How to stop two people booking the same week off

Why it happens even in a careful company

Think about where a holiday request actually begins: somebody at home, on a phone, looking at flights.

At that moment, the information that would prevent the clash — who else is already off those days — is in a spreadsheet on somebody else's laptop, or in an inbox. So they pick dates, and the first time anybody compares them against anybody else's is after the request exists, when it is socially expensive to say no.

The school holidays make it sharper, because they are the same weeks for everybody with children. Half terms and the fortnight after Christmas are not randomly distributed; they are a queue nobody can see the length of.

And a pending request is usually invisible. Even a shared spreadsheet normally records decisions, not requests — so two people can both be waiting for the same week and neither knows.

The thing that actually prevents it

Make the clash visible before the dates are chosen, and most of them simply do not get requested.

That needs three things that are easy to describe and were hard to have.

A chart, not a list. Rows of people against a run of dates, so overlap is a shape you see rather than a comparison you perform.

Pending leave drawn on it. A request that has been made but not agreed has to appear, visibly different from an approved one. Most clashes are between two requests, not between two bookings.

Readable where the decision is made. Which means on a phone, at home, in the evening. A chart somebody has to be at their desk to see prevents nothing.

With those three, the dynamic changes on its own. People shift their dates by a few days before asking, because they can see the week filling up, and nobody had to enforce anything.

What to do with the clash you already have

Sometimes two requests still land on the same week, and somebody has to decide.

Before deciding, the useful facts are: how many days each request costs, what each person has left, and who else is already off in that window. Having those in front of you turns an awkward judgement into an ordinary one, and makes the reasoning explainable afterwards — which is most of what fairness means in practice.

The common tie-breakers are first-come-first-served by request date, alternating the popular weeks year on year, and splitting the week. The one worth avoiding is deciding by who asked most persistently, because that is a policy with a very clear long-term winner.

It is also worth saying no early rather than slowly. A request that sits for three weeks and is then declined costs the person a cheaper flight; the same answer on the day it arrives costs them almost nothing.

Setting your team up so this stops happening

Put everybody on one chart, including the part-timers and the weekend people. A chart that is missing three people is a chart that still produces surprises.

Make sure requests land on it as requests. In Leavebook, leave that has been asked for shows in amber straight away and approved leave in blue, so an overlap is visible to the next person who looks, long before anybody decides anything.

Give the approver the context at the point of decision. The queue shows the cost, the remaining balance and the names of anybody already off those days, which is the whole of what you need to be fair without going looking for it.

And send the result somewhere people already look. The approved leave exports as a calendar file for one person or the whole team, so the week in June that somebody booked in March turns up in the calendar of the person scheduling the meeting.