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Tutorial 08: Cowork Automation for Legal Tasks

Learn to automate contract review, document processing, and legal workflows using Claude's Cowork feature without writing code.

Learning Objectives

By the end of this tutorial, you will:

  • Understand Cowork's agentic capabilities for legal automation
  • Set up Cowork for contract review and document processing
  • Build automated legal workflows without coding
  • Create professional document outputs (Word, Excel, PowerPoint)
  • Extract and process tabular data at scale
  • Integrate Word track changes and comment generation
  • Automate document organization and naming
  • Execute batch translation workflows
  • Manage client collaboration and approval workflows

What Is Cowork?

Cowork brings Claude Code's agentic capabilities to your desktop—no coding required. Instead of responding to one prompt at a time, Claude can:

  • Execute multi-step tasks autonomously
  • Work with your local files directly
  • Generate polished professional documents
  • Connect to external services via MCP

Why Cowork Matters for Lawyers

Traditional ClaudeCowork
Chat-based interactionTask delegation
Manual file handlingDirect file access
One response at a timeMulti-step execution
Generic outputsProfessional documents

Cowork vs. Harvey/Legora Automation

FeatureCoworkHarvey WorkflowsLegora Workflows
Coding requiredNoNoNo
CustomizationUnlimitedTemplate-basedTemplate-based
Document outputWord, Excel, PPTPDF reportsVarious
Local file accessYesCloud onlyCloud only
CostIncluded in ProEnterprise pricingEnterprise pricing
PrivacyLocal-firstCloudCloud

Requirements

  • macOS (Cowork is currently macOS-only)
  • Claude Desktop app
  • Claude Pro, Max, Team, or Enterprise subscription

Accessing Cowork

  1. Open Claude Desktop
  2. Click the Cowork icon (or toggle)
  3. Accept research preview terms

Step 1: Select Working Folder

Choose a folder for Claude to access:

  • Your matter working folder
  • Contract review staging area
  • Template library

Step 2: Install Legal Plugin

If not already installed:

  1. Go to Plugins in Cowork
  2. Search "Legal"
  3. Click Install

Step 3: Configure Playbook

See Tutorial 06 for playbook configuration.

Cowork is in research preview. Don't use it for production-critical workflows requiring strict audit trails yet.


Workflow 1: Batch NDA Processing

Scenario: You receive 20 NDAs weekly. Automate triage and initial review.

Cowork Prompt:

I have a folder of NDAs that need processing. For each NDA in
my /Legal/Inbox/NDAs folder:

1. Run NDA triage (standard/counsel review/full review)
2. Create a summary log in Excel with columns:
   - Filename
   - Counterparty
   - Type (mutual/one-way)
   - Triage Result
   - Key Issues Flagged
   - Recommended Action
3. Move files to appropriate subfolders:
   - /Standard_Approval for green
   - /Counsel_Review for yellow
   - /Full_Review for red
4. Generate a brief email summary I can send to the team

Save the Excel file as "NDA_Triage_[today's date].xlsx"
Save the email draft as "NDA_Summary_[today's date].docx"

What Cowork Does:

  1. Scans the NDA folder
  2. Opens each NDA and analyzes
  3. Categorizes based on playbook
  4. Creates organized Excel summary
  5. Moves files to correct folders
  6. Drafts email summary

Time Saved: 3-4 hours → 15 minutes


Workflow 2: Contract Comparison Report

Scenario: Client wants to understand how competitor's terms compare to market.

Cowork Prompt:

I have 5 vendor agreements in /Legal/Vendor_Comparison folder.
Compare them and generate a professional report:

1. For each agreement, extract:
   - Vendor name
   - Annual cost
   - Term length
   - Liability cap
   - Indemnification scope
   - Data rights
   - SLA commitments
   - Notable unusual terms

2. Create a comparison matrix in Excel with:
   - Side-by-side comparison
   - Color coding (green=favorable, yellow=neutral, red=unfavorable)
   - Our standard position for reference

3. Generate a Word document report with:
   - Executive summary (1 page)
   - Detailed comparison analysis
   - Recommendations ranked by importance
   - Appendix with clause excerpts

Save as:
- "Vendor_Comparison_Matrix.xlsx"
- "Vendor_Comparison_Report.docx"

Workflow 3: Due Diligence Document Processing

Scenario: M&A deal requires reviewing 200+ contracts in data room.

