The best questions to ask at a startup interview cover five things a big-company interview rarely needs to: how long the cash lasts (runway), how the company is funded and growing, what your equity actually is (share count, strike price, vesting and exercise window), what the role will involve week to week, and how the founders make decisions. Ask the business and role questions during interviews, save the detailed equity questions for after you have an offer, and pay as much attention to how openly they answer as to the answers themselves.
Startups are understandably careful with financial details, so you will not always get exact numbers. But a company asking you to take part of your pay in equity should be able to explain what that equity is. For the general questions that work at any company, see our guide to questions to ask the interviewer.
When to ask which questions
Match the question to the person and the stage:
| Stage | Who you are talking to | What to ask |
|---|---|---|
| First call | Recruiter, talent lead, sometimes a founder | Process and timeline, salary range, funding stage, team size, why the role is open |
| Technical and team rounds | Engineers, engineering lead | Day-to-day work, stack and tech debt, on-call, how decisions get made, the first 90 days |
| Founder conversation | CEO, CTO, cofounders | Strategy, runway, next raise, biggest risk, how the founders split decisions |
| After the offer, before you sign | Recruiter, founder, sometimes finance | Fully diluted share count, strike price and 409A, vesting, exercise window, preference stack |
Wellfound's startup guide says its equity questions should wait until you have an offer, and Underdog's says to ask about the full offer after you receive it but before you accept. At that point you have the most leverage, and the company has a concrete reason to share specifics with you.
Runway and funding questions
Runway is how many months the company can keep operating on the cash it has now: cash in the bank divided by monthly net burn (spending minus revenue). As a worked example, $6 million in the bank and a net burn of $300,000 a month is 20 months of runway.
- “Roughly how many months of runway do you have at the current burn, and does that include the hiring plan?” Holloway's guide to equity compensation points out that runway estimates are usually based on current burn and may not include future salaries — including yours.
- “When did you last raise, how much, and who led the round?”
- “Is the plan to raise again, or to reach profitability first? What's the timeline?”
- “If the next round took six months longer than planned, what would you cut first?” This shows whether the founders have thought about the downside.
- “If you didn't raise again, would current growth get you to profitability before the cash runs out?” This is Paul Graham's “default alive” test: with expenses held flat and revenue growing at its recent rate, does the company become profitable on the money it has left?
- “Have there been layoffs or restructuring in the past year?”
There is no universal cutoff for “enough” runway. Underdog's guide offers “we have 24 months of runway” as an example of a confident answer and describes six months at a Series A company as a situation where your job depends on the next round closing. Judge runway against the plan: twelve months is fine if profitability is close, and worrying if the next raise depends on milestones not yet hit.
Revenue and traction questions
- “Who pays you today, and roughly how many paying customers do you have?” If the company is pre-revenue, ask about pilots, active users or design partners instead.
- “Which growth metric does the leadership team watch most closely, and how has it trended this year?”
- “Do you think you have product-market fit? How would you know?” A clear answer about who needs the product and why is what you want. Vague enthusiasm is not.
- “What milestone does the next round depend on?”
- “What is the biggest risk to the business right now?” Naming a specific risk and a plan for it is a good sign; “there isn't one” is not.
Equity questions to ask once you have an offer
“20,000 options” means nothing on its own. You need the denominator and the terms. Holloway's equity guide covers these in depth; this is the checklist:
| Question | Why it matters |
|---|---|
| How many shares are outstanding on a fully diluted basis? | It turns your grant into a percentage: 20,000 options out of 20,000,000 fully diluted shares is 0.1%. If they quote a percentage, ask which share count it uses. |
| Are there convertible notes or SAFEs outstanding? | They convert into shares later and dilute everyone, you included. |
| What is the strike price, and when was the last 409A valuation? | The strike price is what you pay per share to exercise. It is normally set at or above the fair market value of common stock, which a 409A valuation estimates for a private company. |
| What did investors pay per preferred share in the last round? | It tells you the paper valuation. Common stock is usually valued below preferred, so expect the two prices to differ. |
| Are these ISOs or NSOs? | The two are taxed differently. Exercising ISOs can create an alternative minimum tax bill even if you sell nothing. |
| What is the vesting schedule, and is there a cliff? | Four-year vesting with a one-year cliff is common: leave before your first anniversary and nothing has vested. |
| How long do I have to exercise after I leave? | This is the post-termination exercise window. Ninety days has long been the market default, though some companies, Quora and Pinterest among the often-cited examples, have extended it. |
| Can I exercise early? | Early exercise lets you buy shares before they vest. If you do, the deadline to file an 83(b) election with the IRS is 30 days after the exercise. |
| Does vesting accelerate if the company is acquired? | Without it, unvested shares depend on the deal terms. |
| What is the total liquidation preference ahead of common? | Preferred investors are typically paid back before common holders in a sale. The bigger that stack, the higher the exit price needed before your shares are worth anything. |
| Do you give refresh grants, and can the company repurchase vested shares? | Refreshes matter past year four. A repurchase right changes what you actually own. |
The exercise window deserves extra attention. Under US tax law, an incentive stock option generally keeps its ISO status only if exercised within three months after your employment ends, so options exercised later under an extended window are usually treated as NSOs. Leave with a large vested grant and a 90-day window, and you may need to find the exercise cost plus any tax quickly or lose the options.
