What actually breaks
Ask anyone to hand over and they will list their tasks. Tasks are the easy part and rarely what goes wrong.
What breaks is the invisible layer: the login only they have, the supplier who deals with them personally, the report due on the 5th that nobody else knows exists, the judgement call about which customer gets prioritised when two are unhappy.
The question that finds the real gaps
Not "what are you working on" but "what will someone need to decide while you are away, and how would you decide it?" Tasks transfer easily. Judgement and access are what people discover missing on day three.
The two-week runway
List everything they own, not everything they are doing
Ongoing responsibilities, recurring obligations, relationships, and standing commitments. Anything with a date attached, including monthly reports and renewals falling in the window.
Current projects are the visible part. Standing obligations are the part that surprises people, because they only appear on a specific day.
Week 1Ownership, not tasksWrite down the judgement calls
For each area, what decisions normally come up and how they usually get made. "If a customer asks for an extension, we grant one week without asking, more than that needs Priya."
This is the part that is never written down and always needed. Half an hour here prevents most of the messages that reach someone on holiday.
Week 1The highest-value itemTransfer access, and test it
Every account, shared mailbox, supplier portal, and admin login. Then have the covering person actually log in while the owner is still there.
Untested access is the most common day-one failure. A password that works and a permission level that allows the needed action are different things.
Week 1Test it, do not assumeTell external people who to contact
Customers, suppliers, and partners get a short note with dates and a named alternative, sent by the person leaving.
An out-of-office is not enough for anyone who deals with them regularly, and a warm introduction is the difference between a handled question and a stalled one.
Week 2Run a live day before they go
The covering person does the work while the owner watches and answers questions, ideally two or three days before departure.
This surfaces the assumptions nobody could have written down. It also leaves time to fix what it reveals.
Week 2The dress rehearsal
Assigning coverage properly
One person per area, not one person for everything. Covering someone's whole job is a second full-time job, and it usually means both get done badly.
Not everything split six ways either. When five people each hold a fragment, nobody has the whole picture and small things fall between them. Two or three coverers with clear areas is the right shape for most roles.
Name a decision maker for anything unexpected. However good the handover, something will arise that nobody anticipated. One named person decides, and they should know that in advance.
Agree the contact threshold explicitly. One named person may contact the person on leave, and only for something meeting a stated bar. Without this you get one of two failures: everybody messages them, or something genuinely serious goes unhandled because nobody wanted to.
Write the coverage down where people will look. A message in chat is gone in a week. It belongs wherever your team already keeps operational information, following the same rules as internal docs people actually read.
Making it work for unplanned absence
Everything above assumes notice. Illness and emergencies do not give any, and the same preparation works if a few things are permanently true rather than assembled ad hoc.
Nothing should have exactly one route. No account with one login holder, no supplier relationship with one contact, no process only one person can run. Auditing this once a year takes an afternoon.
Recurring obligations should live in a system, not a head. Reports, renewals, and deadlines in a shared calendar or task system, with an owner and a backup. This is one of the most straightforward things to automate, as covered in what to automate first.
The judgement notes should exist before they are needed. The same document written for planned leave works for unplanned absence, and it only helps if it was written in advance.
If preparing for one person's holiday reveals that the business genuinely cannot function without them, that is worth treating as a finding rather than a scheduling problem. Our guide to documenting a process covers how to prioritise: the first things to write down are the ones only one person knows and that would hurt if they were unavailable.
Coming back
Two things make the return work, and both are usually skipped.
Do not let them return to a backlog nobody triaged. The covering person should have a short list of what happened, what was decided, and what was deliberately left. Half an hour on their first morning replaces two days of reconstruction.
Ask what broke. The covering person spent two weeks discovering exactly which parts of this role are undocumented, unclear, or dependent on one person. That knowledge is at its most accurate in the first few days back and gone within a fortnight. It is the same principle as capturing what a new joiner notices, described in onboarding a new hire in their first five days.
Frequently asked questions
- How far in advance should handover start?
- Two weeks for a normal holiday, four to six for extended leave. Starting the week before means the handover competes with finishing everything, and both get done badly.
- Should one person cover everything or should it be split?
- One person per area, not one person for everything and not everything split six ways. Splitting across many people means nobody has the whole picture and small things fall between them.
- What is most often forgotten in a handover?
- Access and recurring obligations. Accounts only they can log into, a report due on the 5th, a supplier who only emails them, an approval that routes to them. Tasks get handed over; standing commitments get forgotten.
- Should someone on leave be contactable?
- Agree one named person who may contact them, and a genuine threshold for what qualifies. Without that, either everyone contacts them or nobody does and something real goes unhandled.
- How do you handle leave when someone is the only person who can do their job?
- Treat that as the finding rather than the constraint. A role only one person can perform is a business risk that exists whether or not they take leave, and their holiday is a useful forcing function for fixing it.