50+ Startup Interview Questions to Ask Founders (Equity & Red Flags)

Most candidates think the interview ends when the hiring manager asks, "Do you have any questions for us?"

They are wrong. That is when the real interview begins.

Asking thoughtful, strategic questions is the single best way to differentiate yourself from the thirty other people applying for the same role. You've nailed your STAR method answers, but answering is only half the battle. Knowing good questions to ask at the end of an interview differentiates you from candidates who just want a paycheck; it shows you are evaluating them just as much as they are evaluating you.

Here is the ultimate list of startup interview questions to ask founders and hiring managers, designed to reveal the financial truth and the cultural red flags. (Also check our Google interview guide for Big Tech-specific questions.)

Top 10 Unique Startup Interview Questions (Founder Vibe Check)

If you want to stand out, you can’t ask the same generic questions as everyone else. These "power questions" are designed to demonstrate critical thinking, confidence, and a results-oriented mindset.

1. "What separates a good performer from a great one in this role, and how does that translate to equity refreshers?"
   • Why it works: It links performance directly to ownership. In a startup, cash is tight; equity is the currency. (Especially critical for Machine Learning Engineer and Backend Engineer roles where impact is measurable).
2. "What is the one thing you wish you knew before you started this company?"
   • Why it works: It invites the interviewer to be vulnerable and honest, building an immediate personal connection.
3. "How does the team handle failure or missed deadlines?"
   • Why it works: Everyone is happy when things go right. You need to know if the culture turns toxic when things go wrong.
4. "If I were to start tomorrow, what would be my top priority for the first 30 days?"
   • Why it works: It visualizes you in the role immediately and shows you are eager to hit the ground running.
5. "What is the biggest challenge the team is currently facing that I could help solve immediately?"
   • Why it works: It positions you as a "solver" rather than just an employee. It shifts the focus to value creation.
6. "Is this a new position, or did the previous person leave? If they left, why?"
   • Why it works: This is a crucial due diligence question. If the last three people in this role quit within six months, you need to know.
7. "How has the company’s goals changed over the last year, and what drove those changes?"
   • Why it works: It shows you are thinking about the macro-business strategy, not just your daily tasks.
8. "What’s a project you’re currently working on that you’re excited about?"
   • Why it works: People love talking about themselves. This ends the interview on a high, positive note.
9. "How do you measure success for this position, and how often is it reviewed?"
   • Why it works: It clarifies expectations upfront so there are no surprises during your performance review.
10. "Is there anything in my background that gives you hesitation about hiring me?"
    • Why it works: This is a bold closing move. It gives you one last chance to address any doubts they might have before they make a decision.

Financial Intelligence: The "Due Diligence" Questions

Keywords: 409a valuation, burn rate, runway, preferred stock

This is where you separate yourself from the juniors. Most candidates just ask "What is the salary?" You need to ask like an investor.

• "What is your current runway in months, and does that assume zero revenue growth?" (If they have less than 12 months, worry).
• "What was the 409a valuation at the last audit, and what is the strike price for the options?" (This determines if your stock is actually worth anything).
• "Is there a double-trigger acceleration clause for my unvested stock in case of acquisition?" (Crucial for protection).
• "What is the current burn rate vs. gross revenue?"
• "Do investors hold participating preferred stock or generic preferred?" (Advanced: Participating preferred gets paid twice, screwing employees. If they get nervous answering this, run).
• "When was the last time the cap table was restructured?"

Questions to Ask About the Role & Responsibilities

You need to know exactly what you are signing up for. When considering questions to ask interviewer about the job, focusing on daily realities is key. Use these questions to uncover the truth:

• What does a typical day look like in this role?
• What are the most immediate projects or deadlines I would be jumping into?
• How does this role contribute to the larger company goals?
• What software, tools, or tech stack does the team use daily? (e.g., Kubernetes, AWS, Terraform for DevOps roles)
• What is the budget I would be working with?
• Will I be working independently or as part of a large team?
• How much travel is expected for this position?
• What are the core hours, and is there flexibility in the schedule?
• Who are the key stakeholders I would be working with outside of this immediate team?
• What is the steepest learning curve for someone coming into this position?

Questions to Ask the Hiring Manager (About Team & Management)

In a startup, your manager is often the Founder or a founding engineer. Relationships are everything.

• How would you describe your management style?
• How big is the team, and what are their backgrounds?
• How often does the team meet for stand-ups or status updates?
• How is feedback given to the team? (Is it formal reviews or real-time feedback?)
• What is the average tenure of someone on this team?
• Is the team currently working fully remote, hybrid, or on-site?
• Who will I report to directly?
• Does the team mentor junior members, or is it a "sink or swim" environment? (Vital for Data Engineer and ML roles requiring deep technical context)

Toxic Workplace Detector: Red Flag Questions

Keywords: toxic culture, psychological safety, founder conflict

Use these questions to detect if the ship is sinking or if the culture is dangerous.

• "When was the last time a key leader left, and why?" (This is the ultimate toxic red flag detector. If they squirm, take note).
• "How do you handle disagreements between co-founders?" (Vital for startups. If they say "we never disagree," they are lying).
• "What is the turnover rate for this specific team vs. the company average?"
• "Has the company undergone any layoffs or RIFs in the last 12 months?"

Questions to Ask About Company Culture & Growth

"Culture" is a buzzword. You need to dig deeper to see if the company actually values its employees.

• What professional development opportunities are available?
• Does the company offer tuition reimbursement or certification support?
• How is work-life balance encouraged here?
• What causes people to stay at this company for the long term?
• How does the company approach diversity and inclusion?
• What is the company's policy on internal transfers or promotions?
• Where do you see the company headed in the next 5 years?
• What values are most important to the company leadership?
• How transparent is leadership about company financials and health?
• Has the company undergone any layoffs or big restructuring recently?

Red Flags: Questions NOT to Ask

While there are no "stupid" questions, there are definitely questions that will make you look unprepared or lazy. Avoid these at all costs:

• "What does your company do?" (You should have Googled this before you walked in.)
• "How soon can I take a vacation?" (Focus on the work first.)
• "Did I get the job?" (It puts them on the spot and is awkward.)
• "Can I work another job while working here?" (Just don’t.)
• "How long does it take to get promoted?" (Focus on excelling in the current role first.)

Conclusion: Be Strategic, Not Annoying

You don't need to ask all 50 questions. In fact, please don't.

Pick 3–5 questions that genuinely matter to you. Choose one Unique question to show your strategy, one Role question to clarify the work, and one Culture question to check for red flags.

Remember: The interview is a two-way street. You are interviewing them just as much as they are interviewing you. And once you get the offer, make sure you use our Salary Negotiation Scripts to get what you deserve.