From the perspective of an employee, I completely agree this is the correct method of getting an idea of what equity is worth. I've had exactly 0 new hires ask me all those questions. Maybe 10% have asked me how many shares outstanding we have. The number of people with the experience to ask the right questions is really low, even for senior hires we've made with 10+ years of experience in startups. I think the onus is on startups to start proactively sharing this information with new hires- not just employees.