Questions to Ask Before Joining a Startup
For a candidate with an offer in hand who wants good questions to ask about working at a startup before saying yes. The list opens with the handful to ask first, then covers funding and the market, what the equity and pay are really worth, the role, and the founders and team, where several are meant for a current start-up employee with no founder listening. It closes with a few to put to yourself before you sign.
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The questions
Each question, and why to ask it
Start here
How much cash is in the bank, what is the monthly burn, and how many months of runway does that leave?
Why ask it
Get the first two and do the division yourself, because a runway quoted in months can assume revenue or savings that have not happened yet. A company that will not share either figure with someone holding its offer is asking you to carry a risk you are not allowed to see.
When did you last raise, how much, and at what valuation?
Why ask it
The date shows how far into its money the company is, and the valuation is the bar the next round or a sale has to clear. If the raise was more than two years ago and nothing has been announced since, ask plainly what has been paying the bills.
Is revenue growing, and what does a typical customer pay?
Why ask it
A company with no paying customers yet is a different bet from one with revenue, and either can be worth joining at the right price. Where there is revenue, find out how much comes from the two or three largest accounts, because one cancelled contract can undo a year of growth.
How many shares am I being granted, and how many are outstanding on a fully diluted basis?
Why ask it
Ten thousand options could be one percent of the company or a hundredth of one percent, and only the total tells you which. If you are quoted a percentage instead, check that it counts the whole option pool and any notes due to convert into shares.
What are the first three things you would want me to deliver?
Why ask it
Three named pieces of work, in a rough order, mean someone designed the job before advertising it. A list that covers the whole function usually means you would be absorbing whatever the founders no longer have time for.
Who has left in the past year, and why?
Why ask it
At a company of thirty, three departures is a tenth of the staff, so the reasons carry weight. Listen to how the leavers are described, and compare the account with the public profiles of people who have moved on.
What is the plan for the company: keep building, sell, or go public?
Why ask it
Shares in a private company rarely turn into money without a sale or a listing, so the founders' intended path decides whether and when yours could. A founder who means to run the business for decades and an employee counting on a payout in four years want different things, and it is better to learn that now.
Money and market
What has to be true for the next round, and how close are you?
Why ask it
Look for a named metric, such as a revenue figure or a customer count, and today's number against it. A milestone described only as growth usually means the target has not been agreed with the existing investors.
What happens if the next round does not come together?
Why ask it
Reasonable answers include cutting to profitability, a bridge from existing investors, or a sale. An answer that treats the question as unthinkable tells you the plan does not exist.
Who led the last round, and have your earlier investors put in more money since they first came in?
Why ask it
Backers who have sat through every board meeting and still wrote a second cheque are telling you something no pitch can. If the earlier investors sat the last round out, ask what reason they gave.
What would the company have to cut to break even, and has anyone worked that out?
Why ask it
You are not asking them to be profitable, only whether survival is in their own hands. The smaller version of the company, headcount included, is something a careful founder can describe without notes. Listen for where your role sits in that version.
Who buys the product today, and what were they using before?
Why ask it
A named kind of buyer and a named thing they replaced, even a spreadsheet, means the problem was real enough that people were already working around it. When the customer is described as everyone, it usually means nobody has been sold to twice.
What tells you customers need this and are not just trying it: renewals, daily use, referrals?
Why ask it
This is the product-market fit question with the jargon taken out. Pilots and letters of intent show interest, while renewals and bigger second orders show demand. If the evidence is mostly enthusiasm, you would be joining the search for a business, which can be a fine job at the right price.
How many customers stopped paying in the past year, and what reasons did they give?
Why ask it
Every company loses customers, so a count and two or three plain reasons is the normal answer. Be warier of hearing that nobody ever leaves, from a company with a year of sales behind it, than of a real number.
Who are you losing deals to, and why?
Why ask it
The reason is the useful half: price, a missing feature, or a rival the buyer already knew. A founder who says there is no competition is usually leaving out the spreadsheet, or doing nothing, which is what a hesitant buyer falls back on.
Can I spend an hour in the product as a customer would before I answer the offer?
Why ask it
An hour of clicking around tells you whether you could stand behind the thing for years, and whether the demo matched what customers get. If access is hard to arrange for someone holding an offer, ask which parts are not ready to be seen.