Cowork Prompt:

I need to process contracts from the data room. They're in
/Legal/DD/Contracts organized by type.

For this batch of /Legal/DD/Contracts/Customer_Agreements:

1. For each contract, extract and log:
   - Contract type
   - Counterparty
   - Effective date
   - Term/expiration
   - Annual value (if stated)
   - Auto-renewal terms
   - Change of control provisions
   - Assignment restrictions
   - Termination rights
   - Key risk flags

2. Create master Excel tracker with all data

3. Flag contracts requiring follow-up:
   - Approaching expiration (next 12 months)
   - Change of control consent required
   - Assignment restricted
   - Non-standard terms

4. Generate summary memo for deal team

Output:
- "DD_Contract_Tracker.xlsx"
- "DD_Contract_Summary_Memo.docx"

Workflow 4: Litigation Timeline Generation

Scenario: Prepare chronology from case documents for trial prep.

Cowork Prompt:

I have discovery documents in /Legal/SmithCase/Discovery that
I need to process into a trial timeline.

1. Scan all documents and extract:
   - Document date
   - Document type
   - Key parties involved
   - Summary of content
   - Relevance to our case theory
   - Helpful/harmful assessment

2. Create chronological timeline in Excel with:
   - Date
   - Event description
   - Document reference
   - Key quote (if applicable)
   - Our assessment (helps/hurts/neutral)

3. Generate Word document:
   - Narrative chronology (suitable for mediation brief)
   - Key events highlighted
   - Supporting document citations

4. Create PowerPoint:
   - Visual timeline for trial
   - Key dates marked
   - Clean professional design

Output:
- "SmithCase_Timeline_Master.xlsx"
- "SmithCase_Chronology_Narrative.docx"
- "SmithCase_Timeline_Presentation.pptx"

Part 4: Tabular Extraction & Portfolio Analytics

Portfolio-Wide Spreadsheet Generation

Scenario: You need a portfolio-wide analysis of all active contracts for risk management.

Cowork Prompt:

Process all contracts in /Legal/ActiveContracts and create
comprehensive portfolio analytics:

1. For each contract file, extract:
   - Contract ID
   - Contract name
   - Counterparty
   - Contract type (vendor/customer/partner/other)
   - Execution date
   - Effective date
   - Expiration date
   - Renewal dates
   - Annual value
   - Liability cap
   - Indemnity provisions
   - IP assignment scope
   - Data protection clauses
   - Termination notice period
   - Auto-renewal terms
   - Change of control restrictions
   - Key risk flags
   - Status (active/expired/pending renewal)

2. Create Excel workbook with:

   Sheet 1: Dashboard
   - Total contracts count
   - Total annual value (formula sum)
   - Expiring in next 30/90/180 days (conditional formatting)
   - Contracts requiring action (count)
   - Risk distribution pie chart

   Sheet 2: Master Data Table
   - All extracted fields
   - Sortable and filterable
   - Expiration date conditional formatting (red if <90 days)
   - Risk level color coding

   Sheet 3: Renewal Calendar
   - Sorted by expiration date
   - Assigned responsible parties
   - Renewal notice deadlines
   - Template action items

   Sheet 4: Risk Analysis
   - Contracts with liability caps <$1M
   - Missing indemnity provisions
   - Unrestricted IP assignment
   - Change of control issues
   - Non-standard termination

3. Generate summary memo highlighting:
   - Top portfolio risks
   - Expiration calendar (next 12 months)
   - Recommended priority actions
   - Estimated renewal values

Save as:
- "Portfolio_Analytics_[date].xlsx"
- "Portfolio_Risk_Summary.docx"

Advanced Extension - Legora Equivalent:

For the Portfolio_Analytics workbook:
1. Add Sheet 5: Vendor Spend Analysis
   - By vendor: contract count, total spend, renewal dates
   - Consolidation opportunities
   - Renegotiation candidates

2. Add Sheet 6: Compliance Checklist
   - Insurance requirements met
   - SOW sign-offs current
   - Required approvals documented
   - Annual compliance actions due

3. Generate compliance report with:
   - Audit trail of completed actions
   - Upcoming compliance deadlines
   - Responsible party assignments

Part 5: Microsoft Word Integration Workflows

Track Changes & Redline Automation

Scenario: You need to redline a vendor's proposed contract with your standard terms.

