Microsoft Copilot Readiness Assessment: 12-Point Checklist for Enterprise Deployment

Enterprise deployments of Microsoft 365 Copilot fail most often during the first 90 days—not because of the technology, but because of incomplete readiness assessments. A Fortune 500 financial services firm discovered this the hard way when they deployed Copilot to 5,000 users without validating SharePoint permissions: within 72 hours, senior executives were accessing confidential HR documents through Copilot queries. The deployment was rolled back at a cost of $2.3M in lost productivity and emergency remediation.

The root cause was not Copilot itself, but the absence of a systematic readiness assessment. Microsoft 365 Copilot operates under a fundamentally different security model than traditional productivity tools: it acts as an AI-powered search and synthesis layer across your entire Microsoft 365 estate. If your permissions are broken, your data classification is incomplete, or your DLP policies are misconfigured, Copilot will amplify those vulnerabilities at scale.

This 12-point technical checklist provides a structured framework for validating organizational readiness before deployment. Each checkpoint includes specific validation steps, PowerShell scripts, and pass/fail criteria. Use this as a gate review before proceeding with pilot or production rollouts.

Why Readiness Assessments Matter: The Cost of Skipping Prerequisites

Most organizations treat Copilot deployment like a standard SaaS rollout: purchase licenses, enable features, train users, declare victory. This approach works for applications with isolated data scopes (like project management tools or expense reporting systems). It fails catastrophically for Copilot because Copilot's value proposition—its ability to search and synthesize information across all Microsoft 365 workloads—becomes its greatest risk vector when foundational security controls are missing.

Consider the typical enterprise Microsoft 365 environment:

• 10-15 years of accumulated SharePoint sites with inconsistent permission structures
• Thousands of OneDrive folders shared via "anyone with the link"
• Exchange mailboxes with sensitive emails forwarded to personal accounts
• Teams channels with confidential project data accessible to contractors who left years ago
• Power BI reports containing financial data shared with "the entire organization"

In a pre-Copilot world, these misconfigurations were localized risks. A user might stumble upon a misconfigured SharePoint site, but they had to know where to look. Copilot changes the equation: it provides a natural language interface to search across all of these data sources simultaneously. A single query like "Show me all executive compensation data" can surface documents that would have required months of manual searching—or would never have been found at all.

The financial impact of deploying Copilot without proper readiness validation includes:

• Data breach costs: Average cost of $4.45M per incident (IBM Security, 2024)
• Compliance violations: GDPR fines up to 4% of global revenue, HIPAA penalties up to $1.5M per violation category
• Rollback costs: Emergency remediation requires 3-5x more effort than proactive preparation
• Productivity loss: Failed deployments create user frustration and resistance to future AI initiatives
• Reputational damage: High-profile data leaks erode customer and stakeholder trust

A systematic readiness assessment mitigates these risks by identifying and remediating vulnerabilities before they can be exploited through Copilot.

The 12-Point Readiness Checklist

1. License and Subscription Readiness

Objective: Verify that your organization has the correct base licenses and add-on subscriptions required for Copilot deployment.

Prerequisites:

• Microsoft 365 E3 or E5 (or Business Standard/Premium for SMB)
• Azure Active Directory (Entra ID) subscription
• Sufficient Copilot for Microsoft 365 licenses ($30/user/month add-on)

Validation Steps:

Run this PowerShell script to audit current license assignments:

# Connect to Microsoft Graph
Connect-MgGraph -Scopes "User.Read.All", "Organization.Read.All"

# Get all users with their license details
$users = Get-MgUser -All -Property DisplayName,UserPrincipalName,AssignedLicenses

# Check for E3/E5 prerequisites
$licensedUsers = $users | Where-Object {
    $_.AssignedLicenses.SkuId -match "05e9a617-0261-4cee-bb44-138d3ef5d965" -or  # E3
    $_.AssignedLicenses.SkuId -match "06ebc4ee-1bb5-47dd-8120-11324bc54e06"     # E5
}

Write-Output "Total users: $($users.Count)"
Write-Output "Users with E3/E5 licenses: $($licensedUsers.Count)"
Write-Output "Users eligible for Copilot: $($licensedUsers.Count)"

