Good explanation Heidi. I wish you would have ended with telling people to ask for preferred shares. it’s not that a company can’t give those but they try to avoid it. You hinted at it when discussing the “essential leadership of the company” but that does not mean regular employees can’t negotiate for preferred shares.
When that is not possible I think it would be prudent for the new employee to negotiate a clause that obligates the company to a detailed explanation of actions and consequences to each employee who holds shares and options whenever there is a change to the status and/or value.
I call that a “honeymoon agreement”. When the company is still early stage, nobody tinks it could fail or not be successful. Getting a clause that requires explanation and protection is much easier to get during that phase than later when the financial acrobatics start.