Legal Redlining in Word: What Law Firms Actually Expect

The Terminology Problem

Ask ten attorneys what "redline" means, and you'll get variations:

• "A document with my proposed changes tracked"
• "A comparison showing what changed between versions"
• "The markup I send back to opposing counsel"
• "Any document with visible Track Changes"

They're all partially right, and the ambiguity causes real confusion. I've seen negotiations stall because one party expected a marked-up document and received a comparison document - or vice versa.

Let's establish working definitions.

Redline, Blackline, and Markup: Working Definitions

Redline: A document showing proposed changes with Track Changes visible. The editor is asserting "here's what I want to change." Attribution goes to the person proposing changes.

Blackline (or Comparison): A document showing what differs between two versions. Generated by comparing Version A to Version B. Attribution goes to "Reviewer" or whoever ran the comparison, not to who actually made the changes.

Markup: Generic term for any document with visible changes. Can be either redline or blackline depending on context.

Clean (or Execution Version): The document with all changes accepted, no tracking visible. What gets signed.

Turn: One party's set of changes in a negotiation. "We received Party A's turn" means Party A sent their redline of our document.

These definitions aren't universal, but they're common enough to be useful.

Why the Distinction Matters

Scenario: NDA Negotiation

Party A sends clean NDA draft to Party B.

Party B reviews and returns a redline - their proposed changes to Party A's draft. The document shows Party B's edits.

Party A reviews Party B's redline and returns their response - another redline layered on top, or a new clean draft with a blackline comparison to Party B's version.

At each step, both parties need to understand: "Am I seeing your proposed changes, or am I seeing a comparison of two documents?" The answer determines how to interpret the markup.

If Party B sends what they call a "redline" but it's actually a blackline comparison of some internal versions, Party A will be confused about what Party B is actually proposing.

Configuring Word for Professional Redlining

Setting Reviewer Identity

Before making any changes:

1. File > Options > General
2. Under "Personalize your copy of Microsoft Office"
3. Set User name to your preferred attribution
4. Set Initials for comment shortcuts

Options for User name:

• Individual name (John Smith)
• Firm/company name (Davis Polk)
• Role (Buyer's Counsel)
• Generic (Reviewer)

Different contexts call for different choices. Establish this before you start editing.

Tracking Display Settings

Review > Tracking > Show Markup controls what appears:

Comparison Settings (for Blacklines)

Review > Compare > Compare > More:

The Anatomy of a Professional Redline

What Good Redlines Have

1. Clear attribution: You can tell who proposed each change
2. Readable changes: Word-level, not character-level, changes
3. Explanatory comments: Why you made substantive changes
4. Consistent formatting: All changes styled the same way
5. Complete coverage: No changes made with tracking off

What Good Redlines Don't Have

1. Personal/internal comments: "Fix this later" or "Sarah will hate this"
2. Excessive noise: Every comma repositioned, every space adjusted
3. Inconsistent attribution: Some changes from "John," others from "Admin"
4. Unmarked changes: Edits made before turning on Track Changes
5. Tracked formatting changes: Unless formatting is actually substantive

Turn Management in Multi-Party Negotiations

Contract negotiations create document versions:

Original Draft (Party A)
    ↓
Party B's Turn 1 (redline on Original)
    ↓
Party A's Turn 2 (redline on Turn 1, or new draft + blackline)
    ↓
Party B's Turn 3 (redline on Turn 2)
    ↓
... continues ...

Each turn adds changes. The challenge: keeping track of what each party has proposed, conceded, or still disputes.

Managing Attribution Across Turns

Option 1: Layer changes Keep all previous track changes visible, add new ones on top. Document becomes visually complex but maintains full history.

Option 2: Accept previous, track new Accept the previous party's changes, then enable Track Changes for your response. Cleaner visually, but loses the layered history.

Option 3: Clean + Blackline Send a clean draft plus a blackline comparison to their last version. Recipient sees both the proposed final state and what changed.

Most sophisticated negotiations use Option 3 - it provides the clearest view of "what are we actually agreeing to?" while preserving the change record.

Tracking Open Issues

Beyond Track Changes, maintain a separate issues list:

This list travels alongside the redline but isn't in the document. It provides context that Track Changes can't capture.

AI-Assisted Redlining

Manual redlining is time-intensive. A typical commercial contract takes 2-4 hours of attorney time for careful review. AI can accelerate this.

