11 tips for your Microsoft 365 Copilot rollout plan

TL;DR: Copilot only surfaces what a user could already open, so every permissions problem you've been putting off shows up the day you hand out licenses. Fix those first, then pilot small and expand in waves.

Feeling overwhelmed by the possibilities of Microsoft 365 Copilot? You're not alone. Leadership wants licenses deployed yesterday. You know the tenant isn't ready. That gap is the whole problem.

In our Copilot deployment webinar, Microsoft MVP and training specialist Andy Huneycutt shared his insights on navigating the pre-deployment phase, driving user adoption, and achieving continuous improvement. This article captures Andy's tips, updated with what we've since learned from IT teams getting their environments Copilot-ready at scale.

One thing to hold onto throughout: Copilot doesn't create access problems. It reveals them. If someone can open a file today, Copilot can surface it. That's the feature and the risk.

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Tip #1: Prepare your Microsoft 365 environment for Copilot 

Before Copilot swoops in and supercharges your productivity, it's important to get your M365 environment in good order. Set up a clear plan for managing your content, keeping things safe, and controlling who has access to what. 

This is the tip that saves rollouts. Plenty of teams buy licenses first and discover afterwards that SharePoint has unchecked permissions, no data classification, and the "Everyone except external users" (EEEU) group applied across half the tenant. Copilot will reflect all of it back to whoever asks.

Take stock of permissions and access

‍Conduct a thorough assessment of how permissions and access controls function across SharePoint, OneDrive, and Teams. Identify areas for improvement and implement measures to ensure the right people have access to the right things, including granting appropriate access rights and clearly defining roles and responsibilities for handling data.

According to Microsoft's rollout guidance, you should review and audit site permissions using SharePoint Advanced Management, which is included with your Microsoft 365 Copilot license. Per the Copilot oversharing blueprint, run the Content Management Assessment to find sites with oversized audiences, EEEU usage, broken inheritance, inappropriate sharing, and inactive or ownerless sites.

Fix what the assessment finds

Finding the problems is the easy half. The list that actually needs closing:

• Remove site-level EEEU access. ShareGate Protect strips the "Everyone Except External Users" role assignment at the site level and on all top-level SharePoint groups.
• Change site external sharing settings, in bulk rather than site by site.
• Remove company-wide sharing links, EEEU included.
• Correct broken inheritance.
• Assign ownership to orphaned sites.

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Declutter and streamline

Minimize content sprawl by cleaning up orphaned teams and inactive team sites. Less clutter means fewer places for sensitive content to hide, and users find what they're looking for faster.

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Combat oversharing

Encourage team and group owners to regularly review externally shared links and guest access so you keep control over sensitive data. ShareGate Protect gives you visibility into oversharing, EEEU, and sharing links so you can fix issues before they become Copilot problems.

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Sensitivity labels for enhanced protection

Use sensitivity labels to classify and protect data within M365. Microsoft's own IT team pairs sensitivity labeling with Microsoft Purview DLP policies to detect and protect sensitive data across SharePoint, OneDrive, and Teams. You can also set default link types based on sensitivity labels through Purview, so company-shareable links replace broad group grants and oversharing gets limited at the source.

As Microsoft's IT team puts it: "It will be far easier to start with a clean data estate."

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Bonus tips: For a more comprehensive guide on preparing your M365 environment for Copilot, check out our checklist: 7 steps to prepare for Copilot for Microsoft 365. Follow the steps on what you need to set up Copilot for Microsoft 365 like basic requirements and specific app prerequisites.      

Tip #2: Plan your deployment  

Now that your Microsoft 365 environment is Copilot-ready, it's time to map out your deployment strategy. Think of it as the flight plan for your Copilot adventure: clear goals, a dream team on board, and a roadmap everyone can follow.

Tips for creating a winning game plan: 

• Set clear, achievable goals before you buy a single license. What should your team accomplish with Copilot? Faster drafting? Fewer hours lost to meeting recaps? Be specific, and define what success looks like at 90 days and at six months. Vague goals can't be measured, and unmeasured rollouts can't be defended at renewal.

• Identify key stakeholders who will be instrumental in the rollout: IT champions, department heads, potential power users. Delegate tasks and lean on their expertise. No superhero does it alone, and neither should you.

• Create designated user onboarding groups, plus a calendar of planned events like training classes and virtual office hours. Supported users get more out of Copilot from day one.

Then phase it

Microsoft recommends beginning with a phased approach: start with a limited rollout to a small group, then expand your user list as the rollout continues. The Copilot oversharing blueprint organizes the work into three pillars: remediate oversharing, set up guardrails, and meet regulations.

• Pilot: Start with 25 to 50 users who will actually use Copilot and give you honest feedback. This phase lets you explore features in a controlled setting, refine configurations, and build internal advocates.
• Deploy: Expand by department or business function. Watch for adoption gaps and address them early.
• Operate: Scale to the full org while keeping governance intact. This part doesn't end.

Assign the right roles as you go. The AI administrator role covers agents, service health, usage and adoption reporting, and support tickets. Copilot licenses get assigned in the Microsoft 365 admin center.

