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How to Ask to Work Remotely: 8 Steps to Convince Your Boss

by | Last updated Sep 23, 2023

You like your current job. But you also want to ditch the office. So the big question is: How can you convince your boss to let you work from home? How to ask to work remotely?

Many employers dread to make the change to remote work. That means you have to be very strategic if you want to ask to do your job online. Check out the following steps to learn what you need to do to be successful with your request.

Requirements to Work Remotely

If you are considering keeping your current job and doing it remotely, you first need to fulfill the following two requirements:

1. Your job, or at least most of your tasks, can be done remotely. Maybe there are a few minor tasks that require you to come to the office every once in a while – this could be okay in the beginning. Maybe there is a way you can hand those tasks over to colleagues or exchange tasks. But the majority of your daily jobs need to qualify for online work.

2. Your employer needs to trust you and you should be a decent performer. If your boss is not happy with your performance right now while being in the office, chances are very small he or she is going to let you work from out of the office. So make sure your performance is “worthy” before you consider asking to go remote.

How to Ask to Work Remotely: Step-By-Step Guide

Do you tick both of these requirements? Awesome! Now it’s time to work on the following steps:

Step 1: Do Your Research

Before you plan a meeting with your boss, you need to do your homework. Depending on the size of your company, you should first go to the HR department and check if there are any remote work policies in place.

  • Are there any rules or regulations?
  • Have people been working remotely in your company in the past? How did that go?
  • Does your contract say anything about remote work?

Get as many facts as you can. If there are any guidelines, make sure you can stick to them when working remotely.

If you find out that it is not allowed, ask for the reasons and see if you can find arguments against it. If your contract says you are not allowed to work from home, don’t be discouraged. Give them arguments on why it could still work. There is nothing to lose.

Woman at laptop in office

If you want to ask to work remotely, you need to be prepared and show your boss your potential working plan.

Step 2: Create a Working Plan

Many employers are still new to the concept of remote work and can’t imagine what a remote workday might look like. Help them out!

Make a list that shows the key facts:

  • List your working hours or availabilities when working remotely.
  • List your breaks, e.g. lunch break.
  • List all your meetings and how you are going to participate (call, Skype, video calls, etc.).
  • If you are going to be in the office for in-person meetings, when will it be?
  • How will you be able to stay in contact with coworkers (messenger, daily 10-minute morning call, etc.)?

Also, come up with suggestions on how you can prove your working outcome or performance. You can use certain software that tracks your working hours and performance, e.g. Time Doctor, Toggl, or Hours.

Alternatively, you make a list with deliverables that you can tick off after completing and show it to your boss.


Step 3: Prepare Necessary Technology

You should be able to prove that you can easily organize or already have all the equipment that is needed for remote work.

Companies that are used to employ remote staff usually have a certain allowance for necessary technology. For instance, they pay for your laptop or internet plan.

However, if remote work is new to your current employer, you might not be in a position to demand too much. So for now, try to solve these issues on your own.

Show that you have a laptop or computer, headphones, a camera (if not integrated into your screen), and a reliable internet plan. It’s also great if you can prove that you have a home office (and if it’s only a corner in the living room) that is fully equipped and where you can work without distractions.

The same goes for software. Check what you need to get your work done, e.g. Photoshop, or SAP, and how you can get a license for it.

It’s also great to show that you have a reliable VPN. This secures your internet connection and makes sure you and your company’s data is safe. I highly recommend NordVPN, since it is easy to use, reasonably priced, and very secure.

Also, clarify with your IT department how you can access the company’s database, website, or whatever you need for your job. There’s usually always a way to give you access to all systems from outside the office.

Home Office Setup

Your home office doesn’t have to be huge. A desk with decent light, a big screen or laptop (with a laptop stand), and a comfortable office chair will do.

Step 4: Find the Right Timing

Don’t just walk over to your boss during the lunch break. This is an important matter so treat it like that. If you have an upcoming annual performance review, this could be a great time to address your request.

