Ideally, you'd get to know one of the employees. Then ask away. Ideally you'd want one of the more employees more capable of cynicism (or realism, if you wish);

Ideally, you'd get to know one of the employees. Then ask away. Ideally you'd want one of the more employees more capable of cynicism (or realism, if you wish); statements like, "It's a really good environment!" are useless. You can ask what would happen if you perturb the system: "What if I do <something often interpreted as upsetting the chain of command>?" If you know the industry, or can speak with a friend in it, that's good. Then you can predict much of what they do/think, and watch out for irrational/ignorant deviations. Will they give you contact info of a normal employee, or leave you alone to speak with them? If they're really good, they'll do it without you needing to ask. Bosses are professional liars. (This includes technically true statements designed to mislead. Whether they're even aware of it is not relevant.) Conditioned daily to say what maximizes their interests, or they fail. They are virtually the worst sources of direct info, unless they open up their books and emails to you (which they won't). They often don't even know some answers due to blindspots. So when speaking with bosses, I try to observe "rationality" (which I agree is subjective). Charismatic talkiness is a flag; it may indicate ego. Evaluating it isn't easy; that practiced charisma may be useful for success, but it can also be a pain to work with. One thing I care about is how much ability I'll have to help the company maximize its success. Part of that is knowing how many employees there currently are, and what kind of people they are, because their work is "legacy code" as far as I'm concerned. Do I have to deal with it? (Because usually it'll suck.) But really, the high-risk sort of startups come with... well, inherent risk.