It depends what you want out of the conversation. Do you want to build the relationship, get an idea of how the company is doing, get advice for your career, etc. All of these require different questions. Also depends on how long you have.

But, my favorite generic question is "what keeps him or her up at night?"

Why?

* People generally love to talk about themselves, VPs included.

* It shows you are thinking about the big picture.

* It gives him or her the chance to talk strategically.

* It might give you some insight into current problems the VP thinks is or will be interesting/important to the org.

do you just literally ask that or rephrase the question to "what are the expectations for me"? I mean sometimes what keep the VP up at night is not sth relevant to or disclosable to you.

I have asked that question directly.

I'm sure most VPs have multiple things that keep them up at night, so I'd expect them to pick one they could legally disclose :) .

If they do talk about something that will get them in legal trouble, well, that's a good piece of data to have about your company (they have a VP who might get in legal trouble).

And probably, if they're good, pick one that is relevant to the person they are in conversation with. So not "I'm worried about my aging father and his health" and more "I think that these zero-days are going to become more and more common", etc etc.

I love the "what keeps you up at night" question as well: it's easy enough to qualify it or in context make it clear that it applies to the business.

I really like this. I wouldn't have thought to ask it either. Thank you!

What sources of revenue are most profitable for the company? How does IT contribute to that?

What books or periodicals should I read to understand more about the company's industry, domain, and history?

What areas of IT are the biggest pain points for the company, in terms of either revenue or expertises?

How is the success of IT measured and rewarded at the senior executive level?

Most companies produce a great deal of information about operations and status, but it can be heard to know which kinds and sources are the most valuable for knowing the real state of the company. Ask how the VP keeps up to date with the most important company directions.

What are the most important issues facing the department? - demonstrate empathy and a desire to contribute to the things that matter

what metrics or signals are most helpful to him in understanding and communicating the value that your department is delivering? - align yourself with the stuff he can actually use

how can I help? of course not the first question, but I’d make sure to ask when you sense it’s a good moment.