409A valuation history and expiration check

What I did: Was about to approve a new batch of option grants and needed to confirm our 409A was still current before authorizing the exercise prices.

The prompt I used:

Show me all 409A valuations for [Company Name], including the effective date, expiration date, and common stock FMV at each valuation. Flag any that are expired or expiring within 30 days.

How it works: Returns the full 409A history with dates and FMV values, then checks whether any valuation is expired or within 30 days of expiration. Grants issued against an expired 409A create IRS risk under Section 409A — this is a quick compliance check that takes 10 seconds.

Result: Current valuation confirmed as valid, with expiration date flagged so we knew when to initiate the next refresh. No grants delayed.