image How to Handle Holiday Requests from Your Team

How to Handle Holiday Requests from Your Team

What if you want to be the nice boss, but you have to be the bad guy at the same time every year due to fielding holiday requests? 

In the insurance industry, this happens frequently when it comes to employees making holiday requests. For several holidays (especially Thanksgiving and Christmas), it’s not uncommon for many people to request time off at the same time. But not everyone can get that time off, which puts you in the awkward position of handling holiday requests fairly and consistently. 

How can you handle holiday requests with your team while maintaining employee loyalty without playing favorites? Keep reading to discover the answers! 

Create a Leave Policy Early and Enforce it Consistently 

As a boss, you never want to be seen as treating some employees better than others or making up arbitrary rules on the spot. So when it comes to time off, you should create a leave policy early on and enforce it consistently. 

For example, your leave policy might include certain “blackout dates” where nobody can request time off. Most leave policies have a simple strategy in place such as “first come, first serve.” This doesn’t mean there is never room for any flexibility (always important for adaptive managers). Still, when you have a policy in place and enforce it consistently, then those who have their time off denied won’t think it’s a personal or insulting decision. 

Use a Vacation Calendar 

Employees rarely realize when their leave requests would conflict with somebody’s previous request, or even with your leave policy, until it’s too late. That’s why we recommend using a vacation calendar (either a physical one or a shared app) that your entire team can access. 

Such a calendar should show any of the blackout dates we mentioned earlier and show who is already off for which dates. This helps limit the number of requests you have to handle personally because employees will better know when they can and can’t get time off. Moreover, having a public vacation calendar like this helps encourage employees to schedule plans and requests further into the future rather than springing leave requests on you at the last minute. 

Allow Employees to Make Tradeoffs with the Schedule 

You may have noticed a pattern here: Some of the best ways to handle holiday requests from your team is to encourage employees to handle things mostly on their own via checking the leave policy, checking the vacation calendar, and so on. 

In that spirit, we recommend you let employees make tradeoffs to suit the company’s scheduling needs. For example, the entire team might sit down and look at something like the month of December and figure out who will cover what days. Employees often like this method because it gives them more agency in the workplace. Managers (even those who have mastered the soft skills of leadership) often prefer this method because it means fewer workers coming to them with schedule problems and special leave requests. 

Young woman at work dreams about where to go on vacation

Consistent Communication is Key 

As a leader in the workplace, you don’t have to invent the wheel. For instance, you have probably often heard that it’s important to openly and consistently communicate with your employees. While that is always true, it’s especially important for modern managers hoping to avoid workplace drama regarding holidays. 

Consider emailing the occasional reminders about your company leave policy. Through both email and weekly meetings, remind employees about upcoming holidays and the need to get their leave requests in sooner rather than later. In addition to helping manage expectations about leave time during this period, consistent communication reduces the chances that you are blindsided by somebody’s sudden requests. Just make sure you aren’t accidentally scaring anyone

Reward Employees Who Make Schedule Sacrifices 

No matter how fair your leave policy is and how consistent your communication is, there will always be some sad workers over the holidays who have had their requests for time off denied. So instead of wishing them better luck next time, we recommend that you offer small rewards to employees who have their time denied or who have willingly made schedule compromises to help your team out. 

These rewards might include anything from buying their lunch to letting them leave a little early ahead of the weekend. Perhaps the best reward is to give this employee “dibs” on getting time off for the next major holiday. This helps refocus workers and lets them know you see them and appreciate the sacrifice they are making for you. 

Allow Some Vacation Days to Roll Over 

You might think that December is so filled with leave requests because of major holidays like Christmas and New Year’s Eve. While those holidays are one big factor, another major factor is that the average employee is worried about losing their vacation days at the end of the year, so if they have any days left, they decide to burn through them suddenly. 

Our advice? We recommend eliminating any “use it or lose it” policy you have and allowing a limited number of vacation days to roll over into next year. This one move will naturally reduce the number of workers rushing to request time off at the same time while assuring any employees who get their end-of-year leave requests denied that they aren’t losing these vacation days. 

Put Your Leadership Skills to Their Best Use Today! 

Now you know how to handle holiday requests from your team. But do you know where you can make the most of your natural skills in management? 

Here at Confie, we need leaders like you today to help train the workers of tomorrow. Ready to learn more about taking your own career to the next level? For more information about Confie, contact us today or call us at (714) 252-2500