Can Employees Really “Work from Anywhere”? 03.8.2022 | Jennifer Connell

work from anywhere

We’ve seen the commercials flaunting scenes of pristine, white sandy beaches, tropical turquoise waters… and a sun-kissed 30-something on a beach chair with a laptop and Pina Colada. No, it’s not an ad for your next beach vacation, but one that boasts the ease of working from Barbados or any other country promoting digital nomad visas for remote workers.

Who wouldn’t be intrigued by the thought of working from a beach, the mountains, or some other location far, far away from the office that promises a lower cost of living and more space. But is it truly feasible?

I recently moderated a virtual roundtable for over a dozen Canadian companies, and it was clear that remote work is a hot topic for mobility managers. Employees who grew accustomed to working from home during the pandemic say the flexibility remote work offers leads to greater productivity. And companies facing talent shortages acknowledge that allowing remote work gives them a broader pool of potential hires to tap into. Either way, requests for remote work are on the rise:

Our conversation zeroed in on some of the concerns and challenges regarding remote work:

  • Most companies are risk-averse, particularly those within heavily regulated industries, and may lack the appetite for the risks that remote work can bring.
  • Many companies are utilizing guidelines rather than formal policies to address remote work. These are often managed ad hoc on a case-by-case basis.
  • A more formal remote work policy may be required as the volume of requests remains high since the pandemic and is primed to grow as offices re-open.
  • Work from anywhere requests are granted on a short-term basis — generally between 10 to 60 days — and are all temporary in nature.
  • Domestic requests are allowed more frequently, as they require less risk on behalf of the employer.
  • Some companies are measuring risk for international requests with predetermined country combinations.
  • The grass is not greener. Organizations are losing talent due to the false perception that other employers allow 100% work from anywhere arrangements. Companies, in turn, need to be more flexible in order to attract and retain talent.

To that last point, one attendee asked the group if any one of them had a policy that allows employees to truly work from anywhere. The answer from the group was a resounding “no.”

Attendees agreed that they evaluate requests based on the location, employee circumstances, nature of the work, local laws and compensation practices, as well as other factors that make Work from Anywhere an impractical (if not impossible) practice that can be applied to an entire workforce. Most attendees noted that they are experiencing pressure from employees and candidates who perceive that other companies are allowing employees to work remotely from any location.

This group of corporate mobility professionals reinforced what has taken up much of their time in the past 18 months: When it comes to creating a global policy, each move must be evaluated from a compliance perspective and local regulations must be followed to minimize the many risks associated with remote work. The areas of risk include:

  • Personal Tax Obligations
  • Social Security Issues
  • Permanent Establishment
  • Corporate Tax, Immigration & Employment Law
  • Implications are Different for Each Country
  • Cyber Security
  • Compensation & Benefits

There is little doubt that the Work from Anywhere discussion is here to stay, so the question of how to structure remote work policies to help organizations remain productive, compliant and competitive will inevitably remain a hot topic in 2022.

Go here to learn how Weichert is developing tech-forward solutions to help our clients rise to the challenges of meeting the duty of care and compliance objectives of their remote workforce.

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Written by Jennifer Connell


Jennifer Connell, SCRP, SGMS-T, is Vice President of Weichert’s Advisory Services group. She has over 25 years of experience in the workforce mobility and employee benefits industries and is a recipient of Worldwide ERC’s Distinguished Service Award. She has spoken on workforce mobility topics at industry conferences throughout North America and written for mobility- and HR-themed blogs and magazines worldwide.

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