If it is not worth paying an attorney, it probably isn’t worth doing in the grand scheme of things. Take the money you would spend on exercising the options and invest it elsewhere.

Some lawyers will do an initial consult for free. You can talk with them for say thirty minutes to determine if it's worth their bother to take the case.

There are lots of situations where a letter from a lawyer gets results without you needing to do anything more beyond that. If you can afford to pay a lawyer and it won't cost more than the value of the thing you seek, I think a letter from a lawyer is a terrific idea.

Having a lawyer write a letter shouldn’t cost more than $1000 or so. I guess the shares are worth more than that?

The end goal is not to go to court, of course.

Yeah people overestimate the costs of a lawyer to help navigate beaurocracy. $1000 bucks can get you really far.

They also underestimate the cost of trials, which is $100k+ for anything serious due to discovery.