This is a checklist, not tax advice. Exercise costs and taxes depend on your situation. Talk to a tax professional before you exercise, especially with ISOs.
Once you have the numbers, our software engineer salary negotiation guide covers how to weigh cash against equity, and new grads should read how to negotiate a new grad offer.
Role scope questions
At a startup, the job description is a starting point. These questions tell you what the job actually is:
- “What would you need me to have shipped in my first 90 days, and by the end of my first year?”
- “When people here say they wear many hats, what does that mean for this role? What non-engineering work would land on my plate?”
- “How does on-call work, and who handles production issues at night?”
- “How are titles and levels decided, and what happens to my role when you hire people more senior than me?” This matters most for early hires.
- “What would you rebuild in the codebase if you had a free month?” The answer shows the real state of the tech debt.
- “Is this a new role or a backfill? If a backfill, why did the last person leave?”
If you would be the first engineer and expected to lead engineering, you are taking on some of a cofounder's risk. It is fair to ask how the equity reflects that.
Founder and team dynamics
At a small company the founders shape almost everything about your day.
- “How do you split decisions between the founders? Who has the final call on product and on engineering?”
- “What did the two of you most recently disagree about, and how did you settle it?”
- “Has the founding or leadership team changed since the company started?”
- “How involved are your investors in day-to-day decisions?”
- “What kind of people, who are otherwise successful, don't work out here?” This one is from Wellfound's startup question list; the answer shows what the culture really rewards.
The most useful technique is consistency checking. Ask each founder the same question separately, such as “Where will the company be in 18 months?”, and compare. Hearing two different visions is a warning. Then ask engineers on the team how decisions really get made; founders rarely describe their own tensions, but the team usually knows.
How to ask without sounding adversarial
Money questions feel awkward because they sound like doubt. Frame them as commitment: you want to understand the company because you are thinking about staying for years.
- Runway: “I'm looking for somewhere I can stay for a long time, so I'd like to understand the runway. Roughly how many months do you have at the current burn, and what's the plan for the next raise?”
- Equity: “To compare offers fairly I need to understand the grant as a percentage. Could you share the fully diluted share count and the current 409A price?”
- Founders: “What's something you and your cofounder disagreed about recently, and how did you resolve it?”
- When they hesitate: “I understand if you can't share exact numbers. Could you give me a range, or tell me whether it's more or less than 18 months?”
Ask the equity questions in writing after the offer when you can, so the answers are on record. And say the founder and runway questions out loud a few times before the call; they feel blunt the first time and normal by the third. A free AI mock interview in CoPilot Interview is one way to rehearse the rest of the conversation: paste the job description and your résumé, answer out loud, and get each answer scored.
Red flags in the answers
One weak answer is not a dealbreaker. A pattern is. Watch for these:
| What you hear | Why it matters | Follow-up |
|---|---|---|
| “We don't share that” about runway, after an offer | You are being asked to take risk without information. Underdog's guide calls that answer a red flag at an early-stage company. | Ask for a range. |
| Short runway and no specific funding plan | Your job may depend on a round that is not lined up. | “What happens if the round slips six months?” |
| No fully diluted share count, ever | You cannot value the grant. | “Can you share the percentage instead?” |
| Nobody can tell you the exercise window | You may face a large bill within 90 days of leaving. | Ask to see the equity plan document. |
| Founders describe different visions | Misaligned founders produce shifting priorities. | Ask engineers how decisions actually get made. |
| The role has been open for many months, or keeps being backfilled | Could be a hiring problem or a role nobody wants. | “What happened with the previous people in this role?” |
| Pressure to sign within a day or two, before you have seen equity terms | You cannot evaluate an offer you cannot see. | Ask for the full offer in writing and a reasonable deadline. |
Context matters: a seed-stage company may have little or no revenue, and that is normal. What you are really testing is candor, because how founders talk about the hard parts now is how they will talk to you once you work there.
Practice your answers before the startup loop
Paste the job description and your résumé into a free AI mock interview: an AI interviewer asks questions built from your résumé, scores each spoken answer, and finishes with a report of likely next-round questions. The free plan includes 15 minutes a day with no credit card.
Try a free AI mock interviewFAQ
When should you ask about equity in a startup interview?
Save detailed equity questions for after you receive an offer, when you have the most leverage and the company has a reason to share specifics. It's fine to ask the recruiter early about the salary range and whether equity is part of the package.
Is it rude to ask a startup about its runway?
No. You are being asked to take on risk, so it is reasonable to ask how long the company can operate on its current cash. Frame it around wanting to stay long term, and accept a range if they won't share an exact number.
How much runway should a startup have?
There is no universal cutoff. One startup jobs guide cites 24 months as an example of a confident answer and treats six months at a Series A company as risky, but what matters most is runway relative to the plan to raise again or reach profitability.
What is a post-termination exercise window?
It is how long you have to buy your vested options after you leave the company. Ninety days has long been the common default, and under US tax rules, incentive stock options exercised more than three months after employment ends generally lose their ISO tax treatment.
How do I work out what percentage of the company my options represent?
Divide the number of options in your grant by the company's fully diluted share count. For example, 20,000 options out of 20,000,000 fully diluted shares is 0.1%.
What should I ask startup founders in an interview?
Ask how they split decisions, how they resolved a recent disagreement, what the biggest risk to the business is and where they expect the company to be in 18 months. Ask each founder separately and compare the answers.