Battling the Expectations and Realities of Copilot: Insights from the Ring

🛎️ Ding, ding, ding!

Gloves were off for the battle of the century—Microsoft 365 Copilot: Magic or Meh? We took to the (virtual) ring with a tag-team showdown, putting Microsoft’s marketing promises head-to-head with the realities of implementation.

In Team Reality's corner were Marc D. Anderson and Julie Turner from Sympraxis Consulting. Michal Pisarek and Joy Apple represented Team Expectations. It was non-stop action from the start with Team Expectations hyping up Copilot as a plug-and-play AI savior and Team Reality throwing counterpunches with governance challenges and content chaos. 

From the opening bell, it was clear—Copilot is a game-changer, but only if organizations are ready (and willing) to play the game. Below, I break down the main rounds of our webinar battle and offer practical strategies for organizations stepping into the Copilot ring.

Get our Microsoft 365 Copilot Guide to learn more about implementation, deployment, best practices, and more.

Microsoft 365 Capabilities 

Round 1: The Promise vs. Reality of Copilot

🥊 Expectation: Copilot is ready for all organizations and offers value across industries.

💥 Reality: Sure, Copilot is flashy in the demo reels, but in real-world scenarios, it will stumble over disorganized content and inconsistent governance. If your “digital estate,” as Marc calls it, is a mess, Copilot will surface the chaos rather than solve it. As we said in the battle, Copilot doesn’t make bad content good—it just makes it faster.

🏆 Winning Copilot Readiness Strategy:

• Assess your digital estate: structured content, permissions, and security policies are key.
• Start a non-IT-led pilot program—pick cohorts within departments, not a random cross-section of users.
• Address industry-specific concerns—Copilot’s value in legal vs. manufacturing varies drastically.
• Conduct cost-benefit planning to ensure it’s worth the $30 per user per month.

Round 2: The Myth of Plug-and-Play

🥊 Expectation: Copilot is an intuitive, plug-and-play tool that requires minimal setup and support.

💥 Reality: Flip the switch, and Copilot works—technically. But “works” doesn’t mean “works well.” Without governance, it’s “a truffle pig sniffing out everything users have access to - including that “final_final_revised_v2” doc from 2018.” Surprise!

🏆 Winning Copilot Governance Strategy:

• Ensure readiness across three battle zones: 
  ✅ Technical (permissions, settings)
  ✅Content (quality, structure)
  ✅ People (training and adoption)
• Pilot in a controlled environment—avoid letting IT or execs be the only test users.
• Provide user guidance before rollout, so employees aren’t left guessing.
• Support and iterate—Copilot is not a “set it and forget it” tool.

Round 3: The Learning Curve of Effective Use

🥊 Expectation: Copilot is easy to use, and its responses are always correct, relevant, and useful.

💥 Reality: “Easy” and “effective” aren’t the same thing. Writing good prompts takes skill, and Copilot is not a mind reader. Sometimes it’s a genius; other times, it confidently hallucinates things that never happened (like when it told Marc D. Anderson that Sympraxis had won awards it never applied for! Flattering?).

🏆 Winning Copilot Prompt Strategy:

• Train users in prompt engineering—Copilot requires specificity.
• Encourage an “AI Copilot mindset”—Copilot is a collaborator, not an oracle.
• Share success stories—motivation matters.
• Develop ongoing AI literacy—search was already hard for users; prompting is harder.
• Remember: “Slow is smooth, and smooth is fast.” Invest in training upfront to go faster later.

Bonus Round: The Importance of Metadata

🎯 I never met a data I didn’t like! Get it? Met a data? Metadata isn’t just a governance geek’s dream—it’s the backbone of a functional IA strategy. But here’s the kicker: Copilot doesn’t yet use SharePoint metadata to filter or refine results. That said, investing in metadata now means better AI outcomes later.

🏆 Winning Copilot Metadata Strategy:

• Stop burying content in deep folder structure—go flat, go metadata-driven.
• Make metadata useful—users hate tagging unless it provides clear value.
• Keep investing in structured content—when Copilot evolves, you’ll be ahead of the curve.

Conclusion

After three intense rounds, what’s the final verdict? Copilot is powerful, but only if organizations do the work to make it useful.

Think of Copilot adoption like training for a marathon - you don’t just show up and expect to win. You need readiness, governance, and user enablement to get the full benefit. Rushing deployment will only lead to frustration, security risks, and AI-generated nonsense.

By addressing the realities of Copilot adoption and following structured recommendations, businesses can maximize AI’s benefits and avoid common pitfalls. The organizations investing in content management, upskilling, and AI literacy today will be best positioned for success tomorrow.

🥊 Who won the battle? That’s up to you! But as Marc said, reality does matter. Let’s keep the conversation going! What are your thoughts on Copilot readiness? And what hot topic do you want to see us battle next time?

And if you're ready to learn more about how Orchestry can help you get Copilot-ready, download our Microsoft 365 Copilot Guide.