Managing Annual Leave: Tackling the Summer Holiday Scramble

by | Jun 9, 2025

The summer holidays present one of HR’s biggest annual headaches. Come May, your inbox fills with leave requests for the exact same fortnight in July, and suddenly you’re playing referee between colleagues who’ve all booked the same villa in Spain. Sound familiar? You’re not alone, nearly every UK business faces this seasonal staffing nightmare.

 

Why Summer Creates Chaos

Let’s face it, everyone wants those prime summer weeks. Parents are tied to school holidays, while other employees fancy guaranteed sunshine, and those precious weeks in July and August become the most contested dates in your annual leave calendar. Meanwhile, you’re left trying to keep the lights on with a skeleton crew during what might be your busiest trading period.

The mistake most businesses make is being reactive rather than proactive. If you’re reading this in June with your inbox already bursting with clashing requests, don’t panic, there’s still time to implement damage control.

 

Immediate Action Plan

Whether you’re planning for next year or dealing with this summer’s chaos, here’s your strategy:

For This Summer: If you’re dealing with immediate requests, set an urgent deadline (give people one week to get their requests in). Explain that you’re implementing a fair system retrospectively and all requests received by [date] will be considered together.

For Next Year: Establish a cut-off date for summer leave requests (we recommend end of February). This gives everyone fair warning and prevents last-minute panic requests.

First Come, First Served: Process requests in order of submission, not based on who shouts loudest or has the best sob story about their deposit in Majorca.

Implement a Rotation System: Keep records of who got prime dates last year. If Sarah bagged the first two weeks of August in 2024, perhaps it’s time for someone else to have a turn.

Set Capacity Limits: Decide maximum numbers for each department during peak periods. If you need at least three people in accounts, don’t approve four leave requests for the same week.

 

Use Technology to Your Advantage

Manual systems create more problems than they solve. HR Chest’s annual leave calendar transforms chaos into clarity by:

  • Showing real-time team availability so employees can see potential clashes before submitting requests
  • Automatically calculating remaining entitlement using their leave calculator
  • Creating an audit trail for all decisions (essential when disputes arise)
  • Enabling managers to approve or decline requests based on live staffing data

This transparency prevents the “it’s not fair” conversations and reduces your administrative burden significantly.

 

Practical Communication Strategies

Be Brutally Honest: Tell your team exactly how the system works. Publish your approval criteria and stick to them religiously.

Use Visual Aids: Display team calendars (with permission) so everyone can see the bigger picture. Often, employees will voluntarily adjust their plans when they understand the impact.

Offer Alternatives: “I can’t approve your first choice, but how about these dates instead?” Come prepared with solutions, not just rejections.

Set Expectations Early: In January’s team meeting, remind everyone about the process and emphasise that flexibility will be rewarded.

 

Keeping Operations Running

Cross-Train Your Team: Ensure multiple people can cover essential functions. That way, you’re not held hostage by one person’s indispensability.

Consider Temporary Staff: Budget for temps during peak leave periods, especially for customer-facing roles.

Adjust Service Levels: Sometimes you need to reduce opening hours or pause non-essential projects during heavy leave periods. Plan these changes in advance and communicate them to customers.

Reward Flexibility: Publicly acknowledge team members who take leave during off-peak times or adjust their plans to help the team. Consider incentives like extra days off or preferred parking spaces.

Remember, if you’re implementing these changes mid-crisis, communicate clearly with your team about the new approach. Explain that you’re putting fairer systems in place and that while this summer might require some compromise, next year will run much more smoothly.

Summer leave management doesn’t have to be a battlefield. With planning (even if it’s reactive planning!), clear systems and honest communication, you can transform this annual headache into a manageable process that keeps everyone reasonably happy and your business running smoothly.