Summer arrives. The sun’s shining and the birds are singing. 

Then you realise three members of your team are all off on the same week. 🤯

Sound familiar? We don’t doubt it.

Managing employee time off requests is vital to keep any business running smoothly. But let's face it, it can sometimes feel like a huge chore, especially when several employees request the same time off.

Whether it's the peak of summer vacation, the festive season, or a long weekend for a national holiday, time off request clashes are unavoidable. 

Poor leave request management can cause grumpy employees and a dip in team morale. So, if you want to build a workplace where everyone feels listened to and respected, it’s important to get it right. 

But how do you make sure everyone feels good about how you make those decisions? 

We’ve got some easy strategies that’ll help turn those time off headaches into decisions everyone can agree with.

Why’s it important to be fair with time off requests? 

Before we get into the “how”, let's have a quick look at why being fair with time off is so important. We’re not talking about ticking a box on your HR list, we mean really making a difference to your company. Here’s how:

  • A happy team is a productive team: When your team feels like you treat their time off requests fairly, they feel valued and respected. This boosts their moods, makes them feel more connected to their work, and generally improves office culture. 
  • Less sick days and more people sticking around: A clear and fair system means less frustration and that means fewer unexpected absences (absenteeism). Happier people will stick with your company for the long haul.
  • Building that trust factor: Clear and consistent rules build trust between the people doing the work and the people in charge. When everyone understands the game and sees it played fairly, it creates a feeling of security and reliability.
  • Keeping the show on the road: Good time off management means you can plan ahead for when people are away. So you can make sure you've got enough people on hand to keep things running smoothly and avoid any major disruptions in your daily operations.
  • Avoiding sticky situations: Having clear rules that you apply consistently can also help protect your business from any potential legal issues down the line if someone feels like they've been treated unfairly.

A step-by-step guide on sorting out clashing holiday requests

The inevitable has happened, you've got clashing requests. Not to worry, we’ve got you covered! Here’s a simple seven-step approach you can take and apply to your very own overlapping time off request situations.

Step 1: Make a clear and effective time off policy

Think of your time off policy as the rulebook for the game – everyone needs to know the rules to play fairly. 

No, it’s not another boring document. It's the foundation for how to manage time off requests fairly. So, make sure it's not just gathering dust somewhere. Here's what your policy should do, and do well:

  • Be crystal clear: No jargon, no confusing language. Explain each type of leave in plain English. What's the deal with annual leave? How does sick leave work? What about those less common ones?
  • Outline the request process: Don't just say "request time off." Walk people through it. Do they need to use a specific form? Is there a particular system or time off tracker you use? What's the ideal notice period for different types of leave? A clear process makes it easier for everyone and reduces the chances of requests getting lost in the void.
  • Explain how you prioritize: This is crucial for managing time off requests fairly. Your policy needs to explain exactly how you'll decide when multiple people want the same time off. Will you consider seniority or use a first-come, first-served basis? Let your team know so they can manage their expectations. We’ll go into more detail on this later to help you decide which is best for you!

Don't just write the policy and forget about it. Review it regularly (at least once a year) to make sure it's still working and relevant to your company's needs. Get feedback from your employees to see if there’s anything they think could work better, and implement changes as needed.

Step 2: Encourage your team to plan ahead

You can avoid many time off request headaches with early planning and open communication. A good way to get ahead of this is to encourage your team to request their time off as early as possible, especially for popular holiday periods. Remind them of the cut-off dates you've got in your policy.

Creating an environment where employees feel comfortable discussing their time off needs with you and their team members also helps. A quick, informal chat can reveal potential clashes early on, making it easier to adjust your schedule.

It’s important to lead from the front here. If you, as the boss, plan your time off in advance and openly chat about it, your team’s more likely to follow suit. Try sending gentle reminders before peak holiday seasons about the time off request process and any relevant deadlines. A simple email or a message in a team channel is all it takes.

Step 3: Let a time off tracker do the heavy lifting

Trying to manage time off requests with spreadsheets or, shock horror, a paper-based system is a lot of extra, unnecessary work! 

A good time off tracker is your answer. Here's how it helps with managing employee time off requests fairly:

  • Centralized hub: A time off tracker provides a single place for all leave requests, approvals, and records. No more scattered emails or lost forms.
  • Real-time visibility: You can see at a glance who's requested time off, who's got time off approved, and who's currently out of the office. This is perfect for spotting potential clashes before they become a problem.
  • Automated workflows: Many time off tracking systems automate the approval process, sending notifications to relevant managers and employees. This saves time and streamlines everything.
  • Enforce your policy: You can often configure a time off tracker to enforce your company's policy. For example, it can automatically flag requests that violate the maximum number of people off at once in a department or remind employees of the required notice period.
  • Fairness through transparency: The process is more transparent with a time off tracker. Employees can often see the status of their requests and, in some systems, even see a team calendar. Transparency will help the whole process feel fair since everyone can see exactly what decisions are being made and how.
  • Data and reporting: A good time off tracker provides some sweet data on leave trends. You can see when your busiest times for requests are, which departments take the most leave, and other insights that can help you improve your policies and planning.

