, a handbook or a weekly meeting, and what was lost that they still miss.
What from the early days have you fought hardest to keep as the company grew?
Why ask it
One for a founder whose company is well past its start-up years. It might be a habit such as answering support email in person, a rule about who gets hired, or lunch together on a Friday. Follow with the thing they tried to keep and could not.
If I joined, what would you want to hand over to me first?
Why ask it
Save this for a conversation where a job is on the table. A founder with a real need names the task at once, and it is often something they dislike or know they do poorly. A loose answer about helping wherever needed suggests the role has not been thought through, so ask what the last person hired ended up doing.
Do early employees get a share in the company, and how does that work?
Why ask it
This opens the subject of equity without turning a first conversation into a negotiation. Listen for whether shares or options go to everyone or to a few, and whether the founder can explain the terms in plain words. Vesting, tax and what happens when you leave differ by company and by country, so get them in writing before relying on any figure.
The founder
What does a normal week look like for you, hours included?
Why ask it
A week gives a truer picture than a day, since it takes in the travel, the evenings and the weekend catch-up. Hours get exaggerated in both directions, so have them walk you through last week in particular.
What do you like most about the job, and what do you like least?
Why ask it
People start companies to build or sell something and end up running payroll, reading contracts and giving performance reviews. The part they love explains why they keep going, and the part they dread shows what the job turns into once the product exists. Ask whether the dreaded task has been passed to someone else yet.
How has your own job changed since you founded the company, and which part was hardest to hand over?
Why ask it
The founder of a company with fifty staff does different work from the person who started it, and not everyone enjoys the change. The task held on to longest, often sales, the product or approving each hire, tends to be the one they believe they do best. Ask what finally made them let it go.
If you had to step away for three months, what would stop working?
Why ask it
The reply shows how much of the company still runs through one person. At a young company the honest answer is nearly everything, and an older one usually has a shorter list. Whatever is on it, ask whether anyone is being trained to take it over.
What skill has mattered most that you did not expect to need?
Why ask it
Expect to hear something like selling, writing clearly, reading a contract or delivering bad news, and seldom anything technical. The answer doubles as a study list for anyone planning to start something. Ask how they picked it up, since few of these are taught anywhere formal.
Who or what shaped how you run the company: a former boss, a mentor, a book?
Why ask it
Take the names as a reading list and the reasons as the real answer. Someone who learned pricing from a former boss, or how to manage people from a sports coach, is telling you where their instincts come from. Then ask what they tried from that source that did not work for them.
What have you changed your mind about in the last year?
Why ask it
Remote work, pricing, a type of customer, whether to raise money at all: a year of running a company tends to overturn at least one firm opinion. Give them a moment to think, then ask what evidence did it.
Who do you talk to when things are going badly?
Why ask it
There is a lot a founder cannot say to staff, investors or customers, which leaves a short list. You might hear about a partner at home, another founder a year further on, a coach or a group that meets monthly. Anyone planning to start a company can borrow the answer, and if the reply is nobody, leave it there.
Have you ever come close to quitting, and what kept you going?
Why ask it
The thought is common among people who run companies, and it is easier to admit once the moment has passed. What kept them at it is the true answer to what motivates them, and it tends to be plainer than a mission statement: a customer who depended on the product, a team they had hired, sheer stubbornness. Let them choose how much detail to give.
What has this cost you outside the business?
Why ask it
Ask it plainly and then wait. Savings, health and time with family are the parts usually left out of the public story, and they matter most to someone weighing the same path. Take whatever they offer and do not dig for more.
What are you proudest of so far?
Why ask it
After a run of questions about mistakes and money, this one lets them enjoy the answer. Notice whether the pride attaches to a number, a product, a customer's result or the people they hired, since that is a fair guide to what they would protect if the company had to shrink.
How do you define success for the company, and for yourself?
Why ask it
The two halves often get different answers, and the gap deserves a follow-up. A company goal might be a revenue line or a sale, while the personal one is control of their own time or building something their town is known for. When the personal half is missing, ask what they would do the week after selling.
What should someone have in place before they quit a job to start a company?
Why ask it
Asking for conditions gets a sharper answer than asking for advice. You may hear a number of months of savings, a first customer who has already paid, or a co-founder who has committed. What is sensible depends on your own costs and obligations, so weigh it as one founder's rule and not a formula.
What advice would you give a first-time founder that they would not want to hear?
