At The Holiday Tracker, we believe in keeping things simple. Our blog is packed with practical articles to help you manage time off, support your team, and stay organised—without the hassle.
We cover everything from handling staff absences to workplace wellbeing, productivity, and even duvet days. No matter what your business is, you’ll find something useful to make your workday easier.
Explore our latest blog posts for straightforward tips to help your business run smoothly.
Summer has a habit of making managing employee holiday requests feel more complicated.
The requests are already coming in.
One person wants the first week of August. Another wants exactly the same dates. Someone else has a wedding. Another booked flights back in January and assumed everything would be fine.
And somehow, you’re the one who has to make it all fit together.
Nobody’s being unreasonable. Everybody has a good reason for wanting time off.
That’s often what makes holiday decisions difficult.
Managing employee holiday requests would be fairly straightforward if requests arrived neatly throughout the year.
But they rarely do.
They tend to arrive in clusters. Summer holidays, school breaks, long weekends and popular weeks in August can all create a surge in requests. Suddenly, several people want time off at the same time and you’re left trying to work out how everything is going to fit together.
The challenge isn’t that employees want holiday. Most businesses expect that. The challenge is balancing what people need with what the business needs.
Nobody’s being unreasonable, and that’s often what makes the decision difficult.
That’s what many managers find hardest: saying no to a reasonable request from a good member of staff because approving it would create a problem elsewhere in the team.
There’s rarely a perfect solution when multiple employees want the same dates.
However, most businesses find it easier to manage employee holiday requests fairly when they:
Employees don’t always expect every request to be approved. What they do expect is fairness and consistency. When people understand how decisions are made, they’re often much more accepting of the outcome.
It can also help to acknowledge requests as quickly as possible, even if you can’t make a final decision straight away.
For example, if several requests for the same week arrive at once, a quick response such as “I’ve received your request and I’m reviewing the team’s availability before making a decision” lets employees know where they stand.
Employees are often trying to book flights, arrange childcare or finalise plans with family members. Even when you can’t give an immediate answer, keeping people informed can reduce uncertainty and prevent them feeling their request has disappeared into a black hole.
This is one of the most common challenges businesses face.
A popular week during the summer holidays arrives and suddenly multiple employees want exactly the same dates.
Sometimes the difficult part isn’t deciding who can have the time off. It’s deciding who can’t, especially when both requests are perfectly reasonable.
If competing requests are a regular challenge, it can help to decide in advance how requests will be assessed.
Many businesses use a first-come, first-served approach because it’s simple, transparent and easy for employees to understand.
Others prefer to rotate popular holiday periods from year to year. For example, if one employee was granted the first week of August this year, another employee may be given priority for the same week next year.
Some businesses also take team coverage and business needs into account, particularly where certain skills or responsibilities need to remain available.
There’s no single right answer. What’s important is choosing an approach that works for your business and applying it consistently.
Whatever approach you choose, make sure employees understand how decisions are made. People are often more accepting of a decision they don’t like if they can see that it has been applied fairly and consistently.
Many holiday-related headaches can be reduced by talking about summer leave before requests start piling up.
That doesn’t mean asking employees to book every day of annual leave in January. It simply means encouraging conversations early enough that potential clashes don’t come as a surprise.
A few simple steps can help:
For example, if you already know that the first two weeks of August are likely to be difficult to cover, letting employees know early gives everyone a better chance of planning around it.
The earlier people start thinking about summer leave, the more options everyone usually has.
When requests arrive gradually, they’re often much easier to manage than when six requests for the same week arrive on the same day.
Approving annual leave isn’t simply about saying yes or no. It’s also about making sure the business can continue to operate effectively while people are away.
Before approving leave, it can be useful to ask:
You may also need to consider minimum staffing levels, customer demand, project deadlines and specialist knowledge within the team.
Thinking through these questions can help managers make decisions more confidently and explain those decisions more clearly.
Sometimes approving a request isn’t possible because it would leave the business short-staffed or place too much pressure on the people who remain. These conversations aren’t always easy, but most employees understand when decisions are explained clearly and honestly.
Most of the difficulty in managing employee holiday requests comes down to information.
More specifically, having the right information available when you need it.
When everyone wants the same week off, making fair decisions becomes much harder if you can’t easily see who’s already off, what cover is available or whether a clash already exists.
This isn’t a management failure. It’s what happens when the information you need is spread across a spreadsheet, a calendar, an inbox and your own memory.
You might be trying to decide whether a request works, but you’re not completely sure who else is off that week. You think something was already agreed, but can’t quite remember the details. Or you approve something that looks fine, only to realise later that it creates a problem you hadn’t spotted.
That’s where visibility can make a real difference.
Visibility can also help employees make more informed holiday requests.
When employees can see who is already off, they’re often able to avoid requesting dates that are already particularly busy. That can reduce the likelihood of disappointment and make holiday planning easier for everyone involved.
This is something we hear regularly from customers.
One customer described The Holiday Tracker as helping them “see who’s on holiday at a glance.”
Another told us that managers can review the full team before approving or rejecting requests.
When people can see what’s happening, making holiday decisions often becomes much simpler.
In The Holiday Tracker, employees can view the Team Calendar for the team they belong to before submitting a request. This helps them see planned holidays within their team and identify dates that may be easier to approve.
Managers can view the Team Calendar for the team they manage, along with holidays, sickness and other absences, making it easier to make informed decisions and spot potential clashes before approving leave.
Managing employee holiday requests isn’t difficult because employees want time off.
It’s difficult because everybody has a good reason for wanting it, and somehow it all still has to fit together.
The key is to plan ahead, communicate clearly and make decisions using the best information available at the time.
When employees understand how decisions are made, and managers have a clear view of team availability, making it all fit together becomes a little easier.
If managing holiday requests is becoming more difficult than it needs to be, The Holiday Tracker helps managers make holiday decisions with confidence by providing a clear view of team availability.
Start your free 7-day trial and see how simple annual leave management can be.
Most people expect the difficult part of their day to be the big tasks.
But often, it’s the smaller jobs that end up taking the most mental energy. Checking, remembering, replying, and following up tend to fill the gaps left by everything else.
That’s often why people finish the day feeling busy, but not like they’ve made much progress.
Approving holiday requests sounds simple.
Until you’re the one who has to decide.
Because it’s rarely just about the request.
It’s a surprisingly common mistake, and most businesses don’t realise they’re making it.
“We treat everyone the same.” It’s what every good employer aims for. But when it comes to part-time staff and bank holidays, a well-intentioned calculation can end up producing very unequal entitlement.
Most small businesses aren’t worried about keeping everyone.
They’re worried about keeping the people who really matter.
The ones who understand how things work, carry responsibility, and quietly keep everything moving. When people like that leave, it is not just a recruitment problem. It affects stability, workload, and confidence across the business.
At The Holiday Tracker, we work with organisations of all shapes and sizes. In this Powered By story, we’re sharing how a charity supporting the local community uses The Holiday Tracker to keep holiday and sickness admin clear, simple and under control.
There are days when you finish work feeling completely worn out, even though nothing dramatic has happened. No crisis. No disaster. Just a steady stream of questions, messages, interruptions and decisions.
And yet your brain feels full. Heavy. Done.
If that sounds familiar, you’re not alone.
The Holiday Tracker app has been an absolute
lifesaver for our company
- Magdalena, Kaktus Vans
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