How to Ask to Work From Home (With Exact Scripts & Templates to Aid Your Negotiation)

Follow these 9 steps to secure a remote work arrangement even in the most skeptical of organizations

negotiate working from home

More and more workplaces offer employees the opportunity to work remotely. Yet, if it isn’t available in your office, it may seem like a nonstarter.

In the year 2019, that’s absolutely not true.

Over two-thirds of the global workforce now works remotely at least one day each week and 50 percent works outside the office for at least half of the week, according to a 2018 study from International Workplace Group.

But while remote work is increasingly common, it’s often up to employees to advocate for it. While 63 percent of employers reported having remote workers, according to Upwork’s Future Workforce Report from last year, the majority of those organizations lacked an official remote work policy.

What can make the difference in whether you’ll enjoy the freedom to work from home yourself is how you ask. The following steps will help to persuade even the most skeptical of managers to let you work remotely:

April 10 is global Work From Home Day. 🌏👩‍💻🏡 It could be the perfect opportunity to start the conversation at your workplace.

1. Research the landscape in your industry and organization

When going into any negotiation about remote work, it’s essential to be prepared. That includes understanding the landscape of remote work in your industry and your organization. Find out how common remote work is in your field with online resources like Flexjobs. (Some of the top fields for flexible work might surprise you, including medical and health, customer service, and education and training.)

Drill a bit deeper and find out if your organization’s competitors offer remote work arrangements. After all, your management should want to offer similar privileges to avoid losing good employees.

Finally, ask around your office and throughout your company to see if there are any teams or departments that already have remote work arrangements. Your organization may even have a remote work policy that you didn’t know about.

“If it’s happening somewhere else [in your organization], find out how it’s going, why it’s being done, and what the objections have been,” says Pilar Orti, director of Virtual Not Distant, a consultancy that helps organizations transition to an “office optional” approach.

Having this information at a meeting will help you show your boss that remote work is more common than they realize, and allow you to offer concrete examples for how the arrangement has worked in similar contexts.

2. Emphasize the benefits to your organization

Go into your negotiation with a list of the benefits a remote work arrangement will have for your employer. This could include potential cost savings, improved morale, and increased productivity. You want to assure your boss that this arrangement is good for everyone, not just you.

Use the following questions from Brie Reynolds, senior career specialist at FlexJobs, to generate concrete examples of how your work will improve with a flexible arrangement:

  • How would you do your job better?
  • Would you be more productive in some ways, and why is that?
  • Would you be better able to focus, and would you be able to drill down into projects without interruption?
  • Would you be able to work hours that better accommodate your company?
  • If you’re able to skip your commute, could you start working earlier?

There’s no need to hide that working remotely will benefit you personally, say in the form of shorter commutes or more schedule freedom; just make sure you’re looking at the benefits from your manager’s perspective.

If you work in an environment where teleworking isn’t common, or is even looked down on, you will likely be educating your boss. Having a few key facts on how employers benefit from remote work could help your case, though unless your boss is particularly wonkish, it’s best not to overwhelm them with a lot of statistics.

Here are some of the most compelling stats to strengthen your case for remote work:

  • Seventy percent of global employees work remotely at least one day a week, more than 50 percent do so for half the week or more, and 11 percent more than five times per week, according to a 2018 study by International Workplace Group. Takeaway: Employers need to get ahead of this trend in order to attract and retain talent.
  • Call center employees at a Chinese travel website who worked from home completed 13.5 percent more calls, quit at half the rate, and reported significantly more job satisfaction than their in-office counterparts, according to a Stanford studyTakeaway: When set up right, remote work helps employers retain talent and can boost productivity at the same time – a win for everyone.
  • Remote workers communicate as well or better than onsite employees, according to a survey by the employee management platform company 15Five. Takeaway: Far from being a barrier to communication, remote work can actually create better lines of communication with more intentional systems and tools in place to regularly check in and make sure things are on track.

3. Create a clear and specific remote work plan

After you’ve done your research, create a short document that outlines exactly how your remote work arrangement could work. This should include your schedule on the days you will work remotely and a summary of how you will communicate and track your output.

“You want to think about communication barriers, how you’ll communicate with your team, and if there are already communication tools in place,” says Reynolds.

You may even want to suggest digital tools for remote communication and project management. (This could even spur your whole team to start more effectively communicating and managing projects).

Ultimately, your goal should be to address potential challenges of working from home from your boss’s perspective and make clear the burden is off your boss for any additional management the arrangement would require. It should also assure that you will work just as well—if not better—when you are remote. Make it as easy as possible for your boss to say yes.

“Make it clear you’re devoted to the work and that working off-site would be beneficial to all parties. Manage reasonable expectations and give measurable, clear results,” says Carrie Anne-Murphy, who negotiated a remote work arrangement when she was a buyer for a kitchen supply store in New York City. “And don’t seem too happy about it all, even though it rules,” she adds.

