25 Questions to Ask a Startup Founder
So you’ve been approached to join a startup or invest in one. How do you know if it’s the right move for you?
Asking the startup founder the right questions is key. It helps you understand their vision, goals, and challenges. This allows you to evaluate if the opportunity is a good fit.
As a potential co-founder, employee, or investor, you want to dig deep. Going beyond the surface will give you a complete picture.
Here are 25 well-rounded questions to ask a founder before joining or funding their startup:
You may be considering involvement with a startup for several reasons:
- As an investor, you want to vet the business model, market, and team. This reduces the risk that your financial resources will be squandered.
- As an employee, you want to evaluate the founder’s leadership skills. Joining a dysfunctional environment can stall your career.
- As a partner, you want to ensure your capabilities complement the startup’s needs. Bringing incompatible solutions to the table leads to frustration.
- As a potential customer, you want to verify their product addresses your pain points. Purchasing an ill-fitted solution results in wasted budgets.
Asking thoughtful questions allows you to complete your due diligence before making a commitment. The founder’s transparency builds trust in the relationship. With your eyes wide open to the pros and cons, you’re better equipped to make the startup decision that’s right for you.
About the Founder
Understanding the founder’s background provides context. It also builds trust when you get to know them as a person.
1. What motivated you to start this company?
This open-ended question reveals their origin story. Listen for a meaningful purpose that goes beyond money. Passion is fuel for the unavoidable roadblocks ahead.
2. What past experiences prepared you to start this company?
Red flags include no relevant experience or unwillingness to talk about past failures. Look for applicable skills and lessons learned.
3. How did you meet your co-founders and why did you decide to work together?
This probes their relationship and alignment. Co-founders need complementary skills and a shared vision to succeed.
4. How do you respond when stakeholders challenge your ideas?
Seeking diverse opinions is positive. But founders need conviction paired with openness. Watch for defensiveness or inability to disagree respectfully.
5. What might your friends say are your weaknesses?
Founders who can acknowledge their faults show self-awareness. This helps them identify threats and mentor co-founders and employees to fill gaps.
About the Company
Moving to the startup itself, you want to assess the core idea and business model.
6. What specific problem does your product solve?
Pinpoint the customer’s pain point. If the founder struggles to explain this clearly, it’s a red flag.
7. Who is your target customer?
Understanding the target customer is essential. Make sure it aligns with your expertise, values, and ability to serve them.
8. How do you make money? What is your revenue model?
Viability requires profits. See if they have a solid plan to generate revenue long-term, not just today.
9. Who do you consider your main competitors and how do you differentiate?
Direct and indirect competitors should be on their radar. But the obsession with beating competitors can be a warning sign.
10. How large do you estimate the total addressable market size to be?
While projections can be unpredictable, unreasonable estimates indicate poor analysis.
11. What are the key technologies or capabilities needed to create your product?
This probes their understanding of technical requirements. Don’t neglect barriers that could derail the timeline or budget.
12. Do you have any patents, trademarks, or other IP protection?
Intellectual property advantages can provide a competitive edge. But not always necessary in the early stages.
13. What major regulatory or legal hurdles could you face?
Savvy founders mitigate potential compliance issues before they become expensive problems.
14. Who are your mentors and key advisors?
External experts provide valuable guidance. Lack of advisors can mean isolation or unwillingness to seek input.
About the Opportunity
Now it’s time to evaluate your potential role and the startup’s readiness.
15. What role do you envision me playing and why?
Look for a clear vision of your responsibilities and fit. Title matters less than the expectations.
16. What are your funding needs and how will you use the investment?
This gauges the financial situation and direction. Ensure you agree with how funds will be allocated before committing.
17. What milestones or traction have you achieved so far?
Progress can demonstrate the ability to execute. But beware of hockey stick projections based on limited data.
18. Can I see a demo of your product or prototype?
Even early versions reveal the feasibility. However incomplete demos could signal delays or overly optimistic timelines.
19. What does your 12-month roadmap look like?
While plans will evolve, vague or illogical goals indicate poor planning.
20. What are your biggest challenges right now?
How they respond provides insight into self-awareness, problem-solving skills, and realism.
21. Why have past employees or co-founders left your company?
High turnover might indicate issues with leadership, culture, or vision. Probe the reasons people move on.
22. May I speak to other team members about their experience?
This provides an unfiltered perspective on the work environment and founder relationship.
23. How much equity or financial return can I expect?
Equity should match contribution. Be wary of undersized offers lacking upside for risk.
24. What’s your proposed vesting schedule?
Long vesting demonstrates commitment. Fast vesting erodes leverage and provides little incentive.
25. Under what circumstances would you step down as CEO?
Inflexibility about moving on when appropriate can harm the company. The most successful founders know their limits.
Joining a Startup is a Leap of Faith
There are no guarantees any startup will succeed. However, asking the right questions allows you to make an informed decision.
Analyze the founder’s motivations, skills, and self-awareness. Dig into the market opportunity and business model viability. Scrutinize financial assumptions and early traction.
Most importantly, evaluate if the role aligns with your experience, values, and passion.
With eyes wide open, you can determine if this startup opportunity is your next step toward purposeful work and potential rewards.