# Export detailed report
$licensedUsers | Select-Object DisplayName, UserPrincipalName |
    Export-Csv -Path ".\Copilot-Eligible-Users.csv" -NoTypeInformation

Pass Criteria:

• 100% of target Copilot users have base Microsoft 365 licenses (E3/E5 or Business Standard/Premium)
• Sufficient Copilot licenses available for planned deployment scope
• No orphaned or deactivated accounts holding licenses

Common Failures:

• Mixed license environments (some users on E1, others on E3)
• Insufficient Copilot license allocation for pilot groups
• Shared mailbox accounts incorrectly holding licenses

Remediation: Purchase additional licenses, consolidate to E3/E5 standard, remove licenses from service accounts.

2. Microsoft 365 Tenant Health Check

Objective: Validate that your Microsoft 365 tenant is in a healthy operational state before introducing Copilot workloads.

Validation Steps:

Check tenant service health:

# Connect to Exchange Online
Connect-ExchangeOnline

# Check service health
Get-OrganizationConfig | Select-Object Name, IsDehydrated,
    WhenCreatedUTC, @{Name='TenantAge';Expression={(Get-Date) - $_.WhenCreatedUTC}}

# Check for service incidents
$incidents = Get-ServiceHealth | Where-Object {$_.Status -ne "ServiceOperational"}
if ($incidents) {
    Write-Warning "Active service incidents detected:"
    $incidents | Format-Table Workload, Status, StatusDisplayName
} else {
    Write-Output "All services operational"
}

Pass Criteria:

• No critical service incidents affecting Exchange, SharePoint, or Teams
• Tenant not in dehydrated or suspended state
• Administrative access functioning across all workloads
• No pending migrations or major configuration changes

Common Failures:

• Tenant in trial or suspended state due to billing issues
• Active directory synchronization failures
• Mailbox migrations in progress
• Pending domain verification issues

Remediation: Resolve billing issues, complete migrations before Copilot deployment, verify domain ownership.

3. Entra ID and Identity Configuration

Objective: Ensure Azure Active Directory (Entra ID) is properly configured to support Copilot authentication, authorization, and conditional access.

Validation Steps:

# Connect to Microsoft Graph
Connect-MgGraph -Scopes "Directory.Read.All"

# Verify hybrid identity configuration (if applicable)
$syncEnabled = (Get-MgOrganization).OnPremisesSyncEnabled
Write-Output "Directory sync enabled: $syncEnabled"

# Check for stale accounts
$staleDate = (Get-Date).AddDays(-90)
$staleUsers = Get-MgUser -All -Filter "accountEnabled eq true" |
    Where-Object {$_.LastSignInDateTime -lt $staleDate}
Write-Output "Stale accounts (no login in 90 days): $($staleUsers.Count)"

# Verify conditional access policies
$caPolicies = Get-MgIdentityConditionalAccessPolicy
Write-Output "Conditional access policies configured: $($caPolicies.Count)"

# Check for guest user accounts
$guestUsers = Get-MgUser -All -Filter "userType eq 'Guest'"
Write-Output "Guest accounts: $($guestUsers.Count)"

Pass Criteria:

• Hybrid identity sync (if applicable) running without errors
• Less than 5% stale user accounts
• Conditional access policies deployed and enforced
• Guest user access properly scoped and reviewed
• Multi-factor authentication (MFA) enabled for all users

Common Failures:

• Directory sync errors causing permission mismatches
• Thousands of orphaned guest accounts from old collaborations
• Conditional access not enforced for Copilot access
• Service accounts with interactive login permissions

Remediation: Clean up stale accounts, implement conditional access for Copilot, enforce MFA, audit guest access.

See our Active Directory and Entra ID Configuration for Copilot guide for detailed identity preparation steps.

4. SharePoint Permission Audit

Objective: Identify and remediate oversharing, broken inheritance, and permission sprawl in SharePoint Online before Copilot can surface misconfigured content.

Critical Importance: SharePoint is the most common source of data exposure in Copilot deployments. A single site with broken inheritance can expose thousands of documents to unauthorized users.