What to include in your remote work plan:

  • Summary statement that highlights the benefits to your employer. Include a statement summarizing your proposal to work remotely and why you are asking for the arrangement. For example: “I am proposing to work from my home office each Tuesday and Friday so that I can have interruption free time to work on my writing and editing responsibilities and be at home when my children come back from school. Below please find the details of my proposed schedule, which ensures I will meet or exceed all of my work responsibilities with this arrangement.”
  • Proposed remote work schedule. Detail your proposed remote work schedule. If you are proposing to start the day earlier, end the day later, or another change from your normal schedule, note how your remote work schedule will allow you to be available when needed. Note whether you’ll be in the office for regular meetings or, if not, how you plan to attend them remotely. (You can also offer to share your work schedule with your boss as a calendar, particularly in the beginning as you transition to remote work). If remote work is new territory for your organization, you could suggest a trial period, or a moderate schedule, like one or two days a week, to ease into it.
  • Your key roles and responsibilities and how you’ll accomplish them remotely. List out each and every job function you currently perform and how you’ll accomplish each of your responsibilities as well or better remotely.
  • How you will communicate with your team. Include the best number to reach you at in case of an emergency, the times of day you will check email, and how you will be present for meetings during which you’re working remotely. If your team doesn’t already have one, you’ll want to suggest a communication tool for remote-friendly workplaces that you’ll use to keep in touch.
  • How your manager and team will know your output. Describe how you and your manager can assess your performance while working from home. You’ll likely want to stick to whatever metrics your team currently uses, but you may need to communicate your accomplishments more regularly if you go remote. Depending on your team’s work style, this could mean sending a weekly email with an update on what you completed during the week, using project management software like Todoist to break down projects into tasks with deadlines, or noting accomplishments at a weekly check-in with your boss. (For ideas, check out Remote.co’s survey of remote companies on how they measure their employees’ output. The list also reinforces just how many companies make remote arrangements work.)
  • Your home office. Describe the location and arrangement of your home office, including the equipment you already have (laptop, wifi), as well as the privacy, quiet, and lack of interruption it ensures.
  • Equipment needs and security. List equipment needs, such as computer hardware or software. Show that you understand the security implications of working remotely by suggesting the use of VPN clients, encrypted chat, and if needed, data encryption software. You may want to talk to your organization’s IT department to find out what digital security resources are available. (Some companies will want to provide a work-issued laptop to ensure proper security measures are followed, but at least you’ve made clear up front that you take privacy and security concerns seriously).

You can download this excellent remote work proposal template from The Escape Series to use as a starting point.

4. Time your request carefully

It goes without saying that your request to work remotely will only be successful if your boss already trusts you and values your work. Even if that’s generally true, it can be helpful to time your request directly following the successful close of a big project you’ve lead or when your boss is particularly impressed with your work.

Lay the groundwork for weeks or even months ahead of time by proactively establishing a system of measuring and communicating your progress to your boss on a regular basis. When the time comes to make your request to work remotely, not only will your boss know your value as an employee, but you’ll also have a proven system in place for assessing your performance.

5. Ask in-person, not via email

Don’t spring your request on your manager in passing or even in an email. If you check-in regularly and have the time, bring it up then. If you don’t, request a meeting. To avoid immediate rejection, don’t say ahead of time that you want to discuss working remotely. Instead, say that you’d like to discuss your job functions and how you do your job, advises Reynolds.

The tone of the meeting should reflect the relationship you have with your boss. If the two of you are close, the conversation can be more casual than if you have a strictly professional relationship.

The email to your manager can look something like this, again, adapting for the tone you use with your boss:

Hi [Your Boss’s Name],

I wanted to see if we could schedule a meeting to discuss some ideas I have for improving my work environment and making it more conducive to accomplishing my job responsibilities.

In the next two weeks I’m free [insert specific dates and times]. Looking forward to talking with you in more detail.

Thanks,

[Your name]

6. Come prepared to lead the meeting

Armed with your research and prep work, make sure you’re ready to lead the conversation with your boss. Start by discussing at a high level your desire to work remotely, including the benefits for your organization and how typical it is where you work and in your industry.

Briefly highlight specific projects you’ve worked on recently in which you managed your time and tasks effectively and proactively. These specific examples give your boss proof that you’ll be able to handle the responsibility of working independently from home.

Then make your request, and make it specific.

“If it’s working from home one day a week or working from home five days a week, you want to make sure that, in an ideal situation, you know what you would ask for,” says Reynolds.

Even though you may not get exactly what you want, it helps to start from this position.

Don’t give your typed up proposal to your boss right away. Instead, use what negotiation expert Ramit Sethi calls “The Briefcase Technique”. Here’s how it works:

When, your boss brings up concerns (“How could I be sure you’ll be working?”, “Won’t we need a lot of equipment?”, etc.), say something like this:

“I’m glad you brought up the specifics. I’ve actually done a lot of research into how other companies have implemented successful remote work arrangements. [pull out your proposal here, actual briefcase optional]

“I wrote up a draft plan that addresses those concerns. It outlines [start walking them through your plan section-by-section] my proposed remote schedule, when and how I’ll be available, my home office setup, the security measures I’ll take to protect company data, how we can work together to track progress, my home office setup, and how often we’ll check in on so we can make sure the arrangement is working for everyone.”

