How to Convince Your Boss to Let You Work Remote (and Why It Is One Of The Best Things You Can Do!)

By Sarah Archer

Posted 1 week agoGROWTH

When the internet went out you might have thought it was the apocalypse. People just stared at their useless computers, refreshing over and over, waiting like zombies, to get back online. My colleagues and I invented some office games, seeing how many trivia questions we could answer, and making baskets with crumpled up reports in the far away trash cans.
How to Convince Your Boss to Let You Work Remote (and Why It Is One Of The Best Things You Can Do!)


Some of us left and got coffee, so it wasn’t all bad. Mostly we just whispered about things we’d watched during the current golden age of television. And waited. Just when we started cleaning old papers out of deep parts of our office drawers, someone had the brilliant idea: Let’s all just go home, where we can get work done.  

There’s nothing like an outage to leave you to discover that you actually cannot do a thing at work without an internet connection. And if, like at my work, you have everything living on Google Drive and Dropbox, being cut off sinks nearly every possible interaction. You can’t even Slack message your friends in the office! 

If you probe this idea deeper you’ll realize just how much you do that requires only strong wifi to accomplish. How many times do you go through a whole workday thinking, “I saw almost no one today and literally accomplished my every action over the internet?” For some of us, that day stretches into weeks. 

Well, many companies and employees are recognizing this same phenomenon. They’ve noticed that there isn’t much point in keeping people in cubicles they pay for on computers they pay for while simultaneously realizing that more flexibility and freedom from traditional office space is a good look on everyone. 


It’s so hard to understand why so many people focus on negotiating their salaries, without thinking that time is something the private time is the most valuable they can fight for.

Today, work from home employment is for more than just for freelancers, permanent telecommuting is getting to be a huge part of our workforce. More than 4.7 million Americans are working from home and that number is growing for good reason.

Employees and companies are looking at ways that remote work saves money and creates healthier work relationships. Not speaking that it leaves you more time to take care and enjoy your personal life and relationship with others.

So, what about you? When is it your turn to reap the benefits of remote work? If you want to convince your boss that it’s a good idea for you to be part of the new trend of telecommuting, what can you do? Marching into your boss’s office and demanding to be sent home probably won’t have the effect you are looking for. 

Instead, here are some ways to convince even the most concervative boss that this new-fangled remote work trend is the way of the future.

How to approach asking your boss about going remote

Don’t ask via email

Even though you are about to ask about the possibility of performing your daily work remotely, for this meeting, you want to be face-to-face. Consider this the same way you might talk about a promotion. You want to come in well-prepared and with good justification. 

Do your research


There are sites and resources that will help you learn exactly what you need to know when you are getting ready to work remotely. Places like Remote How and Remote Work Association give you access to a network of remote workers as well as consultants who can give you further advice.

Create a proposal

A formal request that has outlined the logistics of this move will do a great deal toward getting what you want out of the meeting. Make sure you include all of your obligations and how you feel they can be done as effectively, or more effectively, remotely. 

Consider the company first, not your own needs (if you need to get your kids off to school, for example — don’t talk about that out of the gate). Treat this like you would a big client meeting and make a deck (if you have the skills for it) that really outlines all the benefits to your company. 

How to structure your pitch 

“Remote work is changing the landscape and you are about to make a lot more money because of it.”

Starting off, it’s a good idea to talk more generally about the benefits that companies have seen because of remote work. Most bosses respect the bottom line more than anything else so you can begin with work from home statistics that show how companies have been saving money on a number of aspects of their business because of remote work. 

For example,  A CNN study measured that companies save around 11K annually from each employee that they let work from home just half of the time! And, American Express reports they set to save $15m in real estate costs alone because of telecommuters. 

While not needing to open new offices is likely the largest financial perk, other related savings are in related things like utilities, housekeeping, and K-cups for the Keurig. Aetna Insurance has let slip that they have saved over $70m per year due to the fact that their workforce is made up of around 50% work from home employees of any kind: programmers, customer service assistants, essay writers and so on. 

“My productivity? Well, let’s look at how much more productive I could be without a two hour commute”  

The question of productivity might be the one looming most prominently on your boss’s brow. If that’s the issue, you can point to statistics that show that most companies agree: When they have let their employees work remotely, productivity has gone up

Think of all the time you spend in the office in meaningless meetings that should have been emails or toasting someone’s birthday. With those distractions gone, you’ll really be able to work harder and with improved focus.

“And all the room you’ll have for training” 

Growing companies love being able to make legacy employees work remotely, so they have the space to train new employees without making things too congested in the office. Convince your boss that now is the time for you to give traditional office space to someone new.

“And, you might be able to keep me around forever?” 

While you don’t want to make any kind of ultimatum, it’s true that with the rise of working from home, many employees are looking around and eyeing jobs that give them the flexibility they need. Close to three-quarters of people surveyed said they would consider a new job if it had more flexible hours and was off-site work. 

At the same time, around 75% of female tech employees said that working from home was a good way to retain top talent. In general, telecommuting has been a good retention tool as statistics indicated that retention rates for those companies that offer this kind of work have gone up by around 10%.

The shift means older employees are able to stay on for longer and even workers who may have to change their location for some reason (to take care of a loved one or because a spouse takes on a new job) will be able to stay with the company. 

“You don’t hate the environment… do you?” 

With most companies looking for ways to achieve a greener status, working from home does way more good than a grass patch on the roof of your office building. Commuters are one of the worst pollutants and causes of greenhouse gasses in the world.

Already, those that telecommute are said to save the earth from over 3.5 million tons of greenhouse gas emissions in the US alone.  In addition, just the ability to save space (using just one space for both home and work and not two) has a profound environmental impact. 

How to set expectations, on both sides 

In addition to all the reasons they should be excited to have you work from home, you’ll want to prepare to specifically lay out expectations. Give them an understanding of where you plan to work from and how your hours might change or not. 

The best proposal would likely be for you not to change your work hours at all. And, perhaps you want to start with a part-time remote strategy before proposing full-time off-site. This kind of transition is likely good for both sides, as you’ll want to get used to working from home before you jump in with both feet. 

You will also want to be prepared for a flurry of questions about your proposed situation: 

  • How would your remote work change your management of people or projects? 
  • How would you communicate with your head office and what is your wifi or office needs? 
  • What if you needed to be at a face-to-face meeting or needed to hold a meeting with a client? 

Other questions might involve legal issues:

  • If you are working from over the border of another state, are their tax implications? 
  • What if you are injured on the job, but in your remote location?
  • What are the worker’s compensation rules for this? 

Because of these thorny topics, you might want to consult your legal team before going into the meeting at all. 

Ultimately, in nearly every industry, the pros far outweigh the cons for allowing employees to work on a remote basis. The difficult part is convincing your bosses that the winds of change have shifted in this direction.

Make sure you treat this ask very professionally, practice your pitch with a presentation that will give them good reason to believe in this idea, and be prepared to answer questions. If you have all that down, it’s very likely that there will be a much shorter commute to work in your future. 

About the author Sarah Archer

Sarah is a Content Marketing Manager at Siege Media and Your Best Digs who works remotely while traveling. She’s passionate about developing high-quality content for diverse industries ranging from startups to Fortune 500 companies. When she’s not creating content, she’s likely hiking a new trail or mapping out the next destination.