If someone asked you to share some board slides, you could simply explain they’re company confidential then try to tease out what information they’re after with follow up questions. Or maybe consider that they care enough about the business (or want to appear to) to ask questions like that.

Why is asking where you see yourself in 5 years arrogant? I own my own profitable company, no vc funding. I’ve never been asked that, but if I were, I’d be delighted to give an answer. Totally reasonable question.

If someone asked me why I wasn’t relaxing on the beach, I’d explain to them that it gets old. Sitting idle is a terrible way to spend time, although it might not appear so if you haven’t had the experience. I’d tell them that I hope to get them to a place one day where they could see just how overrated it is and judge for themselves.

"What keeps you up at night" is also a very common question... obviously within the context of an interview, the candidate isn't asking about problems with your marriage or your health or whatever other personal issue you might be thinking of. Typical answers I've heard are figuring out how to scale, hiring fast while maintaining a high quality bar and moving up market. Knowing what the CEO is concerned about is a totally reasonable and relevant piece of knowledge for picking a company.

1. Is a poorly worded "what's your passion" question to the CEO

2. That's a red flag, you can redirect and say minutes are posted ... question to gauge transparency

3. No more arrogant than asking the employee

4. Poorly worded... "how do you plan to keep me here when the market turns in 2-3 years to the next fad"

5. Is a perfectly fine question, not asking about your wife

Some of these are poorly worded, none of them are out of line. If you are not comfortable answering them speaks to your character greatly.

A wordy, trying-to-be-cute way of saying "What motivates you to keep working?" or "Why do you keep working instead of retiring?" which is a pretty good question.

"Will you share slides from the last board meeting?"

A bit presumptuous maybe, but not quite into the realm of arrogance. I would verbally summarize the slides.

"Where do you see yourself in 5 years?"

Nothing arrogant about this one; a CEO should have a 5-year plan at least. Although this particular way of asking it has been used verbatim enough times since I first heard it in the 80s, that it now shuts down my mind immediately due to its blandly mind-numbing cliché quality. Which doesn't speak to the candidate's amazing creativity. Don't ask it this way if you're sitting with a Gen-Xer probably.

"When I leave here in 2-3 years, will it be because of the people, or because I haven't gotten a raise and/or promotion?"

I mean, you tell me. Are you more "I have a terrible personality and poor social skills" or are you more "I get childishly petulant when I don't get promotions and raises I think I deserve?" Both these things are within your control... and so is your exit from the company for that matter. If you were mature enough to take responsibility that is. Terrible question, don't ever say this. It conveys four negative things about you, all of which I would assume are true.

"What keeps you up at night?"

The question is again trying to be all folksy and cute bygoshdarn bygolly, but at its heart it's a pretty good question. In other words right now what's your biggest obstacle / thing you're worried about / thing that's giving you a pain. At work mind you... not your personal life!

Slides from board meeting are about transparency, i do not want to work at organization that is not transparent about fiances(and especially not at one which has high profits, but very volatile cash reserves). If it gets deflected, but a summary is provided ,it isn't a red flag - it means that employees potentially have access to this data.

if you think asking about your future plans arrogant, why are you asking such questions to employees? this is a legitimate question about where you want to take this company towards.

In most western tech jobs - changing job after a year is norm - not an exception. over here it is frowned upon, but 2-3 years is a long enough time in most cases. And there are two main cases of job hopping: increase in salary is way more significant than any rise given; toxic workplace;

Last one isn't personal, but it has implied context of company itself. what are problems that you want to fix, and potential threats.

those questions are even more important if company is paying in equity. I wouldn't want to work there if i didn't get the answer at least to majority of them. It would be a huge red flag - or i would assume that equity is 100% worthless when comparing compensations between offers.

Relationships of power shifted - there is abundance of jobs, and scarcity of good developers. Quite frankly - there are plenty of bad companies, and few good ones - just like with candidates.

You would hate to bring in a bad horrible person in. We would hate to invest time and effort into useless endeavor.

On the other hand, asking for slides from the last board meeting is a good request from someone deciding whether to accept an offer, and "where do you see yourself in 5 years" and "what keeps you up at night" are both perfectly reasonable questions about how you view the potential development of your venture.