How to ask your boss to work remotely

Tips for transitioning into remote work.

Two people in a meeting

In recent years, an unprecedented number of workers have embraced working remotely either some of or all the time. Some managers are now eager for employees to return to the office, though, creating a potential source of conflict between employees and their employers.    

Whether you would like to start working remotely for the first time or are already working remotely and want to continue, you’ll have to have a conversation with your manager about it. This guide to asking your boss to work remotely will help you make your case.  

How to ask your boss to work remotely

The prospect of asking your boss to work remotely can be daunting, because they’re likely to have some questions and concerns. Whether you want the freedom and flexibility working from anywhere allows or want to be remote for family or financial reasons, it’s important to understand why your employer might not want you to do so.

Whether you’re a new or experienced remote worker, dive into Oyster's Global Employment Pass to find resources on how to boost your candidacy and land the job of your dreams.

Complying with local laws

It’s already complicated to run payroll and comply with local labor laws when a business only operates in one area. A distributed team that works across different states or even in different countries makes complying with local laws even more difficult for employers. Some managers may think that the extra time and effort required to tackle these challenges aren’t worthwhile. 

Providing equipment

With a central office, it’s easy for your employer to supply, maintain, and track the equipment you use to do your job. Remotely, this is a bigger undertaking—but there are ways around this issue. Distributed companies often offer a stipend to cover the cost of office equipment so employees can source their own at-home setups. Others ship the required equipment directly to their remote employees. When you leave the company, you can mail the equipment back to your employer if required. 


When you work in an office with all your coworkers, it’s easy for your boss to check in on you and make sure you’re doing what you need to do. Working from home forces your boss to place more trust in you that you’ll continue meeting your productivity goals.

Luckily, several studies have shown that remote workers are more productive than in-house employees. Your boss can rest assured that you’ll be able to get at least as much done at home as you usually do in the office.  

Steps to take to convince your boss

1. Draft a proposal

The worst thing you can do when you ask your boss for a remote work arrangement is to show up unprepared. It’s worth taking some time to think about how you’re going to pitch remote work to your boss. 

Think about the tasks you perform in your role and how you can complete them remotely. Choose a time to have the conversation when both you and your boss are available and calm. Don’t forget to put your proposal in writing, as this will help your boss recognize that you take this seriously and ensure that you’re discussing the same terms. 

2. Show the benefits of remote work

Although you’re probably focused on the advantages of remote work for you, it can also be good for your company. Show your boss the research demonstrating that remote work improves employee retention, helps reduce overhead costs for office space, and increases employee productivity. All these factors can help the company perform better and be more competitive. It’s a win-win situation for you and your employer.   

3. Propose a trial period

Even after going through the previous steps, your boss might still be hesitant to let you work remotely. A good way to offer some reassurance is to propose a trial period of remote work. That way, your boss can see how you’ll perform working remotely without having to commit to the arrangement fully. 

Your remote work trial period could be working at home two days per week and going into the office the other three, for example. Another option would be to work from home full-time for a limited time, like one month to start. Once your boss sees how well the trial period goes, they may be more inclined to allow you to work from home permanently. 

If you follow these steps and your boss still won’t allow you to work remotely, you can always consider looking for a new position on remote job boards.  

4. Tell them about Oyster

If you need some help getting your employer to allow you to work remotely, tell them about Oyster’s global employment platform. The platform will help your employer avoid the typical compliance roadblocks of having a distributed team. It also streamlines global payroll and provides a simple way for bosses to manage all team members, regardless of where they are. 

Oyster makes hiring across borders easy. Let your employer know that we can help.

About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, engage, pay, manage, develop, and take care of a thriving distributed workforce. Oyster lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

Oyster enables hiring anywhere in the world—with reliable, compliant payroll, and great local benefits and perks.

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