How to Convince Your Boss to Let You Work from Home

How to Convince Your Boss to Let You Work from Home
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by Chris Durst       Dec. 5, 2023

If you’re already employed doing something you love – but you’d also love to eliminate or reduce your commute – then this post is for you.

But first, we’ll take a moment to make an important point: Until the law deems otherwise, remote work is a management option rather than an employee right or “benefit,” and is justified by the advantages it offers the company – not the employee.

In other words, until environmental or other imperatives create a right to work remotely, companies – who by and large are much more closely related to sharks and crocodiles than to personal assistants, spa attendants or fairy godmothers – will evaluate  remote work proposals not as service requests, but as they would any other business proposition. In other words, What’s in it for me?

Accordingly, if you plan to broach the topic of  remote work with your boss, keep his or her company perspective in mind at all times: What’s in it for me? Doing so can mean the difference between hearing, “We don’t do that here” and “OK, let’s give it a try, and see how you do.”

And to get to that “yes” point, you’ll want to present a well-considered case for why having you work from home is the right decision for the company.


Over the years, many people have told us that they’ve asked bosses and supervisors if they could work from home, only to be rejected outright. When we ask how they approached the topic, far too often the reply is, “I just told him that I need to be at home with my kids.”

As compassionate people and parents ourselves, we can sympathize with the employee’s – and children’s – needs. (After all, one of the prime reasons we launched our home-based jobs website, RatRaceRebellion.com, was to help parents and children spend more time together.) But as business owners, too, we can also see why the bosses said no.

In most cases, the manager is probably sympathetic to the employee’s plight, but the harsh truth is that child-care issues (or an aging parent, an outrageous commute, unreliable transportation, etc.) are not his or her problem, and solving it is not perceived as a source of profit to the company. The manager – and his or her boss all the way up to the board room – has a list of goals for a given reporting period, and “helping Employee X spend more time with her children” usually isn’t on it.

Indeed, though it may sound cold, if a company starts making decisions based on “feelings” instead of earnings, profits may suffer, and jobs may be put at risk – including yours.

So let’s explore how you can wow the boss with a company-oriented plan, instead of a self-oriented request.


Here, we’ll walk you through a step-by-step process for creating a winning proposal. Those steps will include:

  1. Drafting an attention-grabbing opening statement
  2. Outlining the benefits to the company
  3. Breaking down your daily tasks and commitments
  4. Proposing a schedule and highlighting your flexibility
  5. Suggesting methods for quantifying your productivity
  6. Reminding your boss what a valuable asset you are to the company
  7. Describing your home-based workspace and equipment

1. Drafting an attention-grabbing opening statement

Length: 1-3 paragraphs

Open your proposal with a short statement that will make your boss want to read more. (Though this section will appear first, you’ll want to write it last, so you can weave in supporting statistics and other data you find in your research.)

For example:

Dear Boss,

Now more than ever, corporations large and small are embracing  remote work, and letting employees periodically work from home. Many factors are driving the movement, including increased employee productivity and decreased turnover, business-continuity concerns, rising real estate and fuel costs, and the company’s environmental image.

Companies like American Express, Amazon, U-Haul, Hilton, Neiman-Marcus and many others, are permitting employees – including managers — to work from anywhere as long as they achieve their targets.

I have assessed my duties here at Widget, Inc., and, as this  remote work proposal will show, I believe I can be an even greater asset to the company if I am permitted to work periodically at home. Indeed, a “time and task” audit that I recently completed of my in-office work revealed that eliminating “drop-in” interruptions alone could result in 15% more productivity on days when I am working at home.

I will look forward to discussing this proposal with you, and exploring how a trial remote work period might demonstrate substantial benefits for our team and a positive impact on the company’s bottom line. 


Ms. Work F. Home

2. Outlining the benefits to the company

Length: 2 pages

 We usually refer to this as the “What’s in it for them” section of the proposal (“them” being your employer, of course). Here, you’ll show in detail how you’ve considered a remote work arrangement from the employer’s viewpoint, and you’ll lay out the compelling reasons why it would directly benefit the company.

This is often the “make or break” part of a proposal. Be prepared to roll up your sleeves and spend plenty of time searching for facts and statistics that will “hit home,” so to speak, with your boss.

Using the thought-starters below, and thinking specifically about what motivates your company and its managers, outline what you assume the benefits of a remote work arrangement will be to the business. We’ve listed several “action words” and benefits as thought starters.

Note: For more ideas, consider the buzz words and phrases that recur in company meetings and memos, and conversations with your boss. These can be good indicators of what’s on management’s mind.


Now, with your list as a reference point, you can begin the research that will back up your assumptions with hard facts! Ideally, you’ll want to gather meaningful statistics from respected studies and industry reports.

With these goals in mind, start your research with your favorite search engine. Use search terms that include the form of the information you’re seeking (i.e., statistics, findings, research, studies, etc.) “+” the assumption you are hoping to support (i.e., “ remote work saves time”).

