Running a Readiness Assessment

Overview

You’ve reviewed the prerequisites. You know what Copilot needs—licensing, identity, SharePoint, network. But knowing the requirements and actually meeting them are two different things. A readiness assessment tells you where you stand today and what you need to fix before you can safely enable Copilot.

This video walks through a structured approach to readiness assessment: the tools Microsoft provides, how to evaluate your biggest risk area (permissions and oversharing), how to assess whether your users are ready, and how to build a remediation plan that gets you from “almost ready” to “go live.”

What You’ll Learn

• Microsoft’s Tools: Readiness resources, the Copilot Dashboard, SharePoint Advanced Management, and Secure Score
• Oversharing Evaluation: How to find and prioritize permission problems before Copilot exposes them
• User Readiness: Assessing digital literacy, training needs, and change management readiness
• Remediation Planning: Categorizing gaps, assigning owners, and deciding when to proceed

Script

Hook: don’t guess—assess

Prerequisites tell you what you need. A readiness assessment tells you whether you actually have it.

There’s a difference between knowing that your SharePoint permissions should be clean and actually running a report that proves they are. There’s a difference between requiring MFA and confirming it’s enforced for every user who will get Copilot.

A structured assessment prevents deployment surprises. It turns “I think we’re ready” into “here’s the evidence that we’re ready—and here’s what we still need to fix.”

Let’s walk through how to do this.

Microsoft’s readiness tools

Microsoft provides several tools that help you assess Copilot readiness. None of them does everything, but together they give you a comprehensive picture.

First, the Microsoft Copilot adoption site at adoption.microsoft.com. This is your starting point for readiness resources. It includes readiness guides, assessment templates, and planning tools specifically designed for Copilot deployments. The content is organized by role—IT admin, security, change management—so you can direct the right resources to the right people.

Second, the Microsoft Copilot Dashboard in the Microsoft 365 admin center. Once you have Copilot licenses in your tenant, the dashboard shows readiness indicators and, after enablement, usage analytics. Before deployment, use it to verify that your tenant configuration meets baseline requirements.

Third, SharePoint Advanced Management. This is the most important tool for readiness assessment. SharePoint Advanced Management provides oversharing reports that identify sites and content shared more broadly than intended. It shows you which sites have “everyone” access, which content is externally shared, and where permission inheritance may be creating unintended access. If you don’t have SharePoint Advanced Management enabled, enable it before your assessment. The insights it provides are essential.

Fourth, Microsoft Secure Score. While not Copilot-specific, Secure Score gives you a baseline measurement of your Microsoft 365 security posture. It identifies configuration gaps across identity, device management, data protection, and app security. A low Secure Score in areas relevant to Copilot—like identity and information protection—signals readiness gaps.

These tools complement each other. The adoption site tells you what to assess. The Copilot Dashboard shows tenant-level readiness. SharePoint Advanced Management dives deep on permissions. Secure Score measures overall security posture. Use all four.

Permissions and oversharing evaluation

If there’s one area that deserves the most attention in your readiness assessment, it’s permissions and oversharing. This is the number one readiness risk for Copilot.

Here’s why. Copilot respects existing permissions. It only shows users content they can already access. That’s the right security model. But it means that every oversharing problem in your environment becomes a Copilot problem. If a user has access to a SharePoint site they shouldn’t—maybe because the site was shared with “everyone except external users” years ago—Copilot can now surface that content in search results, summaries, and recommendations.

Before Copilot, oversharing was a latent risk. Users had access to content they didn’t know about because they never looked for it. Copilot actively surfaces content. That latent risk becomes an active exposure.

Start your assessment with SharePoint access reviews. Use SharePoint Advanced Management to generate reports on sites with broad sharing. Look for sites shared with “Everyone,” “Everyone except external users,” or large security groups that may include users who shouldn’t have access.

Next, review Teams membership. Are there Teams with hundreds of members that were created for a short-term project and never cleaned up? Are there Teams with guest accounts that are no longer active? Each Team is backed by a SharePoint site and a mailbox, so overshared Teams mean overshared content.

