How to Ask Your Boss to Allow You to Work Remotely

Working remotely has been in the news virtually every day since the start of the pandemic, but the idea of working from home has always held some appeal for many workers.

Advantages to telecommuting include eliminating a lengthy commute, allowing more flexibility to pick up or drop off children from school or child care, avoiding delays in getting to work due to weather-related concerns, and isolating yourself from contagious illnesses that can be spread in the workplace.

Certain types of jobs are more suited to remote work. Some jobs in information technology, customer service, finance, sales, marketing, and research lend themselves to remote work. Technology has enabled even some jobs that used to require face-to-face interaction—such as counseling, security, and legal jobs—to be telecommute positions, at least part of the time.

If you’ve been thinking about working remotely, there are a few things to consider:

– Do you have the temperament to work from home, at least part time? Can you take the initiative to start (and finish) projects independently? Do you have the self-discipline to give your work the same attention and focus as if you were in the office?

– Do you have the physical facilities at home to enable remote work? This includes a dedicated workspace and the technology tools to support working from home (e.g., high-speed internet and a separate phone line). 

– Does your company already allow remote work? Pitching the idea of telecommuting to a company that doesn’t currently offer remote work opportunities is more difficult than requesting the opportunity in a company that already supports telecommuting.

– Do you already have the opportunity to work from home occasionally? Expanding your telecommuting to a regular occurrence may be easier if you’ve demonstrated your capability for remote work already.

With the answers to these questions in mind, it’s time to put together your proposal to telecommute. This can be a simple one- to two-page document, but it should definitely be in writing.

Here are some of the things to include in your proposal:

The benefits for the employer. There have been considerable research studies over the past several years that outline the benefits of telecommuting on worker productivity and efficiency. In addition, employees who work from home can sometimes offer coverage for other time zones that wouldn’t be possible when working from a traditional office. If multiple employees are allowed to telecommute, requirements for office space can be reduced with the use of shared workspaces, saving the company money. Make sure you are emphasizing the benefits to the company, not to you personally.

How you meet the company’s existing remote work policy requirements. If your company already allows remote work, research the company’s existing policies and procedures. Which type of work is eligible for telecommuting? Do you qualify? What are the company’s guidelines for how often employees can work from home?

Your proposal for telecommuting. Which hours and/or which days are you proposing to work from home? Be specific. Laura Vanderkam in her book I Know How She Does It recommends not pitching to work remotely on Fridays, as it may be perceived as wanting to slack off at home. But instead, aim for your most productive day of the week and explain how you can be even more productive at home.

Describe how you can complete your job requirements remotely. Do you need any additional technology to work from home—for example, a computer, laptop, or tablet? How about a high-speed internet connection? Virtual private network (VPN)? Specific software? Are you asking the company to pay for—or reimburse you—for this additional expense?

Identify tasks that can’t be completed remotely—and offer a solution to address these issues. Are there things you need to do that can’t be accomplished unless you’re in the office? How will you handle these tasks? 

Assess other issues that may arise (and propose solutions). Will being out of the office affect your co-workers? Identify these circumstances and propose a solution. For example, if you mentor another employee, you could suggest ongoing Skype or Zoom calls to continue to provide this support, even when you’re not in the office.

Outline the security of data off-site. Do you work with sensitive client information? How will you secure this information? For example, you might outline your use of a shredder, passwords, antivirus software, and even physical safekeeping of data (locked drawers, safes, or rooms).

Provide your communication plan. How do you plan to stay in touch with your colleagues and boss? Technology such as Slack, Skype, and Zoom provide access, as do texts and conference calls.

Create a plan for reporting your time and results. One of the biggest concerns for managers is that things aren’t getting done while you are telecommuting. Reassure your boss by creating a plan to report your work regularly. For example, you could track your time and projects daily and submit a report of your accomplishments each Friday.

Start small. In your proposal, discuss telecommuting for a trial period. For example, you might propose working from home one to two days per week for a month or three months. Also mention having a plan to review the effectiveness of the arrangement initially (perhaps after the one-month or three-month trial period) and then periodically (for example, every six months).

Call to action. End your proposal with a request for an in-person meeting to review the proposal and discuss any issues.

These are the basic areas that should be covered in your proposal. 

Here’s a sample proposal:

(cover sheet/memo)

To: Jane Manager

From: John Employee

Re: Proposal to Telecommute

Dear Jane,

Attached you will find a proposal to consider my request to telecommute two days a week. I am proposing a 60-day trial period, with an evaluation at the end of the two months to evaluate whether I could continue telecommuting after that time. 

