While some of the rules that govern stock options are dictated by tax and securities laws, many variables in the ways option grants work are left for each company to provide in its stock plan and in the grant agreement that recipients must often accept. Stock options give you the right to purchase a specified number of shares of the company's stock at a fixed price during a rigidly defined timeframe. The purchase is called the exercise , and the fixed price set at grant is called the exercise price. Typically, you must continue to work at the company for a specified length of time before you are allowed to exercise any of the stock options.

That length of time is called the vesting period , which is characterized by a vesting schedule. Under a vesting schedule , an option grant can be set up so that it vests either all at once cliff vesting or in a series of parts over time graded vesting. The graphic below illustrates the concept of a typical graded vesting schedule. While vesting periods for stock options are usually time-based , they can also be based on the achievement of specified goals, whether in corporate performance or employee performance see the FAQ on performance-based stock options.

Stock options always have a limited term during which they can be exercised. The most common term is 10 years from the date of grant. Of course, after the vesting period has elapsed, the actual amount of time to exercise the options will be shorter e. If the options are not exercised before the expiration of the grant term, they are irrevocably forfeited. Employees who leave the company before the vesting date usually forfeit their options.

With vested options , departing employees typically have a strictly enforced timeframe often 60 or 90 days in which to exercise—they are almost never allowed the remainder of the original option term. Since the exercise price is nearly always the company's stock price on the grant date, stock options become valuable only if the stock price rises, thus creating a discount between the market price and your lower exercise price.

However, any value in the stock options is entirely theoretical until you exercise them—i.

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After you have acquired the shares through this purchase, you own them outright, just as you would own shares bought on the open market. Depending on the rules of your company's stock plan, options can be exercised in various ways.

What You Need to Know About Stock Options

If you have the cash to do so, you can simply make a straightforward cash payment , or you can pay through a salary deduction. Alternatively, in a cashless exercise , shares are sold immediately at exercise to cover the exercise cost and the taxes. If your company's stock price rises, the discount between the stock price and the exercise price can make stock options very valuable. That potential for personal financial gain, which is directly aligned with the company's stock-price performance, is intended to motivate you to work hard to improve corporate value.

In other words, what's good for your company is good for you. However, by the same token, stock options can lose value too. If the stock price decreases after the grant date, the exercise price will be higher than the market price of the stock, making it pointless to exercise the options—you could buy the same shares for less on the open market.

Options with an exercise price that is greater than the stock price are called underwater stock options. Companies can grant two kinds of stock options: nonqualified stock options NQSOs , the most common type, and incentive stock options ISOs , which offer some tax benefits but also raise the risk of the alternative minimum tax AMT.

Thus the word nonqualified applies to the tax treatment not to eligibility or any other consideration. NQSOs are the most common form of stock option and may be granted to employees, officers, directors, contractors, and consultants. You pay taxes when you exercise NQSOs.

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When you sell the shares, whether immediately or after a holding period, your proceeds are taxed under the rules for capital gains and losses. For a detailed explanation of the tax rules, see the related sections of the Tax Center on this website. However, to qualify they must meet rigid criteria under the tax code. The vesting period is the length of time that an employee must wait in order to be able to exercise their ESOs.

Forms of Stock Option Agreement and Stock Option Exercise Agreement

Why does the employee need to wait? Because it gives the employee an incentive to perform well and stay with the company. Vesting follows a pre-determined schedule that is set up by the company at the time of the option grant. Note that the stock may not be fully vested when purchased with an option in certain cases, despite exercise of the stock options, as the company may not want to run the risk of employees making a quick gain by exercising their options and immediately selling their shares and subsequently leaving the company.

If you have received an options grant, you must carefully go through your company's stock options plan, as well as the options agreement, to determine the rights available and restrictions applied to employees. The options agreement will provide the key details of your option grant such as the vesting schedule, how the ESOs will vest, shares represented by the grant, and the strike price.

If you are a key employee or executive, it may be possible to negotiate certain aspects of the options agreement, such as a vesting schedule where the shares vest faster, or a lower exercise price. It may also be worthwhile to discuss the options agreement with your financial planner or wealth manager before you sign on the dotted line.

ESOs typically vest in chunks over time at predetermined dates, as set out in the vesting schedule. As mentioned earlier, we had assumed that the ESOs have a term of 10 years. This means that after 10 years, you would no longer have the right to buy shares.