For example, using the action words “save” and “increase” that we listed above, your search phrases might include:

  • statistics + remote work saves time
  • studies + remote work saves time
  • findings + remote work saves time
  • research + remote work saves time
  • statistics + remote work saves money
  • studies + remote work saves money
  • findings + remote work saves money
  • research+ remote work saves money
  • statistics + remote work increases income
  • studies + remote work increases income
  • findings + remote work increases income
  • research+ remote work increases income
  • statistics + remote work increases customer satisfaction
  • studies + remote work increases customer satisfaction
  • findings + remote work increases customer satisfaction
  • research + remote work increases customer satisfaction

Hint: To find additional data, try these searches using “telecommute” or “telecommuting” or “telework” in the place of “ remote work.”

In reviewing your search results, give the greatest weight to information found on sites with a solid reputation in the  remote work arena, or that your boss will otherwise consider reliable.

To strengthen your case for working from home, do some research to see whether your company’s competitors – or firms it simply respects or would like to emulate – have  remote work programs, and cite their successes.

Now, compile your most compelling findings in an easy-to-skim format (most managers don’t have the time to read a heavy narrative-style document). A bullet-point list usually works best, but if you have a knack for organizing data in another format (and you’ll know your boss’s preferences, too), by all means do so.

3. Breaking down your daily tasks and commitments

Length: 2-3 pages, depending on your job description

This section of your proposal is the “reality check” – an assessment of whether your job can actually be done from home.

To show your boss you’ve given this proposal due thought, you’ll need to analyze every aspect of your job – the tasks you manage, who you interact with, what resources you use, how you deliver your work, etc. – and explain which duties you can do from home, and how.

If your company uses written job descriptions, these may be a good starting place. However, as most employees will attest, it’s a rare description that captures a job’s every facet. Therefore, we suggest conducting a “time and task audit,” in which you record during a one-week period (or 2-3 days, if your job is repetitive) everything you really do. While this can be tedious and takes time, the data can reinforce your proposal substantially.

To get started on the audit, create an audit worksheet with the following column headers: time, activity, home, office, and “AI” (avoidable interruptions). Separate your typical work day into ten-minute increments. (The example below shows the first few hours of a work day that begins at 8:00A.M.) This can be done by hand, but your word processor or spreadsheet application will create a clean form that can be printed out or completed on your computer.

Now you’re ready to conduct your audit. Throughout the course of your work day:

1. In the “activity” column, briefly note the task you were involved in during the time specified on the left.

2. If the activity could be done as well or better from home, place an “X” in the “home” column. If better done in the office, place an “X” in the “office” column.

3. Each time your activities are interrupted for non-productive reasons, place an “X” in the “AI” column.

At the end of your audit period, you’ll have a snapshot of your typical work week, and an accurate idea of how much of your work you can do from home.

You’ll also have another important detail – the amount of time you are unproductive each day due to interruptions that could have been avoided if you had been at home – your AIs. (Needless to add, this assumes you’ll take every reasonable measure to fend off the AIs that can beset you in a home office!)

Armed with your audit, you can present your boss with a comprehensive overview of your duties, the percentage of work you can perform from home, and the productive time you’ll gain by relocating yourself to a setting more conducive to uninterrupted work.

4. Proposing a schedule and highlighting your flexibility

Length: 2-3 paragraphs

The key to an acceptable remote work schedule (“acceptable” as defined primarily by management, of course) is to transition into the arrangement conservatively, at a pace your boss can be comfortable with. (If you perform well, the schedule you yourself would prefer will hopefully follow.) While aggressive schedules are easy for management to refuse, a well-planned “trial period” might seem not only eminently reasonable, but even an exciting experiment – one that could spearhead a larger remote work program within the company.

A preliminary schedule of just one or two days per week can often work well, weighted toward the days that would work best for your boss and colleagues. In this early phase, you might want to avoid requesting remote work days on Mondays or Fridays, as co-workers may decide that you’ve finagled a “long weekend” setup, while they’re stuck back at the office. And among other side-effects, their sour grapes won’t help your cause when it comes time to petition the company to make the trial arrangement permanent.

Regardless of the schedule you propose, be sure your boss knows you’re willing to be flexible. Some managers, regardless of how well-weighed the plan, will want to tweak it a bit to “make it their own.” Now is the time to give a little, and show you’re a team player.

Remember, even if the boss concedes to only one remote work day per week, this still gives you the opening to demonstrate the superb value of that day to the company, and the multiple value of more.

5. Suggesting methods for quantifying your productivity

Length: 1 page

It’s important to remember that most managers have never supervised a remote workforce, and you may be asking yours to take a step outside his or her managerial comfort zone. Regardless, managers often note (or by stonewalling even minimal remote work initiatives, betray) their concern that employees will be unproductive if unwatched. In this section of your proposal, you can ease any such concerns by suggesting ways in which your productivity can be measured.

