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. For U.S. trademark registrations, the Section 8 filing is due between the fifth and sixth anniversaries, with a six-month grace period available for an extra fee.
- 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.
- For USPTO trademark registrations, the Section 8 declaration of continued use is due between the fifth and sixth anniversaries after registration, with a six-month grace period available for an extra fee.
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.
