I think we all can agree that the key to employee retention isn’t pizza party Fridays and predictable, but lackluster, 2% annual salary adjustments.
No, it’s power and autonomy over your time, your schedule, and your location. And if the 2020s have taught us anything so far, it’s that remote work isn’t such a lofty dream after all. Maybe you have friends who work remotely and you’re feeling a bit jealous. Or maybe your partner got a job offer in a new city and you’re wondering if your company would support the move. Or, maybe you’ve heard of the world of digital nomads and want to try the lifestyle on for size.
Regardless of your motivations, if your company isn’t one of the many already embracing the remote work movement, you might be asking yourself: could remote work ever be in the cards for me?
How can you ask your boss to let you work remotely, even if doing so isn’t yet the status quo?
While working remotely has become increasingly more mainstream, many jobs still require employees to go into the office. Depending on your industry, you might be feeling the uncertainty as companies teeter between holding ono their cubicles or getting rid of their corporate leases for good.
Because of all the volatility of this emerging workplace shift, asking your boss for permission to work remotely can understandably be intimidating.
The good news is, it doesn’t have to be!
From doing your research to having the actual conversation, consider these tips on how to ask your boss to let you work remotely.
First, Why Should You Pursue Working Remotely?
Perhaps the most obvious and biggest advantage to working remotely is the flexibility.
This flexibility can help you make time for things you want to prioritize, like squeezing in a workout, cooking yourself breakfast, or spending more time with your loved ones.
Working remotely can also save you money, especially if you have a long commute or typically spend your lunch hours eating out.
It can also be a logistical choice, allowing you to relocate to a city or country that makes more sense for your lifestyle or your family needs.
For me, working remotely has opened the doors to traveling more – something I’ve always dreamt of doing but never thought I could when I was in an office.
Which Industries are Best Suited for Working Remotely?
Remote work may sound very appealing, but some industries are better suited than others to working from home. Some jobs require in-person work and collaboration, while others will thrive on digital communication. Is your industry, and your individual role, one of them?
Here are some industries and roles that are typically best suited for remote work:
- Tech and Software Jobs: Jobs like software engineering, web development, computer programming, IT support, and other tech roles can often be done remotely as long as you have a strong Wi-Fi connection.
- Designers, Social Media Managers, and Other Online Creative Jobs: Roles such as marketing managers, graphic designers, copywriters, social media managers, and others are great for remote work since they rely mostly on working and collaborating on the computer.
- Writing and Editing: Writers, editors, copy editors, proofreaders, and translators are all jobs that can easily be done on the computer, as their collaborations often happen on online documents and files.
- Customer Service and Sales: These types of roles often require messaging clients online and sometimes taking calls, making them great roles to do from anywhere.
- Education and Training: You can teach online from anywhere, whether it’s teaching a course, tutoring, doing educational development, and more.
Of course, this list isn’t exclusive – remote jobs and responsibilities can exist in almost any industry. However, if your particular role requires a substantial amount of on-the-ground, in-person tasks, the transition into remote work may be harder if not altogether impossible.
It’s important to assess this upfront and determine whether it’s better to ask your boss for more flexibility or seek new remote-first opportunities elsewhere.
RELATED: The Top Employee Benefits to Look for If You Love to Travel
Different Ways You Can Work Remotely
Fortunately, remote work exists on a spectrum – there is no one singular way to enjoy the benefits of work flexibility! While some work remotely full-time, you may also find that a hybrid or occasionally remote work schedule is ideal for you and your company.
Here are the most common forms of remote work:
- Fully Remote: In a fully remote work agreement, you work for your company 100% virtually, whether from your home or elsewhere. Policies for fully remote companies can vary from having geo-specific requirements (like needing to be in the same city, state, or country as your employer), to supporting fully distributed work where your location and time zone don’t matter as long as you have WiFi.
- Hybrid: In a hybrid work agreement, you have a flexible schedule divided between in-person work and virtual work, typically executed on a regular cadence. One common example of this could be working in the office three days a week. Another could be a floating remote work allowance where you can choose when you work from home as long as you’re spending some time in the office each week.
- Ad Hoc: If permanent hybrid and remote work isn’t as easily feasible in your company, an ad hoc approach might be a more reasonable compromise to suggest to your boss. Perhaps you’d like to work remotely every now and then for extended periods of time so you can travel, or take care of family, or explore new hobbies or pursuits. Requesting ad hoc remote work, or taking occasional workations*, can be a fantastic way to meet in the middle. You never know – these smaller remote work sprints could potentially demonstrate your competence at working remotely and lead to even more flexibility in the future!
How to Ask Your Boss to Let You Work Remotely: 8 Steps
There are many things to consider when planning to ask your boss to let you work remotely. From assessing your own role, to reviewing your company’s policies and culture, to planning out an ideal scenario that balances your individual goals with the needs of your team – this is just some of the leg work that is required before you strike up the conversation with your boss.
To get started, here are eight things you should consider when preparing your case.
