If you manage a small team, holiday requests probably don't feel like a big deal. Someone asks for time off, you check if it's fine, you say yes. Job done.
Until it isn't.
Until two people ask for the same week and you have to tell one of them no. Until someone books flights before they've actually had approval. Until you can't remember whether you said yes to something three months ago. Until the person who always asks first gets the best weeks and the rest of the team quietly starts to resent it.
Managing leave fairly sounds simple. In practice, for a lot of small businesses, it's one of those things that works on trust and goodwill until it stops working - and when it stops, it tends to create exactly the kind of friction that's hard to walk back.
Here's how to do it properly.
Start with a clear process - and stick to it
The single biggest cause of holiday request problems in small teams isn't bad intentions. It's the absence of a consistent process.
When requests come in over WhatsApp, by email, in person, and occasionally via a Post-it note on someone's desk, you're essentially making a new decision every time from scratch. There's no paper trail, no consistency, and no way to compare one request against another.
A clear process doesn't need to be complicated. At its most basic, it just needs to answer three questions:
- How should requests be submitted? (one channel, not several)
- How far in advance do you need to know?
- How quickly can someone expect a decision?
Get those three things agreed and communicated to the team, and you've already solved most of the common problems before they happen.
Set some ground rules upfront
Beyond the process, it helps to have a few basic rules in place - not to make people's lives harder, but so that decisions feel fair and explainable when you have to say no.
A few worth considering:
Minimum notice periods. Most businesses ask for at least twice the length of the holiday as notice - so two weeks off needs four weeks notice. This isn't always practical, and you'll want to be flexible for emergencies, but having a starting point gives you something to point to.
Maximum number of people off at once. Depending on your team size and structure, you might need at least three people in the office on any given day, or you might need cover for a specific role. Whatever it is, make it explicit. "We can't have more than two people off at once" is a lot easier to say than making it up each time.
Blackout periods. If your business has busy seasons - Christmas, school holidays, end of financial year - it's perfectly reasonable to restrict leave during those times. Just make sure people know in advance, not when they're trying to book.
First come, first served - or something else. Most small businesses default to first come, first served, and it's not a bad system. But it helps if everyone knows that's the rule. If you'd rather rotate priority so the same people don't always get the best weeks, that's fine too - just make it explicit.
The goal isn't to be rigid. It's to make sure your decisions feel consistent rather than arbitrary.
Keep a record of every request and decision
This is the part that most small businesses skip - and it's the part that causes the most problems later.
When a request comes in verbally and you approve it in passing, nobody has a record of that conversation. Six weeks later, when the person turns up at the airport and you're wondering why they're not in the office, the paper trail matters.
A record doesn't have to be complicated. A simple log of who asked for what, when, and what you decided is enough. The important thing is that both you and the person requesting can refer back to it.
This is also useful when someone challenges a decision. "I approved Sarah's request before yours came in, so I can't approve both" is a much easier conversation to have when you can show the timestamps.
Think about the whole team calendar, not just the individual request
One of the most common mistakes in small teams is reviewing each request in isolation - does this person have enough leave? Are they needed on that date? - without looking at the bigger picture.
The question isn't just whether you can accommodate this request. It's whether you can accommodate it alongside everything else that's already been approved.
This is where a lot of manual systems fall down. When leave is tracked in a spreadsheet or scattered across emails, it's genuinely hard to see at a glance who else is off at the same time. You approve something in good faith, then discover two weeks later that half the team is out that week.
The fix is having one place where all approved leave is visible - ideally a team calendar that anyone in a management role can check before approving anything. Even a basic shared Google Calendar is better than nothing. It means you're making decisions with the full picture in front of you, not just the piece you can currently see.
Be consistent - even when it's uncomfortable
The hardest part of managing holiday requests fairly isn't the process. It's applying it consistently when it creates awkward conversations.
The long-standing employee who expects a bit of extra flexibility. The person who booked flights without waiting for approval. The team member who always seems to need time off at the busiest possible moment.
These situations are where a clear process actually earns its keep. When you have a policy - even a simple one - you're not making a personal decision, you're applying a rule. That takes a lot of the discomfort out of saying no, because it's not about the person, it's about the process.
"I can't approve this because we already have two people off that week and that's our limit" is a much easier conversation than "I can't approve this because... well... it just doesn't work for me."
What this looks like in practice
A simple, fair holiday request process for a small team might look like this:
- Requests go through one channel - not WhatsApp, not a tap on the shoulder, not an email to whoever's nearest
- Requests include the dates, the number of days, and whether it's a firm booking or still flexible
- You check the team calendar before deciding
- You give a decision within a set timeframe - say, 48 hours for standard requests
- The decision is logged, and the calendar is updated if approved
That's it. No elaborate system required. Just consistency.
When it gets complicated
Even with a clear process, some situations need judgement rather than rules.
Two people request the same week at the same time. Someone has a personal situation that makes the usual notice period unrealistic. A long-serving employee wants two weeks off during a busy period and it's technically within the rules but it puts the team under real pressure.
In these cases, the process gives you a starting point, not a final answer. The goal is to make a decision you can explain and stand behind - one that the rest of the team would recognise as fair, even if it didn't go their way.
That's ultimately what fairness means in this context. Not that everyone gets what they want, but that the same standards apply to everyone, every time.
A note on software
If you're managing all of this manually - requests by email, approvals by reply, a spreadsheet somewhere tracking who's got what left - you already know it works until it doesn't.
A simple leave management tool takes the admin out of this process. Requests come through one place, you can see the whole team calendar before you decide, approvals are logged automatically, and balances update in real time. No chasing, no second-guessing, no cross-referencing three different documents to work out what you approved in February.
Absently is built for exactly this - small UK teams who want a process that actually works, without the complexity of a full HR system. You can try it free for 30 days, no credit card needed.
Or if you're one of the first businesses we work with, you can apply for a founding membership and get lifetime access in exchange for honest feedback.
Absently is leave management software for small UK businesses. Simple, fairly priced, and built to replace the spreadsheet.