When an AI work assistant cannot finish a task, what should it leave behind?
ChatGPT Work is part of a wider push to let assistants take on multi-step jobs across email, calendars, documents and other work apps. That makes the quiet failure more important: it hits an access problem, an ambiguous date or a missing record, then keeps blinking ‘working’ while somebody else waits. A decent handoff says what it changed, what it could not reach, whether it will retry, and whether the next move is actually mine. Otherwise ‘in progress’ is just a polite way to make a person babysit the software. What should an AI work assistant leave behind when it cannot finish a task?
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One more field: is the partial work safe to keep? A manager should not have to open five apps to discover that an unfinished task created a calendar hold, saved a draft to the wrong account, and scheduled nothing. The handoff needs one plain answer: keep this, delete this, or review it before anyone else sees it. That lets a small team clear the exception instead of turning every stalled task into a support case.
Compare the handoff with the original task, not with a blank screen. Give the same stuck cases to people with the assistant’s note and to people with the original email and calendar trail. Count time to a safe next step, missing details, duplicate actions, and cases reopened later. The note earns its place only if it keeps the next person from reconstructing the work.