How To Convince Your Boss to Embrace Work From Anywhere

Despite being a B2B HR technology company, we get a lot of requests from individuals either looking for remote work jobs or asking for advice on how they can convince their managers to allow them to work from anywhere.

So we’ve finally decided to put down some of our thoughts to help every one of you out there who are struggling to make the case to your company that international remote work is a valuable employee benefit.

So what does Work From Anywhere (WFA) actually entail, and how can you convince your boss to embrace it?

What is Work From Anywhere?

Work From Anywhere is not just about answering emails from a beachside hammock.  It’s a structured approach to flexibility, allowing employees to work from different international locations for limited periods – typically 14 to 90 days annually. Think of it as a professional passport for those seeking balance between work and life.

Breaking the Work From Anywhere Myths

Your boss might see WFA as a glorified vacation, but there is much more to it than that. If done well, it empowers employees to:

• Support aging relatives in another country (which is one of the most underappreciated benefits for many employees)
• Stay connected to family abroad without using up vacation days
• Explore diverse cultural environments which can often stimulate personal (and professional) growth

Regional Perspectives on Work From Anywhere

It is fair to say that the openness to work from anywhere is directly correlated with an openness to remote work more generally, which itself varies by country.  So it’s helpful to first start with the local practices and benchmarks in your country and wider region.  If we look at the work from anywhere trends we see more broadly:

• European Union: With freedom of movement within the EU, this helps to somewhat reduce the compliance risks, at least from an immigration perspective for EU passport holders, meaning international remote work is quite common across much of the EU.  Some companies even have a policy for just within the EU.
• United Kingdom: We have found a lot of companies within the UK are open to offering workations as an employee benefit.  While Brexit does pose some immigration challenges, the heavy service industry focus means the industries with the highest share of remote work (e.g. technology, consultancy, marketing, insurance) are well represented here.
• United States: With a very limited number of PTO days, offering international remote work flexibility can be a key retention tool, which is why we are seeing more and more companies in the US offer both state-to-state remote work and international remote work.
• High Expat Countries Like Singapore/Dubai: Countries that have a lot of expats tend to have a high concentration of people who value mobility to stay connected with their roots so will appreciate the ability to work while visiting their family abroad.

The Business Benefits of Work From Anywhere

We have written extensively about the business benefits of having a work from anywhere policy so feel free to access our benchmarking data and case studies to help bolster your business case for introducing a work from anywhere policy.  The ones that are most often cited include:

• Talent Retention and Attraction: Top talent prioritize flexibility and in the metrics we have seen, companies like Spotify reduced attrition by 15% a year after they launched their WFA policy and others like Pinterest reduced their voluntary attrition by over 30%.
• Enhanced Productivity: Employees with autonomy working in a high trust environment almost always outperform versus those without autonomy in a low trust environment..
• Global Competitiveness: Businesses offering WFA policies stand out in the talent marketplace and can market this as a key employee benefit (just take a look at the companies doing so on Flexa Careers).
• The Flip Side Of RTOs: The other side of the argument is that if your company is pushing RTOs, the statistics show quite clearly how devastating these can be for sending talent out the door.

One strategy we have seen deployed by many companies is that if there is still reticence by senior management,  to first start with a pilot, be it in one country or one subsidiary, and test it out as an employee benefit for both prospective candidates and existing employees, then run a survey a few months later to see the results.  When they see the objective data coming in, this can build further internal momentum for the case towards implementing a WFA policy.

The Reality Check: Work From Anywhere is Not Always Truly “Anywhere”

While WFA sounds limitless, most companies impose significant restrictions. Policies often allow WFA only for specific time periods and in pre-approved countries. Legal, tax, and compliance challenges mean your “anywhere” might be limited to a handful of destinations.  For example:

• Time Limits: Many companies restrict WFA to 30-90 days annually to manage tax residency and compliance issues.
• Country Restrictions: Employees may only work in countries where the company has legal entities or operational infrastructure.
• Compliance Hurdles: Payroll, tax laws, and data security vary widely across borders, limiting true global flexibility.

When pitching WFA, it’s essential to understand these constraints and propose realistic plans that fit within the company’s policy framework.

Neither Is Work From Anywhere For All Companies Or Industries

While many companies successfully implementing WFA policies shine the spotlight on the benefits of a WFA model as part of your employee benefits, it’s important to acknowledge that this approach may not be universally applicable. For companies operating in highly regulated industries, such as banking or healthcare, the challenges of implementing WFA are significant. Strict data protection laws, compliance requirements, and security concerns often necessitate a more controlled work environment, making widespread remote work difficult to manage. 

Additionally, if your company’s competitors are not offering WFA – whether due to industry norms or local business practices – there may be less external pressure to adopt such policies. In these cases, companies may quite rightly prioritize other strategies for talent attraction and retention, especially if the broader workforce doesn’t yet demand the flexibility that WFA provides. 

Recognizing these nuances is essential when assessing whether a WFA model aligns with your company’s talent offering  and competitive landscape.

They Key Steps to Convince Your Boss to Embrace Work From Anywhere

So taking all those points above into account, if you’re still convinced that a WFA policy should be a key part of your company’s total rewards offering, there are 4 key steps you can consider to convince your boss to allow you to work from anywhere.

1. Build Your Case with Data

Numbers speak louder than words. Research and present compelling evidence focusing on:

• Productivity: Lots of studies show remote workers often outperform their office-based peers.  Follow thought leaders like Nick Bloom, Kate Lister or many others (like Jobgether’s Top 100 list featuring also Donal Brady from Work From Anywhere) where you can access the latest trends.
• Retention: Companies with WFA policies report higher employee satisfaction and retention.
• Cost Savings: Flexible work more broadly can reduce office space costs and commuting costs.
• D&I: Companies like Spotify and Pinterest who implemented WFA policies pointed to significantly positive changes to their D&I metrics.
• Industry Trends: Benchmark against competitors who have embraced WFA like from the Flexa Careers page above.  Mercer have also done lots of surveys that can be quite helpful here.

