Some of the questions that you need to ask and think about when exercising stock options:

• What type of options do you have?
• Are you aware of the taxation on the different types of options?
• Are you aware that you trigger alternative minimum tax when you exercise an incentive stock option?
• What do you think the stock is going to do over the next 10 years?
• What if the stock goes down at the end of the 10 years?
• Are you going to hold all your options for 10 years?
• Are you better off selling some options each year?
• Is your portfolio concentrated in one stock?
• Should you design a strategy to sell the options? 

Selling incentive stock options or qualified stock options; a glossary of terms

10 Things you should know to get the most from your employee stock options