Workations That Work: Managing Risk, Maximizing Reward


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Have you ever wished you could break free from the daily routine and take your work beyond the office walls—perhaps to a beach, a mountain, or a castle? I know that I have. Travel is a personal passion of mine, and I find the experience enriches and recharges my life. The idea of blending productivity with exploration has captured the imagination of many professionals in recent years. "Workations" (a combination of the words “work” and “vacation”) have surged in popularity as employees seek to experience the world without waiting for retirement. But for the combination of work and travel to be successful, everyone involved needs to be on the same page, with strong guidelines, security protocols, legal obligations, and performance expectations in place.


Clear Expectations and Agreements

When I first considered combining work, vacation, and travel, I understood that there would be several concerns, not just for me, but also for my employer. What obligations did I need to meet to remain an active and productive employee? Could technology and infrastructure around the world live up to the professional standards of my job? How could I effectively blend vacation time into my ongoing work activities while still meeting the needs of my team and clients? As with any business or leadership activity, clear communication is the key step here. Discussion and agreements needed to occur upfront around the scope of my seven-week workation. By establishing a Remote Work and Workation Policy, having honest conversations about expectations, and settings and procedures for data transfer and communication, we were able to set things in motion. These discussions formed the basis of a workation plan—the agreement used to manage the obligations on both sides during my out-of-office experience.


Safety, Security, and Legal Issues

When working for a Canadian organization, there are potential legal issues when an employee works from a different province or country from where they are contractually employed. Part of the workation planning process needs to involve reviewing and documenting these risks or concerns, including taxation, health and safety, and visa requirements. The employee requesting the workation opportunity needs to complete the research to ensure that there will be no negative impact or cost to the employer and that all work will be done in an ergonomic and safe manner, just like in their established office location. Additionally, the safety of travel in the proposed location and any government issued travel advisories should be considered as part of the workation plan.


Working in human resources and leadership, privacy and confidentiality are paramount. Consideration needs to be given to data protection and security in all locations visited (including those that you just fly over). Are all devices used configured with for appropriate cyber security? What about using public Wi-Fi versus secure data networks? How will sensitive data be stored and accessed while travelling? What about device search or seizure at international borders?


Things That Get Measured Get Done

As I am writing this from a stop on my workation, I know that establishing a remote work and workation policy and having a thorough workation plan has made working “from away” much easier than initially expected. I know what is expected of me when, and have been able to plan my travel, accommodations, and activities around these expectations. I know how and when I communicate with my team, when I have scheduled working time (including time zone implications), and what I need to have completed when. This plan has created measurable outcomes and has helped ensure that what I committed to is getting done!


With workations becoming more popular, particularly for professionals and remote workers, it is essential that businesses are prepared to have the necessary discussions and consistently apply best practices. If you need help developing a remote work and workation policy, contact us.  Using a clear policy will reduce risk, will maximize the experience and effectiveness for both businesses and employees navigating a workation.


From the Owl Insight team (formerly Lisa Isaac HR) and lead collaborator, Rebecca Wilkinson. Rebecca.Wilkinson@owlinsighthr.ca


For professional HR advice that you can trust, contact us today!




Blog Photo by Tanner Van Dera on Unsplash

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