Not including compensation, what questions do you regret not asking about culture, daily life, management, vision etc. for your current or previous jobs.
Find out how much money the plan to raise. There's an interesting relationship between how much money a company has the influence that money has on culture.
Find out why the founders started the company, or why other colleagues joined. If the company wasn't started out of strong passion and or opportunity to solve a unique problem, it probably won't work, and won't be very fun.
Ask what the lowest point of the company has been so far and how they overcame that challenge and/or how it's shaped or influence the culture.
I wanted to, but believed I couldn't afford to, ask about the physical working environment.
I can get along with most any personality type. As long as my workspace allows me to concentrate (for me, is (very) quiet unless I choose to make it otherwise, is clean (allergies), and has some natural light).
I mean, I've worked (well) with widely acknowledged jerks. I've fostered genuinely careful and motivated people who were a bit slow to get the tasks at hand and so at risk. I've held my own with "the brightest". I've "networked" far beyond my "station".
But, in many work environments, for HR type issues, you "take what you're given". And workspace seems to fall predominantly into that mold.
In retrospect, I wish I'd blown off more of the "career" advice" that was heavily propagated, and just asked and insisted on knowing what the physical work environment was going to be like. I would have failed to gain some opportunities -- but I would have saved myself a lot of frustration and, ultimately, time in the process.
For some people, it really does matter. And I'm one of them.
-How much tome do teammates socialize outside of work?
-What percentage of your time is support?
-Is mentorship valued?
-Which best describes the engineering culture: deadline or quality driven?
-How many hours of meetings are there a week?
-Would you say your customers love you?
-What's the biggest complaint about the firm?
-Do you do automated testing?
-What software methodologies do you practice?
-Are the hours flexible? Can you work from home?
-Are vacation days counted?