Questions to Ask a Startup
Questions to ask a startup company before you take a job there, put money in or sign on as a customer, written with the early-stage startup in mind, where little of what you need to know has been published anywhere. The list opens with the basics anyone should check, then works through product and customers, the financial questions, the founders, what working there is like, and equity and exit.
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The questions
Each question, and why to ask it
Start here
What problem does the company solve, and who has it badly enough to pay for a fix?
Why ask it
A startup that can say this in two sentences knows what it is selling. Listen for a particular kind of person or business with a cost they already feel, not a market described by its size. If the founder and the first employee you meet give different answers, the company is still deciding.
How does the company make money today, or is it still pre-revenue?
Why ask it
Pre-revenue is a stage, not a fault, so either answer can be a good one. What matters is whether the first paid sale has a date and a named buyer attached, or sits somewhere after the next funding round. If money is coming in, ask whether it repeats each month or arrives as one-off projects.
How much money has the company raised so far, and who put it in?
Why ask it
The total tells you less than the list of names. A known fund, a handful of friends and the founders' own savings each come with different patience and different strings. Compare what you hear with anything announced publicly, and if no outside money has gone in at all, ask what the company has been living on.
How much runway does the company have: what is the monthly burn, and what is in the bank?
Why ask it
Runway is the cash in the bank divided by what the company spends each month, and asking for the two parts lets you do the sum yourself. A figure quoted in months can quietly assume cuts or sales that have not happened yet. Some founders hold exact numbers back at a first meeting, which is fair, as long as they arrive before you have to decide.
Who started the company, and what in their past makes them the people to build it?
Why ask it
You are looking for a reason this team has an edge: years inside the industry, a product they have built before, customers who already take their calls. A good story about passion is not that. If they are learning the field as they go, ask who they call when they do not know something, and how they found that person.
What is the single biggest risk to the company right now, and what are you doing about it?
Why ask it
Every young company has one thing that could end it, and the conversation gets useful once it is named. A contract up for renewal, a rule still being written or one engineer nobody could replace are all answers you can weigh. The second half matters more: a risk with an owner and a date is being managed, and one that is only being watched is not.
What is the one thing the company has to get right in the next twelve months?
Why ask it
Asking for one thing forces a choice, and a company with limited cash cannot afford five priorities. Tie the answer back to the money: if the goal is missed, does the company slow down, cut, or run out? For anyone taking a job there, it is also what their work will be judged against.
Why should someone join or invest now, rather than waiting a year?
Why ask it
Coming in early usually means a bigger share and more say in a company that is less certain to survive, and waiting a year reverses the trade. Hearing a founder describe both halves shows they know what they are asking you to give up. If the only answer is that the chance will be gone, ask what exactly will be different in twelve months.
Product and customers
Who is the customer, in the sense of who signs the invoice?
Why ask it
Founders often describe a user rather than a buyer, and the gap between the two is where young companies stall. If the person who benefits and the person who pays are different, ask how the payer was convinced last time. A clean answer names a job title and a budget line.
What do your best customers have in common?
Why ask it
A company that knows this can go and find more of them. Good answers are traits you could search for: a size, an industry, a tool they already use, a recent event such as an audit or a new head of department. 'Anyone with a team' means they are still selling to whoever will listen.
How many paying customers do you have now, and how many did you have a year ago?
Why ask it
Settle what counts as a customer before you compare the two numbers. Pilots, free accounts and signed letters of intent often get added in, and none of them is the same as someone who has paid. Growth from two to four is a hundred per cent and tells you very little, so take the counts and work out the percentage yourself.
What do you charge, and how did you arrive at that number?
Why ask it
A price can come from talking to buyers, from a competitor's pricing page or from a guess nobody has gone back to, and the reasoning shows which. Ask when it last changed and what happened to sales afterwards. If it has never been raised or tested, nobody at the company knows yet what the product is worth to the people buying it.
How do customers find you today?
Why ask it
At an early stage the truthful answer is often the founder's own contacts, which is a fine start and a poor plan. The thing to find out is whether one channel already brings in buyers without a founder making the introduction. A list of channels they intend to try next quarter means that has not happened yet.
Can I try the product myself, or watch a real customer account in use?
Why ask it
Ten minutes with the real thing beats a slide deck, and how readily they agree is information too. Go off the rehearsed path while you are in there: search for something odd, open the unfinished corner, ask what happens when it breaks. A product that only works with a founder at the keyboard cannot yet be sold without one.
