Why your Copilot prompt failed
A short PDF per edition, built from failures we published, not invented. Every card starts from a documented failure, carries the issue and the date it ran in, and pairs it with the prompt written against it.
One role per edition, because the failures people in your seat actually hit are more useful than a sampler. Free, no signup required.
For project managers
Three failures we published in March 2026: a plan with invented dependencies, a priority order that was really the due-date column, and a risk list that described every project ever. All three are here, each with the prompt written against it, plus the access check to run before you blame your wording.
Download the PDF (free, 6 pages)Editions rotate roles with the newsletter: in-house legal, finance, HR and seven more have documented failures in the archive.
Where the evidence comes from
Where the failures come from
Every failure quoted in the series was published in the AI at Work newsletter, in the "What didn’t work" block of the issue named on the card. The archive is public, so you can read the issue a card cites and check that the card did not improve on it.
How the working prompt was chosen
A documented failure came first, then the prompt that avoids it. Not the other way round. An edition prints all of its role’s archived failures, so the card count varies by role.
Why one role per edition
The 27 failures published so far came from eleven roles, and each edition takes one. The role is on the cover, so you can see from the outside whether an edition is about your job.
What it is not
Not a transcript, not a benchmark, and not the last word on your licence. Nothing in an edition is a screenshot or a claim about your tenant, and its access facts carry their sources.
The archive lives at newsletter.kesslernity.com, so every card can be checked against the issue it cites.
Every edition ships with a newsletter issue
AI at Work goes out every other Tuesday: source-linked news, working prompts, and the ones that did not work, which is where this series comes from. No vendor sponsorship.
Where to next
M365 Copilot Field Guide
Free reference guides for the Copilot surfaces, including Cowork, Work IQ and the admin analytics.
Go→The prompt library
Role collections on GitHub, free, CC-licensed. The count is on the README because it moves.
Open→Copilot Weekly
What changed in M365 Copilot this week, with the guide patches to match.
Go→Kesslernity. Independent practitioner guide, no vendor sponsorship. Not affiliated with, endorsed by, or sponsored by Microsoft. Availability and licensing change; every access fact in an edition carries its source and the date it was read. If a page is wrong by the time you read it, the correction address is on the edition’s back page.