I’ve been thinking about what to ask when someone offers you a job at a startup. The usual questions about salary and benefits matter, but there are deeper ones that tell you whether the place is actually going to survive long enough for you to care about that stock option package.
Here are some questions I’d ask.
How much cash do you have in the bank?
Not how much you’re hoping to raise. Not how much you could borrow if things get tight. Actual cash, right now, in an account.
If the answer is vague, or if it comes with “but we’re close to a round,” take note. Promises don’t pay salaries.
What’s your monthly burn?
Divide the answer to the first question by this one and you get your runway. If they can’t give you a rough number, that’s a problem. If the number depends on hitting revenue targets that haven’t materialised yet, be sceptical.
What was your last valuation?
This tells you what expectations the company is operating under. If there’s barely any revenue or traction and the valuation is over $10 million, the next funding round is going to be awkward. Everyone knows the numbers don’t add up. You’ll be the one picking up the pieces.
What can you do that your competitors can’t?
If the answer is “we’re just better” or “we’re first to market,” walk away. There needs to be something concrete here. A patent. A distribution deal. A technology that’s genuinely harder to replicate than they’re admitting. If the only advantage is price, you’re already losing.
Where are you weak?
This tells you more about the management than about the company. If they can’t name their own weaknesses, or if they dismiss them as “minor,” they’re not being honest with you or themselves. The best answer is something specific and uncomfortable, followed by a plan to fix it.
Who’s invested?
You want to know who’s put real money behind this. Reputable VCs do due diligence. If well-known investors have backed the company, it doesn’t guarantee success, but it means someone with experience looked at the numbers and decided they were worth a shot.
That said, I’ve also seen bootstrapped companies do well. No outside investors means no pressure to hit arbitrary growth targets. It’s a different risk profile, not necessarily a worse one.
Who sits on the board?
Founders and their mates isn’t a board. You want at least one person whose job is to challenge the management, not nod along. Someone with experience who’s been through a funding round before, or a product launch that went wrong, or a hiring crisis. An adult in the room.
Have you shipped anything before?
Not “written code.” Shipped. Delivered to customers. Had to deal with the inevitable bugs and support tickets and angry emails at 2am.
A team that’s never shipped anything will underestimate how much work goes into making something people can actually use. Planning, testing, documentation, deployment, maintenance. The stuff that doesn’t show up in a demo.
How are you going to get customers without a marketing budget?
Most startups don’t have one. The answer shouldn’t be “we’ll figure it out later.” It should be something specific: content marketing, partnerships, a referral programme, building in public. If product-led growth is the plan, the product needs to be genuinely worth talking about.
What keeps you up at night?
If the answer is “nothing,” they’re lying. If it’s “everything,” they’re panicking. Somewhere in between is the truth. Cash flow, hiring, competition, product-market fit. The important thing is that they can name the problems and have a plan, however rough, for dealing with them.
You don’t need to fire all of these at someone in an interview. Pick the ones that matter to you. But if you’re joining a startup, you’re taking a risk. Make sure you understand what that risk actually is before you sign anything.