It should be valued at 0 unless the company takes active steps to encourage you not to, which would include answering dozens of questions about vesting and dilution that they won't.
No one gives a shit. Sometimes it works out well.
You also won't be told when they take on a funding round with priority, even though all their prior rounds were funding with no priority. Personally experienced that one.
If the industry wants employees to value their options above zero, give the employees legal protection that would enable them to do so. Otherwise it's VC firms getting butthurt that people aren't accepting their scrip as real money.
If the industry wants to change this perception, then there should be a widespread standardization on a contract that is fair to the employees and it should be easy for employees to understand any diffs from that standard.
It goes without saying that I've rarely found the contracts I've signed to be opaque.
It's the company who will spend thousand or tens of thousands of dollars having the contract made. It's the company who gets to amortize the costs of a complicated contract over many hiring interactions. It's the company who has the advantage of a strong information and experience asymmetry.
In short, the company has a lot more power. If somebody with power screws somebody without, I save most of my blame for the people who set things up.
It goes without saying that employment contracts all use the same language, I have never personally run into a clause I found opaque or confusing.
It's not just a matter of not understanding the entire legal contract. Someone could understand every single thing, but not realize, like you said above, "you won't be told about funding rounds if your contract doesn't mention it." They wouldn't even think about that because they aren't experts in that field.
I've negotiated plenty of employment and IP agreements. I've found 100% willingness to, at the least, discuss them. But employee options grants must often be the same for everybody. And for a normal employee (as opposed to some C-level executive hire), once you start negotiating "in case I leave early I want more rights" you are signaling bad things.
Really, all I'm telling people is "if you don't understand something fully, assume it's worthless." Your reaction is that, for some reason, employees should jump into the deep end of the pool and try to outsmart the VCs at the game they play every single day of their lives. And for what purpose? The vast majority of the time the options are going to end up at $0 anyway.
I say no. Assume legalese is written in order to screw you over. Smile and accept the options because you might get lucky, but never ever stay late at the office imagining how they will make you rich.
But at the end of the day, they could well be worthless, and they will never mean as much to an employee as they do to me. I had to just accept that people would value them at zero. For those interactions, I just had to think of the options as something we were doing so that in case we won big, we'd all feel good about the outcome.
My critique is not of generic, anodyne advice. It's of your assigning of blame to the weaker party.
I think stock options should be valued at zero. In an a-will employment state you, and with a typical contract, you can get fired at any random day and if you don't have enough money to exercise your vested options within 90 days, they're gone. I don't consider that reliable.
In regards to the parent comment of yours, I think if it was stated as "proactively answer" vs "answer" it'd be less arguable.