Smarter Week

How to automate it

How to automate “compare versions to see what the other side changed”

Here are 2 ways to spend less time on this, best first. Each comes with steps you can follow today and, for AI fixes, a prompt to copy.

20 min
typically, a few times a week
75%
of the time can be automated
Easy
to set up

Fix 1 of 2

Software featureBest fix

Run a proper compare instead of reading for changes

Word Compare, Litera Compare or Draftable show every change between versions, including ones the other side did not mark.

Typically saves about 60% of the time10 min to set up
  1. 1Always compare the returned draft against your last sent version, not the one they marked up.
  2. 2Use Word Review > Compare, Litera Compare or Draftable.
  3. 3Ask AI to summarize the substantive changes from the compare if it is long.

Tools: Microsoft Word Compare · Litera Compare · Draftable

Fix 2 of 2

AI

Have AI do a first pass against your playbook, then a lawyer decides

Contract AI (Spellbook, LegalOn, Ironclad AI, Harvey, Legora, Copilot in Word) flags clauses that differ from your positions and suggests redlines. A qualified reviewer accepts or rejects every change; use only tools approved for confidential documents.

Typically saves about 40% of the time2 h to set up
  1. 1Write your playbook: for the 10 to 15 clauses that matter, your standard position, acceptable fallback and walk-away.
  2. 2Use a contract AI tool or an enterprise AI account your company has approved for client and counterparty data.
  3. 3Run the contract with the prompt below (or load the playbook into the tool).
  4. 4Review every flag and suggested redline yourself; do not send AI redlines unread.
  5. 5Add new positions to the playbook as you negotiate.
Prompt to copy
You are assisting an in-house lawyer. Review the attached [CONTRACT TYPE] from the perspective of [OUR COMPANY] as [CUSTOMER / VENDOR]. Compare it against our playbook below. For each clause that differs, give: clause reference, what it says, our position, risk level (high/medium/low), and a suggested redline in tracked-change style. Then list any missing clauses we normally require. Do not give a final recommendation to sign; quote the contract exactly.

Playbook:
[PASTE POSITIONS]

Tools: Spellbook · LegalOn · Ironclad AI · Harvey · Legora · Microsoft Copilot in Word · Enterprise ChatGPT, Claude, Gemini or Microsoft Copilot (approved for confidential data)

Who does this task

Roles in our library that list this as one of their common tasks. Each guide covers the rest of that role’s week.

In-house counselContract managerParalegal / legal operations

HourLeak · the 8-minute work audit

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Other common tasks for In-house counsel