How to Ask Your Boss to Work Remotely From Another Country

Dear friend, if you are the happiest when on a flight, want to travel the world or simply want to live in a country where you thrive…well, they say we only have about 4,000 weeks in our lives, so I say you give it a go! In this blog post, I will give you step by step guide on how to ask your boss to work remotely from another country.

If your job could be done remotely but your company is not fully remote, I can help you move the first steps and ask to work remotely. I will also give you some tips if your current job is not remote or your company rejects your request. 

If this sounds good to you, keep reading…

How to ask your boss to work remotely

If your job could be done remotely but the company you work for has a hybrid or full attendance policy then try this: 

Step 1: Review the company policy

Head to the HR portal, company Google Drive or anywhere you know you can find your company policy. This is where you will find exactly how your company operates. This means you should be able to check if the company allows more flexibility after x amount of years working for them or maybe they allow 3 to 6 months of “work from anywhere”. If you can’t find any relevant information there, check your contract. Once you review any documentation available, you are fully prepared for the next step.

Step 2: Talk to your manager

If possible, have an honest and open conversation with your manager about your situation and why you would like to submit your request to work from another country. Chances are that your boss will ask you to write down a request to submit to the company, which takes you to step 3.

Step 3: Write down a detailed request

Where you want to go, for how long, time zones and so on. Don’t write what you think they might approve, but what you would like to happen. It’s your life after all!

Here below an example you could use as a template. I’ve sent a similar email to my old company to ask to work from different countries for 6 months. As you can see, it’s important to highlight the exact time zones as well as your commitment to your responsibilities.

Step 4: Wait

This is a waiting game that could last even for months. But chase from time to time and treat this request like a project you are managing, because it matters.

Step 5: They will get back to you with a yes, no or suggestions.

If the answer is no or they come out with suggestions, don’t reply straight away. Take in what you received and tell them you will get back to them soon.

In some instances, the company might approve your plan but with some conditions. These are the ones I have met so far within my community: 

• It’s ok as long as you work within the team work hours. For example, if your team is based in the US you will need to work US hours wherever you are in the world. 
• You can go for 6 months only or less. This might happen for tax reasons. 
• You can only move to countries where the offices are based. 
• A combination of some/all of the above

What if they say no

If the answer is no, it goes without saying that your company doesn’t work for you anymore because it doesn’t meet your personal needs.

From this point, you will need to join a different company which would allow you to work fully remotely. I heard what you are saying! You don’t have time to apply for other jobs. 

My dear, this answer is so 2021! We have chatGBT now and that is not an excuse anymore!

You can use ChatGBT to review your CV and help you write the cover letter and intro messages for Linkedin. And it’s totally free, or at least for now. 

Prepare for all the answers

This process is not necessarily easy or straightforward. Sometimes I hear companies or managers turning fully remote proposals down because “everyone would do it” or “I would do it too but this is not the reality, unfortunately”. When I hear the last one I always think “Why are you not doing it then if it really matters to you?”. I also disagree with “everyone would do it” because working remotely doesn’t mean going on holiday. I want you to know that these answers might come your way and you need to be prepared to keep your motivation high. 

If your job is not remote you can still make it happen

In case your current job cannot be done remotely, then you have two alternatives: 

• Learn a new profession online: If you want to try something new, try a course online! You could start working as a freelancer or fully remote company. Some of these jobs include graphic designer, developer, SEO specialist or social media manager. One of the best places to learn is Udemy. There are many others but this is the one I’ve heard about the most within the digital nomad community.
• Go for jobs which don’t require any experience: Some online jobs don’t require any experience at all. An example of this role could be a virtual assistant. Part of your tasks would include managing the company newsletters, onboarding clients, helping with the database and so on depending on the company.

In both cases, I would make sure you have some sort of passive income or some savings to cover your back. Moving to a cheaper country could also be a good idea until you figure out your next move. An alternative to this could even be house-sitting (take a look at Workaway). This means you move to someone’s house while they are away in order to look after their pets. This is totally free. It also allows you to travel and try out a new career at a low cost. Speaking of saving money, you should check out this blog post on how to save money when booking a trip!

Conclusion

I hope this blog post on “how to ask your boss to work remotely from another country” was useful for you. If you really want to work fully remotely from different countries you should focus on your “why”. This will help keep your motivation high until you succeed in your work-life needs. You’ve got this!

Ciao for now, 

Silvia x

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