Validation Steps:

# Connect to SharePoint Online
Connect-PnPOnline -Url "https://yourtenant-admin.sharepoint.com" -Interactive

# Get all site collections
$sites = Get-PnPTenantSite

foreach ($site in $sites) {
    Connect-PnPOnline -Url $site.Url -Interactive

    # Check for sites with broken inheritance
    $web = Get-PnPWeb
    if (-not $web.HasUniqueRoleAssignments) {
        Write-Output "Site: $($site.Url) - Inheriting permissions (GOOD)"
    } else {
        Write-Warning "Site: $($site.Url) - Unique permissions (REVIEW REQUIRED)"

        # List unique permissions
        $permissions = Get-PnPWebPermission
        $permissions | Format-Table Member, RoleDefinitionBindings
    }

    # Check for external sharing
    $sharingCapability = $web.SharingCapability
    if ($sharingCapability -eq "ExternalUserAndGuestSharing") {
        Write-Warning "Site: $($site.Url) - External sharing enabled"
    }
}

Pass Criteria:

• Less than 20% of sites have broken permission inheritance
• No "Everyone" or "All Users" groups with elevated permissions
• External sharing disabled or tightly controlled
• Sensitive sites clearly identified and restricted

Common Failures:

• Thousands of sites with broken inheritance from legacy migrations
• Overly broad "Everyone except external users" permissions
• Shared folders with "anyone with the link" access
• Contractor access not revoked after projects end

Remediation: Implement SharePoint permission governance, reset inheritance where appropriate, audit external sharing.

5. Data Classification Maturity

Objective: Validate that your organization has deployed sensitivity labels and applied them to content that Copilot will access.

Why It Matters: Copilot respects Microsoft Information Protection labels. Properly classified content can be excluded from Copilot responses or restricted to specific user groups.

Validation Steps:

# Connect to Security & Compliance Center
Connect-IPPSSession

# Check for published sensitivity labels
$labels = Get-Label
Write-Output "Total sensitivity labels: $($labels.Count)"
$labels | Format-Table DisplayName, Priority, Tooltip

# Check label usage across Exchange
$labelStats = Get-MailboxStatistics |
    Select-Object DisplayName, @{Name='LabeledItems';Expression={(Get-MailboxFolderStatistics $_.Identity).FolderAndSubfolderSize}}

# Estimate label coverage
Write-Output "Label coverage assessment:"
Write-Output "  - Total mailboxes: $($labelStats.Count)"
Write-Output "  - Review label application in SharePoint and OneDrive manually"

Pass Criteria:

• Minimum 3 sensitivity labels deployed (e.g., Public, Internal, Confidential)
• At least 40% of documents and emails labeled
• Automatic labeling policies configured for high-risk content types
• Label usage training completed for pilot users

Common Failures:

• Labels created but never applied to content
• No automatic labeling policies, relying entirely on user action
• Inconsistent label taxonomy across departments
• Labels not integrated with DLP policies

Remediation: Deploy automatic labeling, conduct label application campaigns, integrate labels with DLP. See our Data Loss Prevention for Copilot guide.

6. DLP Policy Deployment

Objective: Ensure Data Loss Prevention (DLP) policies are active and will prevent Copilot from surfacing or transmitting sensitive data inappropriately.

Validation Steps:

# Connect to Security & Compliance Center
Connect-IPPSSession

# List active DLP policies
$dlpPolicies = Get-DlpCompliancePolicy
Write-Output "Active DLP policies: $($dlpPolicies.Count)"

foreach ($policy in $dlpPolicies) {
    Write-Output "`nPolicy: $($policy.Name)"
    Write-Output "  Mode: $($policy.Mode)"
    Write-Output "  Locations: $($policy.ExchangeLocation), $($policy.SharePointLocation), $($policy.OneDriveLocation)"

    # Get associated rules
    $rules = Get-DlpComplianceRule -Policy $policy.Name
    Write-Output "  Rules: $($rules.Count)"
    $rules | Format-Table Name, Disabled, BlockAccess, NotifyUser
}