Licensing note: Microsoft 365 Copilot is an add-on plan that requires one of several prerequisite plans, including Microsoft 365 E3, E5, Business Basic, Business Standard, Business Premium, or Office 365 E1, E3, or E5. Commercial Microsoft 365 users can already access Copilot Chat at no extra cost. Give power users the full add-on and start everyone else on the free chat to build momentum.

One pre-project consideration: if your content isn't in Microsoft 365 yet, migration comes first. ShareGate Migrate handles tenant-to-tenant moves with permissions intact. Migrate gets you there clean. Protect keeps you there.

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Tip #3: Create a community blueprint 

People need somewhere to ask questions, share wins, and work things out together. Craft a community plan covering ongoing engagement and support across internal communication platforms, forums, and dedicated user groups.

• Define ownership and roles: Designate a community management team, ideally with representatives from user adoption, training, IT security, product management, and leadership. Give each member a defined role so nothing falls through, including whoever answers the weird questions at 4pm.
• Platform considerations: Decide whether to use a platform your organization already has, like Microsoft Teams, or stand up something dedicated. Weigh user familiarity, functionality, and how well it integrates with your other resources. Viva Engage and Microsoft Forms are both worth a look for broader engagement.

What you want is a space where someone feels comfortable saying "I tried to use Copilot for X and it didn't work." That's the feedback you can act on.

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Tip #4: Craft an effective communication plan 

A successful Copilot deployment depends on clear, consistent communication. You can't flip the switch and expect adoption. Here's how to build a plan that keeps everyone informed and engaged:

• Multi-channel approach: Use a central platform like Microsoft Teams to avoid email silos and reach a wide audience. Supplement it with email newsletters, announcements, and time in team meetings.
• Tailored messaging: Segment your audience. IT leaders need technical depth; everyday users benefit from quick explainer videos and user guides. What excites a finance analyst isn't what a project manager cares about, so speak to their actual workflows.
• Welcome and guide: Communication matters most during onboarding. Welcome users to the program, outline the terms, and provide access information. Point them to the Copilot community as the central hub for questions and support, and repeat it often enough that nobody has to go hunting.
• Embrace feedback: Communication is a two-way street. Surveys, polls, dedicated feedback channels: make it easy for people to tell you what's working and what isn't, then use what they say to refine the rollout.

Build momentum from the top down and the bottom up. Publicize Copilot Academy. Make the wins visible.

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Tip #5: Spice up engagement 

Getting everyone excited about Copilot for M365 is key to driving adoption.  

Strategies for turning Copilot into a hot topic: 

• Keep users informed with regular announcements and updates about Copilot's features and functionalities. 

• Host interactive AMA (ask me anything) sessions, during which users can ask questions and get expert insights from Copilot champions. 

• Show real-world examples of how Copilot positively impacts different departments or teams. Interview key users and share their success stories to inspire others. 

• Organize hands-on workshops or hackathons to help users explore Copilot's full potential. It's a fun way to encourage knowledge-sharing and collaboration! 

• Set up discussions through focus groups or roundtables so you can gather user insights and identify areas for improvement. 

• Keep your finger on the pulse of user sentiment with regular polls and surveys. Gauge user satisfaction and identify any roadblocks to adoption. 

Don't let Copilot become shelfware. The licenses cost money. Make sure people use them.

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Tip #6: Set up a feedback loop 

A feedback loop keeps Copilot relevant and valuable to your users. Successful deployments need ongoing course correction, not a launch and a shrug.

Steps for gathering feedback

1. Implement a system: surveys, user group discussions, a dedicated feedback channel, or regular 60-minute sessions with stakeholders and users to share updates, walk through how-to scenarios, and collect input.
2. Analyze the data and identify trends or areas where Copilot usage can be improved. Are people struggling with prompts? Is one department lagging badly? Acting on what you find shows users their input counts.
3. Adjust your deployment strategy, communication plan, or support model based on what you hear. If nobody uses Copilot in Outlook, find out why, then fix it.

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Tip #7: Establish a Center of Excellence (CoE) 

Create a centralized hub for everything related to Copilot. It will be a go-to place for users seeking answers, resources, technical support, and shared knowledge. A CoE makes accessing Copilot-related information easier by consolidating resources and minimizing one-to-one communications.

A CoE for Copilot can include: 

• How-to guides: Step-by-step instructions for getting started with Copilot in M365. 

• Training materials: Video training sessions of different lengths. 

• Job aids: Quick reference materials to help with common tasks. 

• Standard operating procedures: Detailed documentation on processes and best practices. 

The beauty of a CoE is that you don’t have to start from scratch. Microsoft’s Copilot for Microsoft 365 Adoption Center offers an extensive success kit with short videos and long training sessions, and the launch day kit adds an implementation guide, email templates, and ready-made event assets.

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Tip #8: Unleash the champions  

Every successful deployment thrives on passionate advocates. In the case of Copilot, these champions are your key users–the early adopters and power users who can inspire and support others on their Copilot journey.

Tips for finding your Copilot power users or champions:

• Watch for early adopters who demonstrate a natural aptitude for Copilot for M365. These individuals are likely to become enthusiastic advocates. 

