Copilot Readiness Assessent

Purpose

The playbook is designed to help small-to-medium businesses (SMBs) assess and strengthen their Microsoft 365 security and compliance posture before deploying Microsoft 365 Copilot. Since Copilot can access a wide range of organizational data, any existing security gaps could be amplified if not addressed.

Structure & Key Sections

1. Step-by-Step Assessment Guide

• Provides a detailed checklist for reviewing:
  • Identity security (e.g., enforcing MFA, reviewing admin roles, enabling self-service password reset)
  • Device management (ensuring all devices are enrolled in Intune, compliant, and protected by Defender)
  • Threat protection (configuring Safe Attachments, Safe Links, anti-phishing, and anti-malware policies)
  • Data governance (setting up sensitivity labels, DLP, audit logging, retention, and eDiscovery)
  • External sharing (tightening SharePoint, OneDrive, and Teams sharing settings)

2. Risk Assessment

• Identifies common security and compliance gaps in SMB Microsoft 365 environments, such as:
  • Weak identity security (e.g., no MFA)
  • Excessive permissions or overexposed data
  • Unmanaged/insecure devices
  • Inadequate email/phishing protection
  • Lack of data classification or DLP controls
  • Insufficient monitoring and audit
  • Overly permissive external sharing

3. Risk Mitigation with Business Premium

• Recommends using Microsoft 365 Business Premium features to close gaps, including:
  • Enforcing MFA and Conditional Access
  • Adopting least privilege and regular access reviews
  • Enrolling and securing all devices
  • Configuring advanced threat protection for email and Teams
  • Applying sensitivity labels and DLP
  • Improving monitoring and alerting
  • Hardening external collaboration
  • User education and policy updates

4. Advanced Needs & Licensing

• Explains when Business Premium may not be enough and when to consider advanced licensing (E5 or add-ons) for:
  • Adaptive/risk-based security (e.g., Privileged Identity Management, risk-based Conditional Access)
  • Advanced threat detection and response (e.g., Defender for Endpoint P2, Defender for Office 365 P2)
  • Strict compliance or data controls (e.g., Insider Risk Management, Advanced Audit, Communication Compliance)

5. Final Recommendations & Checklist

• Summarizes the journey: assess, remediate, pilot Copilot, train users, and schedule ongoing reviews.
• Provides a detailed checklist for each security and compliance area, including navigation steps in the Microsoft 365 admin interfaces.

Key Takeaways

• Security First: Addressing identity, device, threat, data, and external access risks is essential before enabling Copilot.
• Business Premium is Powerful: Most SMBs can achieve a strong security baseline with Business Premium, but advanced needs may require E5 add-ons.
• Continuous Improvement: Regular reviews, user training, and policy updates are critical for ongoing security and compliance.
• Pilot Approach: Start Copilot with a controlled group, monitor usage, and gather feedback before a full rollout.