Build an inventory of your awards.
Collect grant agreements, vesting schedules, exercise deadlines, and transaction history. Keep different award types distinct when reviewing your options.
Model the cash requirement.
An exercise or sale may involve an exercise cost, withholding, or other tax payments. Ask your advisor to model your specific situation before committing cash.
Look beyond a single transaction.
Connect timing with your other income, expected liquidity needs, company restrictions, and longer-term financial goals.
Coordinate your advisors.
Your tax professional, financial advisor, and legal team may each see a different part of the picture. A coordinated discussion helps identify questions before a decision.
Disclaimer: This content is for educational purposes only and may not reflect current laws or guidance. Consult your tax advisor before implementing any strategy discussed.