9 ways to avoid vacation scheduling nightmares

Calendar for employee vacation scheduling

There’s no escaping it: employee vacation scheduling can be a serious nightmare. If the idea of your workers all taking off to the beach in the same week leaves you in a cold sweat, it’s time to get a handle on your team’s time off.

Here are nine ways to make vacation scheduling a breeze.

Create a system

The first step is to put guidelines in place for vacation requests and approvals. In some cases, a first-come first-served system works just fine. Other options include approving vacations based on seniority, or a model where the order of priority rotates every year.

Once you choose a system, communicate it clearly to your team. “Whatever those boundaries are, let them be known to everyone – at the beginning of the year,” says Cissy Pau, principal consultant at Clear HR Consulting.

Set a deadline for requests

If you don’t demand their plans early, your staff might not even consider when they want to take time off, increasing the likelihood of a collective late-year exodus. To avoid this, Pau suggests asking for your staff’s vacation demands at the very beginning of the year, so you don’t need to spend the next 12 months chasing people to determine their plans.

Follow up

It’s your job to make sure your staff is actually taking vacation when they said they would. Pay attention to stockpiling vacation time – or you could pay dearly.

“We’ve seen it a lot where employers will say ‘We have the calendar, but employees aren’t requesting time,’” says Pau. “It’s on the employer to say, ‘it’s time for you to really use up your vacation.’”

In other words, don’t be afraid to say, “Hey Jim, you have four weeks of vacation and now it’s August. When are you planning to use that vacation? Because you’re running out of time.”

Use vacation scheduling software

Programs like Humanity can help to create a centralized system for monitoring vacations. Employees send vacation requests (within specific time frames) and receive notification emails automatically when you approve or reject them. With everyone’s vacation automatically dotted across the calendar, potential problems are much easier to spot.

Consider blackouts

If there’s a critical time in your calendar, an across-the-board blackout might be a good idea. “You don’t have a whole lot of people at Amazon taking vacation off in the second week of December,” said Alan Kearns, career coach and founder of CareerJoy. “It’s an all-hands-on-deck kind of season.”

Make it mandatory

Companies like Hewlett-Packard, Sun Microsystems, and Motorola, to name a few, have been known to make their employees take time off (or even just encourage them to do so). And with good reason – mandatory vacation can help to avoid burnout, boosts morale, and ensures that every position has backup support (plus, it can serve as a cost-cutting measure).

Avoid rollovers

Some people just love to stockpile vacation, and generous vacation rollover policies enable them to horde their days off for years. According to Pau, it’s not recommended.

It can be a financial liability, since employees can accumulate vacation at a lower pay grade and then use it when they’ve reached a bigger salary. “We often don’t recommend allowing the carryover,” she says. “As a matter of practice, make your employees take their time off in the year or you’re going to have a problem.”

Prepare for absences

Even if your vacation scheduling is running like a dream, a headache lurks if no one is adequately prepared to fill in. Pay attention to cross-training and keeping precise track of job duties – it will help you to absorb the absences without missing a beat.

Don’t be afraid to say no

Ultimately, you have the right to deny a vacation request – and your managers should know that. “It really is at their discretion,” says Lisa Kay, president and lead consultant at Peak Performance Human Resources Corp. “Train managers that they don’t have to say yes. If someone’s asking for a vacation at a time that’s really impossible, you have the right to say no.”

See also:
How to navigate the unlimited vacation landscape
Why you should pay your employees to go on vacation


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