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The Do's and Don’ts of Allowing Workcations: Tips for Employers


Simon Vreeswijk

Director of Marketing - 22 Aug, 2022


If you are an employer of any sort, then it’s probably no surprise to you that the working world has changed. One of the biggest shifts has come in the form of remote work and the arrangements that it allows. Employees found a silver lining in the unprecedented pandemic: remote work and the rise of the “workcation”. Here’s everything you need to know about granting a workcation for your employees.

A New Trend: The “Workcation”

The term refers to a “working vacation”. It’s a blend of work time and vacation, where people may leave their place of work but not their workload. This arrangement is becoming increasingly common, as employers find ways to provide more flexibility and workers do more work outside of their traditional office.

The pandemic revealed several new trends in the working world, with more remote work being one of them. More employers than ever before are amenable to workcations and other less traditional working arrangements. Research shows that most Americans (67%) agree with taking a workcation to “recharge their mental and emotional batteries”, and 94% plan to go on a workcation again in 2022 and beyond.

A workcation allows workers to have flexibility in their location and more control over their workdays. Additionally, these arrangements allow employees to make the most of limited vacation time policies. There’s been plenty of research that shows Amercians’ work-life balance is far from optimal, leading to burnout and negative impacts on mental health. Being able to work from anywhere allows people to spend more time with family, enjoy their surroundings, and plan travel to new and interesting places.

Additionally, research from Travel Pulse shows that:

  • 86%of employees either agreed or strongly agreed that a workcation boosted their productivity, and 81% said they became more creative at work after taking a workcation.
  • Nearly 69% of workers were less likely to quit their jobs after going on a workcation and 84% felt more satisfied with their job.
  • A combined 83% of participants either agreed or strongly agreed that a workcation helped them better cope with burnout.

Depending on your industry, you may have sent workers home for a period of time over the past two years. Maybe you’ve made accommodations for sick leave or child care that you didn’t before. No matter how the pandemic affected your workplace, you’ve probably had to make some changes. This sort of working arrangement is just one of those trends, and if you aren’t already granting workcations - chances are you’ll be asked to soon.

Related Article: Top “Workcation” Destinations: Where to Work Remotely Around the World


The Do's: A Successful Workcation Program

We suggest giving a lot of thought to your views on workcation even if it hasn’t been brought up before. Again, this is a trend that’s gaining a lot of traction, and it’s likely to be on at least a few of your employees’ minds. Here are some key things to DO:

DO: Understand the impacts on your organization

Obviously, not every industry or business is set up for allowing remote work. Further, not all types of work should be done remotely (for example, people who handle highly sensitive health information). So first you need to understand if this is something that’s even doable in your organization. And then, if you realize that it’s possible, consider the real benefits that could be offered to your company:

  • In addition to the research on increased productivity, you can expect more loyal and engaged employees. Most people won’t be quick to leave a company offering such a benefit and displaying so much trust in employees. Further, a change of scenery might make employees more creative and inspired.
  • Employees may be able to reduce stress and work in more quiet environments than a busy office, which can be great for their own work and their mental health.
  • You’ll get more well-rounded employees. People who travel have exposure to different cultures, different types of people, and different languages. They may make new connections that can benefit your company or learn new skills that can help them to network.

DO: Consider the cons of such an arrangement

Similarly to the point above, you need to think carefully about any downside. Not all job functions are set up for such work. How will others in the company feel if some people are allowed such an arraignment while others aren’t? Furthermore, the lines between work and leisure can get blurred on a workcation, which may have the opposite of the desired effect on the employee’s mental health.

DO: Develop a comprehensive policy

Once you’ve given real thought to the positives and negatives of such a benefit, consider how you’ll roll it out. It’s important to have a detailed policy in place to avoid confusion and maintain fairness. Address questions like:

  • Who is allowed to go on a workcation? How is eligibility determined?
  • What is the length of time allowed? Research shows that workcations of less than two weeks don’t offer much benefit.
  • Do all employees get the same amount of time? Will time be approved on a case-by-case basis?
  • What is the procedure for requesting a workcation? What approvals are necessary?
  • Who needs to be informed of the workcation? What communication plans need to be in place?
  • What tools will you require workers to have, and who is responsible for providing them? You might want to have a list of requirements, such as a strong wifi signal, that need to be met for a workcation to be planned.
  • The security and privacy measures that employees are expected to take (if relevant).

