The questions to ask in a startup interview

Ask about money, the role, the team, and the plan behind the last raise. The five questions that tell you the most: how many months of runway do you have at current burn, why is this specific seat open, who would I work with day to day, how many shares are outstanding fully diluted, and what did you tell investors you would build with this round. A startup interview is a two-way diligence meeting. The company is checking whether you can do the work, and you are checking whether the job and the equity are what they look like on the offer letter.

Most candidates spend their question time on culture and tech stack. Those matter, but they are not where the risk lives. The risk lives in burn, in why the seat opened, and in the gap between the equity number and what it is actually worth. This post gives you the questions that surface that risk, plus what a good answer and a worried answer sound like. The roles.cc board sorts roles by how recently the company raised, so you often walk in already knowing the round. Use the interview to fill in everything the round does not tell you.

Why should you treat the interview as your diligence?

At a public company the numbers sit in filings. At a startup the only place to get them is the room you are in. A founder who just closed a round will usually answer direct financial questions, because they answered the same ones from investors a few weeks earlier. A vague or defensive answer is itself a data point. You are not being rude by asking how long the money lasts. You are doing the work any investor did before they wired funds.

Set the tone early. Near the start of a founder conversation, say something like: I am excited about the problem, and I want to ask a few direct questions about the business so I can commit with both feet. Good founders relax when they hear this, because it signals you think like an owner. The questions below are grouped into five areas. You will not get to all of them in one loop, so pick the three or four that matter most for your situation.

What should you ask about runway and burn?

This is the single most important area and the one candidates skip most. Runway is how many months the company can operate before it runs out of cash at the current spending rate. A seed round typically buys 18 to 24 months, a Series A around 24 months, but those are plans, not guarantees. Headcount and a missed revenue target can cut a 24 month plan to 12 fast.

• How many months of runway do you have at current burn? A good answer is specific: "about 22 months, and the next raise targets 18 months out." A worried answer is a deflection: "we do not really think about it that way."
• What is your monthly net burn, and how has it moved this year? You want a number and a direction. Burn climbing faster than revenue, with no raise in sight, is the thing to catch.
• What has to be true to raise the next round? Good founders name a metric: a revenue target, a usage milestone, a specific logo. "We will figure it out" means they have not.
• Have you done any layoffs or pauses in hiring? Not disqualifying, but you want the story behind it, not a surprise after you join.

If you only get one financial question, ask the runway one. A founder who answers it cleanly is telling you the company is run by people who watch the bank account. For the longer version of this math, see how to evaluate a startup job offer.

What should you ask about the role itself?

A title tells you almost nothing at a startup. "Senior engineer" can mean you own a whole product surface or that you are the fourth person on a crowded team. The question that cuts through it is why this specific seat is open. New roles funded by a raise are a different bet than a backfill for someone who just left.

• Why is this role open right now? Best answer: "we closed a round in March and this seat is in the hiring plan we showed investors." Watch for: a backfill where the last person left after a few months, repeatedly.
• What does success look like in the first 90 days, and at one year? A real answer is concrete and shippable. A fuzzy answer means the role is not yet scoped, and you will spend month one defining your own job.
• What is the split between new feature work, maintenance, and on-call? This is where reality differs most from the job post. Ask for rough percentages.
• Who decides what I work on, and how often does that change? You are probing for thrash. Constant reprioritization is the top complaint engineers have post-join.

If the role is a founding or near-founding seat, the scope is wider and vaguer by nature, which is fine as long as everyone admits it. For what that level actually involves, see what a founding engineer actually does.

What should you ask about the team and how it works?

You will spend more hours with your immediate team than with the founder. Ask to meet at least one engineer you would actually work with, and ask them different questions than you ask the founder. Engineers tend to answer honestly when the founder is not in the room.

• Who would I work with day to day, and can I meet one of them? A no here, or a stalled answer, is a flag. Healthy teams are happy to show you the people.
• What does the deploy and review process look like? You learn the engineering maturity fast. "We ship a few times a day, code review on every change" is a different shop than "we deploy when the founder says so."
• What is the most recent thing that broke, and how did the team handle it? You are checking for blame culture versus a calm post-mortem habit.
• Who has left engineering in the last year, and why? Turnover among early engineers is one of the loudest signals there is.

Pair the founder's answers against the engineers' answers. When they line up, that is a good sign. When the founder describes a calm, focused team and the engineers describe whiplash, believe the engineers. More interview probes are in how to research a startup before you interview.

What should you ask about equity?

An equity grant is meaningless until you know the denominator. "10,000 options" tells you nothing without the total share count and a recent valuation. You need three numbers to value a grant: how many shares you get, how many shares exist fully diluted, and the most recent price per share. With those you can do the math yourself.

Worked example (illustrative, not advice). Suppose you are offered 40,000 options, the company has 20,000,000 shares outstanding fully diluted, and the last round priced shares at $2.50. Your stake is 40,000 / 20,000,000, which is 0.2 percent. At the last round price your grant is worth 40,000 times $2.50, which is $100,000 on paper, vesting over 4 years. That paper value only becomes real in an exit, and the strike price and taxes come out of it. Do this math in the room, out loud, and let the founder correct your numbers.

• How many shares are outstanding fully diluted? This is the denominator. A founder who will not share it is a flag. "Fully diluted" matters because it counts the option pool and convertible notes, not just issued stock.
• What was the price per share at the last round? Combined with your grant, this gives a paper value. It is not a promise, but it is a real anchor.
• What is the strike price and the vesting schedule? Standard is a 1 year cliff then monthly over 4 years. Ask about the post-termination exercise window too: 90 days is common and can be expensive.
• Is there a recent 409A valuation? This sets your strike price and tells you the current common-stock value.

If a founder dodges the share count, the honest read is that the grant is smaller than the headline number suggests. Plenty of founders just have not thought about how it lands for a candidate, so give them room, but get the number before you sign. The full breakdown lives in startup equity: seed, Series A, B, what to ask and how stock options and vesting work.

What should you ask about the last round's plan?

When a company raises, the founders pitch investors a specific plan for the money: hire these roles, build this, hit this metric, then raise the next round. That plan is the most useful thing you can learn, because the role you are interviewing for is a line item in it. Ask what they told investors they would do with this round. You learn the priorities, the timeline, and where you fit.

• What did you tell investors you would build with this round? A crisp answer means there is a plan and you are in it. A rambling answer means the strategy is still forming, which raises your risk.
• What are the one or two metrics the board watches most? This tells you what actually drives decisions, which is often not what the job post emphasizes.
• What would make the next raise hard? A founder who can name the real risk is thinking clearly. One who says "nothing, we are crushing it" is either lucky or not level with you.

You can see the round itself before you ever interview. The recent raises page lists who just closed, and the board is sorted by funding recency, so you can walk in already knowing the stage and rough timing. For why that signal is worth so much, see should you join a startup that just raised.

What do good and bad answers sound like?

The pattern across all five areas is the same. Good answers are specific, include a number, and admit a real risk. Worried answers are vague, deflect the number, or claim there is no risk at all. Here is the contrast in one place.

None of this means you should grill a founder like an auditor. Ask plainly, listen for whether the answer has a number in it, and follow up once. The goal is not to catch anyone out. It is to make sure the offer you might accept matches the company you think you are joining. For the negotiation that follows, see how to negotiate a startup offer.