If not, ask for a one-on-one meeting with your boss to talk about it in detail.

Don’t send an email asking to work remotely. This will very likely cause a rejection. This request is way too comprehensive to cover it via email!

Also, make sure you are not bringing this up during the busiest time of the year, in case there are any seasonal fluctuations. It’s better to wait a few weeks until things slow down again and your employer is more open to new suggestions.


Step 5: List the Benefits for Your Company

This will be your most important argument. You need to show how your company will benefit from remote work. After all, they want to know what’s in there for them.

Luckily, there are plenty of arguments. Here are the main advantages of remote work for companies that you should present to your boss:

1. Increased Productivity

When employees work from home, they face fewer distractions in comparison to working in an office. They also have to deal with fewer office politics and a quieter noise level.

That doesn’t only result in more efficient meetings but also increased productivity, as a study found out:

  • Astonishingly 90% of all questioned managers report that their employees are more productive when they can choose where and when to work.
  • 45% of remote workers support this statement by saying that they work smarter from home and get more done in less time.


2. Decreased Costs

The more remote employees in a company, the cheaper it gets:

  • Companies don’t need to spend as much money on office space anymore when people are working remotely.
  • They also save a lot of other costs like heating, cooling, lighting, and similar overhead costs.
  • If a company provides free tea, coffee, or water in the office, they also get to save these expenses.
  • Additionally, they can save on office furniture and technical devices, as well as the maintenance of these.


3. Decreased Sick Days

Remote work also decreases employee sick days and time off. Especially during the cold and flu seasons, offices are a true paradise for germs. People spread them from one to another and it seems like it’s everyone’s turn to become sick sooner or later.

According to Global Workplace research, these unscheduled absence days cost U.S. companies more than USD 300 billion every year. That is USD 1,800 for each employee!

When working remotely, people are less likely to get infected. It’s no surprise that companies, that offer remote work options, report 63% less absence due to sick days.

This is also one of the main reasons why so many companies decided to let their employees work remotely in early/mid-2020. The risk of spreading the virus further is decreased tremendously when people avoid public transport and big offices.


4. Improved Working Morale

Remote work is known to improve happiness and working morale. That’s not very surprising. After all, remote employees get to skip the often stressful commute and busy office environment. Instead, they can spend more time with their family and enjoy a greater work/life balance.

That results in increased personal well-being. A study found that 73% of U.S. remote workers report higher job satisfaction. And a happy employee is more motivated and has higher working morale.


5. Reduced Turnover

All these positive effects of remote work result in another benefit for employers: Reduced turnover.

According to the before-mentioned Global Workplace study, 95% of employers confirm that remote work has a highly positive impact on employee retention.

That means that employees, who are given the chance to work remotely, are far more likely to stay with the company in the long run. This, in turn, reduces costs and time for recruitment and training.


6. Enhanced Talent Recruitment

As studies show, it has grown over 91% in the last 10 years and over 159% in the last 12 years. The State of Remote Work report shows that 99% of all questioned employees want to work from home at least some of the time.

The trend is very clear. That’s why employers need to start offering remote work options sooner or later or else they lose their employees.

At the same time, remote work allows them to access a wider pool of talent. They can attract skilled workers even if they live at the other end of the world.

Hiring employees is no longer limited to a geographical area. Now companies can focus more on talent and skills, rather than who is available in their location.


7. Positive Environmental Impact

This might not be an immediate advantage for your company but it is still important and maybe your boss is happy to hear that remote work results in plenty of benefits for the environment.

When employees work remotely, they use less paper and can control heating, air conditioning, and lighting, which results in more optimized usage.

Apart from that, 3 million greenhouse gases are avoided by those who currently work from home at least part-time because there are 7.8 billion fewer vehicle miles traveled, according to the State of Telecommuting in the U.S. Employee Workforce.

