Patrick’s tweet below says it all, what questions would you ask to deeply understand a company?
I’ve just gone through the answers and compiled them into a simple little two-page Google doc.

I’ve also included the questions below as just text so you can grab and choose to format for your liking 🙂

Product & Business Ops

• If you were to start over (or start a competitor) which part of the business would be most difficult to replicate?
• Why would people not use your product or service?
• What problem does the company solve? And why does this problem persist?
• What about your business can & can’t be replicated? Why are you different?
• If the business overachieves, what does it look like in 5 years? / If you miss, what might have gone wrong?  
• What is your special insight or your edge?
• What’s a feature request that you get a lot, but that you will never build?
• What’s the most misunderstood thing about your company and industry?

Industry & Competitors

• If you had 1 bullet, which competitor would you shoot with it?
• What are you doing that your competitors aren’t doing yet?
• Who do you envy in the industry?
• Where and how are you building relative advantages vs peers?
• Why is your cost structure different from your competitors?
• What are the critical trends in the industry?
• How do you compete & think about competitive advantage?
• What do you see as the biggest near-term and long-term risks to your business?

Customers

• Why do customers choose you, and will it continue?
• What system is in place to ensure growth and returning customers?
• Tell me about your favourite customer?
• Where do you go to listen to what your customers are saying?

People, Management, & Culture

• What are the 2-3 key metrics that management looks at to drive the business?
• If the current management team left, would the business lose its moat – why or why not?
• If a friend of yours was joining the company today, what would you tell them about how to be successful here?
• What capabilities on your team are you most confident in, and where might you want to supplement?
• Who are the last few people you hired and why/how did you assess and hire them?
• How do you incentivise learning in your team?
• What percentage of your employees exhaust their annual leaves?
• Who is your ideal employee?
• What challenges does the company face to recruit top talent?

Financials

• How do you make $1 profit? Run me through it from top to bottom.
• How do you determine pricing of your products/services?
• What is your view about leverage?
• Would you repurchase shares and if so under what conditions?
• What is your ROIC, how can it be expanded and how much more capital can be invested before it falls?
• If you had unlimited capital – what initiatives would you take on that you currently are not able to

Misc

• What were the hardest moments in the life of the company? And what did you do about it?
• Is your value reinforced over time and with size?
• What was the closest you got to closing up shop, and how did you overcome it?
• What’s one aspect of your business that keeps you up at night?
• What is the one thing you would change about your company if you could? What’s preventing you?
• What do investors never ask you that they should?
• What do other investors not understand about your business/product?