Organizations everywhere are feeling the pressure to embrace AI, and for good reason. According to Microsoft’s Work Trend Index Report 2025, 71% of so-called Frontier Firms (early adopters) say their company is thriving as a result of AI adoption, compared to just 37% of organizations globally.
There’s no doubt Copilot for Microsoft 365 is a powerful solution, we’re big fans here at Cloudwell, but it’s far from plug-and-play.
In a previous blog we covered IT readiness and piloting Copilot, explaining how organizations can navigate the complexities of secure deployment. But even the most technically sound rollout can fall flat without one key ingredient: user enablement.
That’s why Microsoft has created the Copilot User Enablement Workstream, a structured, people-focused approach designed to help organizations roll out Copilot with confidence and with long-term impact. At Cloudwell, we’re aligning our services with this four-phase framework to support our clients every step of the way.
What Is the Copilot User Enablement Workstream?
While technical preparation can help get your Microsoft 365 environment ready, user enablement ensures your people are prepped and onboard too.
Microsoft’s Copilot User Enablement Workstream provides a clear path to widespread adoption, helping organizations like yours not only launch Copilot but embed it as part of company culture.
The framework includes these four key phases:
1. Get Ready
2. Onboard & Engage
3. Deliver Impact
4. Extend & Optimise
Each stage includes practical actions, from training and communication to measuring success and scaling usage. Let’s take a closer look at each phase and how Cloudwell can support your user enablement journey.
Phase 1: Get Ready – Laying the groundwork
This is the strategy phase. The goal here is to prepare your people, processes, and leadership to embrace AI in a responsible and focused way.
To lay the foundations for a successful Copilot rollout, it’s all about getting leadership support. First, it’s important to secure executive sponsorship and establish an AI Council. This leadership group will play a vital role in setting strategic direction, championing change, and ensuring alignment across all your company’s departments.
Next, you should set out and define your Responsible AI principles, drawing from resources like Microsoft’s Responsible AI Standard. These principles should reflect your organization’s values and guide ethical AI usage throughout the business.
To build momentum and spread best practices, we recommend launching a Champions program. Select employees who will use the new Copilot capabilities and share their feedback. These early adopters will also provide support and guidance during end-user onboarding and the initial usage of Copilot features.
At this point you should identify high-value use cases that align with your company’s strategic goals, such as automating routine tasks and enhancing knowledge sharing. Assigning success owners to each use case will ensure accountability and help track tangible outcomes.
You will need to set clear KPIs and success metrics so you can measure progress and demonstrate the value of your Copilot investment. These benchmarks will help guide continuous improvement throughout the rollout.
Finally, take a strategic approach to licensing. Be intentional with license assignments and concentrate them for better evaluation. Cloudwell can help you with this. Review your users’ needs and eligibility carefully by using tools like the Microsoft 365 Admin Center and the Microsoft Copilot Licensing Guide to ensure your team is properly licensed and ready to go.
Pro tip: The Microsoft Copilot Scenario Library has lots of practical, high-value Copilot use cases tailored to specific roles, departments, and industries.
Phase 2: Onboard & Engage – Building skills and trust
Once you’ve got your foundations in place, this next phase is about getting employees confident, capable, and excited about using Copilot in their roles.
So, now’s the time to deploy your Champions.
Champions play a crucial role in showcasing the practical, day-to-day benefits of Copilot, offering peer-to-peer support and encouraging broader usage. Their enthusiasm often drives adoption more effectively than top-down mandates.
It’s also helpful to establish communities of practice using tools like Microsoft Teams and Viva Engage.
Along with the Champions, supporting with adoption and ongoing training, these user enablement communities provide a platform for employees to learn, share knowledge, and support each other, creating a culture of continuous learning and improvement around the new AI technology, which inevitably leads to increased productivity and faster value realization.
Microsoft Copilot Academy
Microsoft Copilot Academy is packed full of resources to help users develop skills related to Microsoft 365 Copilot. Here are some key features:
1. Structured Learning:
Users can learn about, discover and effectively used Copilot through structured educational content within Viva Learning.
2. Accessibility:
Microsoft 365 users with a Copilot license can access Microsoft Copilot Academy through the Viva Learning platform.
3. Comprehensive Content:
Microsoft experts have curated lots of hands-on learning activities and experiences to help users master Copilot.
4. Language Support:
Microsoft Copilot Academy is available in all these languages: including English, French, German, Italian, Spanish, Portuguese, Japanese, and Chinese.
5. Customization:
Customization is available enabling organizations to tailor the academy to fit their unique needs, provided they have a license for Microsoft Viva Suite or Viva Learning.
Other resources include role-specific training available via Microsoft’s Copilot Learning Hub, with accessible resources like bite-size videos and tailored guidance to help different teams understand how Copilot can support their daily work.
The Copilot Prompt Gallery is also a great resources featuring tips on the art of prompting and how to use Copilot in your everyday apps.
To keep your enablement approach user-focused, gather early and frequent feedback using tools such as Microsoft Forms or Viva Glint. Monitoring user sentiment and common pain points allows you to adjust training, communications, or support strategies as needed.
Pro tip: Use the Microsoft 365 Adoption Score to track engagement and understand how effectively your organization is using Copilot features.
Phase 3: Deliver Impact – Measure what matters
Once users are live with Copilot, it’s important to monitor how the tool is being used in real-world scenarios, tracking adoption and measuring impact.
Start by monitoring usage data and behaviour patterns via the Copilot Dashboard in the Microsoft 365 Admin Center. This gives you and your senior leadership team a clear view of what’s working and where Copilot is adding value, as well as where additional support may be needed to create even greater benefits.
In addition to quantitative data, gather qualitative insights through surveys and feedback tools. Understanding employee sentiment helps paint a more complete picture of the rollout’s effectiveness and surfaces areas for improvement. Furthermore, encourage employees to share their feedback whenever Copilot prompts them. This continuous loop of insights will not only enhance their individual experience but also help refine and improve Copilot, making it an even more valuable tool for everyone.
Deliver extended training and continued awareness by creating weekly or monthly targeted M365 App campaigns to continue to raise awareness of the value and benefits of Microsoft 365 Copilot, and the available resources and opportunities for learning and support. These might include Copilot in Teams and how it can make meetings more productive or reducing inbox stress and improving email efficiency in Copilot in Outlook.
Continue to build momentum and encourage wider adoption, share internal success stories. Whether it’s a department saving hours on reporting or a team using Copilot to enhance creativity, real-world wins go a long way in demonstrating value across the business.
Finally, identify and support lagging areas with tailored interventions, whether that means additional training, awareness through communications or campaigns, clearer use cases, or more focused onboarding for specific roles.
Pro tip: Use Microsoft Power BI to visualise adoption data and integrate user sentiment with broader business intelligence dashboards. This helps teams connect Copilot usage to real business outcomes.
Phase 4: Extend & Optimize – Scale the value of Copilot
Now you’ve got the solid foundations in place, it’s time to build on your success and expand Copilot into new areas.
For example, consider building custom agents for advanced use cases using Copilot Studio, or embedding Copilot into the daily routines across departments, from HR, sales or serviceto finance and operations. Users can also automate workflows and create agents to simplify and automate repetitive business processes and workflows, such as submitting expenses, onboarding employees, and updating benefits. By leveraging these agents, organizations can enhance efficiency and ensure that routine tasks are handled seamlessly.
As your organization becomes more familiar with Copilot, it’s important to continually refine and optimize how it’s used. This means regularly assessing evolving business needs, keeping an eye on shifts in user behavior, and adjusting your enablement strategy accordingly.
Whether it’s adapting to new priorities, responding to feedback, or introducing new capabilities, Cloudwell can help with ongoing optimization to ensure Copilot continues to deliver meaningful value and remains aligned with how your teams actually work.
Pro tip: Experiment with Microsoft Loop or Power Automate to build collaborative, AI-powered processes.
Cloudwell is planning a SharePoint Agents Workshop, designed to help organizations leverage SharePoint agents effectively. Register your interest.
Why user enablement matters
AI success isn’t just about having the right tools, it’s about putting people at the center of change and creating optimism around this new technology.
According to Microsoft’s Work Trend Index 2025, 93% of Frontier Firm workers felt optimistic about their future work opportunities, compared with 77% globally.
Copilot has the power to supercharge productivity, reduce repetitive, manual work, and unlock new ways of working. But without proper enablement, organizations risk low adoption, wasted investment, and missed opportunity.
How Cloudwell can support your user enablement program
1. Practical Adoption Tips: If you’re a small or medium-sized business, we can provide you with practical ways you can integrate Copilot into your Microsoft stack. This includes strategies to reduce administrative tasks, streamline workflows, automate processes, and empower your employees.
2. Expert Insights: Our CEO and Microsoft MVP Pat is on hand to share his valuable tips and tricks on Copilot rollout and adoption. He can even run an adoption masterminds meeting – a collaborative environment for adoption leaders to discuss strategies and navigate the evolving landscape of AI adoption.
3. Adoption Playbook: Offered to all our clients, we’ll share our adoption playbook, packed with all the learnings from Cloudwell and informed by the Microsoft Copilot Success Kit. Our playbook provides actionable steps to accelerate your AI transition.
Our resources are designed to arm you and your organization with the tools and best practice insights to effectively adopt and scale Copilot for Microsoft 365, so you can hit the ground running, and realize those productivity gains sooner.
Are there specific areas you’re looking to improve with Copilot? Take the first steps toward a more efficient workplace by contacting our team to get started today!