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Stock options and employee stock purchase programs can be good opportunities to help build potential financial wealth. When managed properly, these benefits can help pay for future college expenses, retirement, or even a vacation home.

But many investors get tripped up, don’t pay attention to critical dates, and haphazardly manage their employee stock option grants. Ultimately, they lose out on the many benefits these stock option plans can potentially provide.

To help ensure that you maximize your stock option benefits, avoid making these six common mistakes:

Mistake #1:

Allowing in-the-money stock options to expire

A stock option grant provides an opportunity to buy a predetermined number of shares of your employer’s company stock at a pre-established price, known as the exercise or strike price. Typically, there is a vesting period ranging from one to four years, and you have up to 10 years in which to exercise your options to buy the stock.

A stock option is considered “in the money” when it is trading above the original strike price. Say, hypothetically, you have the option to buy 1,000 shares of your employer’s stock at $25 a share. If the stock is currently trading at $50 a share, your options would be $25 a share in the money. If you exercised them and immediately sold the shares at $50, you’d enjoy a pretax profit of $25,000.

You may be tempted to delay exercise as long as possible in the hope that the company’s stock price continues to go up. Delaying will allow you to postpone any tax impact of the exchange, and could increase the gains you realize if you exercise and then sell the shares. But stock option grants are a use-it-or-lose it proposition, which means you must exercise your options before the end of the expiration period. If you don’t act in time, you forfeit your opportunity to exercise the option and buy the stock at the strike price. When this happens, you could end up leaving money on the table, with no recourse.

In some cases, in-the-money options expire worthless because employees simply forget about the deadline. In other cases, employees may plan to exercise on the last possible day, but may get distracted and therefore fail to take necessary action.

“Ask yourself how much extra value you may get by waiting until the last second to exercise your award, and determine if that’s worth the risk of letting the award expire worthless,” says Carl Stegman, senior vice president of product management for Fidelity Stock Plan Services.

Monitor your vesting schedule, keep your contact information updated, and respond to any reminders you receive from your employer or stock plan administrator.

Consider these factors when choosing the right time to exercise your stock options:

• What are your expectations for the stock price and the stock market in general?

• If you think the stock has peaked or is likely to fall in the future, consider excercising and selling. If you think it may continue to go up, you may want to exercise and hold the stock, or delay exercising your options.

Mistake #2:

There are two kinds of stock option grants: incentive stock options (ISOs) and nonqualified stock options (NSOs). When you receive an ISO grant, there’s no immediate tax effect and you do not have to pay regular income taxes when you exercise your options, although the value of the discount your employer provided and the gain may be subject to alternative minimum tax. However, when you sell shares of the stock, you’ll be required to pay capital gains taxes, assuming you sold the shares at a price higher than your strike price. You must hold your shares at least one year from the date of the exercise and two years from the grant date to qualify for the long-term capital gains rate.

If you sell ISO shares before the required holding period, this is known as a disqualifying disposition. In such a case, the difference between the fair market value of the stock at exercise (the strike price) and the grant price—or the entire amount of gain on the sale, if less—will be taxed as ordinary income, and any remaining gain is taxed as a capital gain. For most people, their ordinary income tax rate is higher than the long-term capital gains tax rate.

While taxes are important, they should not be your sole consideration. You also need to consider the risk that your company’s stock price could decline from its current level. “Be aware of your tax situation, but also understand where you are in the marketplace, because there are also risks to continuing to hold the shares,” says Stegman. “Know which shares are qualified for special tax treatment, what the holding periods are, and transact accordingly.”

Mistake #3:

Contact HR for details on your stock option grants before you leave your employer, or if your company merges with another company.

If your company is acquired by a competitor or merges with another company, your vesting could be accelerated. In some cases, you might have the opportunity to immediately exercise your options. However, be sure to check the terms of the merger or acquisition before acting. Find out if the options you own in your current company’s stock will be converted to options to acquire shares in the new company.

Mistake #4:

Concentrating too much of your wealth in company stock

Earning compensation in the form of company stock or options to buy company stock can be highly lucrative, especially when you work for a company whose stock price has been rising for a long time. At the same time, you should consider whether you have too much of your personal wealth tied to a single stock.

Why? There are two main reasons. From an investment perspective, having your investments highly concentrated in a single stock, rather than in a diversified portfolio, exposes you to excess volatility, based on that one company. Moreover, when that company is also your employer, your financial well-being is already highly concentrated in the fortunes of that company in the form of your job, your paycheck, and your benefits, and possibly even your retirement savings.

History, too, is littered with formerly high-flying companies that later became insolvent. When Enron filed for bankruptcy in 1999, more than $1 billion in employee retirement savings evaporated into thin air. More recently, Lehman Brothers employees shared a similar fate.

Consider, too, that income from your employer pays your nondiscretionary monthly bills and your health insurance. Should your company’s fortunes take a turn for the worse, you could find yourself without a job, no health insurance, and a depleted nest egg.

Consult with a financial advisor to develop a plan to ensure that your investments are appropriately diversified.

“Stock from an equity plan is usually a large component of an employee’s annual compensation, so it’s easy to become overly concentrated in your employer’s stock,” says Stegman. “But you need to take a step back, consider how these benefits fit into your long-term financial objectives, such as college savings, retirement, or a vacation home, and develop a plan to diversify accordingly.”

Mistake #5:

Employee Stock Purchase Plans (ESPPs) allow you to purchase your employer’s stock, usually at a discount from the stock’s current fair market value. These discounts typically range from 5% to 15%. Many plans also offer a “look-back option,” which allows you to buy the stock based on the price on the first or last day of the offering period, whichever is lower. If your company offers a 15% discount and the stock rose 5% during the period, you could buy the stock at a 20% discount, already a healthy pretax gain.

Unfortunately, some employees fail to take advantage of their company’s ESPP. If you are not participating, you may want to give your ESPP a second look.

“Employees often opt out of their ESPP when they are entry-level employees,” says Stegman. “But as they become more established in their careers and more financially secure, they should reconsider their ESPP. Depending on the discount your company offers, you could be passing on the opportunity to buy your company’s stock at a significant discount.”