Questions You Should Ask When Interviewing at a Startup

Many software engineers dream of joining a startup—the fast-paced environment, the potential for huge growth, and the chance to make a real impact. But here's the reality check: startups are risky business. With the rise of AI in recent years, we've seen plenty of companies that looked promising on the surface but crashed and burned, even after raising millions of dollars.

So how do you identify the right one to join? PostHog CEO James Hawkins wrote an insightful article called Job interview questions engineers should ask (but don't), sharing his perspective as a startup founder on the questions candidates should ask but rarely do.

These questions are perfect for that moment at the end of an interview when the interviewer asks, "Do you have any questions for us?" If you're considering a startup job, you absolutely need to ask these questions.

Has the Company Found Product-Market Fit?

First up: figuring out if the company has achieved product-market fit (PMF). But don't just ask this directly—you need to dig deeper to get real answers.

Product-market fit basically means the company has built something people actually want and use. Here are the key signs to look for:

• User growth: Are people actually signing up and using the product?
• Active usage: Do people who sign up actually stick around and use it regularly?
• Retention: Are users coming back, or do they try it once and never return?

Instead of asking "Have you achieved product-market fit?" (which will probably get you a vague answer), ask specific questions about these metrics.

For early-stage startups that might not have PMF yet, Hawkins recommends asking:

• "What problem are you trying to solve?"
• "What needs to happen for you to achieve product-market fit?"
• "How will you know when you've achieved it?"
• "Who is your ideal customer?"

If the founders can't give you clear, specific answers to these questions, that's a red flag. It means they're building something without really understanding who wants it or why.

For more mature startups, try these questions:

• "Have you ever doubted your product-market fit?"
• "When did you achieve product-market fit? How did you know?"
• "How do you define an active user?"
• "What's your growth rate?"

If the founders dodge these questions or give vague answers, they probably haven't found PMF yet. And if they haven't found it but don't have a clear plan to get there, that's an even bigger warning sign.

Is the Company Going to Survive?

The second big question is whether the company will still exist in a year or two. Hawkins recommends using Paul Graham's concept of "default alive"—basically, can the company reach profitability before running out of money, given their current spending and growth rates?

Ask these questions to get a real sense of the company's financial health:

• "How long will your current funding last?"
• "What assumptions are you making about your burn rate?"
• "What are your fundraising plans?"

You want to avoid companies that don't know if they're default alive, or worse, companies that know they're not default alive but don't have a realistic plan to fix it. Think of it like this: if a company is burning through cash faster than they're growing revenue, and they can't change either of those things, they're in serious trouble.

How Can I Actually Make a Difference?

Many candidates ask, "What would I be working on?" But this question makes you sound passive, like you're waiting for someone to tell you what to do. Startups don't want that—they want people who can spot problems and solve them independently.

Instead, ask questions that show you're thinking about impact:

• "What's the hardest problem you're trying to solve right now?"
• "What important problems are you choosing to ignore for now?"
• "What do your users complain about most?"

Good founders should be talking to users constantly (and so should good engineers, by the way!). If a founder can't immediately tell you what users want or what frustrates them most, that's a red flag. It means they're building in a bubble without really understanding their customers.

Don't Be Afraid to Ask the Hard Questions

These questions might feel uncomfortable or too direct, but here's the thing: if asking these questions offends the company or gets a defensive response, that tells you everything you need to know about the work environment. Good founders welcome these questions because they show you're thinking seriously about the business.

Remember, interviews go both ways. You're not just trying to impress them—you're also evaluating whether this is a place where you want to spend the next few years of your career. Asking tough questions shows you're smart and thorough, not rude.

The startup world is full of opportunities, but it's also full of companies that won't make it. By asking the right questions, you can increase your chances of joining one of the winners. And if you're thinking about your career in tech more broadly, there are tons of resources out there to help you prepare for every aspect of the job search process.

Don't just take any startup job—take the right one.

Support ExplainThis

If you found this content valuable, please consider supporting our work with a one-time donation of whatever amount feels right to you through this Buy Me a Coffee page.

Creating in-depth technical content takes significant time. Your support helps us continue producing high-quality educational content accessible to everyone.