PTO Planning for the Holidays: A Guide for Managers

PTO Planning for the Holidays: A Guide for Managers

With the holidays approaching quickly, you need to think about how to manage PTO for your team.

Maintaining a system that allows your employees to take time away and come back feeling refreshed without sacrificing overall business productivity can be difficult. That’s why this guide will walk you through eleven steps you can take to ensure that holiday PTO is executed efficiently and effectively for everyone. Let’s get started!

1. Clearly Define Holiday PTO Policies

A lack of clarity is the biggest driver of employee dissatisfaction and unnecessary complications for your holiday PTO planning. Make sure you work with your C-suite to clearly define the company’s PTO policies well before the holidays start.

“Ensure you’re clear about your organization’s current time-off policy and communicate it to your team … Being transparent about leave policies allows individuals to consciously weigh trade-offs and enables everyone to operate from the same set of principles,” advises Sabina Nawaz, founder of Nawaz Consulting LLC.

If you can clearly define your PTO policy and expectations for the holidays, then your team will be able to plan what’s best for them and their family. This is especially important for team members with dependents who may have to consider school and care schedules as well.

2. Communicate PTO Guidelines Effectively

Once you have clearly defined and approved your PTO policy, it’s time to communicate it to your team. An email blast with specific guidelines is a beneficial way to provide your team with the information in a format they can look back on.

George Fraguio, Vice President of Bridge Lending at Vaster, notes, “Clear communication is one of the cornerstones of effective management. Regarding PTO, communication is even more important because this is a benefit that is so valuable to your team.”

Before you release your PTO policy to your team, show it to a few select employees and get their feedback on the guidelines. If anything is confusing, make edits to ensure the policy is as straightforward as possible.

3. Be Available To Answer PTO Questions

No matter how hard you work to streamline your PTO holiday policy, questions will inevitably arise from your team. Hold office hours or offer small group information sessions where your employees can get their questions answered.

“It’s important to create an environment where your employees feel comfortable asking questions about every facet of their work. If they sense a willingness on your part to answer their PTO questions, they will feel cared for and valued,” says Greg Hannley, Founder and CEO of Soba Mesa.

As your employees start to come to you with their confusion or concerns regarding holiday pTO, keep a running list of their questions. Release a “Holiday PTO FAQ” list so that employees who may be more hesitant to ask questions have access to the info.

4. Establish a PTO Request System

As beneficial as PTO is for refreshing your team, it has to be carefully managed so that it doesn’t negatively affect the business. Establishing a PTO request system can be useful to ensure you always have enough staff working to keep the company running smoothly.

“An easy-to-use PTO request system can help you balance your employees’ needs and the needs of the business,” adds Emily Greenfield, Director of Ecommerce at Mac Duggal, a company known for their evening gowns. “Make sure your team knows how to submit a holiday PTO request and that you accept or reject requests in a timely manner.”

Some companies will need a slightly more complex PTO request system based on the size of their team and what it takes to maintain business continuity. If this is the case for your company, record and send out an instructional video so that everyone has the information they need to submit requests.

5. Lead by Example

Studies have shown that employees have become more reluctant to take PTO, even during the holidays. One way you can remedy this is by leading by example.

“A business cannot thrive unless its people are energized and working to their highest potential. To achieve this, everyone needs to take breaks, including the managers and leadership team,” says Shaunak Amin, CEO and Co-Founder of ByStadium.

Another benefit of leading by example regarding PTO is that you can show your team exactly how to use the PTO request system. When they see you step away from work and come back refreshed, they will feel more empowered to do the same.  

6. Establish a Backup System

The biggest fear surrounding holiday PTO is that the business will suffer losses without crucial team members. Establishing a backup system alleviates this fear and makes employees feel more comfortable taking time away.

Niki Jorgensen, director of service operations at Insperity, says, “A backup system can look different for every organization. One approach is to cross-train employees — the process of teaching everyone additional skills to perform job functions outside their role.”

