Why this matters
Legal health decays quietly: contracts drift, filings lapse, policies stop matching reality. An annual checkup with the lawyer you vetted earlier in this checklist catches small gaps before they become penalties, lost trademarks, or a diligence disaster when you raise or sell.
What "done" looks like
- A recurring calendar block, same month every year, with your lawyer
- A standing agenda: entities, contracts, employment, IP, compliance
- State filings and renewals confirmed current
- A short punch list of fixes with owners and deadlines
How to do it
- Pick a fixed month — many founders tie it to fiscal year-end or their state's filing season.
- Confirm entity housekeeping: annual reports, franchise taxes, registered agent, licenses.
- Review the contract stack: customer and vendor templates, leases, anything auto-renewing or expiring within a year.
- Audit employment: handbook vs. actual practice, contractor classification, new state laws if you've hired remotely.
- Check IP deadlines — U.S. trademark registrations cancel if the required maintenance filing isn't made between the fifth and sixth year.
- Close with a punch list and book next year's checkup before you hang up.
Common mistakes
- Only calling the lawyer when something is already on fire
- Letting auto-renewing contracts and registrations roll over unread
- Skipping "quiet" years — those are exactly when drift accumulates
Real-world examples
- Delaware corporations must file an annual report and pay franchise tax by March 1; missing it brings penalties and can cost good standing — a standard diligence check.
- USPTO trademark registrations are canceled if the Section 8 declaration of continued use isn't filed between the fifth and sixth year after registration.
From a founder's point of view
An annual checkup reframes legal from emergency service to maintenance, and maintenance is always cheaper. What it catches — lapsed registrations, stale templates, misclassified workers — costs multiples of the hour it takes to find.
Rule of thumb
If you can't say when your next legal checkup is scheduled, the honest answer is "never" — book a recurring one now.