Cheatsheet
Back fromholiday
The first day back costs most of what the holiday gave you. Not because the work piled up, but because you try to catch up on all of it. Copilot is useful here in one specific way: it replaces catching up rather than speeding it up. Reading 800 emails faster still means reading 800 emails. Two of these six steps happen before you leave — those are the ones that matter most.
Before you leave
Hand over in ten minutes
Let Copilot write the handover instead of writing it yourself. It knows the projects, the open threads and who's involved — you correct it and send it to whoever covers for you.
„Summarise my open projects: current status, next step, who's involved, and what a decision would need. Write it for a colleague covering for me who doesn't know the detail."
Block the day you return
The single most effective step. Keep your first day back free of meetings — you need it to read, not to attend. Set it as a calendar instruction before you go.
„Decline all meeting invitations for [date of return] and suggest the following day instead. Exception: my manager."
The first morning
Briefing, not inbox
Don't open your mail first. Ask for a briefing first, then decide what the inbox is still good for. The order is the whole trick.
„What happened between [start] and [end] that concerns me? Structure it as: decisions taken, open questions addressed to me, and things already resolved without me."
What actually needs you
Most of the backlog is copies. Ask specifically where you were addressed directly, not where you were on the list.
„Which messages and mentions from the last two weeks were addressed to me directly and are still unanswered? Sort by how urgent they look."
Meetings you missed
You don't need to watch recordings. Where the transcript is on, the summary is enough — decisions and tasks, not the conversation.
„Summarise /[meeting]: which decisions were taken, and which tasks fall to me?"
The rest of the week
Hand the rest to Cowork
What's left is a multi-step job, and that's Cowork's territory. Give it the backlog as one task and let it run in the background while you do the work that needs you.
„Work through my backlog: draft replies to the unanswered messages, flag anything you're unsure about, and list what I need to decide myself."
Don't catch up on all of it
A good part of two weeks resolved itself. Decisions were taken, questions answered by someone else, threads went quiet. Reading it anyway costs you the day and changes nothing. Read what's still open, and let the rest go — that's not negligence, it's the reason someone covered for you.
FAQ
Wouldn't it be easier to check in briefly during the holiday?
It feels that way and it isn't. Checking in keeps the work present in your head for two weeks, which is exactly what the break is supposed to interrupt — and the backlog is barely smaller for it. The handover before you leave does more than any holiday inbox check.
How far back can Copilot look?
It depends on your tenant, your retention settings and what's been indexed. Treat the briefing as a good start, not a complete record — for anything that matters, ask the person who covered for you.
I don't have calendar instructions. Now what?
They only exist in new Outlook and Outlook on the web, and they need a Copilot licence. Without them, block your first day back as a normal appointment before you leave. Less elegant, same effect.
Cowork or ordinary chat for the backlog?
Chat for the briefing, because you want to read the answer. Cowork for working through it, because that's several steps across several sources. Note that Cowork is billed by usage through Copilot Credits and may be switched off in your tenant.
Last updated: 6 August 2026
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