Who are your main competitors, and which one do you actually lose deals to?
Why ask it
Naming the rival they lose to gets past the usual claim that nobody else does this. The useful answers include something the other product does better. A team that says it never loses is either not selling much or not finding out why deals go quiet.
What stops a bigger company from copying this once it is shown to work?
Why ask it
Being first is not a defence, and neither is a feature. Real answers sound like data nobody else holds, contracts that are hard to leave, a licence, or a cost structure a large rival could not match without hurting its own business. If you are told that big companies are slow, ask which one has already tried.
Does the company own what it is built on: the code, the brand name, any patents?
Why ask it
Work done by a contractor, a co-founder who left or a founder still employed somewhere else can belong to someone other than the company unless it was signed over. A gap like that tends to surface during a funding round or a sale, when it is slowest to fix. Who owns what by default differs between countries, so ask which agreements are in place there.
Who has stopped being a customer, and what did they say when they left?
Why ask it
Lost customers are the part of the story a pitch leaves out, and most founders can recall each one. Sort the reasons into two piles: a budget cut or bad timing can come right, while a product that did not do what the buyer needed is a deeper problem. A company with nobody on the list may simply be too young for a contract to have come up for renewal.
What share of revenue comes from your largest customer?
Why ask it
One large account can end up setting the roadmap, because nobody wants to refuse the customer who pays most of the bills. Ask when that contract comes up for renewal and how much notice either side has to give. If the answer is most of the revenue, you are really weighing up two companies, and one of them is not in the room.
How big is the market, and how did you count it?
Why ask it
The headline figure in a pitch is usually a whole industry's spending. The sum worth hearing starts from the bottom: how many buyers of the kind they already sell to exist, times what those buyers pay now. If that smaller number still supports the company they describe, the large one does not matter.
Which part of the product is currently held together by manual work?
Why ask it
Every early company has some: onboarding done by hand, reports assembled in a spreadsheet, a founder personally reviewing every signup. Naming it openly is a good sign of self-knowledge, and the answer tells you where the next hires and the next outages will come from.
If the product runs on artificial intelligence, is the model your own or one you rent from another company?
Why ask it
Renting a model is a sensible way to start, and it leaves the supplier free to change its price, its terms or the model itself. Ask what the team did the last time that happened and how long a move to another provider would take. The harder follow-up is what the startup adds that the model's maker could not ship as a feature of its own.
What data was the model trained or tuned on, and do you have the right to use it that way?
Why ask it
Customer records, pages collected from the web and licensed datasets each come with different permissions, and the law on training is unsettled and varies by country. A careful team can say where each source came from and which contract covers it. Anyone signing up as a customer should ask separately whether their own data would be used to train anything.
How do you check that the AI's output is right, and what happens when it is wrong?
Why ask it
A demo shows the cases that work. Ask instead about the set of test cases run before each release, how often the output fails on it, and how a customer's bad result finds its way back to the team. Where a mistake could cost money or safety, find out at what point a person reviews the output before anyone acts on it.
What does it cost you in computing each time a customer uses the product?
Why ask it
Most software costs next to nothing to serve one more request, while a product that calls a large model pays for every one. The heaviest users can then be the least profitable, so more usage is not automatically good news. Ask whether the price follows usage, and how last month's bill from the model or cloud provider compared with revenue.
What is on the product roadmap for the next year, and which customer asked for the item at the top?
Why ask it
A roadmap built from what buyers have asked for reads differently from one built from what the founders find interesting, and the second half of the question shows which this is. Ask what was on the plan six months ago and never shipped. If you would be a customer and need a feature that is not built yet, get its date in the contract.
If the company were sold or closed down, what would happen to customers' data and contracts?
Why ask it
This is the buyer's question, and anyone about to depend on a young supplier should ask it before signing. Look for a way to export your data in a format you could use elsewhere, and a clause on how much notice you get if the service ends. What you are owed depends on the contract and on local law, so read that section yourself and do not rely on a spoken assurance.
Financial questions
What was revenue last month, and what was it in the same month a year ago?
Why ask it
A pair of real months is harder to dress up than a growth rate or an annualised figure. Check whether the number is money received, invoices sent or contracts signed, because the three can sit far apart at a young company. Some founders will only give a range before an offer or a term sheet, and a range is enough to see the direction.
Is the company profitable, and if not, what would have to change for it to be?