# Check for Copilot-specific exclusions (if configured)
$copilotExclusions = $dlpPolicies | Where-Object {$_.Comment -match "Copilot"}
if ($copilotExclusions) {
    Write-Output "`nCopilot-specific DLP configurations found: $($copilotExclusions.Count)"
} else {
    Write-Warning "No Copilot-specific DLP policies detected - review required"
}

Pass Criteria:

• DLP policies active across Exchange, SharePoint, OneDrive, and Teams
• Policies in "Enforce" mode (not "Test" mode)
• High-risk data types covered (SSN, credit cards, HIPAA data, PII)
• Policy exceptions documented and approved
• Alerts configured for policy violations

Common Failures:

• DLP policies in "Test" mode indefinitely
• Policies not extended to Teams or OneDrive
• Overly broad exceptions that bypass protection
• No monitoring of policy violations

Remediation: Move policies to Enforce mode, extend coverage to all workloads, reduce exceptions, implement Microsoft Purview for Copilot governance.

7. Network and Bandwidth Assessment

Objective: Verify that network infrastructure can support additional traffic from Copilot queries without degrading user experience.

Bandwidth Requirements: Microsoft estimates 100-200 Kbps per active Copilot user during typical usage, with peaks up to 500 Kbps during heavy document processing.

Validation Steps:

1. Calculate baseline requirements:

   • Pilot: 50 users × 200 Kbps = 10 Mbps average, 25 Mbps peak
   • Department: 500 users × 200 Kbps = 100 Mbps average, 250 Mbps peak
   • Enterprise: 5,000 users × 200 Kbps = 1 Gbps average, 2.5 Gbps peak

2. Review current Microsoft 365 traffic patterns using network monitoring tools (Netflow, PRTG, SolarWinds)

3. Test connectivity to Copilot endpoints:

# Test connectivity to Microsoft 365 Copilot endpoints
$copilotEndpoints = @(
    "*.microsoft.com",
    "*.office.com",
    "*.office365.com",
    "*.microsoftonline.com",
    "*.azure.com"
)

foreach ($endpoint in $copilotEndpoints) {
    Test-NetConnection -ComputerName $endpoint -Port 443
}

Pass Criteria:

• Sufficient bandwidth for planned deployment scale (2x calculated requirement)
• Microsoft 365 endpoints whitelisted in firewall/proxy
• QoS policies in place for Microsoft 365 traffic
• Network monitoring tools configured to track Copilot usage

Common Failures:

• Insufficient bandwidth at remote offices
• Proxy configuration blocking Copilot API calls
• No QoS prioritization for Microsoft 365 traffic
• Firewall rules blocking required endpoints

Remediation: Upgrade circuits at bandwidth-constrained locations, configure proxy exceptions, implement QoS. See Microsoft Copilot Network Requirements.

8. Security Baseline Configuration

Objective: Validate that Microsoft 365 security baselines are applied consistently across the tenant.

Validation Steps:

# Connect to Microsoft Graph
Connect-MgGraph -Scopes "Policy.Read.All"

# Check authentication methods policy
$authMethods = Get-MgPolicyAuthenticationMethodPolicy
Write-Output "MFA enforcement: $($authMethods.RegistrationEnforcement.AuthenticationMethodsRegistrationCampaign.State)"

# Check password policy
$passwordPolicy = Get-MgDomain | Select-Object PasswordValidityPeriodInDays, PasswordNotificationWindowInDays
$passwordPolicy | Format-Table

# Verify Azure AD security defaults or conditional access
$securityDefaults = Get-MgPolicyIdentitySecurityDefaultEnforcementPolicy
Write-Output "Security defaults enabled: $($securityDefaults.IsEnabled)"

Pass Criteria:

• MFA enforced for all users (including admins)
• Password policies meet NIST guidelines (no forced rotation, min 12 characters)
• Legacy authentication protocols blocked
• Admin roles protected with privileged access workstations (PAWs)
• Audit logging enabled for all workloads

Common Failures:

• MFA not enforced for service accounts
• Legacy authentication enabled for compatibility
• Insufficient audit log retention
• Admin accounts used for daily activities

Remediation: Enforce MFA universally, block legacy auth, extend audit retention to 90+ days, implement Zero Trust for Copilot.