DO: Provide tools and training

Employees going on a workcation will require certain tools and devices. Things like laptops, wifi hotspots, and VPNs are needed, as well as any software or hardware that’s specific to the role. Employees should also be trained on cybersecurity, privacy measures, and other best practices for remote work. Additionally, once you begin allowing workcations, you’ll need to make sure your IT team is properly trained and equipped to support remote employees. In many cases, this will require certain software that they may or may not already have. Generally speaking, you want to make sure that the employee has the following available:

  • Mobile hotspot
  • Team collaboration app
  • Screen sharing software
  • Screen recording tool
  • Video conferencing tool
  • Cloud storage
  • To-do list app (like Todoist)
  • Project management app (like Asana)
  • Security or password tools
  • Productivity app (like Shift)

DO: Prepare clearly defined goals and measures of success

A workcation can only be successful if the employee is clear about exactly what they need to do while on their trip. You should also get details about how and when the employee will be working. Is there a difference in time zones? How will they manage this? Will they have support in the office? For each employee who decides to use this benefit, prepare a custom document that lists the necessary responsibilities and which metrics will be used to measure success.

DO: Provide educational resources for planning a workcation

For many employees, this type of arrangement will be new. That means they may not know exactly what to look for in a workcation destination, or how to set themselves up for success. For example, there are common mistakes that occur in a first workcation experience, including having spotty wifi that limits productivity, or choosing a venue that doesn’t have a dedicated workspace. If you’re going to offer workcations, we suggest including a resource in your policy documents to help employees know how to best plan a workcation. You can check out our guide here, where we cover what to look for in workcation destinations and how to make the experience a productive one.

Related Article: The Ultimate Guide to a Successful Workcation


Employers: What Not to Do When it Comes to Workcations

Just like there are several things you’ll want to do before offering workcations, there are pitfalls that you’ll want to avoid. In order to help your employees to be successful, you need to take certain challenges into account and then plan for them. Here’s what not to do:

DO NOT: Ignore compliance issues

The various regulatory logistics that go into a workcation are one of the bigger factors that companies consider. If your employee is interested in going to a foreign country, then a work visa needs to be arranged. There could also be complicated tax implications that your accountant should go over. Additionally, you need to understand how health insurance will apply should a medical emergency come up. We suggest consulting a legal and accounting expert before formalizing your workcation program.

DO NOT: Overcomplicate things

If you don’t micromanage the employee’s daily work in usual circumstances, you don’t need to while they are on a workcation. As mentioned above, prepare a simple document with responsibilities and which milestones are expected to be hit. However, this document doesn’t need to be overly detailed or complicated. Keep a short list of goals and metrics and allow the employee to manage their own work to these objectives.

DO NOT: Allow workcations during high-stress times

You may want to include suggested seasonality in the policy you create. It’s naturally going to be more difficult for employees to work remotely during some projects or periods. Even though employees should arrange support in the office, you don’t want them to rely on other staff so much that it causes resentment. If there are key milestones to be met, you may want to encourage staff to hold off on their trip. If there is a big launch or deadline coming up, it’s not a great time to enter into a different work arrangement.

DO NOT: Expect the same level of communication

In articles we’ve written for staff taking workcations, we strongly encourage them to set up a communication cadence and make sure their management is on board. It’s essential that staff set up a certain communication schedule, but realize it may be different than what is typical in your office. If you normally speak to employees several times a day, you’ll likely see a decrease in communication - but that doesn’t mean the employee is doing less. Work with them to plan specific touchpoints and let them know they are accountable for being available during those times.