Why ask it
Plenty of startups lose money on purpose while they grow, so a no is not the worrying answer. The worrying one is a no with no account of what profit would take: how many more customers, at what price, with how many staff. A company that can describe that point, and roughly when it arrives, is choosing to raise money and not only needing to.
What does it cost to acquire a customer, and how long until that cost is repaid?
Why ask it
Payback decides whether growth pays for itself or eats cash: a customer who returns the cost of winning them within a few months helps fund the next one. If nobody has worked it out, ask what was spent on sales and marketing last quarter and how many customers arrived. The rough division is enough, and you see whether they think in these terms at all.
What is left from each sale after the cost of delivering it?
Why ask it
Software sold to many customers keeps most of each sale, while anything with people, hardware or shipping inside it keeps far less. Neither is wrong, but a company valued like the first and built like the second has a problem that growth makes bigger. Ask what is counted in the cost, since support and onboarding staff are often left out.
Where does most of the money go each month?
Why ask it
For many startups the answer is salaries, which makes the burn hard to cut without cutting people. Heavy spending on advertising or cloud bills is a different shape of risk: it can be turned down within weeks, and the growth may go with it. You also learn what the founders think is worth paying for.
What will the money from the current round have paid for by the time it runs out?
Why ask it
Good answers can be checked later: a product in customers' hands, a revenue figure, a licence, a team of a certain size. 'Growth' is not a plan. Where the round closed a while ago, ask how the spending so far compares with what the investors were told it would be.
What has to be true for you to raise the next round, and who told you that?
Why ask it
The source matters as much as the milestone. Targets that came from conversations with actual investors are grounded; targets the founders set themselves may bear no relation to what the market will fund. Whatever the milestone is, it is also what the company will prioritise while you are involved.
What happens if the next round takes six months longer than planned, or never closes?
Why ask it
Rounds slip for reasons that have nothing to do with the company, so a second plan is ordinary prudence. Listen for specifics: which costs go first, whether existing backers would lend against the gap, how far revenue alone would carry things. 'It will close' is a hope, and you asked for the plan.
What was the valuation at the last round, and was it a priced round or a note?
Why ask it
A valuation is what one investor agreed to on one day, with terms attached that the number does not show. Convertible notes and similar instruments put off setting a price, often with a cap, so ask how and when they convert. A very high figure is mixed news for anyone arriving later, because the next round has to clear it.
Does the company owe anything: loans, convertible notes, deferred salaries, unpaid taxes?
Why ask it
Money owed generally has to be dealt with before shareholders see anything in a sale or a closure, and it rarely appears in a pitch. Deferred pay is the item to press on, since it means people have already been asked to wait. Being able to list all of it without looking anything up suggests the books are in order.
Can I see the accounts for the last full year, and who prepared them?
Why ask it
Figures said aloud in a meeting and figures in a set of accounts do not always agree, and the second kind has somebody's name on it. An early company often has only management accounts kept by a bookkeeper, which is normal, so ask how recent they are and whether an outside accountant has looked at them. A job candidate may be told no, but an investor discussing terms should expect a yes.
Is the company in a legal dispute, or expecting one?
Why ask it
A claim from a former employee, a departed co-founder or a rival holding a patent can absorb cash and attention that a small team does not have. It is the kind of fact that comes out when asked for plainly and seldom before. Listen for the worst it could cost and who is paying the lawyers, and if you are investing, ask for the answer in writing with the rest of the paperwork.
Founders
How do the founders divide responsibility, and where do you currently disagree?
Why ask it
Founders falling out can sink a company that has customers and money, and the strain tends to show before it breaks. Two people who can each name the other's territory and describe a live disagreement calmly are in better shape than a pair who say they agree about everything. With a solo founder, ask who is allowed to tell them they are wrong.
How is the equity split between the founders, and is their own stock still vesting?
Why ask it
A split that roughly matches who does the work is one less thing to fight about later. Vesting matters because without it a founder who walks away next year keeps a full share while everyone else carries on. If one founder holds almost everything, find out what the others can decide without asking.
Are all the founders working on this full time, and what are they paying themselves?
Why ask it
A founder with another job has a way out that you would not have. On pay, both extremes deserve a follow-up: nothing at all cannot last, and a large salary at a company with little revenue shows whose comfort comes first. The reassuring answer is a figure they can live on for as long as the plan takes.
What did you believe a year ago that turned out to be wrong?
