As an IT professional responsible for rolling out Copilot for Microsoft 365 within your organization, you’ve likely heard the promise – Copilot is easy to deploy, simple to use, and transformative in enhancing productivity. However, the reality, as you may have already discovered, is far more nuanced. Beneath the sleek presentations and impressive use-cases Microsoft provides, the IT journey behind Copilot adoption is complex and layered, filled with critical decisions that carry significant implications for your organization.
Initially, enabling Copilot may seem straightforward enough with comprehensive toolkits and checklists provided by Microsoft. Yet, once you engage with these resources, the true depth of complexity emerges. IT teams we’re working with have experienced significant confusion when navigating the documentation and wizards. What appears simple initially quickly reveals itself to be filled with intricate details that demand careful consideration. Yet, managed carefully and in the right order, the road to Copilot for Microsoft 365 roll-out can be a smooth one. Let’s take a look at some of the fundamentals…
Start with a Readiness Snapshot
Before diving into technical implementation, consider completing Microsoft’s Optimization Assessment – a readiness survey designed to benchmark your organization’s current security and governance maturity. This interactive tool can help you surface potential gaps early, enabling better planning and prioritization.
Identifying Key Stakeholders and Clarifying Roles
Then, you’ll need to clearly define who is responsible for what early on. Your stakeholders will include executive sponsors, people in your IT team, as well as identified champion groups (typically tech-savvy early adopters but not from HR or Legal, as they have access to more highly confidential information). Identifying this group from the outset will help you to make critical security and compliance decisions early on. One thing’s for sure, clear governance is crucial to effectively managing risk and communicating expectations throughout the organization.
Understanding Administrative Role Limitations
Next, a significant limitation that’s often overlooked when rolling out Copilot for Microsoft 365 is that enablement typically requires roles such as global admin or privileged identity management. Given the sensitivity of these roles, it’s likely that your policies will severely restrict who has them, presenting a substantial barrier to straightforward enablement (more on this later).
Data Security Decisions and Their Implications
Decisions around default security settings like multi-factor authentication (MFA) enforcement will have immediate, organization-wide implications, so these are not to be taken lightly. Such settings require comprehensive change management strategies and, without proper handling, can inadvertently lock users out of essential services. So, you’ll need to think through your comms plan and prepare and brief your user adoption team (if you have one) to mitigate user disruption.
Exploring Data Oversharing Risks
You’ve probably heard the horror stories of how someone with early access and unchecked permissions to Copilot can inadvertently access confidential project data or executive salary details. Copilot’s powerful data retrieval capabilities can unintentionally expose sensitive organizational information due to insufficient permissions management or absent sensitivity labelling.
Additionally, common behaviors like selecting “Everyone” or “Public” for convenience when sharing documents also pose serious risk – these settings are often chosen simply because they’re listed first or require fewer steps. So, it’s critical to review and revise these defaults to reduce accidental overexposure. Therefore, before the get-go, you’ll need to implement robust sensitivity labelling policies which will significantly reduce these risks.
Integrating Microsoft Purview – A Critical Layer of Data Security Posture Management
Before turning your attention to permissions via SharePoint Advanced Management (next step, see below), it’s vital to ensure your organization is also addressing the foundational layer of data governance with Microsoft Purview. Microsoft Purview’s Data Security Posture Management (DSPM) provides critical oversight into how your data is classified, labelled, and protected.
In the context of Copilot for Microsoft 365, this means applying robust sensitivity labels to files so that Copilot only surfaces appropriate content during searches and interactions. Purview and SAM are two sides of the same coin and go hand in hand, while SAM focuses on who can access content, Purview ensures that the content itself is appropriately governed and secured. Used together, they complement each other forming a comprehensive defence against data oversharing and misclassification risks that Copilot could unintentionally amplify. For a secure and well-governed rollout, we recommend running both Purview and SAM assessments in tandem, ideally during your pre-pilot technical readiness phase.
Clarifying Roles and Licensing for Purview: Purview is typically managed by your information security, network security or compliance teams (depending on your company’s structure), while SAM falls under SharePoint or global IT admins – so coordination between teams is essential. Also, note that while SAM may require an additional license, some features are available during the free 90-day trial. Purview’s availability can depend on your Microsoft 365 license tier (e.g., E3 vs. E5).
Leveraging SharePoint Advanced Management (SAM)
As mentioned above, alongside Microsoft Purview, we recommend using SharePoint Advanced Management (SAM) to identify and fix oversharing risks before Copilot is widely enabled. SAM gives you detailed visibility into your SharePoint environment – helping you spot issues like sites with hundreds or even thousands of users who may no longer need access. These kinds of legacy permissions often fly under the radar, but with Copilot’s ability to surface data across your environment, they can unintentionally expose sensitive content. Fortunately, Microsoft offers a free SAM trial for up to 90 days, giving you ample time to run audits and clean up permissions before your rollout. While only one Copilot license is needed to access SAM features, full functionality is limited to users with global admin rights.