What AI Redlining Does

1. Clause identification: Recognizes standard contract provisions (indemnification, termination, IP, confidentiality)
2. Playbook comparison: Compares clauses to your firm's or company's standard positions
3. Risk flagging: Identifies deviations from standard with risk scores
4. Language suggestion: Proposes alternative language from your clause library
5. Change generation: Creates Track Changes markup automatically

How to Use AI Redlining

from docxagent import DocxClient

client = DocxClient()

# Upload the contract to review
contract_id = client.upload("vendor_services_agreement.docx")

# Run AI analysis with your playbook
analysis = client.analyze_contract(
    contract_id,
    playbook="tech_vendor_standard",  # Your org's standard positions
    generate_redline=True,
    risk_threshold="medium"
)

# Review AI findings
for issue in analysis.issues:
    print(f"Section: {issue.section}")
    print(f"Current: {issue.current_text[:100]}...")
    print(f"Risk: {issue.risk_level}")
    print(f"Suggestion: {issue.suggested_revision[:100]}...")
    print(f"Rationale: {issue.rationale}")
    print("---")

# Download AI-generated redline
client.download(analysis.redlined_doc_id, "vendor_agreement_redlined.docx")

The output is a Word document with Track Changes showing AI-proposed edits. Comments explain why each change was suggested.

AI Limitations

AI is fast but not a substitute for legal judgment:

• Business context: AI doesn't know your relationship with this vendor or why certain terms matter more than others
• Negotiation strategy: AI can't tell you what to concede vs. what to fight for
• Novel structures: Unusual deal structures may confuse models
• Jurisdiction-specific issues: AI may miss state-specific requirements
• Judgment calls: "Is this risk acceptable?" is a human question

Use AI for first-pass review. Human review for strategy and final sign-off.

Common Redlining Mistakes

Mistake 1: Forgetting to Turn On Track Changes

You edit the document, then realize Track Changes was off. Your edits aren't tracked. Now you have to compare your edited version to the original to recreate the changes.

Prevention: Build a habit of checking the Track Changes button before any edit. Consider macros that auto-enable tracking.

Mistake 2: Sending Documents with Internal Comments

"Make sure partner reviews this before sending" shows up in your redline. Embarrassing and potentially damaging.

Prevention: Before sending, Review > Show Markup > Comments. Read every comment. Delete anything not intended for the recipient.

Mistake 3: Inconsistent Attribution

Some changes show "John Smith," others show "jsmith," others show "DESKTOP-ABC123." Looks unprofessional.

Prevention: Before starting, verify File > Options > General > User name is set correctly.

Mistake 4: Tracking Formatting Changes

Every changed space, adjusted tab, or reformatted character clutters the document.

Prevention: Review > Track Changes > Track Changes Options > Formatting > uncheck or set to not track.

Mistake 5: Excessive Redlining

You rewrote every sentence. Even sentences that were fine. It looks like you're rejecting the entire document.

Prevention: Only change what needs changing. Accept acceptable language. Focus edits on substantive issues.

Redlining Workflow for Attorneys

Receiving a Document for Review

1. Save original with descriptive name (e.g., Contract_VendorDraft_2025-01-29.docx)
2. Open in Word, note the state (any existing track changes?)
3. Verify Track Changes is ON before any edits
4. Set reviewer name appropriately

Reviewing and Marking Up

1. Read first, mark second: Understand the document before changing it
2. Substantive changes first: Indemnification, liability, IP - the things that matter
3. Add comments explaining why, not just what
4. Flag issues for team: Use consistent markers like "[DISCUSS]" or "[PARTNER REVIEW]"
5. Clean-up pass last: Minor wording improvements, consistency fixes

Before Sending

1. Review all comments: Delete internal-only comments
2. Check attribution: Is your name/firm shown correctly?
3. Verify completeness: No changes made with tracking off?
4. Run Document Inspector if sending clean version
5. Create cover communication: Summarize major points, open issues

After Receiving Response

1. Compare to your last version: Verify you're reviewing the right document
2. Review their changes: Accept, reject, or counter each
3. Update issues list: What's now agreed, what's still open?
4. Prepare your response: Another turn or clean + blackline

When to Send Clean vs. Marked

Send marked (redline):

• Ongoing negotiations where changes are expected
• When counterparty needs to see your proposed edits
• When attribution to specific changes matters

Send clean:

• Final execution version
• When document is for signature
• When too much markup makes document unreadable

Send both:

• Complex negotiations
• When you want clean for review plus marked for verification
• When dealing with parties unfamiliar with Track Changes

The Bottom Line

Redlining is communication. Like any communication, clarity matters.

Know the conventions. Configure Word correctly. Review before sending. Use AI to accelerate but not replace judgment.

A good redline tells the story of what you're proposing and why. A bad redline creates confusion that slows negotiations. The mechanical steps - Track Changes, comments, attribution - are just tools for that communication.

Master the tools. Focus on the message.