What would you ask the CEO of a company you're looking to invest in?

If you were limited to 3-5 questions to ask the CEO or the founder of a company you are looking to invest in, what would you ask? Obviously you'd leave out most of the technical questions that you could ask the IR team or look into yourself. I'd like to imagine the most valuable information you could extract from meetings with CEOs are related to overall strategy and long-term visions so would probably ask questions more along those lines. The questions would also likely be sector specific but for the sake of discussion, let's focus on questions that one could ask almost any CEO.

Asking this because I have a couple of meetings lined up and want to make the most out of them as the executives are a bit difficult to pin down.

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Notes: -No yes/no questions, more why/how. -Do not lead their answers by framing the question or leading with your opinion. -Be specific, don't open yourself up to an IR sales pitch-type answer.

Some Non-company-specific questions: -Which one of your competitors gets it right, who keeps you up at night? -How do you feel you're priced compared to competitors, do you think you're priced at a premium/discount and why are you priced that way? -What would cause you to cut prices? What would give you the confidence to raise prices? (fluctuations in input prices is not a good answer) -Which one of your competitors has the most price variability/volatility? -Who do you think is the most valuable employee or what is the most valuable department/function of the company? -What percentage of your spend would you say is growth-based vs maintenance-based? -What kind of incremental ROI do you target when making investment decisions? (HATE the "oh, above our cost of capital" answer) -What steps can you take to lower your cost of capital, and is that a focus? -What is the opportunity internationally? What markets do you find most attractive? -What are some longer-term red flags I should be watching for that would make me a seller of the stock? -Who has the best handle on the business on the sell side that you would recommend I speak to? (not relevant if you're on the sell side) -What do you think the market gets wrong about your business/story? -What do you think your competitive advantage is besides scale? (if they have scale...and if they say it's just scale, that is not a great answer) -What would stop a well-capitalized competitor from entering the market or replicating some of your business? -What technology over the last 10-years has had the greatest impact on your business? -What emerging technologies have the potential to impact the business in the next 10-years? -Is there a company outside the industry that you admire or strive to emulate? -What is the biggest mistake the company has made in the last 10-years and what did you learn from it?

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