Here is a thought from a CDN perspective. Exercising options at what appears to be a low point (ie. expecting higher prices in short term) would minimize the capital gains tax and once exercised any future gains from the resulting shares could be sheltered from tax presumably in a TFSA, assuming of course that he has room to contribute.

Can't comment from a US perspective but I suspect it is tax driven irrespective of jurisdiction.

If the shares are subsequently sold then all of the above may not apply

Hogan