Why ask it
The point is to see whether evidence changes their minds. The convincing answers cost something: a sales channel abandoned, a type of customer that never bought, a feature built and then removed. Be wary of a mistake that turns out to be a compliment, such as having been too ambitious.
How involved are your investors, and what do they push you on?
Why ask it
Investors who want growth at any cost make for a different company to work in, or buy from, than investors who want it to pay its own way. Ask what the last investor update spent the most words on. 'They are very supportive', with no example, leaves the question unanswered, so follow it with the last thing the two sides disagreed about.
Who sits on the board, and what needs its approval?
Why ask it
At many companies the board has the last word on a sale, a new round and who the chief executive is, though the detail sits in each company's own documents. Count founder seats against investor seats and ask who the independent member is, if there is one. Where no formal board exists yet, ask who the founders answer to in practice.
Have any founders or early employees left, and what happened to their shares?
Why ask it
You learn about turnover and about how the company behaves when things get awkward. Someone pressed to hand back shares they had already earned, or a departure nobody will explain, is a preview of your own exit. What a leaver keeps depends on the agreements they signed, so ask what those say as well as what happened.
What would this company turn down, even if it paid well?
Why ask it
Values on a wall are free, so ask for the version that cost something: a customer refused, a shortcut not taken, data not sold. A real example comes with a date and a sum of money. If nothing has been turned down yet, ask what would be, and remember what they said.
What would make you shut this down, and how would you handle it?
Why ask it
It is easier to get a straight answer about the bad case while nobody is in it. Find out whether they have thought about paying staff what they are owed, giving customers notice and handing back whatever money is left. If it has plainly never crossed their minds, nothing is being hidden, but you now know there is no plan.
Who should I speak to who will tell me something you would not?
Why ask it
The best answers name a customer who left, a former employee or an investor known for saying what they think. Watch the reaction as much as the name. If you are steered only toward friendly references, thank them and find the others yourself, through people you know in common or anyone who lists the company as a past employer.
Working there
Why are you hiring for this role now, and what is not getting done without it?
Why ask it
The second half gets you the real job, which is often narrower and more urgent than the posting. Work a founder has been doing at midnight will be handed over gladly and watched closely. If nothing in particular is going undone, the role may exist because the money arrived.
What would you want me to have finished by the end of my first three months?
Why ask it
'Finished' asks for an output, where 'success' invites adjectives. If the answer leans on things that do not exist yet, such as a budget, a colleague or a working product, say so out loud and see what they offer. No answer at all means you would be writing your own job, which suits some people and sinks others.
How many people work here, and how is the team split between building, selling and everything else?
Why ask it
The split shows what the company believes its problem is. All engineers and nobody selling means the founders are still the sales team, and a large sales floor around a thin product is the opposite bet. Ask which group grows next and you will know where the attention and the budget are going.
Who would I report to, and have they managed people before?
Why ask it
Someone who was the best engineer or the best seller last year may still be working out how to hand work over, and you would be the practice. That can go well when they know it. Ask them directly what they find hardest about managing, and treat a blank look as the answer.
How does the salary compare with what a bigger employer pays for the same job, and what is meant to make up the difference?
Why ask it
A startup that pays under the market usually knows it and can say by roughly how much. The common answer to the second half is equity, so ask for the share count and the terms in the same conversation. Scope, title and flexible hours get offered too, and only you can say what those are worth against your rent.
What benefits come with the job: health cover, a retirement plan, paid time off, parental leave?
Why ask it
Young companies tend to add benefits one at a time as the team asks for them, so a short list is not a warning by itself. What the law requires differs from country to country and the rest is the employer's choice, so ask what is written down today and not what is planned. If there is one you cannot go without, put a price on it and raise it alongside the salary.
What do the hours look like in an ordinary week, and when was the last week that was not ordinary?
Why ask it
Founders tend to treat their own hours as the norm, so put this to someone who joined in the past year. A launch week or an outage that ran long is part of the deal at a small company. What you are checking is whether anyone noticed, said thanks, or gave the time back.
Is the team in an office, remote or a mix, and has that changed since the company started?
Why ask it
A policy at a small company is whatever the founders currently prefer, and it tends to move after a raise or a new senior hire. Ask where the last three people hired are based, which shows the direction better than any statement. If the arrangement matters to you, have it written into the offer.
How much do employees get to see: revenue, cash in the bank, the updates sent to investors?
Why ask it
Some founders walk the whole team through the numbers every month and some share nothing below the leadership. Open books let you judge your own risk as you go. With closed ones, your first warning of trouble may be the meeting where it is announced, so ask what was covered at the most recent all-hands.
