Running a Successful Microsoft 365 Copilot Pilot: Agendas, Artifacts, and Decision Checkpoints

Why Start with a Pilot?

A pilot creates a controlled environment to:

  • Learn what value Copilot brings to your unique business needs and goals before investing in licenses for everyone.
  • Test Copilot in real workflows without disrupting business.
  • Identify data governance and security considerations early.
  • Gather feedback from a representative user group.
  • Build a roadmap and tools for broader adoption.

Step 1: Define Scope and Success Criteria

Start by answering:

  • Who’s in the pilot? Choose a cross-functional group – think operations, HR, marketing – not just tech-savvy users and get support from their leadership.
  • What scenarios matter most? Draft 3–5 use cases tied to measurable outcomes (e.g., reducing document drafting time by 30%).
  • How will success be measured? Define KPIs like productivity gains, user satisfaction, and compliance adherence.

Step 2: Prepare Your Environment

Before kickoff:

  • Validate licensing and enable Copilot features.
  • Review data quality and access permissions
    • Copilot respects existing security, so gaps here will surface quickly.
    • Utilize tools like SharePoint Advanced Management and Teams usage reporting to identify outdated and abandoned sites and teams
    • Evaluate public Teams and sites using the “Everyone” security context
  • Confirm compliance settings for sensitive content and information lifecycle management.
  • Remediate configuration and content management issues.

Step 3: Build Your Pilot Agenda

Structure your sessions to keep momentum:

  • Kickoff Meeting
    1. Introduce objectives, timeline, and roles.
    2. Interview key stakeholders to understand current workflows, challenges, and opportunities where Copilot can provide meaningful value.
    3. Share pilot guidelines and feedback channels.
  • Hands-On Training
    1. Demonstrate Copilot in Word, Excel, Teams, and PowerPoint.
    2. Provide quick start guides, homework exercises, and FAQs.
  • Midpoint Check-In
    1. Review early feedback and address blockers.
    2. Incorporate feedback into training and support materials.
  • Wrap-Up & Decision Meeting
    1. Collect success metrics and anecdotes. How did using Copilot impact on the quantity and quality of work?
    2. Present findings, KPIs, and recommendations for next steps.

Step 4: Create Supporting Artifacts

Your pilot toolkit should include:

  • Technical Readiness Survey and Remediation Tracking worksheet.
  • Interview Worksheets for capturing user insights.
  • Slide Decks outlining current workflows, challenges, and opportunities.
  • Feedback Forms for structured input.
  • Next-Step Roadmap for scaling adoption.
  • Prompt library with ideas relevant to your business

Tips

Don’t wait until the end to make decisions – schedule regular checkpoints to validate technical readiness, assess user engagement and satisfaction, improve training and support artifacts, and decide whether to expand, adjust, or pause the rollout.

Engage your pilot department during a favorable time of year (not during a busy season or major deadline) to avoid organizational stress.

Try multiple formats of training and support documentation and solicit feedback during the pilot – slide decks, one-pagers, short videos, FAQs, etc.

Next-Step Roadmap should include the scope, timeline, people, tools, strategies, and budget required to roll out Copilot to target departments.  It should also include potential challenges and mitigation steps and success measurement criteria.

Final Thoughts

A well-run pilot isn’t just a test—it’s a strategic investment in change management. By defining scope, preparing your environment, and structuring clear agendas and artifacts, you’ll turn Copilot from a buzzword into a business advantage.

Ready to design your Copilot pilot? Contact Compass365 to leverage our proven frameworks and accelerate your AI journey.

Contact us to schedule a free strategy session