Check OneDrive sharing. Users share OneDrive files and folders with colleagues for collaboration, but those shares often persist long after the collaboration ends. Run a sharing audit to identify OneDrive content shared broadly.

Prioritize what you find by risk level. Not every oversharing instance is critical. Focus first on sites and content that contain sensitive data—personnel records, financial information, legal documents, controlled unclassified information. Remediate those before enabling Copilot. Lower-risk oversharing can be addressed over time.

User readiness and training needs

Technical readiness is half the equation. The other half is whether your users are ready to use Copilot effectively.

Start by assessing your users’ digital literacy baseline. How comfortable are they with Microsoft 365 today? Do they use Teams, SharePoint, and OneDrive regularly, or are they still primarily email-and-desktop workers? Users who are already proficient with M365 will adopt Copilot more quickly. Users who struggle with basic M365 features will need more support.

Identify training gaps. Copilot requires users to write effective prompts, understand what Copilot can and can’t do, and verify AI-generated outputs. These are new skills. Your training plan should cover prompt writing, Copilot’s limitations and responsible use, and application-specific Copilot features.

Evaluate change management readiness. Does your organization have a history of successful technology rollouts? Is there leadership support for Copilot? Are there champions who can model effective use and help peers? These signals predict adoption success more reliably than technical readiness.

For pilot group selection, choose users who are digitally literate, willing to provide feedback, tolerant of issues, and representative of different roles and workflows. A good pilot group gives you diverse usage data and credible advocates for broader rollout.

Build a training plan framework before you enable Copilot. You don’t need polished training materials on day one, but you need a plan: what will you teach, to whom, in what format, and on what timeline.

Building a remediation plan

Your assessment will produce a list of gaps. The next step is turning that list into an actionable remediation plan.

Start by categorizing each gap. Blockers are issues that must be resolved before you can enable Copilot—like MFA not being enforced or critical SharePoint sites being widely overshared. Risks are issues that should be addressed but don’t prevent deployment—like moderate oversharing on low-sensitivity sites or incomplete training materials. Optimizations are nice-to-have improvements that can happen after deployment—like refining Conditional Access session controls or expanding Secure Score.

For each blocker and high-priority risk, set a remediation timeline. Be specific: “Remediate top 20 overshared SharePoint sites by March 15” is actionable. “Fix SharePoint permissions” is not.

Assign an owner for each remediation item. Identity gaps go to your identity team. SharePoint permissions go to your collaboration admin. Training goes to your change management lead. Without clear ownership, gaps don’t get fixed.

Track remediation progress. Use a shared tracker—a spreadsheet, a Planner board, a Teams list—whatever your team actually uses. Review progress weekly.

Finally, decide what level of risk you’re willing to accept. You don’t need a perfect environment to deploy Copilot. You need blockers resolved and high risks mitigated. Some residual risk is acceptable if it’s documented and the authorizing official agrees.

Close: from assessment to go-live

A readiness assessment isn’t a one-time event. After you remediate the gaps you found, re-assess. Verify that the fixes worked. Check that new issues haven’t appeared.

Set clear go-live criteria. Define what “ready” looks like in specific, measurable terms: all blockers resolved, MFA enforced for 100% of pilot users, top oversharing risks remediated, training materials available, support playbooks documented. When you meet those criteria, you’re ready to enable Copilot for your pilot group.

Document everything. Your assessment results, remediation plan, go-live criteria, and final readiness status should all be in your governance records. If you’re operating under an ATO, this documentation supports your authorization. If you’re not, it still gives your leadership and your auditors confidence that you deployed Copilot responsibly.

Assessment is how you turn confidence into evidence. Do the work, document the results, and deploy from a position of knowledge rather than hope.

Sources & References

• Microsoft 365 Copilot requirements — Requirements used as assessment baseline
• Microsoft Copilot adoption resources — Readiness guides, templates, and planning tools
• Get ready for Copilot with SharePoint Advanced Management — Oversharing assessment and remediation tools