Prompt of the day

Redline playbook check: compare a draft against your standard positions

A counterparty sent their paper. Flag where it deviates from your playbook and what to push back on — as a first pass for an attorney.

You are a transactional attorney doing a first-pass playbook comparison on a contract draft for a licensed lawyer's review — a drafting aid, not legal advice.

Produce:

A) DEVIATION TABLE — each clause I flagged or pasted: the counterparty's position, my standard/fallback position (from what I gave you), the gap, and a risk rating (high / medium / low).

B) MISSING PROTECTIONS — the standard clauses absent from this draft that my playbook would expect.

C) SUGGESTED REDLINES — for the high-risk gaps, proposed language that moves toward my position, marked as a starting point to be reviewed.

D) ESCALATION LIST — the 2-3 points worth a partner's or client's decision rather than a standard redline.

Inputs: [CONTRACT CLAUSES — ANONYMIZED] · [MY STANDARD / FALLBACK POSITIONS] · [DEAL CONTEXT] · [MY LEVERAGE]

Rules: Do not invent clauses, law, or market-standard claims I didn't provide — mark anything uncertain "VERIFY". Anonymize — never paste party names, confidential terms, or client identifiers into a consumer LLM (ABA Formal Op. 512). This is a drafting aid, not legal advice; the attorney owns every redline and the final judgment.

Why it works — A manual redline is slow and inconsistently catches deviations; a playbook-anchored deviation table with risk ratings and a missing-protections scan finds the gaps faster than a linear read — while the anonymize rule and VERIFY flags keep client confidences and unverified market claims out of the workflow, leaving the attorney to own every judgment.

Have AI pressure-test your work before your boss does

AI is a free, tireless red-team. Finding your own holes before the meeting is how you look three steps ahead.

Paste your draft/plan and say: 'You are the toughest skeptic in the room. List the 5 weakest points and the exact questions a critic will ask. Then tell me how to fix each.'

1. Paste the plan or draft.
2. Ask for the 5 weakest points + the questions they'll trigger.
3. Patch the holes before you present.