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Startup Red Flags Checklist

Run this before you sign the offer letter. Some of these you can't unsee.

Includes a personalized analysis written by Seth based on 20+ years of engineering and startup experience.

19 questions · ~4 minutes
Question 1 of 19 Finances & Business Model

Can the founders clearly explain how they make money (or plan to)?

Question 2 of 19 Leadership & Founders

How does the founder respond to pushback or bad news?

Question 3 of 19 Culture & Operations

What's the company's relationship with the truth in sales and marketing?

Question 4 of 19 Finances & Business Model

How transparent is the company about its financial situation?

Question 5 of 19 Equity & Compensation

What does the equity offer look like?

Question 6 of 19 Product & Engineering Culture

What's the engineering culture like?

Question 7 of 19 Culture & Operations

How does the company handle work-life boundaries?

Question 8 of 19 Leadership & Founders

What happened to the last person who left?

Question 9 of 19 Equity & Compensation

Is your salary below market rate?

Question 10 of 19 Leadership & Founders

Does the founder have relevant domain experience?

Question 11 of 19 Culture & Operations

Ask the hiring manager: what are the three biggest unsolved problems facing the team right now? How specific is the answer?

Question 12 of 19 Hiring & Team Health

What does the hiring process tell you about how they make decisions?

Question 13 of 19 Finances & Business Model

Have they ever had a conversation about acquisition or exit that they're willing to share the shape of?

Question 14 of 19 Equity & Compensation

What does the cap table look like?

Question 15 of 19 Product & Engineering Culture

How does the team build and ship product?

Question 16 of 19 Hiring & Team Health

Talk to two current employees outside of the interview process. What do they say when you ask them what they'd change?

Question 17 of 19 Hiring & Team Health

How do they handle underperformance on the team?

Question 18 of 19 Product & Engineering Culture

How does the company make technical decisions - who has authority and how are tradeoffs evaluated?

Question 19 of 19 Leadership & Founders

Has the company had to make hard calls - cutting a product line, laying off people, changing direction dramatically - and how did they handle it?

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