Check Your Company’s Policies
Some companies and industries are less remote work-friendly than others. Check your company’s policies to see whether work-from-home and / or remote work is strictly off-limits first. If there’s an established policy against working outside of the office, you unfortunately might not be able to make a request. However, if there’s no policy, that gray area opens the door to give it a shot!
Additionally, if you’re interested in working and traveling, you’re going to want to look into whether your company has any geographic restrictions for remote work. Some companies are more flexible than others. Can you leave the state? The country?
These are important layers to help you learn exactly how much flexibility you’ll have.
Do a Self-Assessment
Before you ask your boss to let you work remotely, do an honest self-assessment of your role to determine which responsibilities you can fulfill remotely. While some companies are more remote-friendly than others, not all roles or teams within that company may be. If your job requires face-to-face interaction with customers or hands-on work, it might not be suitable for a remote setup. It could be helpful to review your job description and explore which aspects of your job are remote-capable, which aren’t, and which could be remote-capable with some modifications.
Beyond assessing your role, you’ll also want to do an honest assessment of what you’re looking for out of your remote work transition. Is your goal to simply work from home for the added flexibility? To travel? To relocate? For health reasons? Depending on the desire for your ask, and whether it’s appropriate to disclose, it could also be helpful to mention when having the conversation with your boss.
Last but not least, don’t forget to assess your work style, too. How adept are you at working autonomously? At managing your own schedule without distractions? At remaining accountable?
Do Your Research
Look up how other companies in your industry have implemented a remote work policy. Ask your friends and colleagues in your industry for advice if they work remotely. If you have any coworkers in your company that already have a remote work arrangement, take them out for coffee or set up a meeting to learn how they approached it.
Use this research as a framework to understand the best practices and potential challenges of working remotely so you can address them in your ask.
Draft a Proposal
Write a comprehensive proposal detailing how you plan to manage your tasks remotely. Include any proposed tweaks to your job description and responsibilities, a proposed schedule (if different than your existing hours), a remote communication plan, and strategies you’ll be committing to ensure productivity and accountability.
You can outline this in a simple Word Document, an email, or a presentation, depending on the format of your conversation.
Highlight the Benefits
Emphasize the advantages of remote work in your proposal, from increased productivity and lower overhead costs to improved employee wellbeing. Lead with benefits for the company before benefits for yourself (“refreshed creativity from working from a beach in Belize” is not an advantage I’d lead with… but I fully support you using your newfound freedom to reap benefits like this 🙂 )
Request the Meeting
Send an email with the goal of setting up a meeting with your boss to discuss your proposal. Come prepared to walk through your proposal and address any questions or concerns they may have.
Keep scrolling for some sample email templates you can steal to ask your boss to let you work remotely next!
Consider Proposing a Trial Period
If you’re worried about what your boss might say, consider offering to start with a temporary or trial remote work arrangement. This could be a workation, or an adjusted schedule of one or two days a week, progressing to full-time remote work if the trial period proves successful.
Be Patient and Flexible
Remote work is rapidly growing in popularity and understanding, but it’s still a new era of work that many companies may still be averse to adopting. You might find that your boss is skeptical at first, and that’s ok. While your boss may be eager to cling to cubicle culture, you may be able to eventually find a compromise that makes you both happy. Your company may just need a little more time to make adjustments to be remote work-compatible!
Either way, don’t worry. What you’re hoping to do is totally valid and you are not alone. Remote work is here to stay.
Asking to Work Remotely (Steal these Sample Email Templates!)
Asking Your Boss for a Meeting to Discuss Remote Work Possibilities
Subject: Remote Work Possibilities at [Company]
Hi [Manager’s Name],
I have been looking into the idea of working remotely, and I’d like to discuss whether this is something we could explore at [Company]. I understand we don’t have a formal policy around remote or hybrid work, but I am happy to be the guinea pig and see whether doing so can benefit our team. Working from home would allow me the opportunity to [focus more deeply, eliminate distractions, improve my productivity, etc] with the added benefit of [insert personal goal here, but keep it reasonable – spend more time with family, focus on my health, save time on the commute, etc].
I have put together a proposal of what this could look like, including a deeper dive into the benefits, a transition plan, any possible concerns and how they will be addressed, and my communication channels / proposed tools for working remote.
Can we set up a 1:1? I’d love to share what I put together and get your thoughts, feedback, and any questions you might have about whether this is a viable option.
Thank you,
[Your Name]
Asking Your Boss to Transition into Hybrid Work
Subject: Request for Hybrid Work Schedule
Hi [Manager’s name],
As you know, [reason for wanting to work from home]. Being able to work from home would [benefits and solutions, both for yourself and the team. Alternatively, if you already have a track record of success working remotely, list that here]. Because of this, I am wondering if we could discuss a trial period where we could explore the possibility of me transitioning into a hybrid role.
Would it be possible for me to begin working from home [frequency of remote work] for the next [duration of time]? These are the days that would be easiest for hybrid work, and would allow me to continue to be in-person on the days with most meetings and collaboration. I am open to exploring different scenarios to ensure continued success for our team and for my role, and would love your support. Could we discuss this further in our next 1-on-1?
