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What to Include in an Annual Legal Checkup (and Why It Matters)

Running a business means juggling a lot — and legal issues often take a backseat until something goes wrong. But just like you schedule checkups for your health or finances, your business deserves the same attention.

An annual legal checkup can help you:

  • Catch small issues before they become big problems
  • Make sure your documents and practices still match your goals
  • Protect yourself from unnecessary risk
  • Feel confident heading into the next phase of growth

Here’s what that checkup should cover — and why it’s worth your time.


What to Review in an Annual Legal Checkup

1. Business Structure

  • Is your current structure (LLC, S Corp, nonprofit, etc.) still the best fit?
  • Have there been ownership changes, new partners, or shifts in how you operate?

2. Operating Agreement or Bylaws

  • Are roles, decision-making, and ownership reflected accurately?
  • Would the agreement hold up if someone left or a dispute came up?

3. Contracts & Templates

  • Are your core contracts up to date and tailored to your current services?
  • Do your templates cover the right legal protections (payment terms, IP, dispute resolution)?
  • Are there handshake deals that should be formalized?

4. Employment & HR Basics

  • Are your workers properly classified (employee vs. contractor)?
  • Do you have updated offer letters, agreements, or an employee handbook?
  • Are you complying with current labor laws in your state?

5. Licenses, Permits & Filings

  • Are all business licenses, permits, and registrations current?
  • Have you filed any annual reports or corporate updates required in your state?

6. Intellectual Property & Branding

  • Are your name, logo, website, and content protected?
  • Should you consider registering a trademark?

7. Insurance & Risk Management

  • Do you have the right insurance coverage in place for your size and services?
  • Are you exposed to unnecessary legal or financial risks?

8. Website, Privacy & Online Activity

  • Are your website terms of service and privacy policy up to date?
  • Do you collect customer or donor data in a legally compliant way?

Real-World Example: The Growing Business With Hidden Gaps

A successful boutique consulting firm reached out for help with a potential investor. They’d grown quickly over the past two years — hired a few contractors, launched new services, and built up a strong client base.

But when we started reviewing the legal side, a few things surfaced:

  • Their operating agreement hadn’t been touched since day one. It didn’t reflect how profits were actually being shared or how a new investor could be brought in.
  • Their client contract didn’t match their current offerings — and was missing important terms like late fees, dispute resolution, and IP ownership.
  • Their contractor agreements were outdated, and one worker should likely have been classified as an employee.
  • They’d rebranded with a new logo and name — but hadn’t taken steps to protect their intellectual property.

They weren’t in crisis — but these issues could’ve created major problems if they’d moved forward without fixing them. After a full legal checkup, we brought everything up to speed and built a plan for growth with a solid legal foundation.


Why It Matters

Legal checkups aren’t about chasing paperwork — they’re about protecting what you’re building.
As your business grows, so does the risk of something slipping through the cracks.

A little legal maintenance each year can help you:

  • Avoid costly disputes or fines
  • Strengthen your position in deals and negotiations
  • Plan with more clarity and confidence

Want Help With a Legal Checkup?

We offer flexible support options for small businesses and nonprofits. Whether you need a simple review or a deeper dive, we’d be happy to help you stay legally healthy.

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