These are investor questions, not employee questions. In my experience, you're either going to get a vague dodge or a flat-out "we're not going to share that / it's confidential" response unless you're applying for a C-level position.

A better approach is to dive into the product and make a judgement... "What does the company need to do to secure its next round of funding?" VC-scale rule-of-thumb is you need a new funding round every 18 months... 12 months to improve the metrics, then 6 to close the next round. Figure out when the last one was, when the next one comes due, and how honest the company goals are from now until then.

I think I have asked these kinds of questions in every one of the interviews I've ever done to whoever was the senior manager/C and they haven't even blinked at answering the question. It is critically important to me to know if the business feels healthy as it directly affects my confidence in the company, the vision that the person across the table is trying to sell me, and if the person in front of me has their head screwed on right. This is the kind of information that I use in combination with external signals to call bullshit or not. To also colour in this perspective a bit a frank 'I don't know, we are too small and we are struggling to get our internal operations on track and are looking for people who can help' is a sane and reasonable answer.

If I join the organization without asking these sorts of questions and realize that the person leading the company doesn't even know how their own company is running that kills my morale. It could also be that when I ask these sorts of questions I am frank about my opinions: I don't mind being part of the machine but I am business oriented and derive motivation/happiness from doing what I can to accelerate that business even further.

If they're offering equity as part of the compensation package, then you definitely become an investor. Investor questions are totally justified.

Even if they don't offer equity, you still have a significant opportunity cost and risk when you decide to work for a startup. These questions attempt to quantify these.

Disagree - as someone who has worked solely with startups for the last 10 years it is crucial to know this. I have (on more that one occasion) been without pay for a period because "the funding ran out" - it is part and parcel of early start ups and knowing where they are on the journey to profitability is important if you are making a commitment!

oh yes they are investor-like questions.

And rightfully so.

Employee is investing time in effort and receives compensation and equity in case of startups. If equity is non-zero, then obviously employee will ask the same questions an investor would.

Salaries in startups are lower than in most corporations - the difference is what employee might consider to be their cost of investing in the company.

if part of the compensation is equity than the financial health of the company is very relevant.

Might annoy or alienate a CEO (maybe that’s a warning sign?). But, these are the right questions to ask.

> Might annoy or alienate a CEO (maybe that’s a warning sign?)

Yes, this is a warning sign. A CEO of a startup should know that employees take on risk by joining and that prudent candidates will want to take the financial health of the company into consideration when comparing offers.

Its really dependent on the candidate and the position. A quality senior engineer may be gauging the feasibility of ideas that may take _years_ to come to fruition. That requires a lot of non-technical information and both trust and a good working relationship with sr. management. If they are not willing to freely share information, they probably won't utilize the caliber employee who would typically request it. Its no guarantee but personally when I've interviewed people who have asked these types of in depth and / or difficult to answer questions they've turned out to be orders of magnitude higher quality. They know what successful companies look like, and aren't interested in taking chances on companies that won't or can't utilize them to their potential. Doing so requires sharing enough information and trust that the employee can help steer the ship.

Def might, if your tone is off/the CEO is neurotic. If some rando came in trying to gauge how long he could hang on to a job rather than how he can contribute to the idea I'd be a bit put off.

The best candidates dig into product and market and get all the info they need from that.

I also like to ask if I can see the "solution" they are advertising on there website.