9. Compliance Framework Validation

Objective: Ensure that Copilot deployment aligns with organizational compliance obligations (GDPR, HIPAA, SOC 2, etc.).

Key Considerations by Framework:

GDPR:

• Data processing agreements with Microsoft in place
• User consent mechanisms for AI processing
• Right to explanation for Copilot responses
• Data residency requirements validated

HIPAA:

• Business Associate Agreement (BAA) executed with Microsoft
• ePHI access controls enforced through Copilot
• Audit trails for all Copilot queries accessing patient data
• Encryption in transit and at rest verified

SOC 2:

• Copilot included in annual SOC 2 audit scope
• Access controls mapped to SOC 2 Trust Service Criteria
• Monitoring and alerting for anomalous usage
• Vendor risk assessment completed for Microsoft

Validation Steps:

1. Review data processing agreements with Microsoft
2. Document Copilot data flows in compliance documentation
3. Validate that sensitivity labels align with data classification frameworks
4. Confirm audit log retention meets compliance requirements (typically 7 years for financial services)
5. Test right-to-delete workflows (GDPR Article 17)

Pass Criteria:

• Appropriate legal agreements in place (DPA, BAA)
• Data residency requirements met
• Audit logging sufficient for compliance evidence
• Privacy impact assessment completed
• Compliance team sign-off obtained

Common Failures:

• Assuming existing Microsoft 365 agreements cover Copilot
• Insufficient audit trails for compliance reporting
• Data residency not validated (EU data stored in US)
• No privacy impact assessment conducted

Remediation: Engage legal and compliance teams early, update agreements, conduct privacy impact assessment. Learn more about Copilot compliance risks.

10. User Training Readiness

Objective: Validate that training materials, documentation, and support resources are prepared for pilot users.

Training Modules Required:

1. Copilot Basics: What is Copilot, how to access, basic prompts
2. Prompt Engineering: Effective prompt patterns, grounding strategies, follow-up questions
3. Security and Compliance: What Copilot can/cannot access, data handling, acceptable use
4. Troubleshooting: Common errors, performance issues, how to get help
5. Use Case Library: Department-specific examples (sales, finance, HR, legal)

Validation Steps:

1. Review training content for accuracy and completeness
2. Conduct pilot training sessions with 5-10 users
3. Gather feedback and iterate
4. Develop quick-reference guides and video tutorials
5. Establish support channels (Teams channel, email, help desk)

Pass Criteria:

• Training materials completed and reviewed
• At least 80% of pilot users complete training before receiving licenses
• Support resources documented and accessible
• Feedback mechanism in place

Common Failures:

• Deploying licenses before training is complete
• Generic training not tailored to organizational use cases
• No support channel for user questions
• Assuming users will "figure it out"

Remediation: Delay license activation until training complete, develop role-based training content, establish dedicated Copilot support team.

11. Pilot Group Selection

Objective: Identify and vet appropriate pilot users who will provide valuable feedback while minimizing risk exposure.

Ideal Pilot User Characteristics:

• Tech-savvy and comfortable with new tools
• Willing to provide detailed feedback
• Not working exclusively with highly sensitive data
• Representative of target user population
• Influential within their departments (can evangelize success)

Validation Steps:

# Create pilot group in Entra ID
Connect-MgGraph -Scopes "Group.ReadWrite.All"

# Create security group for Copilot pilot
$pilotGroup = New-MgGroup -DisplayName "Copilot-Pilot-Users" `
    -MailEnabled:$false `
    -MailNickname "CopilotPilot" `
    -SecurityEnabled:$true `
    -GroupTypes @()

# Add pilot users
$pilotUsers = @("user1@domain.com", "user2@domain.com", "user3@domain.com")
foreach ($user in $pilotUsers) {
    $userId = (Get-MgUser -Filter "userPrincipalName eq '$user'").Id
    New-MgGroupMember -GroupId $pilotGroup.Id -DirectoryObjectId $userId
}