Cowork Prompt:

I have a vendor MSA at /Legal/VendorNegotiations/Vendor_MSA_Draft.docx

Generate a redlined version with track changes showing our position:

1. Review the vendor's current draft
2. Compare against /Legal/Templates/Standard_MSA_Template.docx
3. Apply track changes for:
   - Our standard liability cap language
   - Our standard IP indemnity
   - Our standard data protection terms
   - Removal of problematic vendor liability caps
   - Addition of our standard payment terms
   - Our standard confidentiality provisions

4. For each change, add Word comments explaining:
   - Why we're making the change
   - What our standard position is
   - Why this protects both parties

5. Add a cover memo as first page with:
   - Executive summary of changes
   - Key negotiation points
   - Our red-line positions vs. nice-to-haves
   - Suggested response strategy

Save as "Vendor_MSA_OurRedlines_[date].docx"
This file will show all changes in track changes view

What Cowork Does:

  1. Reads the vendor draft
  2. Compares to your template
  3. Creates tracked changes (visible red deletions/insertions)
  4. Adds detailed explanatory comments
  5. Generates professional memo
  6. Preserves formatting

Verification Checklist:

  • All changes visible in track changes
  • Comments are clear for negotiation
  • Cover memo accurately reflects changes
  • File ready to send to vendor
  • Confidential info properly marked

Comment Generation for Collaborative Review

Scenario: Team members need to review a contract and document their feedback with Word comments.

Cowork Prompt:

Generate detailed Word comments for this contract review:

Open /Legal/Reviews/ClientAgreement_Draft.docx and add:

1. In Definitions section:
   - Highlight ambiguous terms
   - Add comments with suggested clarifications
   - Reference case law where relevant

2. In Liability section:
   - Comment on cap amounts vs. industry standard
   - Flag mutual vs. one-sided caps
   - Suggest negotiation strategy

3. In IP Rights section:
   - Comment on scope of assignment
   - Flag background IP carveouts
   - Suggest protective language

4. In Termination section:
   - Comment on notice periods
   - Flag change of control provisions
   - Note renewal vs. termination mechanics

5. Create summary comment (at top of document) with:
   - Overall assessment
   - Top 3 issues to negotiate
   - Estimated negotiation timeline

All comments should be professional, actionable, and collaborative.

Save as "ClientAgreement_ReviewComments_[date].docx"

Style Enforcement & Formatting

Scenario: Ensure all contract outputs follow firm standards.

Cowork Prompt:

Apply firm standard formatting to contracts:

For all .docx files in /Legal/Drafts:

1. Apply styles:
   - Heading 1 for article titles
   - Heading 2 for subsections
   - Normal for body text
   - Emphasis for defined terms

2. Format consistently:
   - 1-inch margins
   - Times New Roman 12pt body
   - 1.15 line spacing
   - No tabs (use tables for structured content)
   - Page breaks before new articles
   - Headers with firm name/matter name
   - Footers with date and page numbers

3. Generate style sheet with:
   - Required styles defined
   - Formatting guidelines
   - Examples of proper formatting
   - Common mistakes to avoid

4. Create before/after samples showing
   transformation from inconsistent to firm standard

Save formatted contracts with "_Formatted" suffix
Save style guide as "Firm_Contract_Style_Guide.docx"

Part 6: Document Organization & Automation

AI-Suggested Naming & Folder Cleanup

Scenario: Your document folder has thousands of files with inconsistent naming.

Cowork Prompt:

Analyze and reorganize my legal document library:

Process all files in /Legal/Documents (including subfolders):

1. For each file, determine:
   - Document type (contract/memo/motion/agreement/etc.)
   - Key parties involved
   - Date
   - Matter/client name
   - Current filename

2. Suggest new organized structure:
   - /Clients/[ClientName]/[YearQuarter]/[DocumentType]/
   - Example: /Clients/ABC_Corp/2024_Q1/Agreements/

3. Create CSV with columns:
   - Current path
   - Current filename
   - Suggested new folder
   - Suggested new filename
   - Rationale
   - File type
   - Date

4. Generate implementation guide:
   - Which moves are safe
   - Which require manual review
   - Backlinks to maintain
   - Archive recommendations

5. Provide conflict resolution:
   - Duplicate files (by content)
   - Similar files with different names
   - Obsolete versions to archive

Save as:
- "Reorganization_Plan_[date].xlsx"
- "Implementation_Guide.docx"

Duplicate Detection & Resolution

Scenario: Find and consolidate duplicate contracts taking up space and creating confusion.