What is the company building next, and what was dropped from the roadmap to make room for it?
Why ask it
A plan that names what was cut shows somebody is choosing, which a list of twelve priorities never does. If the next item exists because one large customer asked for it, find out how often that happens, since building to order for a single account is a different job from building a product.
How large could this business get if things go well, and what is that estimate based on?
Why ask it
An estimate built from a count of likely buyers and what each would pay is worth more than a vast total borrowed from an analyst report. For you the point is practical: the grant only matters if the company can grow well beyond the value investors have already put on it.
Has the company changed direction since it started, and what happened to the people who worked on the old plan?
Why ask it
A pivot is no mark against a startup. What concerns you is the people: whether they were moved onto the new work or let go shows how you would be treated at the next turn.
Has the company ever cut staff or pay, or run a payroll late?
Why ask it
A past layoff handled openly, with notice and a clear reason, can be a better sign than a spotless record at a company that has never been tested. A late payroll is different: ask when it was, how long it lasted, and whether everyone was paid in full afterwards.
What is most likely to sink the company in the next eighteen months?
Why ask it
Founders live with this question, so a quick and specific answer (one large customer, a regulator, a rival's pricing) is reassuring. Then ask who is working on it now, and what has changed since they started.
Equity and pay
What is the strike price, the current preferred price, and the last 409A or equivalent valuation?
Why ask it
The strike price is what each option would cost you to buy, and the valuation behind it says what an ordinary share is judged to be worth today. Investors paid the preferred price for shares with rights yours will not have, so multiplying your grant by it overstates what you hold. The 409A is a United States valuation, so elsewhere ask how the strike was set.
Are these options, RSUs or actual shares, and at what point would each cost me money?
Why ask it
The three behave differently: one needs cash to exercise, another can bring a tax bill when it vests or when it is sold, and the timing changes from country to country. Ask the company to put its description in writing, then check it with an accountant who handles equity where you live.
What is the vesting schedule, and what is the exercise window if I leave?
Why ask it
Vesting sets how fast you earn the grant, and the window sets how long you keep the right to buy it after leaving. Where the window is ninety days, you would need the exercise cost, and possibly money for tax depending on where you live, within three months or the options lapse. Some companies offer longer, which is easier to ask for before you sign than at an exit interview.
Is there a cliff, and what happens to my grant if I am let go shortly before it?
Why ask it
With a one-year cliff, a departure in month eleven usually leaves nothing vested. Many companies have no written policy for that case, so it is fair to ask what happened to the people it has applied to.
How much liquidation preference sits ahead of common shares?
Why ask it
Preferred investors are normally repaid first, so in a sale for less than the money raised, common shareholders can receive little or nothing. Ask for the total raised and whether any round carries more than a one times preference or a participation right, then set that against a sale price you find believable.
At what sale price would my grant be worth more than the salary I am giving up?
Why ask it
This turns a share count into the one comparison that matters to you. A founder or finance lead who can sketch it on a whiteboard, preferences included, understands the offer they are making. Treat the result as a scenario and not a forecast.
What dilution are you planning for in the next round, and does the option pool get refilled before it?
Why ask it
New shares for investors and a refilled pool both come out of everyone already holding equity. A rough range is all anyone can give, and hearing one means the company has modelled the round it says it is planning.
What happens to my unvested shares if the company is acquired?
Why ask it
The term to listen for is acceleration: single trigger vests shares on the sale itself, double trigger only if you also lose your job afterwards. Many employee grants carry neither, and then the buyer decides, so go by what the plan document says and not by what the founders hope would happen.
Are top-up grants given after the first one, and what did your longest-serving employees last receive?
Why ask it
If the grant you are hired with is the only one, the reason to stay shrinks to salary once the schedule has run. Press for the real example, because a refresh policy nobody has yet benefited from is only an intention.
Is there any way to turn vested shares into cash while the company is still private?
Why ask it
A tender offer or a sale to an incoming investor is the usual route, and at many early companies it has simply never come up. Ask whether a transfer needs the board's consent, which share agreements often require.
How does the salary compare to the market, and what would it take to revisit it in a year?