The Briefcase Technique makes it harder for your boss to say no by showing you’ve already thought out and offered solutions for all potential challenges.

In addition to your remote work plan, have rehearsed responses to all the objections your boss is likely to have:

Responses to Common Objections

Objection: I don’t feel ready to make a policy for remote working.

Response: I understand your concern. I can do a trial period so you can see if this arrangement works before fully committing to it.

Objection: I can understand how some jobs can be done remotely, but I can’t see how your job could be.

Response: Many jobs and industries that seem like they would be most difficult to do remotely are actually some of the fastest growing areas for remote work, such as education (for example, online tutoring) and healthcare (such as online doctors’ visits). In my remote work plan, I’ve outlined each of my responsibilities and exactly how I’ll complete them remotely. I’m confident that I can perform everything my job requires at an equal or even higher level outside of the office. But of course, we should do a trial period to make sure it works for both of us. I’m always open to changing things as we both learn.

Objection: How will I know you’re working?

Response: I give some ideas in my remote work proposal of how I can keep you apprised of my progress from week to week and am sharing a proposed schedule so you’ll know when I’ll be available. I can also work with you to settle on preferred communications methods. I suggest we do weekly check-ins so we can discuss exactly what I’ve accomplished and any roadblocks I’m facing.

Objection: What if I need you and you’re not available?

Response: In my proposal, I’ve outlined the hours I’ll be working and the times of day I’ll check my email as well as recommendations for a digital communication tool we can use as a team to stay in touch. In urgent situations, I’ll always be available by phone during my work hours.

Objection: If I allow you to work remotely, I’ll have to allow everyone to work remotely.

Response: If this is something that proves to be beneficial for both me and the company, it could be something you can offer more widely as a perk to attract more talent and help employees be both happier and more productive. Of course, even for workplaces with some of the most established flexibility policies, managers have discretion to evaluate requests and decide on an individual basis if someone should work remotely.

7. Expect some discomfort, but don’t be dissuaded

Despite its increasing prevalence, many work environments are still skeptical of remote work. Expect that your boss may have reservations, and your coworkers may even be resentful.

“Sometimes the person you’re requesting that flexibility from wouldn’t know how to manage that flexibility themselves,” Orti points out.

Position yourself as a pioneer who could help the rest of your organization rather than an exception who should be envied.

But don’t be dissuaded by the discomfort. Negotiation is uncomfortable. Change is uncomfortable. But a flexible work arrangement is worth it.

8. Build immediate trust during your trial period

You made a great case for working remotely, and your manager has agreed that you can work from home for a trial period. Even though you’re now one step closer to freedom, it’s important that during your early days of remote work, you build trust with your boss. If you’re at a company that isn’t experienced with remote workers, you’ll be setting an example. Make those first months of working offsite a success with these tips:

  • Over-communicate: Especially in the beginning, you will want to make sure that you are communicative about everything. As Jhana marketing associate and remote worker Anya C. Gonzales says on Glassdoor: “I have to over-communicate: about my schedule, my plans, my development goals. I have to be an expert planner: For any given project, I have to think about what I’ll need from my manager and ask for it in advance.” For ideas on how and when to communicate with your boss, follow this guide on how to prove your value at work.
  • Be visible: One of the biggest challenges remote workers cite is feeling like they are forgotten. To compensate for this, on the days you are at work, make sure you have meetings and other face time with your manager and colleagues. If you’re proposing to work remotely full time, try to do video chats with your manager and coworkers rather than phone.
  • Don’t read too much into emails and other virtual messages: One of the hardest parts about working remotely is the greater ambiguity in virtual communication than face-to-face. It can be easy to misinterpret a slow response to an email or a terse instant message as more negative than is intended. If you do feel like issues are coming up or are unsure of where you stand, initiate a conversation with your boss or proactively seek feedback.
  • Be flexible: It’s likely that there will be some initial hiccups when you start working remotely and that some of the tools and methods you originally proposed won’t work. If it turns out the software you’re using to call into a meeting is having problems, be willing to change. If you’re finding it hard to be away from the office for a particular meeting, be open to moving around your remote work days if possible.
  • Be open to being a pioneer: If you work in an office that isn’t accustomed to remote employees, you’ll likely be a pioneer in certain areas, such as using new privacy tools or communication software. In this scenario, help your manager see your working remotely as a valuable resource for introducing new tools to the rest of your team.

9. If you’re turned down, be prepared to walk away

If, after all of the energy you have put into researching remote work arrangements and making a case to your manager, they still turn you down, it may be time to apply for a remote job.

“Chances are, if they can’t meet those needs, there’s something else that’s jarring in the organization. The culture might not be right for you,” says Orti.

After all, remote job opportunities are increasing by the day. There is no reason you shouldn’t find a company that is a better fit.

There are more and more resources available for finding flexible work, like Flexjobs’ job search board, the list of the 100 top companies with remote jobs in 2019 and Remote.co’s list of companies that are primarily remote. (The fully remote team at Doist is hiring.)


Let us know in the comments section about your experience negotiating remote work arrangements with your organization, and good luck!