Cowork Prompt:

Find and flag duplicate documents:

Scan /Legal/ContractPortfolio and identify:

1. Exact duplicates (identical file content):
   - List with file locations
   - File sizes
   - Dates
   - Recommendation: keep newest, archive others

2. Near-duplicates (same document, minor variations):
   - Show differences
   - Suggest which version is "master"
   - Flag which should be archived

3. Multiple versions of same agreement:
   - Create version control summary
   - Identify most recent version
   - Archive previous versions to /Archive/
   - Create version control document

4. Generate Excel with:
   - Filename
   - File path
   - File size
   - Date
   - Match type (exact/near/version)
   - Action recommended
   - Risk if deleted

5. Create archive checklist:
   - Safe to archive immediately
   - Review before archiving
   - Do not archive (active matters)

Save as:
- "Duplicate_Analysis_[date].xlsx"
- "Archive_Checklist.docx"
- Archive old versions to /Archive/[Year]/

Part 7: Batch Translation Workflow

Multi-Document Translation with Formatting Preservation

Scenario: You have contracts in English that need Spanish versions maintaining all formatting.

Cowork Prompt:

Translate contracts while preserving formatting:

Translate all English contracts in /Legal/Contracts/English/:

1. For each .docx file:
   - Extract text with formatting markers
   - Translate to Spanish maintaining legal terminology
   - Preserve all paragraph formatting
   - Keep table structure intact
   - Maintain header/footer
   - Preserve tracked changes if present

2. Translation quality:
   - Use legal Spanish terminology
   - Maintain formality appropriate to contract type
   - Keep defined terms consistent (suggest bilingual glossary)
   - Flag ambiguous English phrases for human review

3. Create bilingual glossary:
   - English defined terms → Spanish equivalents
   - Legal terminology matching
   - Context-specific meanings
   - Usage examples from contracts

4. Generate Spanish versions with:
   - Same formatting as English
   - Matching page breaks
   - Side-by-side comparison document
   - Translation notes where needed

5. Create quality assurance document:
   - Sentences requiring human verification
   - Terminology decisions made
   - Context-specific notes for translators
   - Proofreading checklist

Save as:
- /Legal/Contracts/Spanish/[Filename]_ES.docx
- "Translation_Glossary.xlsx"
- "Translation_QA_Report.docx"

Always have qualified legal translators review AI-generated translations before execution or client delivery.

Advanced: Bilingual Document Generation:

Create unified bilingual contracts:

1. Take English contract /Legal/Contracts/Original.docx
2. Generate Spanish translation
3. Create side-by-side bilingual version with:
   - English on left, Spanish on right
   - Aligned by paragraph
   - Professional formatting
   - Table format for readability

4. Create separate documents:
   - English version (clean, ready to execute)
   - Spanish version (clean, ready to execute)
   - Bilingual reference version (internal only)

5. Generate translator's notes:
   - Terminology decisions
   - Ambiguities flagged
   - Legal system differences noted
   - Future translation consistency notes

Save as:
- "Contract_EN.docx" (English)
- "Contract_ES.docx" (Spanish)
- "Contract_Bilingual_Reference.docx"
- "Translator_Notes.docx"

Consistency Across Language Versions

Cowork Prompt:

Ensure translation consistency across all legal documents:

1. Analyze all Spanish translations in /Legal/Contracts/Spanish/
2. Extract defined terms and terminology from each
3. Create master terminology database:
   - English term
   - Spanish translation
   - Document sources
   - Frequency of use
   - Alternative translations considered

4. Flag inconsistencies:
   - Same English term with different Spanish translations
   - Similar terms with same translation (may be wrong)
   - Potential translation errors

5. Generate revision guide:
   - Recommendations for standardizing terminology
   - Priority fixes (high impact changes)
   - Documents requiring retranslation
   - Going-forward standards

6. Create terminology style guide:
   - Approved English→Spanish pairings
   - Rationale for each choice
   - Legal context notes
   - Examples

Save as:
- "Terminology_Database.xlsx"
- "Consistency_Report.docx"
- "Legal_Translation_Style_Guide.docx"

Part 8: Client Collaboration Portal Equivalent

Secure Document Sharing Workflows

Scenario: Create organized client deliverables with proper documentation.