Why ask it
You are usually accepting a discount in exchange for equity, and naming its size makes the trade explicit rather than assumed. Ask whether the gap is expected to close as the company raises, or never.
Could the offer be reshaped, with more salary and a smaller grant or the reverse, and at what rate?
Why ask it
The rate at which the company swaps one for the other shows how it values its own shares, which is rarely said outright. If rent or dependants rely on your pay, remember that the cash arrives every month and the grant pays nothing until there is a sale.
What will the benefits be on my first day, as opposed to the ones still being set up?
Why ask it
Health cover, retirement contributions and parental leave tend to arrive late at a young company, and the legal minimum differs by country. Put a rough yearly value on anything missing and add it to the pay cut you are already counting.
What notice and severance would the contract give me if the job were cut?
Why ask it
It feels awkward to raise with people who are trying to hire you, and at a company with a finite runway it is simply practical. Whatever is promised belongs in the contract, and minimum notice depends on where you are employed, so ask how it works there.
Could you send me the full option plan and a sample grant agreement to read this week?
Why ask it
An offer letter is a summary, and the terms that bind you sit in the longer documents: repurchase rights, limits on transfer, what termination does to vested shares. A company that has hired before will have the paperwork to hand, so a long delay is worth a second request.
The role
Why does this role exist now, and who has been doing the work until today?
Why ask it
New funding, a departure and a founder running out of hours lead to three different jobs. Whoever has been covering the work will be either glad to hand it over or reluctant to let go, and you want to know which before your first week.
Would I be starting this function from scratch, or taking over something already running?
Why ask it
Starting it means you write the process yourself and have nobody in your field down the corridor to test an idea on. Some people do their best work that way. If you learn mainly from colleagues who do the same job, count their absence as a cost.
Who would I report to, and how long have they been in that seat?
Why ask it
Reporting lines at a young company move, and a manager who arrived last month may not be the person reviewing you next spring. It helps to meet whoever sits one level above them too, since that is who you would answer to if they left.
Where does my authority stop: which calls would be mine, and which go back to a founder?
Why ask it
Ask for the last decision someone at your level made alone, and the last one that was sent upstairs. A senior title with every purchase and hire routed through a founder is a junior job, and that is easier to learn now than in month three.
What budget, tools and people come with the job in the first year?
Why ask it
Goals set without resources are wishes. If the answer is that budget follows results, ask what the last person who earned it had to show, and how long that took.
How will you judge whether I am doing well, and when would I first hear if I were not?
Why ask it
Young companies often have no formal review cycle, so feedback arrives either constantly or as a surprise. A manager who can say what they would look at after three months has thought about the hire as well as the vacancy.
If the company triples in size, do I grow into the senior version of this job or does someone get hired above me?
Why ask it
Having a boss hired over you is a familiar disappointment for early employees. Neither answer is wrong, and an honest 'it depends on how you do' beats a promise. The best evidence is someone it has already happened to here, and whether they stayed.
What hours do people really work, and what does a bad week look like here?
Why ask it
A question about work-life balance gets a rehearsed line, while the worst recent week comes back as a story with times in it. Listen for who stayed late, whether the cause was a launch or an ordinary Tuesday, and whether anyone took the time back afterwards.
Where does the team work, and how often is everyone expected in the same room?
Why ask it
Startups change their minds on this as they grow or raise, so ask what has shifted since the first hires and what would be written into your contract. A remote arrangement agreed verbally with one founder lasts only as long as that founder's view does.
How does a new person get up to speed when nobody has spare time to train them?
Why ask it
The truthful answer at many early companies is that you teach yourself from whatever documents and people you can find. What the last new hire was handed on day one, and who answered their questions that month, is a fair preview of your own start.
What would I learn here in two years that a larger employer would not let me near?
Why ask it
Scope is the main thing a startup pays in besides equity, and it keeps its value even if the company fails. Running a launch or owning a budget is something you can put on a CV later. Vague talk of wearing many hats is not.
Founders and team
How do the founders divide responsibility, and what have they disagreed about recently?
Why ask it
A specific disagreement described calmly is a healthy sign. If they cannot name one, either the relationship is unexamined or one founder is deciding everything.
What were the founders doing before this, and have any of them built a company before?
