Redline is the AI Assistant's editing engine. Where Ask helps you understand a contract, Redline helps you improve it. You point the AI at a clause, tell it what needs to change, and it proposes a tracked change directly in your document. You stay in control of every edit: nothing is applied without your approval.

How to use Redline

1. Open your contract in Word and launch the SimpleAI sidebar
2. Select Redline from the action selector
3. Highlight the clause you want to edit in your document or tell it which area to focus on 
4. Type your instruction 
5. Hit send
6. Review the proposed tracked change and decide what to do with it

💡 The more specific your instruction, the cleaner the output. One clear direction produces better redlines than a long explanation. Tell the AI what you want the clause to do, not the reasoning behind it.

What Redline is built for

Redline works best for targeted, clause-level improvements. It is not designed for full-document analysis (use Ask for that) or for creating clauses from scratch (use Draft for that).

Use Redline when you want to:

• Strengthen or soften a clause
• Add a missing protection to existing language
• Fix an inconsistency or ambiguity
• Align language with defined terms used elsewhere in the contract
• Make a one-sided obligation mutual
• Change a position or threshold
• Tighten loose or repetitive drafting

What to do with the output

Once the AI returns a suggested redline, you have five options.

Apply. Accepts the proposed change and inserts it into your document as a tracked change. You can still accept or reject it in Word afterwards.

Dismiss. Discards the suggestion without making any change to the document.

Edit directly. Opens the proposed language so you can modify it manually before applying. Use this when the AI has the right idea but the wording needs minor adjusting. You get the benefit of the AI's draft without being locked into its exact phrasing.

Regenerate. Asks the AI to try again. There are two options here:

• Retry with no changes generates a fresh attempt using the same original instruction. Useful when the output is simply off and you want a different take without giving more direction.
• Retry with additional instructions lets you give the AI a short correction before it tries again. Use this when the output is close but needs a specific adjustment.

     "Shorter." "Less aggressive." "Use the defined term 'Services' instead of 'Deliverables'." "Match the tone of the confidentiality section."

Find in document. Jumps to the relevant clause in your Word document. Useful when you are working with a long contract and want to see the proposed change in context before deciding whether to apply it.

📝 If you find yourself regenerating the same redline the same way more than twice, the issue is usually the original instruction. Try rewriting the prompt with a clearer direction before retrying.

Prompts that work well in practice

The prompts below assume you have already highlighted the relevant clause before switching to Redline.

Adjusting balance and tone

     "Make this indemnity mutual."

     "Soften this audit right so it requires reasonable notice and limits scope."

     "Reduce the aggressiveness of this termination right."

     "Make this limitation of liability clause more balanced."

Adding protections

     "Add a cure period of 10 business days before default triggers termination rights."

     "Add survivorship language for confidentiality obligations for 3 years post-termination."

     "Insert a data breach notification obligation within 72 hours."

     "Add a cap of 2x annual fees to this liability clause."

Fixing and aligning

     "Fix the defined term reference. This should refer to 'Fees' not 'Charges'."

     "Align this clause with the defined term 'Services' used elsewhere in the agreement."

     "Correct the cross-reference. This should point to clause 8, not clause 6."

Changing positions

     "Update the governing law to English law."

     "Revise the payment terms to 30 days."

     "Tighten the non-solicitation clause so it applies only to current employees."

     "Broaden the license grant to cover affiliates."

How to get better output from Redline

Keep instructions short. One clear direction produces cleaner output than a long explanation. "Make this mutual" outperforms a paragraph explaining why mutuality matters.

Highlight first, always. If you skip the highlight step, include the clause name in your prompt so the AI knows what to target.

     "In the confidentiality clause, add survivorship language for 3 years post-termination."

Use Ask first if you're unsure what needs changing. If you know a clause has a problem but can't quite articulate it, run Ask first. Once you understand the issue clearly, the Redline instruction almost writes itself.

Reference defined terms correctly. If your contract uses "Customer Data," use that term in your prompt. If you use a different term, the AI may introduce inconsistency.

One change per prompt. If you need to make two unrelated changes to the same clause, do them in sequence rather than combining them. The output will be cleaner.

⚠️ Redline tries to preserve the structure of the existing clause. If you want to replace the clause entirely rather than improve it, use Draft instead. Asking Redline to do a full rewrite often produces a hybrid of the old and new language rather than something clean.

What Redline won't do

Redline will not create something from nothing. If the clause you need does not exist in the contract, Redline has nothing to work with. Switch to Draft to generate new language, then use Redline to refine it once it's in the document.

Redline will also not explain or analyze. If you submit a question in Redline mode, the AI will attempt to produce an edit rather than an answer. Switch to Ask for anything that requires explanation.

Redline as part of a workflow

Redline produces the best results when it follows Ask, not when it's used cold.

Ask then Redline: the standard sequence

Ask: "What's weak about this limitation of liability clause?"

Highlight the clause, switch to Redline: "Cap liability at 12 months' fees and insert a carve-out for fraud and gross negligence."

Compare then Redline: responding to counterparty changes

Run Compare to see what the counterparty changed in their latest draft.

Ask: "Which of these changes weaken our position?"

Highlight the relevant clause, switch to Redline: "Restore the liability cap to the version in our previous draft."

Draft then Redline: creating then refining

Draft a new clause and insert it into the document.

Highlight the new clause, switch to Redline: "Tighten the language and align the defined terms with the rest of the agreement."

Next chapter → Draft: Creating New Contract Language

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