Accelerated by the COVID-19 pandemic, the world is shifting to embrace working from home. Since 2010 or so, professionals have gained access to a plethora of tools and technologies for remote teams that make remote work possible—and companies have seen the benefits of remote work.
If you’re not sure how to ask your boss to work from home and get their permission, I’ve got you covered. Use this guide to learn how to ask to work from home, with 15 vital tips to increase your chances of getting the remote work flexibility you want.
Table of Contents
- Why Do You Want to Work From Home?
- How to Ask to Work From Home
- 1. Research your company’s situation.
- 2. Research your industry.
- 3. Arm yourself with statistics that prove measurable benefits of remote work.
- 4. Explain your motivation.
- 5. Cite your performance.
- 6. Come up with a specific schedule and work plan.
- 7. Touch on security.
- 8. Be prepared to discuss your home office.
- 9. Talk with your boss in person (when possible).
- 10. Time your request.
- 11. Be prepared to make concessions.
- 12. Anticipate objections.
- 13. Get comfortable with discomfort.
- 14. Know when to walk away.
- 15. Regroup.
- Making a Good Impression
Why Do You Want to Work From Home?
Before I get into the main tips, you should spend some time introspecting. Why is it that you want to work from home in the first place? Here are some common reasons people want to work from home:
- Wanting more flexibility. Some people want to work from home so they’re no longer locked into a strict 9 to 5 schedule. Scheduling flexibility isn’t always associated with working from home, but in most cases, they go hand in hand.
- Avoiding the commute. Working from home means you’ll no longer have to drive or travel to the office every day. Depending on how far you live, that could mean a time savings of an hour or more every day—not to mention lower stress due to reduced traffic.
- Limiting distractions. Offices are designed to make people more productive, but they can also be hotbeds of distraction. You’re surrounded by people talking to each other and people more than willing to interrupt your day with a new task or a friendly anecdote. Working remotely is often less distracting.
- Improving your environment. Working from home also gives you more control over your work environment overall. You’ll be in charge of things like lighting, the temperature, the furniture, and even the equipment (in many cases). You can set things up to be as favorable as possible, allowing you to do your best work.
It’s important to realize that while working from home is largely beneficial, it isn’t right for everyone. While working remotely, communication is more difficult to manage, and even if you like the sound of alone time, after a few months of working remotely, you may find yourself feeling isolated.
On top of that, working from home relies on self-discipline and intrinsic motivation; you won’t have supervisors or coworkers looking over your shoulder to hold you accountable, so you’ll be wholly responsible for your own productivity.
For some people, this is the perfect environment for success, but for others, it’s a nightmare. Make sure you understand these aspects fully before making the ask.
How to Ask to Work From Home
When you feel ready to ask your boss if you can work from home, follow these important tips:
1. Research your company’s situation.
The first tip for how to ask to work from home is to do your homework first! Start by making sure you understand the full context of your working environment before you make the request. For starters, are there currently other people already working from home? If so, your chances of success will be higher. Do you know what your boss’s attitude toward remote work is? Do they think it’s something worth considering, or feel like it’s an excuse to slack off? Even if it seems like your chances are low, it’s worth making the ask. Understanding the situation just helps you frame your request in an appropriate and conscious way.
2. Research your industry.
It’s also worth taking a look at your industry, and your specific position. Are there competing companies in the industry that allow their employees to work from home? If so, how have they benefitted from the arrangement? Do many other people in your position work from home already? Don’t use this information as a way to state, “that person over there gets to work from home, so I should get to as well!” Instead, use this as supplemental information to normalize working from home.
3. Arm yourself with statistics that prove measurable benefits of remote work.
This is one of the most important tips for how to ask to work from home: list the measurable benefits of doing so. If you can convince your boss that working from home will be objectively beneficial not just for you, but for the organization, they won’t have much of a rebuttal. We’ve got a massive list of remote work statistics you can use to prove the value of remote work. Explain how working from home boosts productivity and morale while also reducing costs.
4. Explain your motivation.
Don’t lead with this, but during the discussion, make it a point to explain your personal motivation. Are you interested in working from home so you can spend more time with your family? Do you want to avoid the stress of a daily commute? Do you think you can accomplish more focused work on a regular basis? There are many valid reasons here, so make sure you’re providing them sincerely.
5. Cite your performance.
Bosses are much more likely to reward high-performing employees with remote work benefits than employees with a questionable past. if you’ve been a responsible, valuable employee, don’t be afraid to cite your past performance. Explain how you’ve consistently exceeded expectations, and point to your history of effective communication as justifications for why you’ll be valuable when working from home.
6. Come up with a specific schedule and work plan.
The more specific your remote work plan is, the more favorably it’s going to be seen. Explain exactly how your workday is going to change when working from home, such as the different types of tasks you’re going to take on, a new schedule, and the new types of tools you’re going to use. Putting this together proactively shows how serious you are about the possibility of working from home, and may prove the value of the transition.
7. Touch on security.
Many employers are nervous about allowing employees to work from home because of security concerns. When working from home, you won’t have access to the same devices, network, and security protocols as you would in a conventional office. Provide a proposal on how to improve security, such as investing in a better network, using a VPN, or installing remote employee monitoring software.