Why ask it
First-time founders are not a warning sign, though you should expect them to be learning management on the job. What you are checking is whether their past explains why they understand this customer, and whether it matches what you can find out about them independently.
Is every founder full time, and are their own shares still vesting?
Why ask it
A founder with another job, or one whose stock has nothing left to vest, can walk away more easily than you can. Investors often insist on founder vesting, so its absence at a funded company deserves a follow-up.
What made you start this company, and what would make you stop?
Why ask it
The first half you will have heard in the pitch. The second half is rarely rehearsed, and founders who can say what evidence would end it tend to tell staff the truth early, while there is still time to plan.
Where do you want the company to be three years from now, and what has to go right to get there?
Why ask it
Hold the answer up against the hiring budget and the next-round milestones and see whether all three describe the same company. The size of the ambition matters less than whether two founders, asked separately, describe a similar place.
Who sits on the board, and what was the last thing it pushed back on?
Why ask it
The board can usually replace the chief executive and has a say in any sale, so it is part of who you would be working for. Pushback described without resentment suggests a relationship that functions. None at all means either a very young company or a board that is not paying attention.
When a founder's instinct and the numbers point different ways, which usually wins?
Why ask it
A real case is what you want here, such as a feature a founder loved that customers ignored, and how long it took to drop. Instinct winning is not always wrong at a young company, but you should know before you join how much weight your own analysis would carry.
Does the whole team see the bank balance and the runway, and how often?
Why ask it
Where the numbers are shared every month, employees can make their own decisions in good time. Where finances stay with the founders, the first sign of trouble staff get is often the announcement itself.
When did the team last get bad news, and how was it delivered?
Why ask it
A lost customer, a failed round or a missed launch comes to every startup sooner or later. You are listening for speed and directness: a company that calls everyone together the same week is a different place from one where people pieced it together from rumours.
How big is the team today, and how many hires does this year's budget assume?
Why ask it
Set the planned headcount against the cash and see whether the plan fits inside the runway you were quoted. Doubling the team on money that lasts a year assumes a round that has not happened yet.
Who does well here, and who has struggled despite being good at the job?
Why ask it
The strugglers describe the culture better than any values page does: people who needed clear instructions, people who needed quiet, people who disagreed with a founder in public. Check the description against yourself as honestly as you can.
What do you wish you had known before you joined?
Why ask it
Save this for the employees you meet, not the founders. They usually offer a small, true thing, such as how often priorities change or how long expenses take to be repaid, and small true things are what a hiring process tends to smooth over.
How often have your priorities changed this year, and how did you find out each time?
Why ask it
Put this to someone who has been there at least a year. A change explained at a team meeting with the reason attached is ordinary startup life, while one discovered when a project quietly lost its people shows how you would hear about the next one.
What do you spend time on in a normal week that was never part of the job you were hired for?
Why ask it
At a small company everyone picks up extra work, so the existence of extras is not the test. Notice whether they sound like chosen stretch, such as running a customer call, or like gaps nobody was hired to fill, such as fixing the payroll export every month.
When did you last take a full week off, and did work follow you?
Why ask it
A date within the past few months and a shrug is the answer you are hoping for. If an employee has to think back more than a year, or was the only person who could fix something while away, the team is thinner than its headcount suggests.
Did what you were told about the money and the equity when you were hired turn out to be accurate?
Why ask it
An employee two years in has seen whether the quoted runway held and whether the grant paperwork arrived when promised. Some distance between the pitch and what followed is normal, so pay attention to its size and to whether anyone owned up to it.
May I speak with someone on the team without a founder present, and with someone who left?
Why ask it
Employees tend to be more candid alone, and former employees will explain the part nobody volunteers. Refusing both requests at offer stage is a decisive answer in its own right.
Ask yourself
How many months could I pay my bills if the company closed without warning?
Why ask it
A startup can go from fine to finished inside a quarter, and what happens to unpaid wages or severance once the money is gone depends on where you are employed. If the honest answer is weeks, a safer offer or more salary in place of equity deserves a serious look.
If the shares never pay out, are the salary and the work enough on their own?
Why ask it
Plenty of grants never pay out, so treat this as the ordinary case and not the gloomy one. A yes means the equity is a bonus. A no means you are being paid partly in hope, and the size of the pay cut needs another look.
