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Contract Checklist

The Contract Red-Flag Checklist

10 things to scan for before you sign — ordered fastest to slowest, no legal training required.

Chandra Kumar9 min
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A business owner highlights a red-flag clause on a printed contract before signing

Chandra Kumar

Founder & CEO, WiselyWise · Builder, SmartMaya AI · MIT Sloan AI Certification · 29 years enterprise technology

The short answer

Scan a contract for red flags by working through a fixed checklist in order: auto-renewal terms, liability caps, and payment terms first (fastest to check), then termination rights, non-compete scope, IP assignment, indemnification, confidentiality duration, dispute resolution, and amendment rights. Manually this takes 15-20 minutes; an AI contract scanner runs the same checklist in under 5 minutes.

Key Takeaways

  • 10 checks, ordered fastest to slowest — start with the 10-second ones before the 1-minute ones.
  • Most red flags are asymmetries: one side gets an advantage the other doesn't — that's the pattern to look for.
  • A red flag isn't automatically a dealbreaker — most are a one-line ask to fix before you sign.
  • An AI contract scanner runs this exact checklist in under 5 minutes if you'd rather not do it by hand.

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Why a checklist beats reading the whole thing

Most people either read a contract cover to cover — which takes an hour and buries the risky lines in boilerplate — or skip reading it entirely and hope for the best. Neither works well. A fixed checklist gets you most of the protection of a full read in a fraction of the time, because the clauses that actually cause problems repeat across almost every commercial agreement.

The 10 checks below are ordered by how fast they are to run — start at the top, work down, and stop early if you're short on time. Even just the first 3 catches the highest-frequency issues. For the full breakdown of what AI can and can't catch beyond this checklist, see what AI actually spots in a contract.

The 10-point checklist

1

Auto-renewal with a short cancellation window

10 sec

Where to look: Look in the "Term" or "Renewal" section, usually near the top or bottom of the contract.

A contract that renews automatically with only a 30-day (or shorter) window to cancel can lock you in for another full term if you miss it by a week.

What to do: Note the exact cancellation deadline and put a calendar reminder 45 days before it — before you sign, not after.

2

No cap on liability

15 sec

Where to look: Search for the word "liability" — there should be a specific dollar figure or multiple of fees paid.

Without a cap, you could be on the hook for damages far beyond what you paid for the service if something goes wrong.

What to do: If there's no cap, that's a real ask for a revision — market standard is 12 months of fees paid.

3

Payment terms that don't match what was discussed

20 sec

Where to look: Compare the written payment schedule against your email thread or verbal agreement.

Net-60 written in when you agreed to Net-30 verbally is the most common silent change in vendor contracts.

What to do: Flag any mismatch in writing before signing — verbal agreements don't hold up once the contract is signed.

4

One-sided termination rights

30 sec

Where to look: Read the termination clause for both parties, not just one.

If the other party can exit anytime with 10 days notice but you're locked in for the full term, that asymmetry rarely favors you.

What to do: Push for matching termination rights on both sides, or at minimum a "termination for convenience" clause you can also use.

5

A non-compete or exclusivity clause bigger than expected

45 sec

Where to look: Check the geography, time period, and market scope of any non-compete or exclusivity language.

A non-compete written for "12 months, direct competitors" is standard. One written for "5 years, the entire industry" is not — and may not even be enforceable, but it's still worth catching before you sign it.

What to do: Compare the scope against what the relationship actually requires. Anything broader is negotiable.

6

IP assignment broader than the actual deliverable

1 min

Where to look: Read the intellectual property section carefully — check if it's scoped to the specific deliverables or written more broadly.

Some agreements assign rights to "all work product," which can unintentionally capture pre-existing tools, methods, or ideas that weren't part of the engagement.

What to do: Confirm the assignment is limited to what was actually created for this specific engagement.

7

Indemnification with no carve-outs

1 min

Where to look: Look for the word "indemnify" and check whether it excludes the other party's own negligence or misconduct.

Without carve-outs, you could end up indemnifying the other party even for damage they caused.

What to do: Standard practice is mutual indemnification with explicit exclusions for gross negligence and wilful misconduct on both sides.

8

Confidentiality obligations that never expire

30 sec

Where to look: Check the confidentiality section for a stated end date or survival period.

Indefinite confidentiality isn't always unreasonable, but it's worth knowing you're agreeing to before you sign, especially if it covers information that will naturally become public or outdated.

What to do: A 2-5 year survival period after the contract ends is typical for most commercial agreements.

9

Vague or missing dispute resolution

30 sec

Where to look: Check for a governing law and dispute resolution clause — arbitration, mediation, or court jurisdiction.

No dispute clause usually means defaulting to expensive court litigation, potentially in a jurisdiction inconvenient for you.

What to do: Confirm the governing law and venue are reasonable for your business, not automatically favoring the other party.

10

Unilateral amendment rights

20 sec

Where to look: Search for "amend" or "modify" and check whether changes require your written consent.

Some agreements let the other party change terms — including pricing — without needing your sign-off on the update.

What to do: Amendments should always require written consent from both parties. This is a straightforward ask to fix.

Related in this series

Frequently asked questions

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