I would appreciate the opportunity to meet with you later this week to discuss this in further detail. Thank you.

(proposal document)

With winter weather approaching—and a 45-minute commute even when it’s sunny and dry out—I am interested in exploring the possibility of working from home two days per week. Remote work has grown in popularity within the financial services industry as a whole as a way to boost productivity and efficiency, especially when working on client research and longer-term projects, like our strategic planning initiative. Telecommuting also has proven to provide a positive impact on employee morale and employee retention.

I believe I can be more productive working from home two days a week. Research shows that remote workers are typically able to achieve 10-30 percent more work, due in large part to the reduced number of interruptions compared to a normal day in the office.

I would propose working from home on Tuesdays and Thursdays, although I am open to your input on the specific days. Mondays are obviously a heavy client contact day, in addition to having our weekly status meeting, so that would be a day that I would probably not suggest. In addition, if there is an important meeting or client event on one of the days designated for me to work remotely, I would be happy to adjust my schedule to accommodate that specific need.

I am open to starting my workday at 7 a.m. and working until 3 p.m. on my telecommute days. Without my usual commute, I would be available to start work earlier than normal, and finishing at 3 p.m. would allow me to pick up my children from school on those days.

With our current technology systems, I can access my files and client documents at home securely. I already have a dedicated home office with high-speed internet access and an ergonomic chair. I have a desk with a locking file drawer to ensure the security of hard-copy client data that I would bring home with me. In addition, I have a shredder for secure document disposal. 

By utilizing the company’s existing VPN and remote access software, I can ensure secure access of client data on my work computer as well as on the company’s network. I would also be open to using a company-issued laptop for my work at home, if that would be preferable. If a separate phone line is required, I can install a landline at the cost of $35/month (including taxes and fees) with my existing provider.

You may have concerns about my accessibility to you, my co-workers, and my clients, and my ability to work independently while at home. I will be available and accessible during our regular office hours. I will keep in contact with you, co-workers, and clients via either my cell phone or a dedicated phone line, in addition to staying in touch through email and text messages. My work voicemail message will refer callers to this alternate number.

The specific job responsibilities that are appropriate for remote work include client research, writing, strategic planning, working on monthly and year-end reports, and preparing for upcoming meetings (both internal and external). 

Each week, I will create a status report outlining what I expect to complete on my telecommuting days and how much time I anticipate devoting to each task. I will track my time during remote days and report what I have completed at the end of each week. I will save the tasks that are best completed without interruption for my telecommuting days.

I have identified a couple of potential issues and solutions:

– I currently see clients in person up to four days a week. In anticipation of working from home two days a week, I will communicate my future availability to clients on the three days a week that I will be in the office. In fact, with your approval, I will work to schedule in-person meetings on two specific days per week in order to maximize my productivity. I will continue to maintain open communication with clients through email, regular phone calls, and using Zoom to facilitate virtual calls. (I find more and more of my clients are receptive to Zoom calls as it allows them to minimize their travel time and we can collaborate on reviewing their financial documents virtually.)

– I currently provide backup coverage for Pamela. I can continue to provide some support services remotely, but for those that need to be completed in person, I suggest training Ben to handle these tasks. Not only would this increase his knowledge base, but it would also improve our team’s ability to provide seamless support.

I hope you will consider my request based on my past work performance and my contributions to the company over the last four years. 

Thank you for your consideration. I look forward to discussing this with you further.

The pandemic has reshaped how we work and if you’re not planning to return to the office, would prefer not to return, or are looking for a 100% remote role, consider how you want to present your request to your supervisor using the tips and templates above. 

You may not need to submit a formal proposal, especially since the pandemic has made working from home accessible to millions of professionals. Perhaps you only need to schedule a time to chat with your boss. Either way, I strongly encourage you to at least discuss the benefits to the employer and the benefits on your productivity as a result of working remotely.

More people than ever are working from home with their kids around—and if you’re new to this balancing act, I’d like to share some strategies that have worked for me over the years: 10 Ideas to Manage Working From Home With Your Kids Around.

If you’re at that place where you’re feeling like something’s gotta give or there has to be a better way to get everything done that needs doing, I want to offer you four strategies I’ve found that have maximized my time and helped me balance work, kids, homeschooling, and life. 

I would love to connect and continue the conversation on Linkedin. You can send me an invite here.