As an example, you might:

  • Provide your boss with a list of measurable goals, against which he or she can gauge your performance.
  • Suggest applications like Zoom, Microsoft Teams, and Slack, to enable you to work on your office computer from your home computer. This will permit your boss to monitor your activities simply by looking at your in-office computer screen.
  • Agree to email a report at the end of each day, summarizing activities and outcomes.
  • Make yourself available by instant messenger during business hours.
  • Commit to check messages and return phone calls within a certain time.
  • Set a schedule for phone check-ins.
  • Make it known that you can be at the main office within a certain time if urgent situations arise.
  • Set up a pager or other backup communication methods your boss can rely on in the event normal systems fail.

As you, your boss and colleagues adapt to your home-based work arrangement, you may find that your boss doesn’t require the reassuring touches he preferred in the beginning. But regardless, the more pains you take to make the trial period “transparent,” the more likely you’ll be moving toward a permanent and liberal remote work schedule.

6. Reminding your boss what a valuable asset you are to the company

Length: 1 page

Making a case for “you” as a viable work-at-home candidate is an important step in sealing your remote work deal. (Indeed, it helps to approach the entire campaign as if you were applying for a job.) After all, it would be a pity to persuade the boss to embrace the idea of remote work – but not for you! Use this section of your proposal to “strut your stuff,” and remind your boss of all the wonderful attributes and accomplishments that make you the ideal candidate for off-site work.

If written performance evaluations pertinently sing your praises, be sure to quote them often in your proposal. The goal is to get your boss to focus on the traits that ideal teleworkers also share. For example, you want your boss to know that you are:

  • A self-starter
  • An excellent organizer of time, tasks, and priorities
  • An independent problem-solver
  • A solid team player
  • Self-disciplined
  • Self-directed
  • Technically savvy and able to manage basic troubleshooting
  • An excellent communicator

Naturally, your list will need supporting evidence, with clear examples of accomplishments and contributions that demonstrate your Ideal Teleworker qualities.

7. Describing your home-based workspace and equipment

Length: 1 page

It may sound mundane, but it’s important to “paint a picture” of your work environment for your boss. This will not only help him or her visualize you working there, but also show that the space is professional-grade and free of distractions. Ideally, your proposal will include photographs of your home-based work space, but you can make do with a diagram and a written description.

To help make the sale, you might also consider inviting your boss to your home office before the remote work arrangement begins, and smooth the way thereafter with scheduled visits when you are working from home. (Again, as his or her comfort level increases, your boss may find this reassurance unnecessary.)

In your office description, be sure to include details that show you’ve given due consideration to security and safety issues. For example:

  • The home office is free from excessive noise.
  • The wiring will accommodate a computer and other office equipment, and surge protectors are in place.
  • The desk and chair are ergonomically correct, and there is excellent lighting in the work area.
  • The computer is connected to a battery backup/surge protector to ensure no data loss in case of a power loss or surge.
  • The office is well ventilated and has an exit in case of emergency.
  • The office is equipped with smoke detectors and a fire extinguisher.
  • The office is in a secure area where no one, including family members, will have access to work equipment or data.

Be sure to address any unique or extraordinary concerns your company might have about the confidentiality of information and system security. Similarly, if remote work will require the company to provide equipment for your home office, address those issues here.

Other points to consider include:

  • Will you need a fax machine, an additional phone line, or external hard drive?
  • How will you handle backing up your system?
  • Will the company provide insurance to cover any loss of equipment or data from the home office?

Finally, diffuse any concerns there might be about your personal life encroaching on your work at home. For example, tell your boss up front what childcare or eldercare arrangements you’ve made for your remote work days. Note that your loyal Mastiff or beloved Macau will be kept beyond sound’s reach, and won’t disturb you or be heard by colleagues and clients on the phone.

Anticipating questions like these in your proposal and solving them wherever possible will reassure your boss and improve your chances of a green light.

Be Prepared to Talk About Your Proposal

Don’t sit back and let your proposal do the talking – you should be as prepared to “state your case” live as you have in writing. Take the time to anticipate any oral questions your boss might have, and be ready to address them.

You probably know your boss well, and have a sense of what he or she will want to cover in person. Perhaps as you write your proposal, you’ll hear his or her voice in your head – questioning facts or assertions, or wondering how certain aspects of the arrangement will work. Your ability to answer questions with confidence and clarity will strengthen the likelihood of the “yes” you’re hoping for.

Even so, the fates may intervene. If the thumb turns down, remember the points your boss had a hard time getting past, and take steps to help him or her overcome those obstacles. For example, if you have an opportunity to work at home to finish up a project after hours or over a weekend, take it. In business, nothing speaks as loudly as results, and you may soon give your boss reason to reflect on the error of his ways.

For real work from home jobs and gigs, check our Newest Jobs & Gigs page. To be the first to hear about jobs like these, like our Facebook page. Good luck as you make your work from home plans a reality!

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