You’re off for a week. The bags are half packed, it’s late, and you’re typing a handover email from memory. You hit send, close the laptop, and on day two your phone buzzes with a question you could have answered in one line before you left. It isn’t anyone’s fault. The handover just had gaps, because most of what we know about our own work lives in our heads.
These days I spend ten minutes with AI on a handover before any time off. Not to write it for me, but to get everything out of my head, sorted, and checked for gaps. Here’s how.
Step 1: Dump everything that’s live
Open a blank note and list everything you’re in the middle of. Projects, promises, things waiting on other people, anything with a date in the next two weeks. Don’t tidy it. Before anything goes into a chat, take out client names, people’s details and anything confidential. “Supplier contract, waiting on legal” is plenty.
Step 2: Sort it by what actually needs someone
Paste your list in and use this prompt:
“I’m going on leave for a week. Here’s everything I’m working on. Sort it into three groups: things that will need action while I’m away, things that can safely wait until I’m back, and things someone just needs to know about.”
You’ll usually find the first group is shorter than you feared. That alone makes the evening before you go a lot calmer.
Step 3: Give each live item a status and an owner
Next prompt:
“For each item that needs action while I’m away, write one line on where it stands, one line on the next step, and leave a space for who makes the call if it goes wrong.”
Fill in the names yourself, and check with those people that they’re happy to be named. A handover without clear owners just means everyone assumes someone else has it.
Step 4: Ask what you’ve missed
“Imagine you’re the colleague covering for me. What questions would you ask that this handover doesn’t answer?”
This is the step that saves your week off. It tends to surface the things that only live in your head: where the latest version of a file sits, which deadline is real and which one is soft, who needs a gentle chase on Thursday. Add the answers you can, and drop the questions that don’t matter.
Step 5: Send it early and talk it through
Rewrite the handover in your own words so it sounds like you, then send it a day or two before you go rather than at midnight. Book ten minutes with whoever’s covering so they can ask questions while you’re still around. Then set your out of office, say when you’re back, and leave it.
Where AI stops
AI doesn’t know your colleagues, your clients or the history behind a piece of work, and it can sound confident while missing what matters most. You still decide what’s important, what’s fair to ask of someone covering, and what can genuinely wait. Keep names and confidential material out of the chat, never paste passwords or sensitive files into it, and only use AI tools your workplace has approved for work information.
Quick questions
Is it okay to put work details into AI for a handover?
Only if your workplace allows it. The safer route is to use rough notes with client names, personal details and anything confidential taken out. Never paste passwords or sensitive files.
How early should I send a handover?
A day or two before you go is ideal. It gives the person covering time to read it and ask questions while you're still around.
What if nobody is covering for me?
Still sort your list. Tell people what will wait until you're back, set a clear out of office with your return date, and name a contact for anything genuinely urgent.