Would I buy or recommend this product if I had never met the team?
Why ask it
Belief carries people through the long stretches when a startup is not obviously working. Doubt about the product is hard to hide from customers, from candidates you interview and from yourself, and it grows under pressure.
Do I want to work for these founders in a bad month as well as a good one?
Why ask it
A company this size has no other department to transfer to and no layer of management between you and the top. Think back to a moment in the process when one of them was under mild pressure, and how they behaved.
Am I comfortable with a job description that could change twice in a year?
Why ask it
Some people find shifting scope energising and others find it exhausting, and neither is a flaw. Your last few jobs are better evidence than your hopes, so recall how you felt the last time priorities were rewritten in the middle of a project.
If this job lasts only a year, what will I have to show for it?
Why ask it
Skills, a title, something shipped and people who would hire you again all survive a shutdown. A role where you can name what you would carry out with you is a reasonable bet even at long odds on the company.
Have I talked the risk through with whoever shares my finances?
Why ask it
A pay cut and an uncertain employer land on a household, not only on you. A partner who has seen the numbers and agreed to them is in a very different position from one who learns the details when a payday is missed.
Which answer, or refusal to answer, would make me turn this down?
Why ask it
Decide before the final conversation, while your head is clear. Once an offer feels within reach it is easy to explain away a withheld runway figure or a vague equity answer that you would have called a dealbreaker a week earlier.
Evaluating the offer
Practical guidance for the conversation itself
Who to ask, and when
During the interviews
Customers, competitors, the role and how the founders work together are fair in any round, and asking them shows you understand what you would be signing up for. Leave the cash balance and the cap table until the company has decided it wants you.
Once the offer is in hand
This is when the money and equity questions get full answers, because a company shares more with someone it is trying to close. Put them to a founder or whoever runs finance. A recruiter rarely has the share count or the preference terms, and should not be guessing at them.
With startup employees, on their own
The bad week, who does well, how bad news travels, how often priorities change and what people wish they had known are questions for future colleagues, without a founder in the room. Ask two people the same thing and compare the answers.
By yourself, last
Work through the Ask yourself group before the final call, not after it. Write down the answer that would make you say no, so the decision is made by the version of you who is not yet holding a deadline.
Working out what the equity is worth
- 1Get the share count granted and the fully diluted total, then calculate your percentage yourself.
- 2Ask for the strike price and the most recent valuation, and multiply the strike by your share count to see what exercising would cost you.
- 3Ask what sits ahead of common shares in a sale, including preference multiples and any participation.
- 4Model three outcomes: a sale at the last valuation, a sale at three times that, and a shutdown. Work out all three, including the one nobody at the company will bring up.
- 5Ask how long the exercise window stays open after you leave, because it decides whether the equity is real or theoretical for anyone who does not stay until an exit.
- 6Before exercising anything, take the paperwork to an accountant who knows equity where you live, because the tax treatment differs by country and by type of grant.
Checks worth doing yourself
Look up the funding history
Press coverage, and public company filings where your country has them, will often tell you when the company last raised and roughly how much. A long gap with a growing team is the pattern to ask about directly.
Track the team over time
Public profiles show who joined and who left. Departures clustered in one quarter or one function are worth raising in the interview, politely and specifically.
Talk to a customer if you can
One conversation with someone who pays for the product tells you things a demo cannot: why they bought, what annoys them, and whether they would renew. Ask the company for an introduction, and notice how readily it gives one.
Get everything in the written offer
Share count, fully diluted total, strike price, vesting, exercise window and title. A promise about equity made in conversation can leave with the person who made it.
Traps that catch experienced people
Treating a percentage as fixed
Your percentage normally shrinks each time the company issues new shares to investors. What matters is whether the value of the company grows faster than your slice of it gets smaller.
Accepting a large salary cut on optimism
Work out what you are giving up over four years in cash terms, then ask whether the equity plausibly covers it. Sometimes it does, but it should be a calculation rather than a feeling.
Skipping the reference calls
It is easy to research the market carefully and never speak to anyone who used to work there. Former employees have no reason to sell you the job, which makes that call one of the more useful hours you can spend.