Why many people shy away from the first step
Many remote employees dream of a workation but don't dare to start the conversation. Yet the starting position is often better than you'd think: if you already work fully or mostly remotely, your employer has little objective reason to turn down a time-limited stay abroad, as long as availability, data protection and tax questions are sorted out.
This guide helps you prepare the conversation so it comes across as professional and convincing.
Step 1: Get clear on your own position
Before you ask for the conversation, answer these questions for yourself:
- How long? One to four weeks is easier to get approved than three months. Short pilots are more convincing than big announcements.
- Where? Within the EU, the red tape is considerably lighter than in non-EU countries. Choose an EU destination for your first attempt.
- Which time zone? A difference of up to two hours from your home base is usually not an issue. More than four hours needs clear rules on availability.
- Which project? Plan the workation for a phase with few meetings and lots of focused tasks.
Step 2: Know the legal basics
Not legal or tax advice, no guarantee. Always check the current rules against official sources or with a tax or legal adviser.
Social security (A1 certificate)
If you work temporarily in an EU/EEA country or Switzerland, the social security law of your home country generally continues to apply, provided you have an A1 certificate. Your employer applies for it with the responsible Krankenkasse (your statutory health insurer) or the pension insurance agency. Without an A1, you risk becoming liable for social security contributions in the host country.
Income tax / permanent establishment risk
Beyond a certain length of stay (which varies depending on the double taxation agreement), the host country can claim the right to tax your employment income. Your employer could also face a Betriebsstätte (permanent establishment) risk if your work is treated as a permanent presence abroad. So agree the duration with your employer and, if necessary, a tax adviser.
Employment law
As a rule, German employment law continues to apply to your employment relationship (Art. 8 Rome I Regulation), unless agreed otherwise. Even so, local minimum standards in the host country may apply.
Step 3: Prepare the conversation
Documents that build trust
- A short concept paper (one page): destination, period, time zone, availability, tech setup, data protection measures (VPN, encrypted devices), planned return date.
- A reference to company policy: if there are already home office rules, show that a workation is an extension of the same principle.
- An A1 checklist: show that you know what needs to be applied for. That takes work off your employer's plate.
Arguments that count
- No change in performance or availability
- Clearly defined tech security
- Time-limited and reversible
- A positive effect on motivation and retention (employee retention is a real business problem)
What to avoid
- Framing the conversation as a demand: present it as a pilot proposal instead
- Asking for several months the first time
- Playing down the time difference when it matters
Step 4: Put it in writing
An approval by email is enough as documentation. Better still is a short supplementary agreement that covers the following:
- Period and destination
- Availability hours
- A note that data protection and IT security rules continue to apply
- Clarification that German employment law applies
- What happens if the A1 certificate doesn't arrive in time
Conclusion
Preparing the conversation in a structured way signals professionalism and takes away your employer's biggest concerns. The most common mistake isn't asking in the first place, but asking without a plan. With a clear concept, a realistic destination and a short trial period, your chances are good.