Diligence Questions for management meatings?

So lets say it is a hypothetical case where you are asked to draft questions for a hypothetical meating with a hypotherical CEO. Obviously dependent on the opportunity and what information as present in the CIM, but what are generally some good diligence questions/topics that show another level of thinking beyond just basic questions?

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You alluded to it but I think it just takes a good understanding of the company and industry and will differ wildly. You can't put together diligence questions or topics that show another level of thinking if you aren't doing that other level of thinking. Could be through Google search and news articles, equity research, expert calls, third party data providers, comparable internal deal research, etc. 

 
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