8. Be prepared to discuss your home office.
Your home office may be at the bottom of your boss’s priorities for consideration, but it’s still worth acknowledging if the discussion turns this way. Explain that you have a room set aside for your home office, and that you have all the furniture and equipment you need to be as productive as possible. For help, see our guide to work from home office setups.
9. Talk with your boss in person (when possible).
When making the request to work from home, it’s a good idea to have the discussion in person, whenever possible. Look your boss in the eyes and make your case as confidently as possible. It’s possible to make your request with a simple email, but this could convey a lack of effort, or imply that you’re not taking the matter seriously. Additionally, email is not conducive to dialogue, and this is a topic that demands an exchange.
10. Time your request.
Be careful when timing your request. On a Monday, when your boss seems irritable and stressed, and when the team is bombarded with overdue projects, it’s not a good time to ask to work from home. Wait until conditions are more favorable, with a lighter workload and better moods all around. It’s even better if you can wait until you achieve something excellent—that way, your request will be seen in an even better light.
11. Be prepared to make concessions.
Asking to work from home typically introduces a negotiation, so be prepared to make some concessions. Let’s say you ask to start working from home full-time, but your boss isn’t having it. Consider requesting to work from home three days out of the week. If that doesn’t work, consider asking to work from home just one day a week until you can prove it’s feasible. If your boss seems immovable, ask them what would make them reconsider—there may be a specific apprehension preventing them from giving you the go-ahead.
12. Anticipate objections.
No matter what, your boss is going to have some objections or concerns, so be prepared to address those concerns proactively. You likely understand how your boss thinks, and what types of requests get granted or denied in your organization. How will your boss respond to your request, and how can you counteract those challenges? Providing objective evidence as a counterpoint is your strongest tool here.
13. Get comfortable with discomfort.
Asking to work from home is probably going to be uncomfortable for you, even if you like your boss, and even if you feel good about your chances of success. Try to be comfortable with that discomfort. Acknowledging your discomfort proactively and accepting it as your reality will make you feel less anxious, and more confident in your meeting.
14. Know when to walk away.
If your boss is reluctant to accept your request and you’ve attempted to negotiate in a few different ways, don’t be afraid to walk away. If you keep pushing or if you seem overly stubborn, you’re only going to make your boss more likely to stick to their guns. Instead, accept the denial gracefully and move on with your normal workday.
If you’re forced to walk away from the initial conversation, don’t give up hope. Take this time to regroup and come to your boss with another request in the future. Think about their objections, and come up with new rebuttals and responses that might help them see the arrangement in a new light. You may also convince your coworkers to come to your boss with similar requests, increasing their perception of the concept’s normalcy. Just by mentioning the idea of working from home, you’ll be tapping into the mere exposure effect, by which people begin to see things more favorably the more they’re exposed to them. Over time, as long as you’re not stubborn, annoying, or unprofessional in your approach, you may effectively persuade your boss.
Making a Good Impression
Okay, let’s say you’ve reviewed these tips for how to ask to work from home, and your boss grants you permission. Congratulations!
Now, even if it’s in limited capacity to start, it’s important to go out of your way to make a good first impression. Otherwise, your privileges may be revoked.
- Be transparent. First, try to be transparent. Make it clear when you’re working and when you’re taking a break, and tell your supervisors and coworkers what you’re working on. If you’re struggling, or if you need time away from the computer, just let someone know. Your team will be reassured by your transparency.
- Achieve more. Some people argue that the boost in performance associated with working from home is due to workers overachieving on purpose so they can keep their privileges. If that’s the case, so what? Your boss is still seeing the bottom-line benefits. Go out of your way to pump up your numbers, especially at the beginning of your remote work career.
- Over-communicate. Err on the side of over-communication. Notify your supervisor or your coworkers when switching tasks, taking breaks, or undertaking any other significant action. It’s also a good idea to be extra detailed and meticulous in your written posts, including your task descriptions, your emails, and your reports.
- Remain flexible. Be prepared for some growing pains as you and your team members get used to this new arrangement. If you want to be successful, you’ll need to be as flexible as possible. Be open to experimenting with new tools and techniques, and if someone makes an easy request of you, comply with it.
- Make yourself a guinea pig. If you’re one of the first people in your company to be working from home, don’t be afraid to make yourself a guinea pig. You’re going to be setting the tone for the rest of your organization, so do your best work and take notes on what works for and against you while working remotely.
Now you know how to ask to work from home, and how to keep your remote work privileges once you get them.
Working from home should increase your productivity as long as you’re self-motivated and willing to make the arrangement work. But if you want an extra boost, you’ll need a productivity tool that can help you keep track of your ongoing productivity and workload.
One of the best tools for the job is EmailAnalytics, which you can use to track your incoming and outgoing emails, monitor your average email response time, and more. Best of all, you can have your boss receive a daily or weekly report of your email activity so he or she can monitor your email activity, which may help your case when asking to work from home.
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Jayson is a long-time columnist for Forbes, Entrepreneur, BusinessInsider, Inc.com, and various other major media publications, where he has authored over 1,000 articles since 2012, covering technology, marketing, and entrepreneurship. He keynoted the 2013 MarketingProfs University, and won the “Entrepreneur Blogger of the Year” award in 2015 from the Oxford Center for Entrepreneurs. In 2010, he founded a marketing agency that appeared on the Inc. 5000 before selling it in January of 2019, and he is now the CEO of EmailAnalytics, and co-host of the podcast The Entrepreneur Cast.