20 Questions

Questions to Ask Startup Interview

Strategic questions to ask during startup interviews, helping you assess the opportunity, understand the risks and rewards, and determine if the company is a good fit for your career goals.

1

What problem is the company solving, and why does it matter?

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Why this works

Reveals the company's mission and market need, helping you understand whether they're addressing a real problem worth solving.

2

What is your runway, and what are your funding plans?

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Why this works

Shows financial stability and how long the company can operate, helping you assess job security and growth potential.

3

What does success look like in the next 6, 12, and 18 months?

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Why this works

Reveals the company's goals and trajectory, helping you understand their ambitions and realistic growth plans.

4

What is your business model, and how do you make money?

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Why this works

Shows whether they have a viable path to profitability and understand their revenue streams.

5

Who are your main competitors, and what's your competitive advantage?

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Why this works

Reveals market positioning and whether they understand their competitive landscape and differentiation.

6

What does the team look like, and what key hires are you planning to make?

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Why this works

Shows the team composition and hiring priorities, helping you understand the culture and future team dynamics.

7

What is my role's impact on the company's success, and what are the expectations?

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Why this works

Clarifies your specific contributions and responsibilities, ensuring you understand how you'll be measured.

8

What is the company culture like, and what values drive decision-making?

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Why this works

Reveals the work environment and values, helping you assess cultural fit and work-life balance.

9

What is the equity compensation structure, and what percentage of the company does it represent?

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Why this works

Helps you understand the value of your equity offer and your potential upside if the company succeeds.

10

What are the biggest risks and challenges the company is facing right now?

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Why this works

Shows honesty and self-awareness about obstacles, helping you assess whether you're prepared for the challenges.

11

What opportunities for growth and learning exist in this role?

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Why this works

Reveals professional development potential and whether you'll be able to grow your skills and responsibilities.

12

What is the decision-making process, and how much autonomy will I have?

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Why this works

Shows the organizational structure and whether you'll have the freedom to innovate and make decisions.

13

What happened to the last person in this role, and why did they leave?

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Why this works

Reveals potential red flags or challenges in the role and shows whether there's a pattern of turnover.

14

What is the work-life balance like, and what are the typical working hours?

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Why this works

Helps you understand the time commitment and intensity of the work environment.

15

How do you measure success for this role, and what are the key metrics?

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Why this works

Establishes clear performance expectations and shows how your work will be evaluated.

16

What resources and support will I have to do my job effectively?

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Why this works

Reveals whether you'll have the tools, budget, and support needed to succeed in your role.

17

What is the founders' vision for the company in 5-10 years?

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Why this works

Shows long-term thinking and ambition, helping you understand their ultimate goals for the company.

18

What is the customer feedback like, and how are you addressing it?

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Why this works

Reveals market validation and responsiveness to customer needs, showing product-market fit.

19

What benefits and perks are offered, and how do they compare to other startups?

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Why this works

Helps you understand the complete compensation package beyond just salary and equity.

20

What questions should I be asking that I haven't thought of yet?

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Why this works

Shows humility and openness to guidance, potentially revealing important considerations you've missed.

Best Practices for Startup Interview Conversations

Expert tips and techniques for getting the most out of these questions.

Best Practices

Research Thoroughly

Study the company, founders, competitors, and industry before the interview to ask informed, specific questions.

Assess Risk and Reward

Understand that startups involve higher risk but potentially higher rewards. Evaluate whether the trade-off makes sense for you.

Look for Red Flags

Pay attention to evasive answers, unrealistic claims, or lack of clarity about business model and funding.

Question Sequences

The Business Assessment

1
What problem is the company solving?
2
What is your business model?
3
Who are your main competitors?
4
What is your runway and funding plans?

The Role Understanding

1
What is my role's impact on success?
2
How do you measure success for this role?
3
What opportunities for growth exist?
4
What resources will I have?

Common Pitfalls

Don't Get Blinded by Hype

Look beyond the exciting pitch and evaluate the fundamentals: business model, team, market, and funding.

Don't Accept Vague Answers

Push for specifics about funding, equity, expectations, and success metrics. Vague answers are red flags.

Don't Underestimate the Risk

Most startups fail. Ensure you're comfortable with the risk and have financial runway if things don't work out.

Conversation Templates

The Startup Evaluation

1
Step 1: Start with: "I'm excited about the opportunity. Can you tell me what problem you're solving and why it matters?"
2
Step 2: Follow with: "What is your business model, and how are you making money?"
3
Step 3: Deepen with: "What are the biggest risks and challenges you're facing right now?"

Further Reading

"The Lean Startup" by Eric Ries
"Zero to One" by Peter Thiel
"The Hard Thing About Hard Things" by Ben Horowitz

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