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Draft an ISO grant memo with the math done

This page lists three turns, the messages you send to the AI one after another in the same chat, and then a check of the answer. Keep it open next to your chat. Each turn shows the next thing to paste, with the values you entered already filled in. Nothing is sent from this page, and your conversation stays in the AI tool you are using.

Name, role, and whether this is a new hire, promotion, or refresh.

Share count, strike and its valuation source, vesting schedule, acceleration.

Plan name and date, permitted exercise methods, post-termination exercise windows.

Where the grantee is taxed and where the company is incorporated; both change the answer.

Sets the register and how much technical detail sits in the body versus a footnote.

Watch for these throughout

  • The $100,000 limit is measured on FMV at grant of shares first becoming exercisable in a calendar year. Acceleration, an early-exercise feature, or a second grant in the same year can push a previously compliant grant over the cap. Recompute whenever any of those happen.
  • Section 409A requires the strike to be at or above FMV on the grant date. A stale 409A, or a grant dated before the board actually approved it, creates penalty exposure for the grantee, not the company.
  • ISO status is lost if the option is exercised more than three months after termination (twelve for disability). Plans routinely give a longer window, which means the option survives as an NSO. Say so explicitly or the grantee will be surprised.
  • State tax treatment of the AMT preference item and of disqualifying dispositions varies. Confirm the grantee's state of residence at exercise, not at grant.
  • Net exercise and share withholding generally disqualify the netted shares from ISO treatment. Confirm what the plan permits before describing exercise methods.