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What Issues Should I Consider Regarding My Non-Qualified Stock Options?

Updated: Jun 7, 2023

Non-Qualified Stock Options (“NQSOs”) are a common form of equity compensation, offering a share in the potential appreciation of a company’s value. Many of our clients have been (or will be) granted NQSOs as an employee of an issuing company or as an officer, directors, contractors, or consultants. Deciding whether and when to exercise NQSOs and sell shares can be difficult and requires cash flow analysis, complex tax planning, and a long-term strategy.

This checklist helps guide your conversations when advising clients regarding their NQSOs. It covers:

  • Issues to consider at grant

  • Implications of exercise, including early exercise and post-vesting

  • Tax considerations and the IRC 83(b) election

  • Share ownership and sale strategies

  • Concentration and other risks

In today's rapidly evolving business landscape, employee compensation packages have expanded beyond traditional salary and benefits. Equity compensation, such as non-qualified stock options (NQSO) or NSO, has become increasingly prevalent, offering employees a stake in the potential growth and success of their companies. However, understanding the intricacies of non-qualified stock options and making informed decisions regarding their exercise and sale can be a challenging task. In this blog post, we will delve into the key aspects of NQSOs and provide a helpful checklist to guide you through the process.


Grant Issues:

The first step in navigating non-qualified stock options is understanding the options granted to you. Collaborating with your HR department and financial advisor can help you gain clarity on the type of options you have received. It is crucial to differentiate between incentive stock options (ISOs) and non-qualified stock options, as they have different tax implications. Consulting with a qualified tax preparer or CPA can shed light on the tax implications associated with your stock options, including when and how they will be taxed.


Vesting Schedule and Expiration:

Non-qualified stock options often come with a vesting schedule, which determines when you gain full ownership of the shares. Monitoring the expiration of relevant time periods is essential to avoid missing out on exercising your options. Additionally, understanding whether your options have an early exercise feature allows you to make informed decisions about when to exercise them based on your individual circumstances. Considerations such as clawback provisions and the impact of termination of employment should also be evaluated.


Exercise Issues:

When it comes to exercising your non-qualified stock options, several factors must be taken into account. Determining the value of your interest, including the grant price and fair market value, is crucial. It is important to assess whether your options are "in the money" (exercisable at a profit) or "underwater" (exercisable at a loss) and evaluate the potential for future stock appreciation. Additionally, examining dividend policies, any discounts on underlying shares, and the long-term viability of the company is essential to make informed decisions.


Tax Implications:

Non-qualified stock options have tax implications that should be carefully considered. Understanding the income tax limitations associated with exercising your vested options is crucial. The spread between the exercise price and the fair market value at exercise is a key factor in determining the tax owed. Seeking guidance from a tax professional can help you navigate the tax landscape effectively. Exploring options like the 83(i) election, which allows for the deferral of income tax, can also be advantageous.


Cash Flow and Ownership:

Determining the availability of funds for a cash exercise is an important consideration. If you lack the necessary funds, alternative strategies such as borrowing, cashless exercise, or a stock swap can be explored. However, it is essential to carefully assess the tax consequences associated with these alternatives. Understanding the basis of your shares, especially in the case of early exercise, is crucial for accurate tax reporting and minimizing potential tax liabilities.


Sales Strategies and Risk Mitigation:

When it comes to selling shares acquired through non-qualified stock options, understanding the tax consequences is paramount. Considerations such as pre-clearance requirements or blackout windows that restrict trading activities should be taken into account. Additionally, mitigating concentration risk by diversifying your investment portfolio and avoiding over-reliance on your employer's stock is essential. Assessing other risks such as price decline and addressing options within your estate plan or during a divorce are also important aspects to consider.


Non-qualified stock options offer employees an opportunity to participate in their company's growth and success. However, navigating the complexities of NQSOs requires careful analysis and consideration. By following the checklist provided in this blog post and seeking guidance from qualified professionals, you can make informed decisions regarding the exercise and sale of your non-qualified stock options. Remember, understanding the tax implications, assessing risk, and aligning your options with your financial goals are crucial steps towards maximizing the potential benefits of your stock options.


Feel free to visit our website at www.mygatewaymoney.com to access the checklist mentioned in this blog post. If you have any further questions or require assistance, please reach out to us via email, as provided on our website. We appreciate your support and encourage you to share this valuable resource with others who may benefit from it. Together, let's empower ourselves with knowledge and make informed decisions about our financial future.

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