Imagine if your job required you to maintain an updated handoff doc, something the boss could give to a new hire that would let them immediately get caught up on the work. All the file names, locations, assumptions, choices, dilemmas and contacts, organized and ready to go.
Creating something like this would be annoying and time consuming, and eventually we’d get very little done. In addition, we like leaving our intuition a bit unexamined and our choices somewhat undocumented.
But…
This is something your AI should be very good at. Clarity, documentation, commented analysis, all there, every day, an ongoing roadmap that makes it easier to unwind activities or transfer them to a different platform. Here’s a prompt you can cut and paste into the AI you use the most:
Maintain a handoff doc for this work. Its reader is a smart stranger
who has to take over tomorrow with no access to me or to our chats.
At the end of any session where something changed, update the doc before
you finish, without being asked. If nothing changed, say so in one line.
The doc has these sections, always in this order:
1. WHAT THIS IS — two or three sentences: the project, who it's for,
what "done" looks like.
2. CURRENT STATE — what works, what's half-built, what's broken. Dated.
3. WHERE THINGS LIVE — every file, folder, account, URL, and tool, with
the exact name and location. No "the spreadsheet." Name it.
4. DECISIONS — each choice we made, the alternatives we rejected, and why.
Never delete a decision; if we reverse one, mark it superseded and
note the date and reason.
5. ASSUMPTIONS — things we're treating as true but haven't verified.
Flag which ones would hurt most if wrong.
6. OPEN QUESTIONS & DILEMMAS — unresolved tensions, stated plainly,
with the leading options.
7. PEOPLE — who's involved, their role, how to reach them, what they're
waiting on.
8. NEXT STEPS — the first three things a newcomer should do.
9. HOW TO UNWIND — what it would take to stop, hand off, or move this
to another platform.
Rules:
- Distinguish what I told you from what you inferred. Mark inferences.
- Record the reasoning, not just the outcome. The "why" is the valuable part.
- Be specific enough that someone could act without asking a question.
- If something I say contradicts the doc, point it out instead of
silently changing it.
- Keep it tight. Cut stale detail into a dated one-line summary rather
than letting the doc bloat.
- If you're unsure whether something belongs, include it under
Open Questions.The prompt needs a permanent home: put it in stored instructions (along with the doc itself), so it loads every time instead of depending on you to paste it.
Over time, the document will get larger, but that’s okay, it’s better than not having it.