How would you describe the culture, and how has it changed as the team has grown?
Why ask it
The first half will get you adjectives, and it is the second half that produces facts. In a small team the culture is mostly how the founders behave, and it shifts with each group of new hires. Ask for one habit they deliberately kept and one they let go, then put the same question to the newest person you meet.
What would I get to do here that a larger company would not let me do for years?
Why ask it
This is the real argument for a startup job, so let them make it with specifics: owning a product line, talking to customers, hiring your own team. Then ask who you would learn from, because wide responsibility with nobody to check your thinking is a slower education than it sounds. Talk of wearing many hats often means the job is whatever is left over.
If money got tight, which teams would be cut first, and where does this role sit?
Why ask it
It sounds blunt, and a founder who has thought about survival will have an answer ready. Roles tied directly to revenue or to keeping the product running tend to be safest, and anything described as an investment in the future tends to go early. It also opens the subject of notice and severance, which depend on the contract and the country, so ask how they work there.
Equity and exit
How many shares are outstanding, and how much has been promised but not yet issued?
Why ask it
A grant of ten thousand options means nothing until you know what it is ten thousand out of, so ask for the fully diluted total. Shares promised to advisers and early staff but not yet issued count too, because they shrink every slice once the paperwork is done. Divide your number by the total and you have the percentage you are really being offered.
If the company were sold, who would be paid first, and at what sale price would ordinary shareholders get nothing?
Why ask it
Investors usually hold preferred shares that are paid back before anyone else, so a company can sell for a large sum while staff and small holders receive little or nothing. The price at which ordinary shares start to be worth something sums up the whole arrangement in one number. These terms are set round by round in the company's own documents, so ask which rounds carry a preference and how large each one is.
What is the vesting schedule, and does anything speed it up if the company is sold?
Why ask it
Schedules differ between companies and countries, so ask for this one in writing: the length, any waiting period before the first shares are yours, and what a sale does to the rest. Some agreements vest the remainder early if you are let go after an acquisition, and many do not. People who joined a year before a sale care about that clause more than any other.
What would it cost me to exercise my options, and how long would I have after leaving?
Why ask it
Multiply the option count by the strike price and you have the cheque you would need to write, before any tax. Then ask about the deadline, because a short one can force that decision in the months after you leave. Tax treatment depends on the scheme and on where you live, so ask who advises employees on it and plan on an hour with an adviser of your own.
What kind of exit are you aiming for, and when do you realistically expect one?
Why ask it
Venture funds generally have to return money to their own backers within the life of the fund, which puts a clock on the company whether the founders mention it or not. Ask who the likely buyers are and whether any has shown interest. If the plan is to stay private and profitable, ask how shareholders would ever be paid: dividends, buybacks, or not at all.
Has anyone ever offered to buy the company, and what did you do?
Why ask it
An offer turned down tells you the price the founders think is too low, which is the nearest thing to a floor you will hear. It also shows who had a say: the founders alone, the board, or one investor with a veto. Many founders cannot share details, and 'yes, and we said no' is still worth knowing.
What are the terms of this round: the instrument, the valuation or cap, and the rights attached?
Why ask it
This one is for anyone putting money in. Ask for the term sheet itself and read what sits beside the price: the liquidation preference, any right to invest in later rounds, and what you are entitled to be told. Terms vary widely and local law shapes them, so have a lawyer who does this work read them before you sign.
Who else is investing in this round, and how much of it is already committed?
Why ask it
When a lead investor has set the price, someone with experience has negotiated from your side of the table. A round made up of small cheques on terms the company wrote itself has had no such test, and you would be relying on your own reading. Ask how much has to be raised for the round to close at all, and what happens to your money if it falls short.
How much of the company would my money buy, and what happens to that share in later rounds?
Why ask it
Your starting percentage is the amount you put in over the valuation once the round has closed. Every later raise issues new shares and shrinks it, unless you hold a right to buy in again and have the cash to use it. A smaller slice of a more valuable company can still be a good result, so ask the founders to walk you through one worked example.
What is the smallest amount you will take, and would I hold the shares in my own name or through a pooled vehicle?
Why ask it
Small investors are often gathered into a single entity or a crowdfunding nominee so that the company deals with one shareholder. That can be perfectly reasonable, and it changes who votes, who receives the updates and what fees come off the top. Rules on who may buy shares in a private company also differ by country, so ask how it works where you live.
