When you exerices your options you are taxed on the difference between your exercise price and the market price. Therefore you have money at risk. If you hold for long term capital gains there is a risk that the stock will go down--why take the risk? You are better off exercising and selling to avoid that risk. The only advantage of stock options is their leverage and after you exercise there is no leverage.
Yes, if you are knowledgeable about your company and the prospects for future appreciation. If you're not sure, you might want to consult with a financial advisor.
Whoa . .. Has your advisor talked to you about NUA? If not, fire them. Net unrealized appreciation is a tax strategy. In English, you may be able to take your company stock out of a 401k (or move your allocation to company stock from a deferred compensation account and repurchase in your 401k), pay tax on your basis, then qualify for capital gains on the appreciation. Many CPAs don't understand this, but hey - most advisors are salespeople that wouldn't know livestock from preferred stock. You know your company, and with a strong financial plan you can make a business decision on how much risk you want to take. We are working with a client near retirement now. We found how he could decrease his potential tax liability by using a NUA strategy. What is the catch? The stock has to go up, not down. That's the trick, isn't it? It is also inside a 401k - and you may not. The main thing an advisor that knows what they are doing will want to know is - do you pay the tax on the options or does your company? Good luck! Drop us a line if you want to talk.
J, there are a gazillion answers to that. My colleagues have touched on some. Mostly, it depends on your goals or purpose for the money. If you don't have a specific purpose for the stock, you may want to leave it alone. If you are leaving the company, you will want to be sure to take your equity with you, though. However, if you are concerned about tax consequences, maybe your 'exercise and hold' plan will work. There are too many variables to consider here, so you best bet is to find a financial planner (not a salesperson) and spend some time discussing your situation. Good luck!
These stock options may be inside a qualified plan or outside a qualified plan. As you can see from the responses, this could be a hand grenade or a cornucopia. We would all need a discussion and have a plethora of questions for you before really know which path to recommend. It is very important that you find someone who is competent to help you sort it all out. Most of the choices that you could make have irreversible consequences and could be very costly to you. Go forth and conquer.