Step 4: Come up with a fair prioritization method

This is the heart of managing time off requests fairly. You need a clear and consistent way to decide who gets the nod when you have conflicting requests. As mentioned in the policy section, here are a few ways you can go about prioritizing:

  • First-come, first-served: Put simply, the first person to request the time off gets it. This method can get tricky, though, since it can disadvantage those who can't plan far in advance due to their job role or personal situations.
  • Seniority: Some companies allow time off based on seniority,  with employees who have been there longer getting approved first. With this method, you’ve got to make sure you clearly state it in your policy and consistently apply it to requests.  But this system can sometimes lead to newer employees feeling overlooked, overworked, and underappreciated.
  • Departmental needs: This is a more practical way of prioritization. Certain departments or roles might have important deadlines that need all hands on deck, so time off requests could be rejected across the board. Your policy should mention this,  and your team should understand that their leave requests might get declined if this is the case. 

Whatever criteria you choose, the most important thing is to be consistent and transparent. Everyone should understand the system and see that it's applied the same way for everyone.

Step 5: Keep communication open and honest

Once you've made a decision about a conflicting time off request, the way you communicate that decision is almost as important as the decision itself. A few things to remember:

  • Try not to leave people hanging. Let them know the outcome of their request within the timeframe you've outlined in your policy. 
  • Let them know the decision directly, ideally in person or over a quick phone call. Especially if the request is being denied, an email can feel impersonal for a denial.
  • If you're denying a request, clearly and calmly explain why. Let them know if there is something in your policy that backs up your decision. Be empathetic and acknowledge the employee's request and any potential disappointment. 
  • They might start asking questions, and they have the right to, of course.  So, make sure that you’re prepared for that by knowing your policies inside and out. 

Step 6: Get creative and offer alternatives

Denying a time off request outright should be a last resort. Before you say a flat "no," check if there are any alternative solutions that could work for your employee and the business. This shows that you're trying to be flexible and supportive.

If the original dates aren't possible, can you suggest alternative dates close to their original request that work better for coverage? Could you approve part of the requested time off, even if you can't approve the entire period? For example, could they take a few days if they wanted a full week?

The key here is to work with the employee to find a solution rather than just making a decision. Time off is important for them, and if you can find a way for them to get some time off while still keeping the business running smoothly, that's a win-win! 

Step 7: Fine-tune the process

Managing time off requests isn't a one-time fix; it’ll be a continuous process. To make sure your system stays fair and effective, you need to regularly review it and be willing to make changes. 

Ask your employees for feedback on the time off request process. What's working well? What could be improved? You could also ask for their opinions on things like the prioritization method and the deadlines for leave requests, and make changes based on their feedback. After all, they’re the ones using it, so make sure they’re happy with it.

Use the data from your time off tracker to pick up on trends. Are there certain times of the year when you consistently have a high number of requests? Are there particular departments that struggle with coverage? Knowledge is power, and that’s certainly the case here. All this data can help you make changes to improve your processes and make life easier for everyone.

Easy mistakes to steer clear of

Now that we have a clear step-by-step process in place, let’s have a look at some of the common mistakes people make when it comes to managing clashes in leave requests. To make your life easier, stay away from: 

  • Having favorites: If it looks like you always say yes to certain people and no to others, it's going to cause a few issues and a breakdown of trust. This is where looking at the data can be a lifesaver. Make sure you’re fairly approving or denying all leave requests for all employees.
  • Being secretive: Not being upfront about your policy or why you make certain decisions will just lead to frustration and the feeling that things aren't fair.
  • Changing the rules on the fly: If you move the goalposts and suddenly start doing things differently without a good reason, it'll just confuse people and make them think the system's inconsistent. 
  • Forgetting about team needs: Don’t make the mistake of approving everyone’s requests and being left with empty teams. This can really mess things up in terms of getting work done. 

The bottom line? Keep it fair and keep talking

At the end of the day, dealing with time off request clashes effectively boils down to two main things: 

  1. Being fair 
  2. Keeping the lines of communication open 

By having clear rules, being transparent about them, and handling requests with both empathy and a consistent approach, you can keep the peace and create a workplace where everyone feels good about coming to work.

A well-managed time off system shows your team that you care about their work-life balance while also making sure your business keeps rolling along. It's a balancing act, but with the right approach, you'll be a time off management maestro in no time!

Tired of the time off request headache? A good time off tracker can make a world of difference. And Timetastic offers a simple way to manage employee time off, see who's available when, and automate approvals. 

With a clear overview of your team's schedule and the ability to set up your own rules, you can create a fair and stress-free system for everyone. Why not see how Timetastic can help you ditch the time off drama and try our FREE 30-day trial!