What would I be sent as an investor after the round closes, and how often?
Why ask it
Small shareholders often have no automatic right to see the numbers, depending on the company's documents and where it is registered. A founder who already writes a monthly update can simply add you to it, and one who has to think about the question has not been reporting to anyone. Ask to read the last update as a sample.
Besides the money, what do you want from the people who invest?
Why ask it
Some founders are after introductions to customers, some want help with hiring, and some want a cheque and silence. Finding out which one you are dealing with spares both sides a mismatch that otherwise shows up at the first request for a favour. The answer also hints at whether they chose their investors or took whoever said yes.
Doing your own diligence
Practical guidance for the conversation itself
Verify outside the room
- Talk to a customer and a former employee. Between them you learn whether the product does what the deck says and whether the company behaves the way the founders describe.
- Check the public record: filings, funding announcements, job postings, and how long roles have stayed open. Slow hiring after a raise, or a sales role open for nine months, are facts worth asking about.
- Ask for the same number twice at different points and see whether it holds. Revenue, headcount and burn are the three worth repeating, because each has a flattering version and a plain one.
- Get anything about equity in writing and read the actual agreement, not the summary. Vesting, cliff, exercise window after leaving and the strike price all change what the grant is worth to you.
- Put the same question to more than one person. A founder, a recent hire and an investor each answer the runway question or the priority question from where they sit, and the differences between them are the finding.
Reading the answers
Choose by what you are risking
A candidate risks a salary and a few years, an investor risks money, and a customer risks depending on a supplier that may not last. Begin with the opening group whichever you are, then spend most of the conversation on the part that matches your risk: working life and equity for a job, money and founders for an investment, customers and cash in the bank before you sign a contract.
Ask for the number, then the source
Any figure a founder gives you came from somewhere: a dashboard, an accountant, an estimate. Asking where it comes from is not aggressive and it separates measured businesses from remembered ones.
Prefer questions about the past
Projections are free. What happened last quarter is not. Convert any forward-looking question into a backward-looking one whenever an answer starts to feel unfalsifiable.
Watch how they handle not knowing
The best answer to a question they cannot answer is that they do not know and will find out. Founders who improvise a number instead will improvise other things, including things you are relying on.
Separate the market story from this company
Much of a pitch is about how large the opportunity is, which is often true and tells you nothing about whether this particular team will capture any of it. Judge the two separately.
For artificial intelligence startups
The product group has a run of questions for a company whose product depends on a model: whose model it is, what it learned from, how its output is checked and what each use costs. A demo of a rented model can look the same as a product with something of its own underneath, and those four answers tell the two apart. Skip them where the software would work just as well with the AI taken out.
Common pitfalls
Valuing equity as though it were cash
Early-stage equity often ends up worth nothing, and even a good outcome can take years and be reordered by whoever is paid first in a sale. Decide whether the salary alone is acceptable, then treat the rest as a bet you can afford to lose.
Ignoring how the founders behave with each other
Interruptions, corrections, one person answering every question: these cost nothing to observe. Ask a question that needs both of them to answer and watch what happens.
Mistaking momentum for traction
Press coverage, awards, a busy office and a large round are not customers paying repeatedly. Ask what changed for customers last quarter, not what changed in the company's profile.
Stopping when the answers get uncomfortable
The point where a founder becomes vague is often where the information is. Ask once more, politely, and note what happens instead of smoothing past it to keep the meeting pleasant.
Before you commit
Write down the two facts that would change your mind
Name them before the next conversation: a runway figure, a concentration ratio, a churn reason. Deciding in advance is how you avoid rationalising once an offer and a deadline are in front of you.
Model the middling outcome, not the good one
Work out what your position is worth if the company sells for a modest multiple of the money raised, and what happens if the next round is priced lower than the last. The pitch describes the best case, and most of the ways this can go sit below it.
Agree what happens if the plan slips
Ask directly what changes for you if the next round is late: role, scope, salary, timeline. Getting that answer while everyone is optimistic is much easier than negotiating it during a cash crunch.
When you are investing in a startup
The opening group, the financial questions and the last part of equity and exit are what to ask a company before investing in it. Take the answers that matter from the documents as well as the conversation: the term sheet, the accounts, the list of shareholders as it will stand after the round. Shares in a private company can be hard or impossible to sell for years, so put in only what you could leave there, and take advice from someone qualified where you live before you sign.