In recent years, an unprecedented number of workers have embraced working remotely, especially in certain fields; as of November 2023, about 1 in 3 workers in management and professional occupations teleworked. Some managers are now eager for employees to return to the office, though, creating a potential source of conflict given the massive shift during the pandemic, when surveys indicated the switch to remote work affected between 35 and 45 percent of workers.
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.
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.
Prepare Your Case for Remote Work
Get Clear on Your Motivation
Before you approach your manager, take time to understand exactly why you want to work remotely. Is it for better focus, to accommodate family needs, or to reduce commute time and stress? Having a clear, professional reason will make your request more compelling than simply saying you want to work from home.
Research Your Company's Remote Work Policies
Your next step is to do some homework. Check your company handbook or HR portal for any existing policies on remote or hybrid work. Understanding the official stance will help you frame your request and show that you've considered the company's perspective.
Address Your Manager's Likely Concerns
To ask your boss to work remotely, you need to prepare a business case, address their concerns proactively, and propose a trial period. The key is understanding what worries managers most about remote work - compliance issues, equipment logistics, and productivity oversight - so you can offer solutions rather than just making requests. Whether you want the freedom and flexibility working from anywhere allows or want to be remote for family or financial reasons, addressing these concerns head-on is crucial.
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.
Trust and Productivity Oversight
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, studies have shown that remote work is linked to higher productivity; research from the U.S. Bureau of Labor Statistics found a 1 percentage-point increase in remote workers is associated with a 0.08 percentage-point increase in TFP growth (Total Factor Productivity). 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.
Your proposal should cover these key elements:
- Task analysis: How you'll complete your current responsibilities remotely
- Written format: A formal document showing you're serious about this request
- Clear terms: Specific details so you're both discussing the same arrangement
2. Show the benefits of remote work
Here's the thing - your manager cares more about business outcomes than your personal preferences. Focus on these company benefits:
- Higher retention: Remote work improves employee retention
- Lower overhead: Reduced office space and utility costs, as studies show that an increase in remote work correlates with a decrease in growth in unit capital, energy, material, and service costs.
- Better productivity: Studies show remote workers often outperform office-based colleagues
When you frame it as a win-win situation, you're speaking their language.
3. Time Your Conversation Strategically
So when should you have this conversation? Timing can make or break your request.
Avoid these moments:
- During busy seasons or project crises
- Right after missed deadlines or team struggles
- When your manager is clearly overwhelmed
Choose these opportunities: After delivering strong results or when your manager has bandwidth for strategic discussions.
4. 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.
Consider these trial period options:
- Hybrid schedule: Two days remote, three days in office
- Short-term full remote: One month working from home completely
- Gradual increase: Start with one remote day, expand if successful
Once your boss sees the trial period working well, they'll be more open to making it permanent.
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.
5. 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.
What to Do if They Say No
Even with the best preparation, your manager might say no. If this happens, try to understand their specific reasons without being defensive. Ask if you can revisit the conversation in a few months or what milestones you would need to hit to make them more comfortable with the idea.
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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