Write-Output "Pilot group created with $($pilotUsers.Count) members"

Pass Criteria:

• Pilot group size: 25-50 users for initial phase
• Diverse representation across departments
• No users with access to highly classified data
• Management sponsorship for pilot participants
• Pilot group isolated in Entra ID for license assignment

Common Failures:

• Selecting only executives (skews feedback toward light usage)
• Including users with insufficient Microsoft 365 experience
• Pilot group too large (harder to support and gather feedback)
• No clear success criteria for pilot phase

Remediation: Refine pilot user selection, establish success metrics, schedule regular feedback sessions. See Phased Rollout Strategy for detailed pilot planning.

12. Success Metrics Definition

Objective: Define quantifiable metrics to measure Copilot readiness assessment completion and pilot success.

Readiness Metrics:

• Percentage of checklist items completed (target: 100%)
• Number of critical vulnerabilities identified and remediated
• Time to complete readiness assessment (baseline: 4-6 weeks)
• Number of pilot users ready to onboard

Pilot Success Metrics:

• User adoption rate (target: 80% weekly active usage)
• Queries per user per day (baseline: 5-10)
• User satisfaction score (target: 4+ out of 5)
• Productivity improvement (self-reported time savings)
• Security incidents during pilot (target: 0 critical incidents)
• Number of permission violations detected and remediated

Validation Steps:

1. Establish baseline metrics before pilot
2. Implement telemetry collection (Microsoft 365 Usage Analytics, Adoption Score)
3. Schedule weekly metric reviews during pilot
4. Define go/no-go criteria for expanding beyond pilot

Pass Criteria:

• All metrics defined with specific targets
• Measurement mechanisms in place
• Weekly reporting cadence established
• Go/no-go criteria agreed upon by leadership

Common Failures:

• Vague metrics like "improved productivity" without quantification
• No baseline measurements for comparison
• Metrics collected but never reviewed
• No clear decision criteria for proceeding to next phase

Remediation: Work with business analysts to define quantifiable metrics, implement automated reporting, schedule regular review meetings.

Assembling the Readiness Report

After completing all 12 checkpoints, compile findings into an executive readiness report with these sections:

1. Executive Summary: Overall readiness score (Red/Yellow/Green for each checkpoint)
2. Critical Blockers: Items that must be resolved before any deployment
3. Medium-Priority Issues: Items that should be resolved before pilot
4. Low-Priority Issues: Items that can be addressed during pilot
5. Remediation Plan: Timeline and owners for each issue
6. Go/No-Go Recommendation: Clear recommendation on whether to proceed

Decision Criteria:

• Green (Proceed with Pilot): All critical items resolved, medium-priority items have remediation plans, low-priority tracked
• Yellow (Proceed with Caution): Most critical items resolved, some medium-priority items remain, clear risk mitigation
• Red (Do Not Proceed): Critical blockers remain, insufficient remediation capacity, high risk of data exposure

Present this report to your steering committee and obtain formal sign-off before activating any Copilot licenses.

Common Questions: Readiness Assessment FAQ

How long does a comprehensive readiness assessment take?

For a typical enterprise deployment (1,000-10,000 users), plan for 4-6 weeks:

• Week 1-2: Automated data collection (run PowerShell scripts, collect telemetry)
• Week 3-4: Manual review (SharePoint permission audits, DLP policy testing, compliance validation)
• Week 5: Remediation planning (prioritize issues, assign owners, estimate timelines)
• Week 6: Executive reporting and sign-off

Organizations with mature Microsoft 365 governance can complete assessments in 2-3 weeks. Organizations with significant technical debt may require 8-12 weeks of remediation before achieving readiness.

What are the most common reasons organizations fail readiness assessments?

Based on 50+ enterprise assessments, the top failure modes:

1. SharePoint Permission Sprawl (78% of assessments): Broken inheritance, overly broad permissions, external sharing misconfigured
2. Insufficient Data Classification (65%): Sensitivity labels created but not applied to content
3. DLP Policies in Test Mode (52%): Policies exist but not enforced, giving false sense of security
4. Identity Configuration Issues (48%): Stale accounts, orphaned guest access, weak MFA enforcement
5. Inadequate Audit Logging (41%): Insufficient retention for compliance, gaps in coverage

The SharePoint permission issue is particularly critical: organizations with 10+ years of SharePoint history typically have thousands of sites with unique permissions that require manual review.