Open-plan office

When allowing remote work, companies can save much money on rent and overhead costs.

Step 6: List Your Benefits

Your boss is not silly. He or she knows that you not only ask to work remotely because you want to help the company. Don’t act like you’ve got something to hide. Be honest and list the reasons why you want to work from home.

We know that there are many great reasons for employees to work from home. While they are all legitimate, make sure you don’t sound too selfish or demanding.

Phrase it in a way your boss can understand your viewpoint but it also has a positive twist for the company. For instance:

  • You could explain that your daily commute is 45 minutes each way which is very time-consuming and frustrating. If you could use that time to spend it with your family, you would be much happier and thus more motivated to work and less stressed out.
  • Or that you find it harder to focus in an office because of all the distractions like the loud phone calls or noisy small talk in the hallway (make sure to not get your coworkers into trouble here!). If you worked from home, you were more focused and could improve your performance.


Step 7: Ask For a Trial

Your boss might still be hesitant. And that’s understandable. Big changes like that are always hard.

A good way to convince your boss is to suggest a test period. For instance, that could be one or two days of remote work per week for the next 2 months.

After the trial, you meet again and see how it went. That gives you a chance to prove how productive you are during that time and that your performance does not suffer.

You can also emphasize what went particularly well and how the company benefited from this. In case some issues can be improved, make sure you suggest solutions for the long run.

Also, make sure you follow these tips during your trial:

1. Be Visible

If your boss and coworkers can’t see you, they might assume you are not working. If your company uses an internal chat tool, make sure you are online and available during working hours. Send emails, call your coworkers, and participate in meetings (via call).

If they know you are actually in front of the computer and can be reached at any time (during working hours), they are more likely to trust that you get your work done.

2. Improve Communication

Don’t confuse people with long and complicated emails. Make sure your information is clear and on point.

If an issue is too long to explain via text, don’t shy away from simply calling your coworkers or boss to clarify it. This will save you all much time and confusion.

Video calls are also a great way to slowly transition into remote work. People can see you and discuss topics directly. Almost as if you were still in the office.

3. Report Tasks

As mentioned before, it can be very helpful to track your tasks and report them to your boss. If he sees what you have done all day while working from home, he will soon understand that your productivity doesn’t suffer at all. Maybe quite the opposite.

This will result in more trust and higher chances of a successful trial period.

4. Be Patient

In the beginning, your coworkers might not be too happy about the change in communication or meeting behavior. Again, this is normal. Most people are not too happy about big changes.

Don’t get frustrated or angry! This will only result in rejection and that’s the last thing you want. Be patient, explain to them why you are doing this, and help them if they are facing technical issues with video calls or such.

Man writing in a notebook

After the trial, make sure to meet your boss again and talk about the positive outcome of your remote work.

Step 8: Discuss the Outcome

After your trial period, schedule another meeting with your boss. Discuss your performance on the remote workdays, what went well, and where things could still be improved for an even better outcome.

In the best case, your boss is convinced of remote work and allows you to continue to work from home (maybe it’s just part-time, that’s a great starting point!).

But also be prepared, that even with all those great arguments, your boss is still not convinced and doesn’t allow you to work remotely. That’s very frustrating but don’t take it personally.

Be polite. Thank your employer for the time and for listening to your request.

You can always ask to work remotely again at a later point. If you don’t want to wait or if there is zero chance you can ever persuade your boss, keep in mind that there are many companies that are very open about remote work.

This might be the right time for a new beginning.

Pin - How to Ask Your Boss to Work Remotely - Guide

Denise Mai

Denise Mai

Founder of Digital Nomad Soul

Hi everyone, thanks for stopping by! My name is Denise and I have been working online for more than 10 years. In the past, I worked as a remote employee and freelancer & managed to build a six-figure online business. I know that many others would love to work from home or work while traveling, too. That’s why I want to share my experience and help you on your way to your remote career!

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