2. Address Stakeholder Concerns

Your manager isn’t the only decision-maker, and there is actually quite a lot of cross-department agreement needed to implement a WFA policy. WFA impacts multiple departments:

• HR & Global Mobility: Will the policy attract and retain talent?  Will the compliance workload be too much?
• Tax: How will tax laws be managed across borders?  How do we manage social security risks and documentation?  How will permanent establishment risks be addressed?  This last one in particular comes up as the biggest stumbling block for many companies, especially corporate tax departments.
• Legal/Compliance:  How will  labour laws be managed across borders?How will the right to work element be addressed?  And what about immigration?  Insurance?  
• IT and Security: Can sensitive data remain secure in a global work setup?  Will laptops and other physical property be secure?

So bear this in mind and try to address these concerns. What helps is there are award-winning technology platforms available, like what we do here at Work From Anywhere, that help address many of the key compliance elements at a fraction of the cost of going to external advisors.

Whatever you do, make sure to proactively address the concerns above in your pitch, showcasing that you’ve done your homework, and made an effort to gather feedback from any of the key departments above.

3. Present a Clear, Tailored Proposal

Once you have your final proposal ready, make sure it is detailed, structured, and aligned with company goals. A great place to start is our Workation Policy Builder.  Make sure to include:

• Countries: Make the case for a limited number of countries to begin with, that will help build confidence and can be expanded later.  Then as your company evolves, you can make sure to flag countries that have well structured digital nomad visas, as these countries can be added to your programme.
• Duration: Make sure to have a clear maximum number of days people can work remotely abroad.  If your company is conservative, they’re likely to only allow anywhere from 7-30 days work from anywhere annually.  If they’re not, they may allow more (although the maximum we tend to see is typically 90 WFA days per year).
• Compliance Plan: Address tax, legal, technology and regulatory requirements and ensure you have already included some third party technology solutions to help put the case forward for automating the compliance assessments where possible.  
• Clear Owner: It would be helpful to have one department having clear ownership of the policy, otherwise it can become a mess.  With no clear owner, these initiatives can lose momentum.

4. Competitive Benchmarking: What Are Other Companies Doing?

Nothing speaks louder in corporate strategy than understanding your competitors’ moves. Platforms like Flexa.careers provide invaluable insights into which companies are leading the Work From Anywhere revolution. By researching WFA policies of similar companies, you can demonstrate that flexible work isn’t just a trend – it’s a talent retention and attraction tool that your C-Suite cannot ignore.

For instance, tech companies like Spotify offer up to 20 days of international work annually, while Dropbox provides a fully remote-first model with location-flexible options. Fintech companies like Wise and Revolut offer 60+ days work from anywhere while companies like Hubspot and Airbnb offer up to 90 days work from anywhere. They all recognise that rigid location policies could mean losing top talent. Using resources like Flexa.careers, you can compile a detailed landscape of WFA policies across your industry, transforming your pitch from a personal request into a competitive strategy.

The Future of Work is Hybrid – and Global

We are starting to see a settled pattern over the last year with most companies blending the best of both worlds:

• Hybrid Work: For their domestic remote work policy, we see most companies have settled on hybrid which is typically 2-3 days in the office, with flexibility depending on the team..
• WFA As A Perk: This domestic hybrid policy is then complemented by a targeted WFA policy which allows limited periods of international workations (e.g. 30 days/year).

Pro Tips for Your Personal Work From Anywhere Pitch

If trying to implement a company-wide WFA policy feels like too much of a stretch, there are other ways to make the argument to your HR team if you’d like to push for an exception to their standard “no WFA” rule.  It helps to be transparent about your goals and intentions, as lying about the reasons for your trip can make life difficult for your employer down the road.

• Highlight the company benefits (e.g. productivity, commitment to key projects and deadlines), not just personal perks.
• Ensure that the right to work and immigration components, as well as insurance aspects are researched.  Not having these answers in advance increased the burden on your HR and global mobility team, so having these researched will help speed up the process and likelihood of approval.
• Check if there is a well designed digital nomad visa in that destination, as these often help reduce immigration, right to work and some tax risks.
• Propose a trial period to test the arrangement and show your boss you can do a workation productively.

The bottom line is you need to show you’re properly researched the compliance risks and have a clear commitment to meeting your personal and team targets while on workation.

Final Thoughts

Work From Anywhere is more than a trend – it’s a strategic shift in how we view work. With the right preparation, data, and a well-crafted proposal, you can help your company embrace a future that balances flexibility with productivity.

A Word Of Caution: WFA policies vary widely, and not all companies can accommodate every destination or duration. Always consult your HR and legal teams to ensure compliance with company guidelines.

Helpful Resources

Did you know that we have other benchmarks we have put together over the last few years?

• In 2022 we originally put together a benchmark of The Companies Allowing Work From Anywhere 
• We have also put together deep dives on the work from anywhere policies of Pinterest, Airbnb and Spotify
• We have likewise done articles on the RTO policies of Amazon and Bolt
• We often refer to this survey done by International Remote Working and Virtual Assignments Survey done by Mercer in 2023 that has extremely helpful benchmarks.

John Lee

John is Co-founder of Work From Anywhere, a platform to help companies execute a work from anywhere strategy.  John is a Chartered Accountant who speaks 6 languages and was previously the senior finance leader of a €4 billion division of FTSE-listed CRH Plc.  John and his family are passionate about travelling and his eldest daughter, Rosa, while only 5 years old has already travelled to 25 different countries.