Staff holidays are an essential part of running a business, and regular breaks help everyone do their job better. Managing this should be straightforward - but for many organisations, it’s anything but.
Here’s what can derail employers, and how you can get back on track.
❌ Mistake 1: Poor Visibility of Team Availability
Why it’s a problem
A team member grabs you at the start of a busy day to ask for time off.
You're about to head into a meeting/deal with something urgent but they promise they’ll be quick.
You haven’t got the right information in front of you so don’t know if this will clash with anyone else’s holiday. And - let’s be honest - it’s hard to say no when it’s last minute time off to attend their nephew’s school nativity play.
When leave is booked via quick conversations, emails that disappear into a clogged up inbox, or entered into the dreaded holiday spreadsheet, no one has a reliable view of who’s off when.
If teams only discover clashes once rotas are written, upset and resentment can build because things don’t feel fair. As a manager you’re on a hiding to nothing, and can end up firefighting to avoid being understaffed during the busy Christmas season. It’s stressful, inefficient and completely avoidable.
The Solution
A reliable system that lets you manage holiday requests efficiently and fairly.
✅ How WorkSmarter helps:
- It’s easy for employees to request a holiday any time from their platform account or via WorkSmarter’s mobile app.
- Team members see at a glance how much leave has already been taken and what they have left.
- Once a new request is made, the system will instantly flag up any clashes or conflicts so staff are fully informed before deciding whether to continue or change their dates.
- Once submitted, the manager will see all the details and know if there are any conflicts so they’re fully aware before making a decision.
- Once a request is approved, WorkSmarter’s shared holiday calendar is instantly updated - giving everyone full insight and visibility into who’s off and when.
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Mistake 2: Estimating Holiday Balances Instead of Calculating Them ProperlyWhy it’s a problemIt’s approaching the end of a long year and a colleague emails to ask, “Can you confirm how much leave I’ve got left?”
It’s a little irritating as it’s the third holiday query this week.
You open the spreadsheet, cross-check against old emails and try to remember whether that extra day off in May was taken as holiday, unpaid leave or TOIL. There are different rules for part-time staff, people on flexible contracts and those who started mid-year. Somewhere along the way, a formula has been overwritten and you are not entirely sure the numbers are right.
If people end up taking more leave than they are entitled to, you have difficult conversations to manage and potential costs to recoup.
If they take less than they should, staff are more vulnerable to physical exhaustion, mental burnout and at increased risk of going off sick. Not only that, but it leaves employers at risk of their staff falling short of the
5.6 weeks’ statutory minimum annual leave they’re legally entitled to.
The SolutionAccurate, real-time balances for every employee, calculated automatically - powered by reliable HR software that does the hard work for you.
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How WorkSmarter helpsWorkSmarter’s clever holiday calculator does all the hard work for you. Once you’ve set your company holiday rules, the system automatically:
- Calculates each employee’s entitlement based on their individual working pattern and start date
- Includes any policy settings such as bank holiday entitlement, carryover rules and TOIL
- Deducts approved holiday and updates remaining entitlement in real time
- Shows both managers and employees exactly how much leave has been taken, what has been requested and approved/declined, the amount remaining in the current holiday year so you can stay compliant with your legal obligations.
❌ Mistake 3: No Clear or Consistently Applied Holiday Policy
Why it’s a problem
As the year flies by you realise you still haven’t confirmed with your team what’s happening over Christmas.
Is the business closing completely between Christmas and New Year, or just over the bank holidays? Do you need a core team to cover key days? Will those days be taken from people’s holiday allowance, or treated differently?
By the time it’s sorted, some staff have already booked holiday on the assumption the business will be closed, while others have kept days back just in case. Inevitably, someone feels hard done by and you’re left trying to unpick what’s become a bit of a mess.
When holiday rules are vague or applied differently from person to person, it becomes very difficult to show that you’re treating employees fairly and following clear policies and procedures. That can create real problems if a complaint is raised later.
The Solution
A clear, written holiday policy that’s shared, understood and applied in the same way across the business, backed up by the support of a powerful HR software system.
✅ How WorkSmarter helps
Our HR software makes it simple to professionalise your leave management, so there’s no more confusion and frustration.
- Ringfence any ‘no leave’ days in advance. Add custom dates to your holiday calendar so your team has full transparency. Simply block out in-work days you need to reserve, so staff are aware before they make a request.
- Use our Batch Updates feature to manage multiple accounts in one go, making it simple to book pre-approved holidays for multiple users, or change holiday start dates without having to update everyone individually.
- Every affected employee is notified and their holiday balance updated automatically. The shared holiday calendar is adjusted straight away, so everyone’s in the know.
- Add non-working days for your entire company. When you reserve non-working days, these won't be deducted from holiday entitlements.
- Your holiday policy documents can be stored in one place, shared with all staff and easily updated when things change.
Instead of relying on manual processes or memory, WorkSmarter takes care of it all with an automated admin process that’s simple for managers and employees to follow. That means fewer last-minute surprises, fairer decisions and much less admin when you’re already under pressure at the end of the year.
🚀 Now’s the perfect time to make sure your holiday tracking is ready to meet the challenges of 2026. Our friendly team is on hand to help.
Get in touch.