Therefore, the ESOs must be exercised before the year period counting from the date of the option grant is up. It should be emphasized that the record price for the shares is the exercise price or strike price specified in the options agreement, regardless of the actual market price of the stock. In some ESO agreements, a company may offer a reload option. A reload option is a nice provision to take advantage of. We now arrive at the ESO spread. As will be seen later, this triggers a tax event whereby ordinary income tax is applied to the spread.

The following points need to be borne in mind with regard to ESO taxation:. This spread is taxed as ordinary income in your hands in the year of exercise, even if you do not sell the shares. This aspect can give rise to the risk of a huge tax liability, if you continue to hold the stock and it plummets in value.

The ability to buy shares at a significant discount to the current market price a bargain price, in other words is viewed by the IRS as part of the total compensation package provided to you by your employer, and is therefore taxed at your income tax rate. Thus, even if you do not sell the shares acquired pursuant to your ESO exercise, you trigger a tax liability at the time of exercise. The value of an option consists of intrinsic value and time value. Time value depends on the amount of time remaining until expiration the date when the ESOs expire and several other variables.

Given that most ESOs have a stated expiration date of up to 10 years from the date of option grant, their time value can be quite significant. While time value can be easily calculated for exchange-traded options, it is more challenging to calculate time value for non-traded options like ESOs, since a market price is not available for them. To calculate the time value for your ESOs, you would have to use a theoretical pricing model like the well-known Black-Scholes option pricing model to compute the fair value of your ESOs.

You will need to plug inputs such as the exercise price, time remaining, stock price, risk-free interest rate, and volatility into the Model in order to get an estimate of the fair value of the ESO. From there, it is a simple exercise to calculate time value, as can be seen below. The exercise of an ESO will capture intrinsic value but usually gives up time value assuming there is any left , resulting in a potentially large hidden opportunity cost. The value of your ESOs is not static, but will fluctuate over time based on movements in key inputs such as the price of the underlying stock, time to expiration, and above all, volatility.

Consider a situation where your ESOs are out of the money i. It would be illogical to exercise your ESOs in this scenario for two reasons. The biggest and most obvious difference between ESOs and listed options is that ESOs are not traded on an exchange, and hence do not have the many benefits of exchange-traded options. Exchange-traded options, especially on the biggest stock, have a great deal of liquidity and trade frequently, so it is easy to estimate the value of an option portfolio.

Not so with your ESOs, whose value is not as easy to ascertain, because there is no market price reference point. Many ESOs are granted with a term of 10 years, but there are virtually no options that trade for that length of time.

The Downside Risk

LEAPs long-term equity anticipation securities are among the longest-dated options available, but even they only go two years out, which would only help if your ESOs have two years or less to expiration. Option pricing models are therefore crucial for you to know the value of your ESOs. Your employer is required—on the options grant date—to specify a theoretical price of your ESOs in your options agreement.

Be sure to request this information from your company, and also find out how the value of your ESOs has been determined. Option prices can vary widely, depending on the assumptions made in the input variables. For example, your employer may make certain assumptions about expected length of employment and estimated holding period before exercise, which could shorten the time to expiration.

With listed options, on the other hand, the time to expiration is specified and cannot be arbitrarily changed. Assumptions about volatility can also have a significant impact on option prices. If your company assumes lower than normal levels of volatility, your ESOs would be priced lower.

Exercising Stock Options

Listed options have standardized contract terms with regard to number of shares underlying an option contract, expiration date, etc. This uniformity makes it easy to trade options on any optionable stock, whether it is Apple or Google or Qualcomm. If you trade a call option contract, for instance, you have the right to buy shares of the underlying stock at the specified strike price until expiration.

Similarly, a put option contract gives you the right to sell shares of the underlying stock until expiration. While ESOs do have similar rights to listed options, the right to buy stock is not standardized and is spelled out in the options agreement. For all listed options in the U. If the third Friday happens to fall on an exchange holiday, the expiration date moves up by a day to that Thursday. Thus, if you owned one call option contract and at expiration, the market price of the underlying stock was higher than the strike price by one cent or more, you would own shares through the automatic exercise feature.

Likewise, if you owned a put option and at expiration, the market price of the underlying stock was lower than the strike price by one cent or more, you would be short shares through the automatic exercise feature. Note that despite the term "automatic exercise," you still have control over the eventual outcome, by providing alternate instructions to your broker that take precedence over any automatic exercise procedures, or by closing out the position prior to expiration.

With ESOs, the exact details about when they expire may differ from one company to the next. Also, as there is no automatic exercise feature with ESOs, you have to notify your employer if you wish to exercise your options. With ESOs, since the strike price is typically the stock's closing price on a particular day, there are no standardized strike prices.