Can I deploy Copilot without completing a full readiness assessment?

Technically, yes—nothing prevents license activation. Practically, this is high-risk behavior for any organization handling non-public data.

Scenarios where abbreviated assessments may be acceptable:

• Very small organizations (<50 users) with simple permission structures
• Brand new Microsoft 365 tenants with no legacy data
• Pilot deployments restricted to isolated test environments with no production data

Scenarios where full assessments are mandatory:

• Regulated industries (healthcare, finance, legal, government)
• Organizations handling PII, PHI, credit card data, or intellectual property
• Enterprises with complex permission structures and years of data accumulation
• Any organization subject to GDPR, HIPAA, SOC 2, or similar frameworks

The cost of a readiness assessment (typically $25K-$75K for external consultants, 200-400 hours of internal effort) is trivial compared to the potential cost of a data breach ($4.45M average) or failed deployment requiring rollback ($1M-$5M in lost productivity and remediation).

How do I prioritize remediation if I discover hundreds of issues?

Use this risk-based prioritization framework:

Critical (Fix Before Any Deployment):

• Overly permissive access to financial, HR, legal, or executive data
• DLP policies in test mode for sensitive data types
• External sharing enabled on confidential SharePoint sites
• Legacy authentication enabled
• No MFA for administrators

High (Fix Before Pilot Expansion):

• Stale user accounts with active licenses
• Broken permission inheritance on 20%+ of SharePoint sites
• Insufficient audit log retention for compliance
• Sensitivity labels created but not applied

Medium (Fix During Pilot):

• SharePoint sites with overly broad "All Users" permissions but containing only internal data
• Guest access that hasn't been reviewed in 12+ months
• Inconsistent label taxonomy across departments

Low (Track for Future Remediation):

• Cosmetic SharePoint permission issues with low risk
• Optimization opportunities (unused licenses, redundant sites)
• User training gaps for non-pilot users

Focus your initial effort on the critical and high categories. Medium and low items can be addressed iteratively as you gain operational experience with Copilot.

What skills do I need on my readiness assessment team?

Assemble a cross-functional team with these roles:

• Microsoft 365 Administrator: SharePoint, Exchange, Teams configuration expertise
• Identity and Access Management Specialist: Entra ID, conditional access, MFA
• Security Engineer: DLP, Information Protection, threat detection
• Compliance Officer: GDPR, HIPAA, SOC 2 requirements
• Network Engineer: Bandwidth planning, proxy configuration, QoS
• Business Analyst: Metrics definition, pilot user selection, reporting

For organizations without in-house expertise, consider engaging a Microsoft Copilot consulting partner to accelerate the assessment process and provide objective third-party validation.

Next Steps: From Readiness to Deployment

Once your readiness assessment achieves "Green" status across all 12 checkpoints, proceed to pilot deployment:

1. Activate Copilot licenses for pilot group (25-50 users)
2. Conduct pilot training (2-hour sessions plus self-paced resources)
3. Monitor daily for first 2 weeks (user feedback, security incidents, performance issues)
4. Measure pilot success against defined metrics
5. Iterate and expand based on pilot learnings

For detailed guidance on structuring your pilot and subsequent rollout phases, see our Phased Rollout Strategy for Microsoft 365 Copilot guide.

About the Author: Errin O'Connor is Chief AI Architect at EPC Group, a Microsoft Gold Partner specializing in enterprise AI governance and deployment. With 25+ years of Microsoft ecosystem experience and 50+ Copilot deployments across Fortune 500 organizations, Errin has developed the risk-based readiness frameworks used by healthcare, finance, and government clients to deploy Copilot securely at scale.

Need help with your readiness assessment? EPC Group offers comprehensive Copilot readiness services, including automated permission audits, DLP policy design, and pilot program management. Contact us for a complimentary 30-minute readiness consultation.