Working from home has become increasingly popular in recent years. With advances in technology making remote work easier than ever more and more employees are interested in telecommuting. If you want to ask your boss if you can work from home there are several things you should do to increase your chances of getting approved.
Do Your Research
Before approaching your boss, take some time to research working from home in your industry and at your company Look at how common remote work arrangements are for other employees in similar roles. You can check job boards to see if remote options are listed in job postings similar to yours This will give you a sense of whether your request is feasible and aligned with existing policies.
You should also look into any formal policies your company may already have around flexible work locations. Some organizations have established rules about eligibility for remote work, what positions can be done virtually, and how frequently employees can work from home. Understanding these policies will allow you to craft your ask in a way that fits within existing guidelines.
Highlight the Benefits
When presenting your request to work from home, put together a list of benefits for your manager and the company. Emphasize how the arrangement would be a win-win scenario improving your productivity and performance.
Explain how working from home will allow you to:
- Work with fewer distractions and interruptions
- Better focus on high-priority projects
- Avoid wasting time commuting
- Work during hours you are most productive
- Improve your work-life balance
You should also highlight benefits to the company like:
- Increased employee retention (since remote work is a highly desired benefit)
- The ability to hire talent from a wider geographic pool
- Reduced operating costs related to office space
- A more diverse and inclusive culture supporting flexible work
Having clear examples of how remote work will be mutually beneficial will help get your manager on board.
Create a Detailed Plan
Asking to work from home indefinitely with no plan is unlikely to be approved. You’ll be more successful if you propose a well-thought-out arrangement. Be as specific as possible about what you’re requesting.
Consider factors like:
- How many days per week or month you want to work remotely
- Whether there are particular days you want to be in the office vs. at home
- Your proposed remote work hours and schedule
- How you’ll remain engaged, collaborative, and accountable when working virtually
Think through how you’ll adapt your day-to-day work habits to a remote environment. Address things like communication, availability, meetings, accessing systems and files, and productivity. Outline the tools and tactics you’ll use to ensure you can seamlessly do your job and collaborate effectively from home.
Pick the Right Time
Timing your request carefully can impact whether it gets approved. Avoid asking right when your boss or team is facing deadlines or heavy workloads. Similarly, don’t ask when the company is going through layoffs or financial struggles, as they may be less inclined to support remote work during periods of uncertainty.
Look for a time when things are operating smoothly and your manager seems relaxed. Come prepared with your research and plan so you can ask in a professional, thoughtful manner rather than on a whim.
You may choose to schedule a meeting specifically for the purpose of making your request. This will allow you to have an engaged discussion rather than trying to fit it in impromptu.
Ask Face-to-Face
Email is convenient, but having an in-person conversation shows this is an important request you want to thoughtfully discuss. It also allows your manager to get clarification, ask questions, and raise any concerns they may have on the spot.
When asking, remain positive. Don’t threaten to quit if you can’t work from home. Frame this as an exploration of an arrangement you genuinely believe could benefit you and the company long-term. Offer to do a trial period so your boss can see firsthand how productive and engaged you can be while working remotely.
Being willing to compromise and find solutions to any hesitations your manager expresses also demonstrates maturity and flexibility. Maybe starting off gradually with one remote day per week is more comfortable for both sides before ramping up gradually to more time out of the office.
Follow Up Appropriately
Ideally your boss will approve your request to work from home, at least on a trial basis. Make sure to follow up with a thank you note expressing your appreciation and excitement about the opportunity. Reiterate your commitment to making the arrangement successful for all involved.
If your request gets denied, try not to take it personally. Rather than arguing, ask what concerns they have and if there is any additional information you can provide to alleviate those worries. See if there might be potential to revisit the discussion in the future once those limitations are addressed.
Regardless of the outcome, follow up with a brief email summarizing the key points covered. This ensures there is written documentation of the conversation and next steps agreed upon. Send calendar invites for any planned check-ins to evaluate how the remote work trial is going.
Make the Transition Seamless
Once your remote work arrangement is approved, take steps to make the transition as seamless as possible. Communicate the change to colleagues and share your contact information and availability details. Set up your home office to be conducive to productivity and communication.
Most importantly, make sure to deliver on the benefits you highlighted. Come through with top-notch work and complete engagement with colleagues while working from home. This will allow your arrangement to become a mutually beneficial staple of your employment that serves you and the company well.
With some planning, tact, and follow-through, requesting to work from home can be straightforward. Take the right steps and emphasize the advantages, and you may just find yourself joining the growing remote workforce. A well thought out proposal backed by research typically gets better results than an impulsive ask. As remote work becomes more normalized, managers are becoming more receptive to flexible arrangements. Put in effort on your end to show working from home can be a “win” for everyone.
Go Ahead, Ask to Work Remotely. (You Won’t Get Fired)
What is the one thing holding you back from working remotely? Are you afraid of what other people might say if you stop living your life the “normal” way? Do the logistics of the decision overwhelm you so much that you find yourself adding it to the “list of things you’ll do one day” instead of taking action? Does your boss’s potential reaction to what you want to ask keep you up at night?
It all boils down to this: fear.
Fear of doing the ‘wrong’ thing. Fear of discomfort. Fear of consequences. Fear of change.
This mindset, when applied to any aspect of life, is pretty dangerous. Fear will stop you from pursuing any path that has an unknown outcome (which *ahem* describes most of the paths out there) and keeps you inside the bubble that you’ve created for yourself, or that someone else has created for you. It will make you weigh every last pro and con when making a decision so that in the end, all you are focusing on is the worst-case scenario. Fear is growth-inhibiting, stress-inducing and, most of the time, irrational.
