When this workflow applies
Use it when multiple grants overlap, when you are planning a house purchase or relocation, when your company stock is a large part of net worth, or when you need a clear CPA packet.
Step-by-step workflow
- List grants, vesting dates, exercise windows, cost basis, and holding-period start dates.
- Separate decisions by tax type: RSU ordinary income, ISO AMT spread, ESPP qualifying disposition, and capital gains.
- Run side-by-side scenarios for sell now, hold, exercise gradually, and defer action.
- Choose a strategy that fits taxes, liquidity, risk tolerance, and career uncertainty.
Common risks to check
- Optimizing for tax alone can increase concentration risk.
- A good exercise plan can fail if you cannot cover the cash cost and potential tax.
- Incomplete lot records can lead to wrong cost basis and wrong gain estimates.
How EquityTax Pilot fits
EquityTax Pilot keeps lots, holding periods, reminders, and scenario reports connected so equity planning is not scattered across spreadsheets.