Missing Monday

Imagine it’s Monday morning. Your most experienced colleague calls in sick. A customer needs an answer, but their order is an exception. The handbook doesn’t explain what to do, and nobody else knows the answer. Missing Monday helps teams find these knowledge gaps before an absence stops the work. An employee works through a fictional order using the existing handbook. When essential information is missing, the AI asks the expert a focused question. Their answer becomes a short handover note that the expert reviews and approves. The team then tests the note on a fresh order and harder exceptions to see where the advice holds up. We tested 12 fictional orders under three information conditions, making 36 model requests. Of seven orders requiring a final accept-or-reject decision, the handbook alone resolved one without asking the expert. Adding the original expert answer resolved six; adding the approved note resolved seven. None made an incorrect accept-or-reject decision. These are early synthetic results, not proof of workplace productivity or an accuracy advantage over the original expert answer. Our contribution is a practical workflow for capturing knowledge, approving it and testing its limits.