So why are you letting it hold you back from pursuing your dreams of working remotely?
Why, when life is so fleeting, would you stop yourself from living every single day in a way that sets you on fire? Why would you give up the chance to pursue every passion that you’ve been putting off, while making moves in your career?
Working remotely could be the first step you take toward creating your dream life. It allows you to become even more engaged in your work, while taking you outside of the traditional workplace and giving you control over your environment. If the idea of working remotely sounds enticing, or if it’s something that’s been on your mind for awhile, now is the time to take the leap.
First, you’ll need to change your mindset. Though you probably felt a bit of apprehension creeping up again with just the mention of the word ‘change’, you’ll need to turn your fear dial way down and switch on your capacity for hope and opportunity to make this happen successfully. This is not the time to worry about your boss firing you (they won’t) for bringing up the idea of remote work. It’s the time to consider what life could be like if you worked remotely, and fuel yourself with those possibilities.
Think about what remote work can offer you – not only personally but professionally. In addition to an adaptable schedule, you could see increased productivity, better health and you’ll feel so much more happy and fulfilled by your work.
So… how do you start to have the “remote work” conversation?
If you’ve shaken off that fear that we talked about earlier (good riddance!) and are feeling like you’re up to the challenge of talking to your boss about working remotely, there are a few things that you should do to prepare.
If you want to start small…
Ease your way into working remotely by beginning with one day a week outside of the office. This small ask is the simplest conversation to have with your employer as it shouldnt noticeably impact your weekly schedule or routine. Even so, you’ll want to make sure that you go into the meeting fully prepared to answer any questions that your boss may have about why you want to work remotely and how it will impact your role. Good news: we’ve already put together some tips and tricks on how to have that conversation.
If you want to consistently work remotely…
If working from home one day a week isnt enough, or you’re already working remotely one day a week and you want to take it to the next level, you may want to ask to work remotely for a week or two at a time. Just think of the joy that would fill your life if you had an extra week of time every month to be around your family. Maybe youre even ready to go fully remote. Working remotely everyday gives you the freedom you’ve been yearning for, and its effectiveness is backed up by some serious stats. For this more intensive conversation with your employer, it is pertinent to create a presentation deck outlining the why, the how and the KPIs that you’re going to track as you test the remote work waters.
If you want to go big or go home…
If you’re thinking of taking your job completely remote and want to learn how to work remotely and travel the world, you might want to consider talking to your employer about taking your job on the road. In this situation, you have two options: you can either go out on your own, or look into a work and travel program. These programs will take care of all of the heavy lifting for you, from booking flights to setting you up with accommodations and impressive workspaces, so your boss will have peace of mind. Like the point above, you’ll need to be prepared to walk through every angle of this decision with your boss, so do your research!
If you’re interested in joining Remote Year (we knew we liked you!), we can help you plan the conversation that you’ll need to have with your employer. In fact, we’ve developed an entire process to make sure that your talk goes as smoothly as possible.
How to Talk to Your Boss About Working Remotely: A Case Study
Katelyn is currently traveling the world and working remotely with Remote Year Ohana, and she’s just one of the many examples of how preparation and an open mind can turn any conversation with your employer into an opportunity to stand out and advocate for yourself.
“In my journey to pitching Remote Year to my company, I went through three stages,” Katelyn said.
“Stage one is all about proving your worth. Remote Year can be a big ask, particularly if your company doesnt already have remote employees, so being really diligent about showing up every day and doing your best work matters when it comes time for you to bring up Remote Year to your manager.”
“Stage two is all about the lightweight ask. For me, this came in the form of a casual professional development 1:1 I had with my manager. I hadnt created a pitch deck or anything yet – I simply brought up the idea of remote work and asked what he thought about it. That conversation was a casual way to set the tone for a more formal presentation about why Remote Year would be a great option for me and for the company.”
“And last, but certainly not least, stage three is about doing your homework. When I presented my Remote Year pitch to my manager and eventually my company, I felt confident that 99.9% of the questions that would be asked were already researched and answered either in the deck or in my own notes. This preparation showed my team that I was serious about this experience and that I had thought it through from every single angle.”
While every professional situation is unique, Katelyn’s three step system worked for her – and now she’s working from places like Cape Town, Lisbon, Buenos Aires, and Mexico City. Don’t worry if you felt a bit of anxiety while reading through Katelyn’s process. We’ll work with you to develop a plan that works for you and your company.
If you’re still worried that your boss will have a bad reaction to you bringing up a remote work agreement, we’re about to blow your mind. In our experience, many employers think more highly of you after you bring up the idea of working remotely.
How To Ask Your Boss To Work Remotely / Work From Home
How do I request to work from home?
When requesting to work from home, provide your employer with one or more reasons for your request. This helps them understand why you want to work from home and why they should consider the possibility. Common reasons include family obligations, health conditions and commuting stress.
What should you talk about when working from home?
Then talk about how others in the industry compare and if it’s a common occurrence for them to work remotely occasionally or full-time. Finally, discuss the steps you’ll take to avoid miscommunication and stay on top of your work. Having backup plans will show you’re ready to go above and beyond and exceed expectations when working from home.
How do I Ask my Boss to work from home?
Instead of sending a request letter asking to work remotely 100% of the time, you could begin by suggesting you work from home occasionally. For example, Tuesdays and Thursdays (or two other days per week). I like Tuesday and Thursday so that your boss and colleagues won’t think you’re trying to get an extended weekend by working from home.
Should I send a request to work from home?
Working remotely will impact your manager and team most directly, so this is a request that you should send directly to your manager when possible. You may find yourself wanting to send a request to work from home temporarily, for personal reasons, health reasons, family issues, etc.