Cowork Prompt:

Create a client deliverable package:

Prepare documents for /Legal/ClientDeliverables/ABC_Corp_Matter/:

1. Gather documents:
   - Opinion letter (if applicable)
   - Summary memo
   - Supporting documents
   - Forms for execution
   - Cover sheet

2. Organize by document type:
   - Executive summary (first)
   - Documents requiring execution
   - Reference documents
   - Appendices

3. Generate client-facing cover memo:
   - Overview of documents
   - Required actions from client
   - Timeline for next steps
   - Key dates/deadlines
   - Responsible contacts
   - How to return executed documents

4. Create execution checklist:
   - Which documents need signatures
   - Who needs to sign
   - Signature authority verification
   - Witness/notary requirements
   - Return instructions

5. Add document index:
   - Document name
   - Purpose
   - Action required
   - Execution requirements

6. Create tracking spreadsheet:
   - Document name
   - Date sent
   - Status
   - Date received
   - Signature status
   - Notes

Save as:
- "Client_Deliverable_Package_[date]/" folder
- "Cover_Memo.docx"
- "Execution_Checklist.docx"
- "Document_Tracking.xlsx"

Status Update Generation

Scenario: Generate periodic client status updates from matter files.

Cowork Prompt:

Generate client status update:

Create monthly status report for ABC_Corp matter:

1. Gather all recent activity:
   - Recent actions taken
   - Pending items
   - Upcoming deadlines
   - Issues requiring client input
   - Cost summary

2. Generate client-facing memo with:
   - Executive summary (1 page)
   - Detailed activity summary (what we did)
   - Current status (where we stand)
   - Next steps (what's coming)
   - Pending client actions
   - Timeline for next phase
   - Budget status
   - Contact for questions

3. Create action items section:
   - Items pending client response
   - Deadline for each
   - Impact if deadline missed
   - Instructions for client action

4. Add timeline visual:
   - What happened this period
   - Upcoming key dates
   - Milestones
   - Deadlines

5. Generate parallel internal memo:
   - Internal status for file
   - Risk flags not shared with client
   - Strategic notes
   - Next actions for team

Save as:
- "Status_Update_[Month]_[Client].docx"
- "Internal_Matter_Status.docx"

Client-Facing Summary Creation

Scenario: Transform detailed analysis into client-friendly summaries.

Cowork Prompt:

Create client-friendly summaries of technical documents:

Review /Legal/Matters/ABC_Corp/Research_Memos/:

1. For each detailed research memo:
   - Identify key conclusions
   - Extract legal standards
   - Note practical implications
   - Identify risks and opportunities
   - Simplify technical language

2. Generate two-version documents:

   Internal Version:
   - Detailed analysis
   - All legal citations
   - Nuanced analysis
   - Strategic considerations

   Client Version:
   - Executive summary (1-2 pages)
   - Plain-English explanation
   - Practical implications
   - Recommended actions
   - Simple visuals/charts
   - Minimal citations
   - No internal strategy

3. Create FAQ document:
   - Common client questions
   - Plain-language answers
   - Links to relevant sections
   - Contact for follow-ups

4. Add decision framework:
   - Options available
   - Pros/cons of each
   - Cost implications
   - Timeline
   - Recommended approach with rationale

Save as:
- "[Topic]_Internal_Analysis.docx"
- "[Topic]_Client_Summary.docx"
- "[Topic]_FAQ.docx"

Approval Workflow Automation

Scenario: Automate document approval tracking and escalation.

