This assumes your shares are worth more than your exercise price. :) In order to get long-term capital gain treatment you will need to hold the shares for 1 ye

This assumes your shares are worth more than your exercise price. :) In order to get long-term capital gain treatment you will need to hold the shares for 1 year + 1 day. And more than 2 years from the grant date (this part usually isn't an issue). By exercising every month after the 1 year cliff you essentially dollar-cost averaging your purchases. You might also want to use a similar strategy when it comes time to sell. Also keep in mind that the long term capital gain rate is currently 20% plus 3.8% net investment income tax. (Again this if federal only).