Additionally, a backup system can make it easier when employees leave the company and you have to look for new hires. Cross-trained employees can fill in when these gaps occur and make the hiring and onboarding process less stressful and more seamless for you.

7. Provide Flexibility for Your Team

If the main goal of PTO is showing your team that you care about and value them as people, then providing flexibility in your PTO policy is one way to ensure this goal is met. A tiered PTO system that affords different team members more PTO is one way to achieve this flexibility.

“It’s important to recognize that some team members may need more PTO, whether it’s due to more demanding job expectations or considerations regarding their personal life. Make sure the expectations of the tiered system are clearly outlined before the holiday season so people know how much time off to expect,” notes Brianna Bitton, Co-Founder of O Positiv, a company that specializes in women’s vitamins.

Generally speaking, those in leadership positions who hold more responsibility get more PTO due to the nature of their jobs. For less hierarchical companies, a different form of PTO flexibility may be more useful.

8. Use PTO Technology

Woman using an iPad and iMac

Rely on different software solutions that are designed to handle PTO specifically. Technology can be particularly helpful if you have a larger team or a geographically widespread workforce.

“Managers should embrace different PTO software that will help streamline the planning process. Using this kind of technology, they can create shift plans, swap employee shifts, and allow their team to choose their PTO,” says Dovas Zakas, CMO & Co-Founder of The Pets Table.

When it comes to planning your teams’ PTO, work smarter, not harder. Lean on different technology solutions to simplify the process and create more flexibility for your team.

9. Offer Holiday Vacations of Different Durations

Depending on their position and your company’s current business cycle, your team members may not want to take a long vacation during the holidays. However, if they can choose the length of their holiday PTO, they may be more open to taking it.

“When it comes to PTO, recognize that everyone’s holiday needs are going to be slightly different,” notes Cody Candee, Founder and CEO of Bounce. “Allowing employees to choose exactly how much time off they want to take will make them feel more in control of their working conditions and schedule.”

Holiday vacations of different durations within your team will also help the business overall. If some people need more time off during the holidays, then those who don’t need as much time can fill in where needed and take more PTO at another time.

10. Create PTO Support Teams

Another reason employees avoid taking PTO is that they believe it will create more work for them when they return. PTO support teams can help encourage employees to take the time they need without worrying about coming back to chaos.

“A large benefit of PTO support teams is that they create a network of people who can monitor an employee’s tasks and communication for them while they are away and vice versa. Knowing that work won’t pile up exponentially while they are away can make taking PTO seem more attractive,” says Griff Duncan, Digital Marketing Manager of CON-CRĒT, a company that specializes in creatine gummies.

Don’t be afraid to leverage these support teams for other types of leave, such as sick leave, maternity leave, or paternity leave. Support teams within your company will also improve company-wide communication and functioning.

11. Encourage PTO

After spending so much time fleshing out a PTO policy and creating a PTO request system, you’ll want your team to use it. Encouraging PTO directly and often is one of the best ways to ensure employees feel comfortable taking time off.

Charlie Melvoin, Co-Founder of Zygo, a company known for their swimming headphones, highlights, “Frequently, employees may feel shame or hesitance to take PTO. It’s your job as their manager to encourage them to do so and make it known that you care about their overall well-being.”

You can create a positive culture surrounding PTO by setting up a company-wide photo board where employees can share holiday photos. Sending out holiday gifts or cards is another way to celebrate the holiday spirit and get your team in a vacation mindset.

Keep Your Team Happy and Refreshed

PTO is an essential part of the holiday season that employees look forward to and cherish.

“Making a clear PTO policy, communicating it effectively, and being open to your team’s questions regarding the system will make the holidays more enjoyable for everyone,” says Lance Patterson, CEO of Juice Beauty, a company known for their CC cream. “In the midst of planning your team’s PTO, remember to take time off for yourself and set an example for your team.”

With these tips, you’re ready to expertly plan your team’s PTO policy for this season. Instead of something that may set your company back, with a little bit of planning, PTO can be a tool that reinvigorates your team and your business as a whole.

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