Why ask it
Advice to new founders is mostly encouragement, and this wording gives permission to skip it. The replies tend to be blunt and practical: keep the job longer, charge sooner, do not start with a friend you have never worked beside.
What does the company need most right now, and is it something I could help with?
Why ask it
Founders are asked for favours all day, so an offer going the other way stands out. Needs at a small company are usually concrete: an introduction to a certain kind of buyer, someone to test a new feature, a candidate for an open role. Offer only what you will follow through on, and do it within the week.
What should I have asked that I did not, and who else should I talk to?
Why ask it
The first half lets a founder raise the subject they were hoping for, which is often their best story. The second is how one coffee turns into three, because an introduction from a founder gets answered when a cold message would not. Ask for one name and not a list, and tell them afterwards how it went.
Getting past the pitch
Practical guidance for the conversation itself
How to run the conversation
Do the reading first
Skim the website, the pricing page, any funding announcement, and recent posts. Founders answer differently once it is clear you know what the company does, and you avoid spending the first ten minutes on things you could have looked up.
Choose a few for the time you have
Half an hour over coffee has room for six or seven questions once the follow-ups are counted. Take two from the opening group and the rest from whichever section you came for, and keep the ones about the founder's own life for the end, when there is some trust in the room. A podcast or a written interview can go wider, but it still reads better with one section covered properly than with all of them skimmed.
Questions to ask a founder of an older company
Runway, pivots and product-market fit are start-up vocabulary, and someone who has run the same firm for fifteen years may find them beside the point. Lead with how their own job has changed, what they kept from the early days, the size at which the place began to feel different and whether anyone has tried to buy it. Then ask about the first years as history, where the stories are settled and often better told.
Ask about specific past events, not general policy
'How do you hire' produces a philosophy. 'Tell me about the last person you hired' produces facts. Anchor questions to a real decision with a date attached whenever you can.
Let the silence sit
Founders are practised at filling airtime. The useful material often arrives a moment after they finish the version they have said before, so resist the urge to move on.
Ask for the number, then stop pushing
Revenue, runway and headcount are often confidential, especially with investors involved. Ask once, accept a range or a refusal gracefully, and do not trade the rest of the conversation for a figure you cannot verify anyway.
Reading the answers
- If every story is one where the founder was right, the company is very young or the stories are rehearsed. Ask about a decision that did not work.
- Watch for we in place of I on decisions, especially firings and pivots. It can signal a real team or a founder distancing themselves from a call they made alone.
- Any claim about the size of the market deserves the follow-up of where the number came from and how they counted it.
- If growth, hiring and fundraising are all described as going well at once, ask which one is hardest this quarter. One of them usually is.
- When the answers lean on investor vocabulary, ask the same thing again in terms of one customer. It brings the conversation back to what somebody pays for.
If you are asking because you are thinking of doing it yourself
- 1Talk to a founder or two whose company closed, not only ones still standing. People whose companies survived know the path that worked, and the others know where it gives way.
- 2Ask what they lived on in the first year or two. It tells you whether the same route is open to you.
- 3Ask what they would need to see before advising someone to quit a stable job, and take the answer seriously.
- 4Ask what part of the work takes most of their time now, since that is the actual job rather than the version in the founding story.
- 5Follow up in six months. A second conversation lands in a different week, and what has changed between the two is worth hearing.
If you are asking because you might work for them
- The Team questions do double duty. How a founder talks about hiring, letting people go and being told they are wrong is the closest preview you will get of reporting to them.
- Ask about funding and how long the money lasts the way a curious outsider would, then ask again once there is an offer. Exact figures may be held back at a first meeting, which is fair, as long as you have them before you have to decide.
- Have any share of the company put on paper: how many shares or options, what total they are a slice of, the vesting schedule and what happens if you leave. The rules and the tax treatment vary by country, so have someone qualified read the documents.
- Speak to one person who works there now and, if you can find one, somebody who has left. Set their account beside the founder's.
- Notice how your questions are received. Irritation at a fair question about cash or staff turnover is an answer in its own right.
Questions worth skipping
- Asking for the idea in confidence, or hinting you might build something similar. It ends the candour immediately.
- Any variation of what is your secret. It invites a slogan.
- Requests for advice on your own venture in the first conversation, unless you were introduced for that reason.
- Asking what the company is worth out of curiosity. Over coffee or on a podcast it rarely gets a real answer. It becomes a fair question once you hold an offer that includes shares, because the figure decides what the offer means.