Here's an example - say I'm hired with 1000 units of stock over four years. Each year I receive a refresher grant of 250 units of stock, again vesting over four years. Once I reach Year 4, my stock compensation stabilizes, assuming my refreshers remain the same (I'm am obviously grossly simplifying - you could be promoted and get larger grants, the company could do badly and your dollar value be significantly reduced).
But what you can do, and what the parent is alluding to, is jump ship around year 3-4 and get the company you're going to match your current amount of outstanding stock, meaning your initial grant becomes much higher, and your refreshers do too. At least, that's the idea. It's worked for me.
Additionally, although personally I did very well on my refresher grants I know other people at my employer did not. So that's another factor.
Some places offer a bunch to start, but very little after that, which means people tend to leave once they have vested all their options/RSUs.
After the first year, sometimes your vesting schedule will be monthly, quarterly, twice a year, or once a year. As to why they don't allow everyone to be monthly - it's probably because they get to claw back a fair amount of the equity if people leave.
I may be being a little cynical, but if you vest annually or bi-annually you can get a pretty good idea of when your employees are going to leave and use that to plan your crunch periods accordingly. People are rather unlikely to quit the month before the annual vesting date.
To me, the first rule of rewarding someone is to make sure the recipient did all of the work before the reward. If you make them work afterward then it sours the desserts.
I would end up holding onto those little blocks until the next batch of original stocks vested because I had to push a bunch of buttons like a monkey (in a UI designed by monkeys) for a couple hundred bucks. Which just reminded me that I could be making more money and a bigger impact working just about anywhere else.
And then they cancelled the only project that any of us thought had any strategic value to the company. So my direct manager quit. Then someone else quit. Then I gave about 3 weeks notice, but was the 5th one out the door because 2 other people resigned in the week after I gave mine. In all about 8 people left in something like 12 weeks.
Because we all quit right after the end of the fiscal year, we were all owed a bonus from the previous one. When we got the bonus check (mine was a little over 2 month's pay, but the majority of the others got better reviews so got bigger payouts) we went out for beers. Someone, probably me, asked if it was worth it to stay for the last four+ months when things started going sideways. Only one person said yes, out of eight.
For executives and directors, I disagree completely. The shareholders are paying them to make and execute decisions that will grow the company (and share price) over a long period of time. The share-based compensation plan should reflect (and help align) that they are being paid to make long-term decisions.
Those are inherently "promise/award before the hard work is done" type of grants as I see it. (Why would I pay you more for a decision you've already made or work you already did, unless we're just talking about a modest spot bonus for a job well done?)
Others do performance based refreshes, so job hoppers often think they’re never getting more stock, because they had their eye on the next gig or their side hustle or whatever.
