Basically a casual ask for "can you share how many options are outstanding?" is about as good as you are going to get. Totally good. Non-stand demands? Not so good.
If the VC has preferential shares (they do) just realize that's ok - and probably fair. Don't join the company if you don't think it can exit above it's funding amounts if you are in for the stock - but hopefully you're in it because you really will love the position and the stock is just a bonus if it makes it.
That's the most important thing :) You don't want to be in a job you don't like just because it's profitable IMHO.
It's tricky to share that with employees and not have it get out.
That being said, if it were all public, I think that would be fine, I'm not sure what results that would cause if every company did that, and it might be cool if every company were required to by law (hint, hint, congress!).
And absolutely none of them are valid. If you're going to have this person work on the core of your company, there is absolutely no reason to not be up front with them.
I do however strongly believe in tempering expectations, it's wrong to try to retain people by thinking they have more than they do.
It will influence your relationship, positively.
Executives and managers always pay attention to these details and negotiate them when joining a company. The fact that you're paying attention signals that you actually understand what's going on and demands respect.
Some companies will refuse to give you this info and resent you for asking, but you should automatically reject such offers.
If a "rank and file" developer goes back and forth grilling them over offer terms, and is exceptionally picky above his peer group, this DOES make it back upstream in negative ways.
Some companies will not give you this as a matter of policy - , if you are ok with the salary, you could still enjoy working there - and may also make a great deal of money (or you might not).
Then don't work for those companies.
Ones goal in life should not be to get exploited at shitty startups as a "rank and file" developer (aka chump).
All being said, if at that stage of a job offer, you don't want to be looking like the most important thing to you are your options. If you get a decent salary and like the work, you are not being exploited.
The approach you imply is the approach I've taken. Work with founders that I trust, verify the details of the deal to the best of my ability and assume that good people do the right thing for other good people.
A right of first refusal (ROFR) is a reasonable transfer restriction. So is a lock-up period, e.g. you may not sell these shares within N years of getting them. Bans, on the other hand, are not. For a common stockholder, requiring board approval is a cutesy way of saying "ban".
Employees usually get restricted stock until there is a liquidity event.
ROFRs are the only restriction I've seen widely enough to merit calling "standard". Everything else exists in different forms in different companies, all the way up to being wholly non-existent for some combination of employees, executives and institutional shareholders.
My work involves helping private companies raise capital and investors (mostly institutions) sell privately-held positions.
Your experience is working with investors. Your advice makes more sense from that point of view. Employees are rarely (read Never) afforded the same privileges as the investors.
No need for us to boot-lick and perpetuate a minor injustice against employees and labor here...especially one that is causing long-term harm to the ecosystem.
You could also get early exercise. That, personally, is what matters the most to me in a company with common valuation <$100mm. I have very very little interest in holding options; shares (either directly via grant, or via early exercise), or RSUs (which are even flimsier than options, but at least come in public companies.)
Generally, you'll want to hold your options until the company is public or acquired, so you wouldn't need to worry about this.
If you are receiving NSOs, it is best to be at a company where they expire 7 years after leaving.
Even if you cashlessly exercise, you are still going to have a tax-bill problem, which can be a huge problem if current FMV is far higher than strike.
If the company hadn't done this before, they'd need to think through the implications for their processes, and probably get a legal stamp of approval. They might not be willing to do this, and instead pass on even a potentially great employee.
I wouldn't encourage anyone to turn down an offer for its lack of cashless exercisability. The lack thereof, however, causes pain. That should be compensated for. On transferability, I would mark down non-transferable stock to zero in any salary-or-equity trade-off calculation.
1. TRANSFERABILITY. If you are given options to buy privately-held common stock in lieu of compensation, you must demand transferability. Rights of first refusal (ROFRs) are fine. "Board approval" is not. "Board approval" means "you may not sell your shares until we go public, except to us, if and when we feel like it, and at a price we get to unilaterally decide".
2. CASHLESS EXERCISABILITY. Always ask for cashless exercisability. In the public market, if you ask your broker to "cashlessly exercise" in-the-money options, here is what happens. First, your broker lends you the money to exercise the options. Then, the broker sells some of the resulting stock. Finally, the broker pays herself back, plus a pre-disclosed fee, and returns the rest to you.
This also works with private stock. (Unless you forgot Rule No. 1; if your shares aren't transferable you've already been screwed.) But you may not require a broker. Some companies allow for direct cashless exercise. Suppose you hold options for 100 shares struck at $100 per share. You need $10,000 to exercise. The company figures its stock's "fair market value" is $110. You check with outside sources, e.g. a private-stock broker, and conclude this is not much less than what you could sell your stock for in the market. Your stock is worth $11,000 to the company; it is $1,000 in the money. After cashlessly exercising with the company you would get $1,000 of stock, i.e. 9 shares. (Fractions of shares are usually lopped off in these calculations.)
Plus: you got shares without putting up capital. Minus: you lost the upside (and downside) on ninety-one shares. That said, 9 shares is better than 0 because you had no capital to exercise upon termination.