Microsoft Copilot is quickly becoming one of the most talked-about AI tools for business productivity. From summarizing emails and meetings to drafting documents and analyzing data, the promise is real.
But before turning Copilot on, there’s an important question many organizations skip:
Is our Microsoft 365 environment actually ready for AI?
Based on what we see working with Ohio businesses, the answer is often not yet. Below are the most common questions we hear when companies start exploring Copilot — and what you should know before enabling it.
A Copilot Readiness Assessment is a structured review of your Microsoft 365 environment to determine whether it’s secure, organized, and properly governed for AI tools like Microsoft Copilot.
Copilot doesn’t create new permissions — it uses the access users already have. That means any existing security gaps, oversharing, or outdated configurations can be exposed instantly once AI is enabled.
A readiness assessment looks at:
Microsoft 365 security and identity settings
User access and permissions
Teams and SharePoint structure
Data governance and compliance controls
Licensing alignment for Copilot
The goal isn’t to slow AI adoption — it’s to make sure it’s safe and effective.
This assessment is ideal for:
Small and mid-sized businesses considering Microsoft Copilot
Organizations with internal IT teams that want a second set of expert eyes
Companies that have grown organically in Microsoft 365 over time
Leadership teams that want clarity before approving AI tools
Even businesses that feel “pretty secure” often discover hidden risks once permissions and data access are reviewed more closely.
Copilot is powerful because it can access files, emails, chats, and documents across Microsoft 365. But that power comes with responsibility.
Common issues we uncover include:
Files shared too broadly across Teams or SharePoint
Former employees still having access
Legacy authentication still enabled
Too many global administrators
Low Microsoft Secure Scores
Licensing that doesn’t match how the tools are actually used
Copilot doesn’t know what should be private — it only knows what users can access.
A typical Copilot Readiness Assessment includes:
Security & identity review
MFA, Conditional Access, admin roles, legacy authentication, Secure Score
Teams & SharePoint analysis
Site sprawl, ownership, permissions, external sharing, inactive content
Data governance review
Retention policies, sensitivity labels, oversharing risks
Licensing review
Confirmation that licenses support Copilot and recommendations to avoid overspending
AI readiness roadmap
A clear plan for what to fix now vs. later
Businesses receive a clear, actionable deliverable — not just a list of problems.
This typically includes:
An executive-level summary
Key security and data exposure findings
Copilot go / no-go guidance
Prioritized recommendations
A 90-day roadmap for safe AI adoption
For organizations with internal IT teams, findings are shared in a way that’s easy to implement and aligned with existing workflows.
Yes. Cloud Cover is co-managed IT friendly.
Many of our Copilot Readiness Assessments are done in partnership with internal IT teams. We provide clarity, recommendations, and structure — while your team stays in control of the environment.
This approach works especially well for organizations that want to move quickly with AI without introducing new risk.
Most assessments are completed within 5–7 business days, depending on the size and complexity of your Microsoft 365 environment.
Microsoft Copilot can absolutely improve productivity — but only if the foundation is solid.
A Copilot Readiness Assessment helps businesses slow down just enough to avoid costly mistakes, data exposure, or security issues later.
If you’re thinking about Copilot and want a clear picture of where things stand, starting with readiness is the smart first step.
Learn more about our Copilot Readiness Assessment
Ready to talk to us about Copilot for your business? Schedule an introductory call with our team.