The Developer’s Guide to Startup Interviews: Questions That Actually Matter

After years of interviewing at startups and watching talented developers join companies that eventually collapsed, I’ve learned something crucial: the questions you ask during interviews matter more than the answers you give to their technical challenges.

Most developers focus entirely on showcasing their coding skills while completely ignoring whether the company they’re joining will even exist in six months. I’ve seen brilliant engineers waste years at startups that were doomed from day one—not because of technical failures, but because they never asked the right business questions.

Here’s what I wish I had known earlier: the best technical skills in the world won’t save you if the company runs out of money or never finds customers who actually want their product.

The Product-Market Fit Reality Check

This is the make-or-break question that most developers never ask: Does this company actually have product-market fit?

I can’t stress this enough—without product-market fit, even the most exciting technical challenges become meaningless when the company shuts down. Yet I’ve watched countless developers get seduced by cool tech stacks while ignoring this fundamental question.

Here’s how I approach it now. For early-stage startups (under a year old), I ask:

• “What specific problem are you solving, and how do you know people actually have this problem?”
• “What needs to happen for you to achieve product-market fit?”
• “How will you measure success along the way?”
• “Can you describe your ideal customer in detail?”

For more mature startups (2+ years), I dig deeper:

• “When did you know you had product-market fit? What were the signals?”
• “What’s your current growth rate?”
• “How do you define an ‘activated’ user?”
• “Do you ever question whether you still have product-market fit?”

The red flags I watch for are founders who can’t articulate their customer, talk more about their solution than the problem they’re solving, or get evasive when discussing growth numbers. These are warning signs that you might be joining a company that’s building something nobody wants.

I learned this the hard way at my second startup job. The founders had convinced themselves they had product-market fit because they had paying customers, but their retention was terrible and growth had stalled. Six months later, we ran out of funding.

The Money Question: Will This Company Survive?

The most uncomfortable question I now always ask is: “Are you default alive?”

This term, coined by Paul Graham, means the company will become profitable before running out of money at their current burn rate. It’s a simple concept that cuts through all the startup BS about “hockey stick growth” and “changing the world.”

I follow up with:

• “What’s your current runway?”
• “What assumptions are you making in that calculation?”
• “What’s your fundraising timeline?”

Any founder who can’t answer these questions clearly either doesn’t understand their own business or isn’t being honest with you. Both are bad signs.

The fundraising environment matters too. Right now, AI startups can raise money more easily than others. If you’re interviewing at a capital-intensive startup that isn’t AI-related, they better have exceptional growth and revenue to justify their existence.

I avoid companies that don’t know if they’re default alive, don’t care about it, or are banking on unrealistic revenue projections to survive. The last startup I nearly joined was predicting 10x revenue growth in six months with no clear plan for how to achieve it. I walked away, and they folded eight months later.

Finding Your Impact: Beyond “What Will I Work On?”

Most developers ask terrible questions about their potential role. “What will I be working on?” signals that you need hand-holding. Startups need problem-solvers, not task-followers.

Instead, I ask:

• “What keeps you up at night as a founder?”
• “What’s the hardest technical problem you’re facing right now?”
• “What problem are you currently ignoring that you know you’ll need to solve eventually?”
• “What’s the biggest complaint your users have about the product?”

These questions serve two purposes: they help you understand where you can add the most value, and they demonstrate that you think like an owner, not just an employee.

Good founders should be able to instantly rattle off user pain points and technical challenges. If they can’t, it’s a sign they’re not talking to users enough—a classic startup death spiral.

Evaluating the Technical Team

As a developer, you need to understand if you’ll be working with people who will make you better or hold you back. I ask:

• “How did you find your first few technical hires?”
• “What qualities do you look for when hiring engineers?”
• “How do you compensate and retain strong technical talent?”
• “Do you share company metrics and board updates with the engineering team?”

Red flags include founders who immediately name-drop FAANG companies their team came from rather than discussing the qualities they value. A team full of ex-Google engineers doesn’t guarantee success—it often means they’ve hired expensive talent without considering culture fit or startup mentality.

I also watch for signs that engineering is viewed as a cost center rather than a strategic advantage. Startups that treat developers as code monkeys rarely succeed.

Understanding the Culture You’re Joining

“What’s the culture like?” is a useless question that gets you marketing-speak answers. Instead, I ask:

• “What are your company values, and can you give me specific examples of how you’ve lived them?”
• “Who decides what features to build and why?”
• “What does a typical workday look like for engineers?”
• “What behaviors would cause someone in this role to fail?”

I’m looking for intentionality and specificity. Startups with vague answers about culture usually don’t have one—they’re just winging it.

Watch out for companies where founders micromanage everything, where there are excessive meetings for a small team, or where it’s obvious no one has thought about what kind of company they want to build.

Culture is a startup’s biggest competitive advantage. Big companies can outpay you and offer better benefits, but they can’t move as fast or give you the same level of ownership. A startup that doesn’t leverage this advantage is missing the point.

The Long-Term Vision Test

Finally, I always ask about the founders’ motivations and long-term plans:

• “Why did you start this company?”
• “What are you most proud of so far?”
• “Do you plan to sell the company?”
• “What’s your strategy, and why?”

Founders planning a quick exit will make short-term decisions that might conflict with your career goals. There’s nothing wrong with this approach, but you should know what you’re signing up for.

I also look for simple, clear strategy statements. If founders can’t explain their strategy in one sentence, the company will likely become a confused mess of features that don’t connect.

One question I’ve started asking after seeing too many startup founding teams implode: “How do you and your co-founders handle disagreements?” Founder breakups kill more startups than technical failures.

The Bottom Line

These questions might seem aggressive or overly business-focused for a developer interview. But here’s the reality: if the company fails, none of your technical contributions matter. Your GitHub commits won’t pay rent when the startup shuts down.

A company that reacts badly to these questions probably isn’t a place you want to work anyway. Good founders appreciate candidates who think strategically about the business, not just the code.

Remember, you’re not just interviewing for a job—you’re betting months or years of your career on these founders and their vision. Make sure it’s a bet worth taking.

The best career moves I’ve made were joining startups where I asked hard questions and got honest, thoughtful answers. The worst were where I got distracted by cool technology and forgot to evaluate the fundamentals.

Don’t make my mistakes. Ask the hard questions. Your future self will thank you.