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4 Tips to Make Sure Your Company's Vacation Schedule Doesn't End up a Hot Mess If you have multiple employees taking PTO simultaneously, what do you do? In a word, "prepare."

By Heather R. Huhman

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.


It's officially summertime, and small companies everywhere are feeling the heat. In fact, a 2017 survey of 400 employees by TSheets found that 30 percent of employees polled said they would take a vacation with their paid time off. Nearly the same number -- 28 percent -- said they'd use that time to spend with family.

Related: Is 'Paid Time-Off' Actually Possible?

Chloe Mitchell, director of talent relations at The Social Select, an influencer marketing agency in Los Angeles, said that in her experience the summer months are the most popular time for vacations. "Last week, we had three out of four members of our talent rRelations team out of the office," Mitchell reported via email.

"Because we have a shared team calendar on which everyone indicates their vacation time, we were aware of this weeks prior and had time to devise a plan."

Preparing for employee vacations is key, Mitchell pointed out. It ensures that the company will operate smoothly and that employees can enjoy worry-free time off. "Once the three employees arrived back from their time off, we met as a team and discussed how things went, in an effort to improve the process for next time," she added.

When running a small company, having multiple employees leave on vacation simultaneously can be disruptive. However, preparing ahead of time as a means to ensure employees enjoy their time off leads to a successful summer for everyone.

With summer under way, here are four ways to handle your own company's vacation scheduling.

1. Rally the troops.

The worst thing employers can do during the summer vacation months is take on all the work themselves. That's why Andrew Schrage, CEO at Denver-based Money Crashers, a personal finance website, suggests rallying the troops.

"Since you'll usually know about these vacations in advance, it's a good idea to conduct a meeting. Take some time and plan out which employees will be taking on specific responsibilities," Schrage suggested via email.

Make sure your entire team is on the same page, by handing out specific duties. Once everyone knows who will cover what tasks, schedule a time for each "fill-in" person to meet with the employee taking vacation. This will help team members understand what is expected of them and give them the opportunity to ask any questions.

Also, providing direction and details to those filling in will help employees relax and enjoy their time off even more.

Related: Give Us a Break: Millennials Are Suffering From 'Vacation Shame'

2. Stay transparent.

One employee's vacation time is another's extra-busy work week. David Cancel, CEO of Drift, a marketing and sales messaging service in Boston, helps his team push through the "summer slump" by keeping everyone informed.

"We made sure everyone's vacation time was documented multiple weeks, if not months, in advance," Cancel explained in an email. "We also make sure we message our upcoming time off to each other in Slack. A month out, you might send a Slack message to your team: 'Just a reminder; next month I'll be out during this week.' Then, two weeks out, you can send another reminder."

Drift's vacation transparency policy doesn't just help everyone remember who is off and when, but also holds everyone accountable to ensure that work doesn't suffer.

To stay organized, use an all-in-one HR platform like Wurk, a one-stop shop for tracking employees' vacation time, communications about their time off and payroll issues. With an online system like that, employees can eliminate paperwork and let one another know their time-off requests.

To help ensure transparency on this issue, set deadlines by which employees must enter their vacation times into the system. This will prevent co-workers from feeling overwhelmed or caught off guard by a last-minute vacation update.

3. Go above and beyond.

Employees who pick up the slack for their vacationing co-workers are true team players. Gary Beckstrand, vice president of O.C. Tanner, an employee-recognition company in Salt Lake City, Utah, went above and beyond to celebrate the team members who helped out when a fellow employee took an extended vacation.

"Honestly, we had a couple of intense days, but it did build camaraderie and strengthened relationships," Beckstrand reported. "I built in a budget for food and drinks as a token of my appreciation. I also spent a lot of time encouraging, by saying 'thanks' and acknowledging those who went above and beyond, with formal recognition, as well."

When it comes to showing employees appreciation, Niki Jorgensen, manager of HR services at Insperity, a strategic HR services company based in Houston, suggests that companies host special events for employees.

"A few examples might include hosting a pizza party or buying lunch for workers," Jorgenen suggested. "Some companies host a visit from animals at a local dog shelter whereby employees can interact with the animals and even consider an adoption. Workplace games and competitions can also be a good way to keep employees engaged and energized during the summertime."

4. Offer shorter weeks

Shorter weeks during the overflow of vacation time are another way to reward employees and give them a reprieve from extra work.

"As an organization, a clear and consistent policy must be implemented so that the company's business is not disrupted," Jay Starkman, CEO of Engage PEO, an HR solutions company in Hollywood, Fla., told me via email. "Companies may want to consider allowing seasonal perks such as compressed work weeks, revised work schedules, flextime or shorter hours on Fridays to help employees achieve a better work/life balance."

Starkman isn't the only one giving his team seasonal perks. In fact, a recent Gartner poll of 220 HR leaders found that 42 percent of the organizations sampled said they are offering their employees "summer Fridays" off this year.

So, think about these policies for your company: Sit employees down to discuss a flexible summer scheduling policy, and ask what will help them relax and refocus this summer. Find out what will give them the motivation to be more productive.

Related: Being a Work Martyr Doesn't Help You Advance Your Career, Study Finds

The policies they suggest, once implemented, will help them feel less overwhelmed when their colleagues take off; and supervisors will likely find that they're also better able to manage workflow.

Heather R. Huhman

Career and Workplace Expert; Founder and President, Come Recommended

Waldorf, Md.-based Heather R. Huhman is a career expert, experienced hiring manager and president of Come Recommended, the PR solution for job search and HR tech companies. She writes about issues impacting the modern workplace.

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