Questions to Ask Startup
Critical questions to ask a startup before joining as an employee, investor, or partner—covering product-market fit, funding runway, team, culture, equity, and viability.
1What problem are you solving, and who is your target customer?
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What problem are you solving, and who is your target customer?
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Why this works
Core product-market fit question—clarity here determines viability.
2What's your current traction—revenue, users, growth rate?
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What's your current traction—revenue, users, growth rate?
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Why this works
Reveals whether the business is gaining momentum or struggling.
3How much runway do you have, and when do you plan to raise more funding?
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How much runway do you have, and when do you plan to raise more funding?
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Why this works
Critical for job security and operational stability.
4Who are your competitors, and what's your competitive advantage?
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Who are your competitors, and what's your competitive advantage?
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Why this works
Assesses market positioning and defensibility.
5What's your business model, and how do you make money?
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What's your business model, and how do you make money?
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Why this works
Path to profitability is essential—many startups lack this.
6Who are the founders, and what's their track record?
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Who are the founders, and what's their track record?
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Why this works
Founder experience and relationships predict success more than ideas.
7What is the cap table, and how is equity distributed?
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What is the cap table, and how is equity distributed?
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Why this works
Reveals ownership structure and whether early employees get meaningful equity.
8What are the key milestones for the next 6-12 months?
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What are the key milestones for the next 6-12 months?
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Why this works
Shows strategic focus and realistic goal-setting.
9What's your biggest risk or existential threat right now?
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What's your biggest risk or existential threat right now?
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Why this works
Honest answer reveals self-awareness and transparency.
10How would you describe the company culture and working style?
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How would you describe the company culture and working style?
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Why this works
Culture fit matters immensely in small, intense startup environments.
11What does the equity package look like, and what's the vesting schedule?
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What does the equity package look like, and what's the vesting schedule?
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Why this works
For employees—understand stock options, strike price, and dilution.
12What percentage of the company does my equity represent on a fully diluted basis?
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What percentage of the company does my equity represent on a fully diluted basis?
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Why this works
Absolute number of shares means nothing without knowing total shares.
13What happens to my equity if the company is acquired or goes public?
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What happens to my equity if the company is acquired or goes public?
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Why this works
Liquidation preferences and exits affect whether your equity is worth anything.
14What's your customer acquisition cost and lifetime value?
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What's your customer acquisition cost and lifetime value?
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Why this works
Unit economics determine whether growth is sustainable or burning cash.
15How do you prioritize product development and feature requests?
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How do you prioritize product development and feature requests?
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Why this works
Shows whether they're customer-driven or founder-driven.
16What are the expectations for work hours and work-life balance?
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What are the expectations for work hours and work-life balance?
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Why this works
Startups can be intense—understand the reality upfront.
17What benefits, salary, and perks do you offer compared to market rate?
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What benefits, salary, and perks do you offer compared to market rate?
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Why this works
Startups often pay below market—equity should compensate for risk.
18Who are your investors, and how involved are they?
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Who are your investors, and how involved are they?
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Why this works
Investor quality and support matter—smart money adds value beyond capital.
19What would cause you to pivot or shut down, and how would you handle that?
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What would cause you to pivot or shut down, and how would you handle that?
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Why this works
Shows contingency planning and founder integrity.
20Why should I join your startup instead of a more established company?
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Why should I join your startup instead of a more established company?
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Why this works
Forces them to articulate the unique opportunity and sell you on the vision.
Evaluating Startup Opportunities
Expert tips and techniques for getting the most out of these questions.
Best Practices for Due Diligence
Do Your Own Research
Talk to current and former employees, check Glassdoor, research the market—don't rely only on what they tell you.
Get Equity Details in Writing
Verbal promises mean nothing—review the stock option agreement before accepting.
Assess the Team, Not Just the Idea
Great teams can pivot to success; weak teams fail even with great ideas.
Key Risk Factors to Evaluate
Startup Risk Checklist
Common Pitfalls
Overvaluing Equity in Early-Stage Startups
Most startups fail—don't sacrifice salary for equity unless you can afford the risk.
Ignoring Red Flags in Founder Dynamics
Co-founder conflict is a top reason startups fail—observe team dynamics closely.