6 Files. 3 People. Can Copilot Cowork Figure It Out?
I gave Microsoft Copilot Cowork six PDFs for three different people and asked it to figure out who should receive each file. It worked. A full YouTube demonstration is coming next week.
I've been putting Microsoft Copilot Cowork to the test, and this might be one of my favorite experiments yet.
I gave Cowork 6 PDF files for 3 different people. Cowork had to figure out which files belonged to whom, match them with the correct recipients, and prepare three separate emails with the correct attachments.
And yes, it worked.
I gave Cowork the OneDrive folder and let it work through the files rather than providing a master spreadsheet telling it exactly what to do.
What impressed me wasn't simply that Copilot could understand the PDFs. It was that Cowork could take that information and turn it into a multi-step task: files → people → email addresses → correct attachments → emails ready to send.
Cowork showed what it was going to do
Outlook Sent Folder - Cowork Worked!
Gmail - External Account - Cowork Worked!
🎥 Full Video Coming Next Week
I'm putting together a YouTube video showing the entire test, including the prompt I used, how Cowork handled the six files, and what happened after I added more files.
More coming next week!
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Training can be tailored to your organization's needs, from practical Copilot workflows and prompting to Teams collaboration and advanced Excel productivity.
Interested in training for your organization? Contact Chris Menard to discuss a customized session for your team.
Chris Menard