Cowork Prompt:

Set up approval workflow tracking:

Create approval system for /Legal/ToBeApproved/:

1. Scan folder for documents needing approval
2. For each document, extract:
   - Document name
   - Type of approval needed
   - Required approver
   - Date submitted
   - Client impact
   - Urgency level
   - Required turnaround

3. Generate approval tracker Excel with:
   - Document name
   - Submitted date
   - Approver assigned
   - Status (pending/approved/rejected/revise)
   - Days pending (formula)
   - SLA deadline
   - Status indicators (color coding)

4. Create escalation rules:
   - Flag if >3 days pending
   - Escalate if >7 days pending
   - Alert if SLA about to breach

5. Generate daily/weekly reports:
   - What's pending approval
   - Days pending for each
   - At-risk items (approaching deadline)
   - Action items for approvers

6. Create automated reminder emails:
   - For pending approvals >3 days
   - For approaching deadlines
   - For stakeholders waiting on approval

Save as:
- "Approval_Tracker.xlsx"
- "Approval_Status_Report.docx"
- Automated reports to /Reports/Weekly/

Part 9: Professional Document Generation

Word Documents

Cowork can generate professional Word documents with:

  • Proper formatting
  • Styles and headings
  • Tables and charts
  • Track changes (for redlines)
  • Comments

Example: Contract Redline Request

Review the contract at /Legal/CurrentDeal/Draft_MSA.docx

Apply our standard playbook and generate a redlined version
with track changes showing:
- Deletions struck through
- Additions in red
- Comments explaining each significant change

Save as "Draft_MSA_OurRedlines.docx"

Excel Spreadsheets

Cowork creates functional Excel files with:

  • Working formulas
  • Conditional formatting
  • Multiple sheets
  • Charts and graphs
  • Data validation

Example: Contract Portfolio Analysis

Analyze all contracts in /Legal/ContractPortfolio and create
an Excel workbook with:

Sheet 1: Summary Dashboard
- Total contract value
- Contracts by type (pie chart)
- Expiration calendar (next 12 months)
- Risk distribution

Sheet 2: Detailed Log
- All extracted contract data
- Conditional formatting for expiration dates
- Risk flags highlighted

Sheet 3: Renewal Calendar
- Contracts requiring action by month
- Responsible party assignment column

Save as "Contract_Portfolio_Analysis.xlsx"

PowerPoint Presentations

Cowork generates presentation-ready slides:

  • Professional layouts
  • Charts and visuals
  • Speaker notes
  • Consistent formatting

Example: Board Legal Update

Generate a board presentation covering Q1 legal matters:

Slide 1: Title - "Legal Department Q1 Update"
Slide 2: Key Metrics (contracts closed, disputes resolved, spend)
Slide 3: Major Matters Summary (table format)
Slide 4: Litigation Status (timeline visual)
Slide 5: Regulatory Developments (bullet points)
Slide 6: Looking Ahead Q2 (priorities)
Slide 7: Questions

Use professional business style. Include speaker notes
with key talking points.

Save as "Legal_Q1_Board_Update.pptx"

Part 10: Automated Monitoring & Alerts

Setting Up Contract Expiration Monitoring

Cowork Prompt:

Set up a contract monitoring workflow:

1. Every Monday, scan /Legal/ActiveContracts for:
   - Contracts expiring in next 90 days
   - Auto-renewals with notice deadlines approaching
   - Contracts requiring annual compliance actions

2. Generate weekly report:
   - List of approaching deadlines
   - Required actions
   - Responsible parties

3. Create draft reminder emails for each deadline

Save to /Legal/WeeklyReports/[date]_ContractAlerts/

Regulatory Update Monitoring

Cowork Prompt:

Search for recent regulatory developments in [practice area]
and generate a client alert:

1. Research recent [FDA/SEC/FTC/etc.] announcements
2. Summarize key developments
3. Analyze impact on our clients
4. Draft client alert memo
5. Create short version for LinkedIn post

Save:
- "Client_Alert_[Topic].docx" (full memo)
- "LinkedIn_Post_[Topic].txt" (short version)

Combined Workflow Example

Process the new vendor agreement in my inbox:

1. /triage-nda first to categorize urgency

2. If RED or YELLOW, then:
   /review-contract for full analysis

3. Based on review, generate:
   - Internal memo summarizing issues
   - Redlined contract with suggested changes
   - Email to business team with summary

4. Save all outputs to /Legal/[VendorName]_Review/

5. Log the review in our tracking spreadsheet

Do's

  • Do start with small batches to test workflows
  • Do review all outputs before sending/filing
  • Do maintain organized folder structures
  • Do back up important documents before processing
  • Do document your workflows for team replication

Don'ts

  • Don't automate privileged analysis without controls
  • Don't rely on Cowork for final legal conclusions
  • Don't process client documents without proper security
  • Don't skip verification of extracted data
  • Don't use for regulated workflows without compliance review

