[BlewisJS]

You can't presume that they exercised early voluntarily. If you leave the company, you typically have 90 days to exercise options or they are forfeited back to the company. In other cases, they actually just expire after enough time passes, which again forces employees to exercise before a liquidity event.

[tvladeck]

Fair point. I did make that assumption.

[alttab]

To your point though, and to press it further - if companies require that you exercise your options in a window after they vest or they expire - they were never really options to begin with. In essence, the vesting schedule on expiring options is a timeline for you forking over risk-filled cash or forfeit part of your "compensation."

The advice seems to suggest if their options expire if you don't buy them at a certain point (except for leaving the company, which makes sense), say no and ask for cash. If they can't pay, now you know where you really stand.

[JonFish85]

Again though nobody forced them to exercise. It accelerates the timeline, but it's not forcing anyone into anything more than having to make a decision.

[tptacek]

Typically, when you leave a company that issued you incentive options, you are forced to execute within 90 days or forfeit the shares entirely.