What’s the most exciting problem you’re trying to solve?

I like this one alot, as it establishes where the CEO falls on the innovative vs. reactive spectrum and gives you a feel for his actual passion for the product/service/user base.

I know a company that shares a lot in common with startups. And whilst the CEO spent about 6 months creating a 5 year business plan (which contained answers to all of your growth related questions), no where did it address what it is they actually *do*, who their target userbase is, and what kinds of products/services they’re bringing to the table. The CEO has only ever been able to articulate his dreams as being “bigger than Microsoft.” Because of that lack of identity, the [co] has been completely unable to reach its growth goals; no amount of pretty “projected revenue” graphs will change that.

When a line programmer complains of their CEO not being a “tech guy,” I think it points to the above being a major problem (the other problem being a lack of confidence in his tech staff). There’s a huge difference between a CEO who is excited about making cool stuff and a CEO who only ever says he wants to be the next YouTube or Microsoft.

first and foremost, make sure you fit in culturally, or you will be hating life.

As important as the CEO meeting is the meeting with the people who live in the trenches. Oftentimes, C-level people have an exaggerated sense of their company’s awesomeness, the staff’s morale, etc. Meeting with a line programmer is a quick way to dispel those myths and understand the real company culture.