Best,
[Your Name]
Asking Your Boss to Work Remotely Temporarily for Travel
Subject: Remote Work Request for Upcoming Trip
Hi [Manager’s name],
I am looking into [traveling, going on vacation, spending extended time with family, etc] and am wondering if we could discuss allowing me to work remotely while I am there. Is this something you would be open to permitting?
The dates I will be traveling are [dates] and I am thinking that a schedule like [proposed schedule] would be ideal so that I could strategically use my vacation time and continue working towards our goals. I am confident that I will have reliable WiFi, a dedicated workspace, and a time zone that would enable me to work remotely successfully while I am there.
If it would be helpful, I am open to exploring a trial period of working from home ahead of this trip in order to iron out my processes and provide you with a proposed game plan of how I will continue to execute my work.
Thank you for the consideration & looking forward to chatting through any ideas or concerns you might have.
Best,
[Your Name]
Asking Your Boss to Transition from Hybrid to Full-Time Remote Work
Subject: Remote Work Schedule Change Request
Hi [Manager’s name],
Now that I have been working remotely for [current hybrid schedule], I have found that doing so has helped me to gain increased focus, productivity, and [any other relevant benefits]. In addition, I have been monitoring my output and am happy to share that [status of any projects, goals, or concrete examples of increased productivity].
Given this, I am wondering if it be possible for me to transition into a full-time remote work agreement? I would continue to prioritize attendance for any in-office meetings and company events, and in the meantime, leverage the increased work flexibility to double-down on the value that I add to the team. I would welcome any feedback from you on how we might be able to make this happen, as I value your input and want to ensure a smooth transition.
Thank you for the consideration!
Best,
[Your Name]
What to Do Once You’re Approved to Work Remotely
If your boss takes you up on your request, amazing!
Now, you’ll need to make sure you hold up your end of the bargain and prove that you’re cut out to thrive working remotely, whether for a temporary period or for the long haul. This is your time to shine!
Also, if you’re one of the first people to work remotely in your company, you could find yourself being a trailblazer for others. Keep this in mind – your success could pave the way for others looking to transition to remote work, too.
Establish Your Remote Work Setup
To maintain productivity, you’ll want to ensure you have everything you need to work remotely, including equipment, strong WiFi, a dedicated workspace, and anything else you may need.
In addition to your home office and equipment, this list of additional remote work tools can help you optimize your transition into the world of telecommuting from anywhere.
Some companies, particularly those already set up to support remote work, may offer certain stipends or perks to help you offset the costs of establishing your home office. Others may allow you to borrow equipment from the office and bring it home, like desk chairs, laptop stands, and keyboards. If you are unsure, it can’t hurt to ask!
Over-Communicate and Stay Disciplined
Working remotely is not yet the default for most industries – it’s a privilege. Make sure you do what you need to do in order to stay on top of your workload now that you’re working remotely. Overcommunicate and take advantage of your remote work tools to keep your boss and your team up-to-date on your status so you leave absolutely no room for doubt.
If you can stay disciplined, maintain your strong performance, and effectively operate autonomously, you’ll not only validate your boss’s decision but establish the trust needed for even more flexibility in the future.
Plan Your First Remote Work Adventure
Once you’ve managed to get your boss on your side, and you’ve proven your chops as a remote worker, why not plan a little remote work adventure?
Whether it’s working from your favorite coffee shop for the day, or signing up for a fun coworking space, or planning your very first workation, think about how you want to leverage your newfound flexibility and try out new work scenarios, new schedules, and new scenery to see where it is you thrive. Just keep in mind your company’s policies and whether there are any location restrictions to your remote work.
Check out my guide on how to be successful working remotely from anywhere next to help you navigate any new workplace environment with ease.
What If Your Boss Says No?
You might still be wondering this, and I hear you. What if, even after all this preparation, your boss says no?
This could very well be your reality, and you’ll need to be patient and prepared for the possibility of rejection. If your boss denies your request, respect their decision and – if you feel comfortable doing so – ask for any feedback or insight into the decision that was made. You may find that their hands were tied due to company policies, the timing isn’t ideal, or they need a bit more convincing before giving you the green light. If you find that the door isn’t closed entirely on your remote work discussion, you can use this as an opportunity to work together on future possibilities.
However, if you find that your boss or your company policies won’t budge, you may want to consider whether your desire to work remotely outweighs the perks of staying with your current company.
If that’s the case, looking for a remote job might be your next step. Fortunately, there are endless remote jobs and career paths out there, and you’ll never know unless you look for yourself!
Ready to ask your boss to let you work remotely? You got this! Let me know if you have any other questions in the comments below.
Read This Next:
- How to Work Remotely from Anywhere: The Ultimate Guide
- What is a Digital Nomad vs a Remote Worker? Pros, Cons, and Choosing What’s Right for You
- How to Nail the Virtual Interview: Tips for the Modern Job Seeker
- How to Find a Coworking Space You’ll Love
- How to Find a Remote Job: Everything You Need to Know
- How (and Why) to Include Travel on Your Resume
- The Top Employee Benefits to Look Out for If You Love to Travel
- Essential Remote Work Tools for Successful Work Anywhere
- 18 Careers That Allow You To Work Remote
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