My goals when talking to a CEO are to get a feel for the strategic direction of the company and culture fit. I try to ask these questions to a variety of people

My goals when talking to a CEO are to get a feel for the strategic direction of the company and culture fit. I try to ask these questions to a variety of people at the company to evaluate how aligned everybody is, but usually the CEO has the best insight into strategy. To that end, I don't really have any generic questions because they vary greatly by situation. Some examples: Company was beginning to enter the enterprise market so I asked questions about the direction of the sale team, their comfort with enterprise sales cycles, etc. Company was tightly integrated to a third party platform so I asked questions about that relationship, wether they wanted to move that tech in house, how they would do that, etc.