This is also the right moment to consider introducing restricted search settings, especially if you’re concerned about data exposure in early phases. While restrictive measures can slightly impact user experience, they offer greater control during the pilot and rollout phases – helping you strike a balance between productivity and protection. By combining SAM with Purview and implementing restricted search where necessary, you can build a secure, well-governed foundation for your Copilot deployment.
Managing Productivity and Security Trade-offs
While some Copilot advocates recommend introducing restricted SharePoint searches from the outset, stringent security measures like this can significantly impact user productivity. Like with everything, you must carefully weigh-up these trade-offs, clearly looking at potential productivity impacts against the security benefits gained.
Recommended Pilot Practices
Before your formal pilot begins, consider starting with a small pre-pilot phase – typically a technically proficient group within IT. This group can help you identify glaring oversharing or permission issues quickly, before you expose Copilot to a broader audience.
Next, identify your formal pilot group, which should ideally consist of a mix of technical users, executive assistants, and business knowledge workers from departments like marketing or finance. You may choose to avoid including Legal and HR participants at this stage, as they typically deal with the most sensitive data and can generate unnecessary resistance if sensitive content is inadvertently surfaced, according to the Director of Microsoft 365 Jeremy Chapman, who advised to add these teams in at the end of the pilot, when you’re just about ready to roll Copilot out, in his ‘Copilot implementation essentials session’ earlier this year.
However you approach your pilot, this phase should task your group explicitly with attempting to uncover data vulnerabilities. Have them conduct structured scenario-based security tests, such as attempting access to sensitive information through Copilot prompts. The pilot duration should realistically span at least three months to allow for comprehensive and iterative security testing.
Path-Based Decision Framework
The Copilot roll-out path you decide to take will depend on a number of considerations. Choosing your path will depend significantly on your organization’s risk tolerance, industry compliance requirements, security maturity, and internal readiness. Here we’ve outlined three possible approaches:
Rapid Deployment: Quick productivity gains but heightened security risks.
If you’re under pressure from your top executives or want to have early-mover advantage, you might opt for a rapid rollout. While this will quickly enable productivity enhancements, it does also introduce significant risks of data oversharing – potentially exposing sensitive data like salary information or confidential projects inadvertently. This risk is heightened without proper sensitivity labelling and security management, mentioned above.
A Balanced Approach: Controlled exposure, structured vulnerability testing, and manageable risk.
For a steadier approach, we recommend incorporating critical security measures using Microsoft Purview and SAM upfront to introduce sensitivity labels and clearly defined permissions. It’s best practice to run a pilot test involving technically proficient users who actively probe the system for vulnerabilities. For instance, use pilot groups to perform structured scenarios asking Copilot pointed security-related questions to identify gaps proactively. Such pilots should typically last around three months, allowing adequate time to identify and address vulnerabilities effectively.
Cautious Security-First Approach: Maximizing security with potential short-term productivity limitations.
This strategy prioritizes extensive security readiness measures before widespread deployment. This includes advanced security auditing using tools like SharePoint Advanced Management (SAM) with restricted search to identify and rectify oversharing vulnerabilities comprehensively. Although this approach guarantees high security standards, it may temporarily limit productivity, as overly restrictive search and restricting sharing policies could disrupt daily operations initially.
Realistic Timelines and Setting Expectations
Whichever route you take, we suggest setting realistic expectations from the outset. Best practice is to allocate at least three months for your initial pre-pilot, pilot and testing phases. Organizations with lower security maturity should prepare for even longer timelines. It’s important to have transparent communication regarding these timeframes with stakeholders to prevent frustration and align executive expectations.
Continuous Engagement and Iterative Improvement
Copilot for Microsoft 365 adoption isn’t a one-time event but an ongoing journey. You will need continuous support from initial technical readiness through ongoing user enablement. As Microsoft continues to roll out new Copilot features, you will need to manage evolving security requirements and sustain user productivity. Therefore, we recommend you create dedicated adoption team or work with a trusted external partner like Cloudwell to help you through this transformative yet complex transition.
If you’re evaluating your Copilot strategy or facing challenges adopting Copilot for Microsoft 365, Cloudwell is ready to guide you. Together, we can ensure your Copilot journey is secure, productive, and aligned with your business objectives. Reach out to us for expert guidance, tailored specifically to your needs.