20 Questions

Questions to Ask Startup CEO in Interview

Strategic questions to ask a startup CEO during an interview to understand the company's vision, culture, and growth potential.

1

What is your company's mission and vision, and how do you see it evolving over the next 5 years?

Click to see why this works

Why this works

Critical for understanding the company's direction and whether it aligns with your career goals and values.

2

What are the biggest challenges your company is currently facing, and how are you addressing them?

Click to see why this works

Why this works

Important for understanding the company's current situation and the CEO's approach to problem-solving.

3

What is your company's culture like, and how do you maintain it as you grow?

Click to see why this works

Why this works

Helps you understand the work environment and whether it's a place where you can thrive and be happy.

4

What are your company's key metrics and KPIs, and how do you measure success?

Click to see why this works

Why this works

Important for understanding how the company defines success and what drives its decision-making.

5

What is your company's funding situation, and what are your plans for future growth?

Click to see why this works

Why this works

Critical for understanding the company's financial stability and growth potential.

6

What are your company's competitive advantages, and how do you differentiate from competitors?

Click to see why this works

Why this works

Helps you understand the company's market position and what makes it unique in the industry.

7

What are your company's biggest opportunities, and how do you plan to capitalize on them?

Click to see why this works

Why this works

Important for understanding the company's growth potential and future opportunities.

8

What is your company's team structure, and how do you plan to scale it?

Click to see why this works

Why this works

Helps you understand the company's organizational structure and growth plans.

9

What are your company's biggest risks, and how do you mitigate them?

Click to see why this works

Why this works

Important for understanding the company's risk management approach and potential challenges.

10

What is your company's customer base, and how do you acquire and retain customers?

Click to see why this works

Why this works

Helps you understand the company's business model and customer relationships.

11

What are your company's technology stack and infrastructure, and how do you plan to scale them?

Click to see why this works

Why this works

Important for understanding the company's technical capabilities and growth plans.

12

What is your company's approach to innovation, and how do you encourage creativity?

Click to see why this works

Why this works

Helps you understand the company's innovation culture and whether it's a place where you can contribute and grow.

13

What are your company's biggest achievements, and what are you most proud of?

Click to see why this works

Why this works

Important for understanding the company's track record and what the CEO values most.

14

What is your company's approach to diversity and inclusion, and how do you promote it?

Click to see why this works

Why this works

Helps you understand the company's commitment to diversity and whether it's an inclusive workplace.

15

What are your company's biggest lessons learned, and how do you apply them?

Click to see why this works

Why this works

Important for understanding the company's learning culture and approach to continuous improvement.

16

What is your company's approach to work-life balance, and how do you support your employees?

Click to see why this works

Why this works

Helps you understand the company's employee support and whether it's a place where you can maintain a healthy work-life balance.

17

What are your company's biggest opportunities for improvement, and how do you plan to address them?

Click to see why this works

Why this works

Important for understanding the company's self-awareness and commitment to improvement.

18

What is your company's approach to feedback and communication, and how do you ensure transparency?

Click to see why this works

Why this works

Helps you understand the company's communication culture and whether it's a place where you can have open and honest conversations.

19

What are your company's biggest goals for the next year, and how do you plan to achieve them?

Click to see why this works

Why this works

Important for understanding the company's short-term priorities and how they align with your role.

20

What is your company's approach to failure, and how do you learn from mistakes?

Click to see why this works

Why this works

Helps you understand the company's learning culture and whether it's a place where you can take risks and learn from failures.

Interviewing Startup CEOs

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

Best Practices

Research the Company

Take time to research the company's history, products, and market position. Understanding the company will help you ask more informed questions.

Prepare Thoughtful Questions

Prepare questions that show your interest in the company and your understanding of the industry. This will help you stand out as a candidate.

Listen Actively

Pay attention to the CEO's answers and ask follow-up questions. This shows your engagement and helps you gather more information.

Question Sequences

The Vision Explorer

1
What is your company's mission and vision?
2
What are your company's biggest challenges?
3
What are your company's key metrics and KPIs?
4
What is your company's funding situation?

The Culture Assessor

1
What is your company's culture like?
2
What is your company's approach to diversity and inclusion?
3
What is your company's approach to work-life balance?
4
What is your company's approach to feedback and communication?

Common Pitfalls

Don't Ask Generic Questions

Avoid asking questions that could apply to any company. Make your questions specific to the startup and its unique challenges.

Avoid Being Too Aggressive

While it's good to be direct, don't be overly aggressive or confrontational. Maintain a professional and respectful tone.

Don't Ignore Red Flags

Pay attention to the CEO's answers and look for any red flags that might indicate problems with the company or culture.

Conversation Templates

The Vision Seeker

1
Step 1: Start with: "What is your company's mission and vision?"
2
Step 2: Follow with: "What are your company's biggest challenges?"
3
Step 3: Deepen with: "What are your company's key metrics and KPIs?"
4
Step 4: Complete with: "What is your company's funding situation?"

The Culture Explorer

1
Step 1: Begin with: "What is your company's culture like?"
2
Step 2: Explore with: "What is your company's approach to diversity and inclusion?"
3
Step 3: Investigate with: "What is your company's approach to work-life balance?"
4
Step 4: Assess with: "What is your company's approach to feedback and communication?"

Further Reading

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

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation