Microsoft 365 Copilot is the hot ticket for businesses embracing AI. But how can organizations make the most of their investment in the fast-growing technology?
According to Microsoft’s most recent Work Trend Index Report – 2025: The year the Frontier Firm was born, nearly half of leaders (47%) say upskilling their existing workforce is a top priority in the next year and a half, with expanding team capacity using digital labor (45%) a close second.
So, ensuring successful adoption isn’t just a nice-to-have, it’s a business imperative.
In our latest Q&A series, Cloudwell Conversations, we’re talking to members of the Cloudwell team about their areas of expertise, gaining insights into the challenges businesses are facing and more importantly, the solutions.
First up is Maureen Stein, Microsoft 365 consultant and adoption specialist.
Kelvin Helmholtz (KH): You’ve led Microsoft 365 adoption strategies at scale, what’s the biggest mistake enterprises make when rolling out new tools like Copilot?
Maureen Stein (MS): I think not providing adequate training and outreach is a major mistake. Adequate support and training are essential for users to gain knowledge and understanding, and to integrate Copilot into their everyday routines effectively
KH: From your experience, what role should IT leaders play in driving user enablement, beyond just technical readiness?
MS: It’s important that business leaders sponsor and champion the change, driving the strategy throughout the rollout. Leadership and sponsorship are essential for aligning AI investments to business priorities and defining high-value scenarios.
Creating an AI Council from leaders across the organization can help guide and measure adoption. This includes user enablement programs, communications and a Copilot dashboard, along with communities of practice, skilling and training, and authentically receiving feedback and then taking action on that feedback as well.
KH: Copilot is a hot topic right now. What’s your advice to CTOs trying to cut through the hype and deliver real value?
MS: I believe having a clear vision and strategy for its implementation. It’s crucial to define what success looks like and align the goals with measurable outcomes to ensure the pilot delivers actionable insights. While IT is often the earliest adopter of new technology, they might have less impactful business use cases for Copilot. Instead, it would be more beneficial to provide Copilot licenses to users who are actually creating content, performing data analysis, organizing meetings etc.
KH: What makes a great Copilot Champion and how do you find and support them?
MS: A great Copilot Champion is someone who is enthusiastic about technology and has a good understanding of the business needs and goals. I also think, they should have the ability to inspire others to try new technology tools and practices. It’s important to provide them with necessary training and resources to become a subject matter expert in Copilot.
I think it’s also essential to encourage Champions to share their knowledge and experiences through the community of practice and during workshops or training sessions. Lastly, you’ll want to offer continuous support and recognition for their efforts as a way to keep them motivated and engaged in the community.
KH: For IT pros building their own Copilot strategies, what are your top three tips?
MS: My top three tips are:
1. Start with a clear vision and strategy with a ROI Focus: Before jumping into implementation, it’s key to define specific, high-impact use cases where Copilot can deliver the most value to the business.
Consider things like time savings (e.g., automating documentation, code generation, or ticket triage); error reduction (e.g., guided troubleshooting or compliance checks) and user empowerment (e.g., enabling non-technical users to query data or generate reports).
It’s best to start with a pilot of a small group of users and track KPIs like task completion time, satisfaction, or support ticket volume.
2. Establish robust data infrastructure and governance: Copilot’s success depends on access to high-quality, well-structured data. IT needs to ensure technical readiness and data governance are in place with permissions and sensitivity labels, connectors are configured for all platforms like SharePoint, Teams, Jira, or ServiceNow, and semantic indexing is enabled for enterprise search and grounding
3. Support guided use and evolving intelligence: Copilot is more of a collaborative partner, not meant to be a replacement. Design workflows that allow users to review, edit, and approve Copilot-generated outputs. Encourage continuous feedback to improve prompts, plugins, and grounding data.
Most importantly, include training and change management to drive adoption and use Copilot prompt engineering and custom tools to make it work better with your organization’s unique language, terminology, tools, and workflows.
Could your organization use Cloudwell’s expertise on Copilot adoption? Take a look at our recent blogs on IT readiness and user enablement, or reach out to our team to get started on your Copilot adoption journey.