DO NOT: Apply your new policy unfairly

It’s very important - especially when everyone is just learning about your new workcation option - that you don’t play favorites as you allow workcations. Granting them based on performance is one thing: if you offer this perk to people who go above and beyond, that’s fair, as long as everyone understands that the policy is such. You may want to grant based on seniority or tenure with the company. Some roles are better suited to a workcation, and most employees are going to understand that. In that case, try to think of other perks for individuals who must work from the office. Remember, you want this to be a tool for making employees lives better - not garnering resentment. If you only allow a workcation for your best friend at work and no other employees, word will get around pretty quickly - and not in a good way.

Workcations and Employee Retention: New Benefit Trends

Some employers have chosen to go beyond simply allowing employees to take a workcation. As a talent acquisition and retention tool, several organizations have planned a workcation program. A workcation arrangement can be a formal benefit offered to employees.

Here are some of the latest trends we are seeing:

  • Some companies organize an internal workcation where groups of colleagues can team build. The trip can be organized by internal staff, and opened to all employees or certain departments. For example, you might organize a two-week ski trip in the mountains for your marketing staff. They will collaborate and complete normal work during the day and enjoy leisure activities or downtime after hours. This arrangement can range from completely employer sponsored - where the company pays for travel, boarding, etc. - all the way to simply letting staff know that the option is available.
  • A few organizations have offered employees up to $2,000 to go anywhere in the world for a week or two while still doing their jobs. Having a financial contribution to offer will encourage more employees to take advantage.
  • Some travel or tourism companies have begun to specialize in workcations. Several luxury resorts have set up specialized areas with state-of-the-art work stations, the latest technology, and reliable wifi. Companies are able to partner with these resorts to offer a pre-planned experience to employees. TUI is a global tourism company currently pitching remote work holidays to employers.
  • You might offer a canned workcation benefit where every employee is entitled to a certain amount of time (when meeting specific criteria) that they can take as desired. For example, you could provide every employee a 30 day workcation option where they can work from anywhere without taking PTO.
  • As a real life example, HubSpot offers a 90 day workcation policy, where employees can combine being abroad with working. As long as employees can adjust to the time change, they are able to live and work in another country for up to 3 months. At ​​Thomson Reuters Corp in Canada, employees can work anywhere in the country for up to 6 weeks. You’re likely to see several companies follow suit, especially those who are heavily recruiting Generation Z employees.

Encourage the Use of Productivity Tools

When it comes to a workcation - or most forms of remote work, really - connectivity is key. Without being able to properly complete tasks, manage a workload, or collaborate and communicate with colleagues, staff is unlikely to have a successful workcation. When one workcation doesn’t go well, it’s unlikely your company will want to offer them more widely.

Fortunately, there are a variety of tools that can improve a remote working experience. Shift can help people to manage any accounts that employees use regularly, whether for personal or work reasons. Anyone who uses online platforms will find Shift to be a powerful resource.

Related Article: Top Productivity Tools & Apps for 2022


With Shift, you can organize and manage the following:

  • Mail - Connect all of your Gmail, Outlook, and Office 365 accounts and manage everything from one centralized workstation.
  • Apps - WhatsApp, Slack, Messenger—we have everything you need to get it done. Browse our Apps Directory, connect yours, and switch between them easily.
  • Search - Save time and find exactly what you're looking for across any of your Mail, Calendar, and Drive accounts.
  • Chrome extensions - Enjoy access to Boomerang, Grammarly, LastPass, and many of your other favorite Chrome Extensions.
  • Focused web tabs - Access the web from inside Shift. Manage your tabs and organize them by account for a better browsing experience.
  • Workspaces - Create a Workspace with the exact apps, tabs, and bookmarks you need, then share it with your team to get the job done.
  • Account management - Toggle between your most-used accounts, check notifications and streamline your workflow.

If you’re considering allowing workcations, make sure employees have installed Shift and can use it to manage logging in and out of accounts, saving them time and streamlining their efforts. View all of the apps and extensions that can integrate with Shift for maximum productivity, or download Shift to explore.