Questions to take to a tax adviser before an option exercise

Prepare the facts

Record jurisdiction, option type, grant date, vesting, exercise date, shares, strike, fair market value method, sale plan, prior exercises, and relevant household tax information. Bring the plan documents and company-provided valuation or reporting material.

For US taxpayers, incentive and nonqualified options can produce different regular-tax, payroll, alternative-minimum-tax, basis, and reporting questions.

• Option classification
• Exercise spread
• Fair value source
• Holding period
• Withholding and estimated tax

Ask about the full sequence

Discuss exercise, holding, sale, disqualifying disposition where applicable, loss, expiration, and state mobility. Confirm basis reporting and how company forms should be reconciled with broker records.

Tax rules change and individual facts matter. This workbook is a preparation aid, not a tax calculation or recommendation.