In any small business, especially one with a tight-knit team, holidays can be a bit of a balancing act. When two or more employees want the same time off- particularly during popular periods like school holidays, summer, or Christmas -it can quickly lead to tension if not handled fairly and clearly.
Managing conflicting holiday requests is part policy, part people skills. With a little planning and the right approach, you can keep your team happy while maintaining business continuity. Here’s how to stay on top of it.
1. Start with a clear holiday policy
The best way to avoid disputes is to set expectations from the start. A simple, written holiday policy should explain:
- How to request time off (e.g. notice periods, written/email requests)
- How requests are approved (first-come, manager discretion, rotation, etc.)
- Any “blackout” periods (busy times when leave is restricted)
- The process for resolving overlapping requests
Having this in place gives you a clear framework to refer to if conflict arises, and shows employees that decisions are based on fairness, not favouritism.
Tip: Keep your policy consistent, but allow for flexibility if needed. For example, an employee needing time off for a significant life event might be prioritised over a less time-sensitive request.
2. First-come, first-served: a common approach
Many small businesses operate on a first-come, first-served basis. This can work well if employees are proactive in planning their time off and you encourage early booking.
Make it fair by:
- Communicating when popular holiday times are approaching
- Reminding staff to get requests in early
- Documenting when requests are submitted (a shared calendar or email trail is helpful)
But remember, being first shouldn’t always mean guaranteed approval -business needs come first.
3. Use a holiday calendar everyone can see
Transparency goes a long way. Having a shared calendar (digital or even a whiteboard in the office) allows everyone to:
- See when others are off
- Plan their requests more thoughtfully
- Understand when a request might impact cover
This helps encourage a team mindset and often reduces the number of clashes to begin with.
4. Balance fairness with business needs
As an employer, you have the right to refuse holiday requests, especially if multiple people want time off that would leave the business short-staffed. You’re not obliged to approve all leave – just to make sure everyone can take their statutory entitlement (5.6 weeks for full-time staff) over the course of the year.
When deciding between overlapping requests, consider:
- Who submitted the request first
- Whether either person had similar leave approved recently
- Any special circumstances (family events, childcare, etc.)
- The overall impact on the business
If both requests are equally valid, rotating who gets preference year to year can be a good compromise.
5. Communicate decisions clearly and kindly
No one enjoys disappointing someone, especially in a small team. But how you communicate a declined request matters.
- Be prompt – don’t leave people hanging.
- Explain the reason clearly and refer back to your policy.
- Offer alternative dates or compromises if possible.
- Be empathetic -it’s not just about the policy, it’s about people.
Handling the situation with openness and consideration can maintain trust, even if the decision isn’t what the employee hoped for.
6. Encourage team flexibility
If you’ve got more than one employee wanting the same time off, encourage them to talk it through together first. In many cases, team members are willing to compromise if they understand the other person’s reason.
Sometimes a swap, staggered leave, or splitting the time can solve the issue without management needing to step in.
7. Plan ahead for peak periods
If you know Christmas, summer, or school half-terms are always tricky, get ahead of the rush. Ask staff to submit leave requests well in advance (e.g. three months before Christmas) so you can review them fairly and find solutions before things get heated.
You might also set a cap on how many team members can be off at the same time – just make sure this is clearly explained in your holiday policy.
Final thoughts
Conflicting holiday requests are almost inevitable in a small business, but they don’t have to lead to conflict. With clear policies, open communication, and a little empathy, you can handle overlapping requests fairly – keeping both your team and your business running smoothly.
And remember, your employees need and deserve their rest. Managing holiday leave well helps keep morale high, stress low, and your small business a great place to work.
If you’d like any further advice on managing annual leave, do get in touch.