Whitepapers / The Complete Copilot Readiness Assessment Guide
The Complete Copilot Readiness Assessment Guide
A Technical Framework for Enterprise CIOs
Published: January 15, 2026
50 min
12,500 words
Author: Copilot Consulting Team
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This whitepaper provides a step-by-step technical framework for conducting a thorough Copilot readiness assessment. Includes PowerShell scripts, audit checklists, risk scoring methodology, and remediation roadmaps for common deployment blockers.
Table of Contents
Executive Summary
Page 2
Introduction: The Copilot Readiness Challenge
Page 5
Phase 1: Permission Audit & Data Exposure Assessment
Page 10
Phase 2: Data Classification & Sensitivity Labels
Page 18
Phase 3: DLP Policy Configuration
Page 26
Phase 4: Compliance Validation (HIPAA, SOC 2, GDPR)
Page 34
Phase 5: Risk Scoring & Remediation Roadmap
Page 42
Conclusion: Next Steps
Page 48
Appendix: PowerShell Scripts & Checklists
Page 50
Key Takeaways
Comprehensive permission audit methodology using PowerShell scripts and Microsoft Graph API
Step-by-step data classification framework with sensitivity label templates
DLP policy configuration guide for preventing data exposure via Copilot
Compliance validation checklists for HIPAA, SOC 2, GDPR, and attorney-client privilege
Risk scoring methodology: Red/Yellow/Green tenant readiness assessment
Remediation roadmap templates with timelines and resource requirements
Topics Covered
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