Quality Control Checklist

For every Cowork-generated deliverable:

  • Spot-check extracted data against source
  • Verify document formatting is correct
  • Review any legal conclusions
  • Check privilege/confidentiality handling
  • Confirm file saved to correct location
  • Test any Excel formulas
  • Review before client/counterparty sharing

Part 13: Limitations and Workarounds

Current Cowork Limitations

LimitationWorkaround
macOS onlyUse Claude web for basic tasks on other platforms
Research previewDon't use for production-critical workflows yet
No WindowsRun in VM or wait for Windows release
File size limitsSplit large documents
Complex formattingMay need manual polish

When to Use Traditional Approach Instead

  • Highly confidential matters (privilege concerns)
  • Regulated workflows requiring audit trails
  • Complex formatting requirements
  • When human judgment is critical
  • One-off tasks that don't justify setup

Homework Before Tutorial 09

  1. Set up Cowork on your Mac

  2. Create a working folder structure for legal documents

  3. Process a batch of 5-10 documents using Cowork

  4. Generate one professional document (Word, Excel, or PPT)

  5. Document one workflow you could automate

  6. Extract tabular data from documents into Excel

  7. Create a track changes document with comments



Quick Reference: Cowork Command Patterns

Batch Processing

For each [document type] in [folder]:
[list of actions]
Save results to [output location]

Report Generation

Analyze [documents/data] and create:
1. [Excel tracker with columns: X, Y, Z]
2. [Word memo with sections: A, B, C]
3. [PowerPoint with slides: 1, 2, 3]
Save all to [location]

Tabular Extraction

Extract from [documents in folder]:
[list of data points to extract]
Create Excel with columns: [X, Y, Z]
Add [formulas/formatting/charts]
Save to [location]

Track Changes & Comments

Review [document] and generate:
1. Tracked changes version
2. Detailed comments explaining each change
3. Summary memo of key issues
Save as [output filename]

Translation Workflow

Translate [documents in folder]:
[source language] → [target language]
Preserve all formatting and structure
Create glossary of terminology
Generate QA report
Save originals and translations to [location]

Client Collaboration

Create client deliverable package:
1. Organize documents by type
2. Generate cover memo
3. Create execution checklist
4. Set up tracking spreadsheet
Save to [folder]

Sources

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Learning ObjectivesPart 1: Understanding Cowork for LegalWhat Is Cowork?Why Cowork Matters for LawyersCowork vs. Harvey/Legora AutomationPart 2: Setting Up Cowork for Legal WorkRequirementsAccessing CoworkConfiguring Your Legal WorkspacePart 3: Core Legal Automation WorkflowsWorkflow 1: Batch NDA ProcessingWorkflow 2: Contract Comparison ReportWorkflow 3: Due Diligence Document ProcessingWorkflow 4: Litigation Timeline GenerationPart 4: Tabular Extraction & Portfolio AnalyticsPortfolio-Wide Spreadsheet GenerationPart 5: Microsoft Word Integration WorkflowsTrack Changes & Redline AutomationComment Generation for Collaborative ReviewStyle Enforcement & FormattingPart 6: Document Organization & AutomationAI-Suggested Naming & Folder CleanupDuplicate Detection & ResolutionPart 7: Batch Translation WorkflowMulti-Document Translation with Formatting PreservationConsistency Across Language VersionsPart 8: Client Collaboration Portal EquivalentSecure Document Sharing WorkflowsStatus Update GenerationClient-Facing Summary CreationApproval Workflow AutomationPart 9: Professional Document GenerationWord DocumentsExcel SpreadsheetsPowerPoint PresentationsPart 10: Automated Monitoring & AlertsSetting Up Contract Expiration MonitoringRegulatory Update MonitoringPart 11: Integration with Legal PluginCombined Workflow ExamplePart 12: Best Practices for Cowork Legal AutomationDo'sDon'tsQuality Control ChecklistPart 13: Limitations and WorkaroundsCurrent Cowork LimitationsWhen to Use Traditional Approach InsteadHomework Before Tutorial 09NavigationQuick Reference: Cowork Command PatternsBatch ProcessingReport GenerationTabular ExtractionTrack Changes & CommentsTranslation WorkflowClient CollaborationSources