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Insights
Expert analysis, insights, and opinions

Calibrating Copilot
Real-World Tests and Lessons Learned from evaluating Microsoft Copilot Chat, M365 Copilot, Cowork, and various agents on different use cases. We spend our AI credits so you don't have to!


Calibrating Copilot Ep. 8: Can Copilot Predict the Future?
We asked Copilot and Cowork to forecast August 2026 US flight delays and cancellations, then checked the predictions against what actually happened. A simple statistical average beat them all.

Kevin Kieller
Oct 304 min read


Calibrating Copilot Ep. 7: Creating Interactive Training with Copilot and Cowork
We turned an AI policy into a five-minute interactive training experience. The included Microsoft 365 Copilot won, while Cowork Max built something beautiful that we could not share.

Kevin Kieller
Oct 234 min read


Calibrating Copilot Ep. 6: A 90-Second Explainer Video for Under $15?
One short prompt, a 90-second animated explainer with narration and captions. Copilot struggled, Cowork Light stumbled, and Cowork Medium and above delivered results that genuinely surprised us.

Kevin Kieller
Oct 184 min read


Calibrating Copilot Ep. 5: Which Copilot Builds a PowerPoint You Would Actually Present?
We asked Copilot Chat, Microsoft 365 Copilot, Copilot in PowerPoint, and Cowork to turn our website into a 12-slide customer deck with speaker notes. The free option surprised us, and so did the paid one.

Kevin Kieller
Sep 284 min read


Calibrating Copilot Ep. 4: We Gave Copilot 191 Pages and Asked It to Build an App
Can Copilot vibe code a working insurance quotation app from a 191-page manual? We tested Copilot Chat, M365 Copilot, Researcher, Cowork, and Claude. The results varied dramatically.

Kevin Kieller
Sep 224 min read


Calibrating Copilot Ep. 3: More Cowork Effort Does Not Mean a Better Answer
We tested every Cowork effort setting, from Light to Max, building an Excel executive dashboard from Canadian wildfire data. The most surprising result: a polished dashboard that reached the wrong conclusion.

Kevin Kieller
Aug 314 min read


Calibrating Copilot Ep. 2: Can Copilot Make the Bid or No-Bid Call on a Complex RFP?
We gave four Copilot options a real nine-document RFP for a Cisco-to-Teams Phone migration and asked for a bid recommendation. Only one caught the risks that really mattered.

Kevin Kieller
Aug 254 min read


Calibrating Copilot: Which Copilot Writes the Best Executive Project Summary?
In the first episode of Calibrating Copilot, we run the same project-summary prompt through Copilot Chat, M365 Copilot, Researcher, and Cowork, and rate each on accuracy, completeness, speed, and cost.

Kevin Kieller
Aug 174 min read
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