How to Ask Your Boss to Work Remotely | The Desired Desk

How to Ask Your Boss to Work Remotely

Everyone else is doing it. So, why not you? You want in on the action and freedom of working from home, but you’re not quite sure how to ask your boss to work remotely. According to a Gartner survey, 80% of company leaders will permit employees to work remotely even after the pandemic.

You’re tired of the commute, getting stuck in traffic, packing your lunch, losing an hour of sleep and of course wearing pants. Today we’re going to teach you how to ask your boss to work remotely.

Can Your Job Be Done Remotely?

How to Ask Your Boss to Work Remotely

Before you even begin thinking about asking your boss to work remotely, ask yourself “can my job be done remotely?”. If the answer isn’t a resounding “Yes!”, it isn’t the end of the world. Here are 15 example job types that can generally be done from home:

  • Admin
  • Customer Service
  • Recruiter
  • Accountant
  • Web Designer/Developer
  • Writer
  • Editor
  • Engineer
  • Accountant
  • Teacher
  • Project Manager
  • Consultant
  • Sales Representative
  • Account Manager
  • Data Analyst

If your job isn’t listed above, no big deal.

Let’s take a look at what these positions all have in common. They can all be done with the use of a computer and telephone, and that’s it! If your job only requires the use of those two items then you can surely work your job from home.

Related: Top 4 Work From Home Jobs With Benefits

Unfortunately, if you do something that involves direct interaction with others and physical service it is going to be very hard (if not impossible) to work remotely. Think truck driver, police officer, grocery clerk, barber, janitor, etc.

How’s Your Performance?

How to Ask Your Boss to Work Remotely

When your boss gives you the opportunity to work remotely they effectively are saying that they trust you immensely. Working from home is a lot different than working in the office. There isn’t someone there to look over your shoulder to make sure you are doing the right thing or actually that you are actually working. Your boss is trusting that you are going to do the right thing for the company.

COVID forced a lot of business owners and managers to deploy their staff remotely. However, if you’ve made it this far into the pandemic and you still aren’t working remote, I’m going to assume COVID isn’t the most pressing reason for you wanting to work remotely.

Before asking your boss to work remotely, make sure you are a top performer, someone that your boss has great things to say about and you are a contributing member to the team and organization as a whole. This will make the question a lot easier to ask and it will cause your boss to not have as much resistance to the idea.

If your performance is slacking at this moment and time, maybe take the next few months to ensure that you really take your work seriously. Meet your deadlines, hit your quotas, please your customers. This is a very important step. It can make or break your dream of working from home.

Your Employer Saves Money

How to Ask Your Boss to Work Remotely

Did you know that when you work from home, you’re actually saving your employer money?

Many people don’t realize this, but there are tons of expenses that get slashed when employees begin to work from home. It can cost up to $14,800 per year per employee just for office space in some large corporations!

Your employer will not only be saving on office rental space, they will also be saving on utilities, insurance, vendor fees, etc.

Also, when you work from home, your employee satisfaction level will most likely rise which will translate into you staying with the company longer. If you’re good at your job, your employer doesn’t want to see you go. They want you to stay with the company as long as possible. Hiring and firing can be very expensive.

Related: What Expenses Should My Employer Pay If I Work From Home?

Things to Consider

How to Ask Your Boss to Work Remotely

If you’ve never worked from home before, there are some things that I want you to consider before you pop “the question” to your boss. Working from home is great, don’t get me wrong. There are a few things, however, that can be difficult.


Working from home can be very lonely. You might not realize at this moment how important the physical interaction you’re getting at work is. Make sure to supplement this human interaction in other ways after your work day. Join a gym, go to meetups, go to social clubs, hang out with friends, see your family (within reason and always abide by your local restrictions).


When your desk is just feet away from your bed it can sometimes be hard to get motivated. What you wear at home, your diet and your default personality will all have an affect on your ability to get motivated at home. When you work from home you need to be able to extract your internal motivation and complete the task at hand. This can be a challenge.


I know work at an office can also be boring, but when you work in an office you have a commute that exposes you to various interesting and exciting things around the world. You don’t realize how this stimulates your mind, but it does. When your commute is a walk to the other bedroom or next to the bed, you’re not getting exposed to as many things as you once were. This can leave you feeling bored.

Similar to the solution for loneliness, you want to make sure you are proactively taking steps to combat the boredom. Get some nice pictures for your desk. Buy some plants. Listen to music while you’re working (if you can). Call your friends on your lunch break and after hours. There are many things you can do to help combat your boredom.

Related: How to Have a Social life While Working From Home

Asking the Question

It’s time for the big question. How are you going to do it? It’s pretty simple, really. You just ask. There are, however, a few things you want to include when asking your boss to work remotely.

First, express your interest. Simply let your boss know that you’re interested in doing your job from home. This might be enough for you to get a yes. Your boss might not have a single rebuttal. This is great news! Your job is done. Welcome aboard remote employee.

If your boss doesn’t seem to be fond of the idea, see if you can find out the reason for their hesitance. It’s probably because they don’t believe your work is going to get done at the same levels it is currently. If so, simply ask your boss if you can work remotely for a probationary period. This way if your performance doesn’t meet their standards, you can continue to work in the office. No harm no foul.

If your boss isn’t open to this idea, there are just going to be some nuts you can’t seem to crack. That’s ok. If working remotely is something that you are desperately searching for there are plenty of remote work opportunities available (especially in today’s day). Whatever you do, don’t get discouraged. You’ll find the right job eventually, or maybe it’ll even find you.

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