A Manager's Checklist for the Week Before Someone Goes on Leave

Most leave problems are not caused by the leave. They are caused by the week before it, when everyone assumes someone else has covered the gap. The week before someone goes on leave is when a manager should do four things: reassign the work that cannot wait, freeze the work that can, check who holds the access nobody else has, and pull forward every decision that would otherwise sit for a fortnight.

Here is the short version. Anything that needs this person's judgement should be decided before they leave or explicitly parked until they return. The middle ground, where it waits quietly in someone's inbox, is most of what a two week leave request costs the timeline.

Start with decisions, not tasks

Task lists are the easy part and the least useful. Tasks can usually be picked up by whoever has time. Decisions cannot.

Go through the next three weeks and find every point where this person is the one who says yes or no. Approvals on spend, sign off on a release, the final word on a design, an answer a client is waiting on. For each one, do one of three things:

• Decide it now, even if it feels early
• Give someone else the authority in writing, naming them
• Agree openly that it waits, and tell whoever is affected

The third option is fine. What is not fine is nobody knowing which of the three applies.

What to reassign and what to freeze

Split the person's open work into two piles.

Reassign anything with an external date attached: a client deliverable, a compliance filing, a payment, anything a customer is expecting. Also reassign anything another person is blocked on, and check those dates against public holidays on the other side of a border while you are in there. Name one person per item, not a team. A shared owner is no owner.

Freeze the rest. Work that only matters internally and has no hard date is usually better paused than handed over badly. Half a handover costs more than a two week pause, because the person picking it up spends longer understanding it than doing it, and then the original owner comes back and redoes it anyway.

Write the freeze down somewhere visible. Otherwise someone will find the task, assume it was dropped, and start it.

Access is the part people forget

This is where a two week absence turns into a two week block. Check, before they go:

• Shared accounts and admin logins only this person holds
• Approval chains in finance or HR tools where they are the only approver
• Anything scheduled to renew or expire during the absence
• Signing authority on documents in progress
• Access to a client system granted to them personally

The fix is usually to add a second person rather than transfer anything. Adding takes minutes while they are still here. Recovering an account while they are on a boat somewhere takes days.

The handover conversation, kept short

A thirty minute conversation with the covering person beats a long document nobody reads. Cover four things and stop:

• What is in flight and what state it is in
• Who to contact for each thing, by name
• What is already agreed and should not be reopened
• What the person taking over should refuse to decide, and who to escalate it to instead

Ask the covering person to repeat back the escalation path. If they cannot, the handover has not happened yet.

Pull the awkward conversations forward

If there is a difficult conversation due with this person, a performance discussion, a scope disagreement with a client, a decision you have both been avoiding, have it before they go. Leaving it hanging over two weeks of holiday is unkind, and coming back to it stale makes it harder for everyone.

The same applies in the other direction. If you owe them an answer, give it before they leave.

The day before

A short list, done properly:

• Out of office set, with a named person in it rather than a team address
• Calendar cleared, recurring meetings either declined or given a stand in
• Anything they own on the project board reassigned or marked as paused
• One message to the wider team saying who is away, until when, and who to ask instead

That last message costs two minutes and prevents most of the interruptions that follow someone onto their holiday.

Why this keeps happening

The reason teams repeat this every time is that the leave calendar and the work plan usually live in different systems. The leave is approved in one place months ahead, and the project plan is built in another by someone who never sees it. The gap only becomes visible in the week it matters, which is exactly when there is no time left to fix it.

You can close that gap with a calendar reminder, a shared document and notice periods people will actually follow. You can also close it with a tool that shows both together. Either works. What does not work is assuming that an approved leave request means anyone has planned for the absence.