• Nurture the ones you find. Give them in-depth training materials, early access to new features, and chances to share their expertise. Early access is its own incentive.

• Promote a sense of community among your champions. Encourage them to collaborate, share best practices, and support each other in their advocacy efforts. You can also create a dedicated Copilot champion forum or host regular sessions. 

• Keep your Copilot community informed. Part of this translates to recognizing your champions' contributions! Recognize their achievements publicly and give them opportunities to showcase their Copilot expertise through presentations, workshops, or blog posts. 

By empowering your Copilot champions, you create a powerful network of user advocates who can drive adoption, answer questions, and inspire others to use the tool to its full potential. 

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Tip #9: Train, support, repeat 

Equipping business users with the necessary knowledge and resources is paramount to a successful Copilot deployment.

Steps to user enablement:

1. Get the ball rolling with a friendly notification welcoming users to their Copilot journey. 

2. Clearly outline any relevant terms of service or privacy policies users must agree to before setting sail.  

3. Provision the Copilot license, granting users access to all its features and functionalities. 

4. Welcome users to the Copilot community, a dedicated space for learning, collaboration, and support. 

5. Send a warm welcome email with valuable resources, including links to training sessions and a comprehensive FAQ section. 

6. Offer a variety of training options that cater to different learning styles. These could include online modules, interactive workshops, or live Q&A sessions.

7. Once users have completed the onboarding process and training, they'll be fully equipped to use Copilot with confidence and unlock its full potential. 

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Tip #10: Monitor and evaluate progress 

A successful Copilot deployment is an ongoing journey; tracking your progress is key.

• Use the Microsoft 365 Copilot usage reports in the admin center to measure adoption, usage patterns, and business impact. 
• Use the Microsoft Copilot Dashboard to find power users and expansion candidates. They're your next wave of champions.

• And don't underestimate the power of user feedback!  

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Good to know 

• Users are active in Copilot when they engage with its features. For example, interacting with the chat pane by submitting prompts constitutes active usage. Simply opening a feature doesn’t count. 

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Where native tools stop

Microsoft gives you solid native tooling. Purview handles labeling, DLP, and retention. SharePoint Advanced Management covers site governance and Restricted Content Discovery, including Restricted Content Discovery for sites you want held back from Copilot. The admin center handles license assignment and usage reports.

The gap most teams hit isn't in what Microsoft offers. It's in operationalizing it. Getting one view across SharePoint, OneDrive, and Teams means jumping between consoles. Bulk remediation means PowerShell. And ongoing monitoring that a non-technical stakeholder can read is hard to produce from any of it.

Permissions also don't hold still. New sites appear, external sharing happens, access drifts. Fixing permissions once before launch and assuming you're done is the most common mistake in the operate phase, and it's the one that turns a clean pilot into an exposed tenant at 4,000 users.

ShareGate Protect's Permissions Matrix Report answers "who has access to what" across SharePoint and OneDrive in seconds, refreshing roughly every 24 hours. Delegated Reviews route governance decisions to the workspace owners who actually know the content, and they act in a reviewer app through Microsoft 365 SSO. It's not a security platform, a DLP replacement, or a SIEM, and it doesn't replace Purview. It makes the native controls something you can act on, and it lets you monitor Copilot access and right-size Copilot licenses as the rollout matures.

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Tip #11: Evaluate potential challenges unique to your organization

Even the smoothest deployment hits bumps. Name yours early.

Tips for anticipating and addressing potential challenges:

• Technical hurdles: Check your current IT infrastructure and identify any technical hurdles that could disrupt your smooth Copilot deployment.
  • Ensure compatibility across your M365 environment. Check for potential issues with older versions of M365 applications or limitations in your current hardware.
  • Confirm your operating systems (Windows 11 or macOS) and security policies line up with Copilot's functionality. Are there policies restricting desktop, web, or mobile app usage that need adjusting? Watch for security measures that block specific features, like recording Teams meetings or generating transcripts.
  • If you have a remote workforce, work with InfoSec and cybersecurity to close any gaps between working remotely and on the network.
• Adoption barriers: User adoption is a journey, not a destination.
  • Rapid tech change causes change fatigue. Copilot is a new way of working in M365, so build a change management strategy that addresses real concerns instead of talking past them.
  • Address worries about Copilot replacing jobs directly. It's a co-pilot, not an autopilot. It assists. It doesn't replace.

Now that we've covered the challenges, here’s what you can do to overcome them:

• Technical support: Provide your IT team with the necessary resources so they can help you address any technical hurdles that emerge.

• Change management: Develop a plan to address user concerns and encourage adoption. This might involve clear communication about the benefits of Copilot, addressing privacy and security anxieties, and providing support throughout the deployment process.
• Transparency is key: Openly address data privacy and security concerns. Provide clear explanations of how Copilot handles user data and emphasize the security measures in place.

Follow these tips and you can navigate the Copilot rollout with some confidence. A good governance plan for your M365 environment lays the foundation, and our 5 essential steps to prepare for Microsoft 365 Copilot covers the readiness work in more detail. Get the permissions right first, and the rest of the rollout is just project management.