As long as it's legal and not weird/personal/insulting and you're polite, you should never be scared of asking a question! In fact, you should find a question

As long as it's legal and not weird/personal/insulting and you're polite, you should never be scared of asking a question! In fact, you should find a question they don't want to answer "yes" to, and you should push on it. It will tell you volumes about who they are, how much they respect you, and their skill as professionals, negotiators, and more. I've lost offers in the past for being insistent about things. That's fine. I dodged a bullet and saved years of my life. Directly responsive to your question: you want to know the shares outstanding, the liquidation preferences (if any) of prior investors, if there are any weird share structures (e.g. series FU preferred, which converts 10,000:1 to common and is held exclusively by the CEO's dog), if there's a single- or double-trigger clause for employees, the terms of the stock agreement...there are lots of things you might ask about.