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 indicators do you watch closely on a weekly/monthly basis?
- 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 to 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?
- Why do customers choose you, and will it continue?
- What system is in place to ensure growth and returning customers?
- Tell me about your favorite customer?
- When are customers wrong?
- 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?
- Who's most difficult to replace and why?
- What decisions can only you make and why?
- 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?
- How do you make $1 profit? Run me through it from top to bottom.
- How do you determine pricing of your products/services?
- What are the 3 biggest margin opportunities in the business?
- What is your view about leverage?
- Walk me through the company’s last 3 major capital allocation decisions
- 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?
- 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?