How to ask your boss to work remotely (step-by-step guide)

by Liam Martin
how to ask to work remotely

Wondering how to ask to work remotely?

With the COVID 19 pandemic and the subsequent virtual work transition, several companies recognize the benefits of remote work

However, many businesses plan on opening their doors soon and resuming regular operations. So if your employer is planning to discontinue the remote work option, you may want to give them a little nudge to let you continue working from home.

In this article, we’ll highlight the advantages of working remotely and provide you a step-by-step guide to help you write the perfect remote work proposal.

This Article Contains:

(click on the links below to jump to a specific section)

How to ask to work remotely (4-step guide)

What are the key benefits of working remotely?

Let’s get started.   

How to ask to work remotely (4-step guide)

Here’s a step-by-step guide to help you prepare your remote work (also known as telework and work from home) pitch before approaching your manager:

Step 1 – Work out the details

Before you ask your manager to let you work remotely, work out all the details. This shows that you’re serious about this proposal and takes the guesswork out of the situation for your manager. 

Here are a few details to consider:

  • Does your office have a VPN (Virtual Private Network) that you need to connect to at home? How will you connect to this network? 
  • Do you require any special tools or software to complete your work at home? If so, how will you access it?
  • Do you need to regularly check in with others (a coworker, clients, etc.) to do your current job? How will you do this while working from home?
  • Do you supervise others? How do you plan to continue to do this effectively from home?

The more details you have covered, the more prepared you’ll be and the more comfortable your manager will be letting you work remotely.

Step 2 – Create a proposal

Using the benefits we’ve already mentioned (and those that attracted you to remote work in the first place), create a proposal

Highlighting the benefits of working remotely to your supervisor is the key to backing up your request. 

Tell your employer or manager how working remotely will increase your ability to effectively perform your job and how it will positively affect the rest of your team — by boosting their productivity. 

Having a formal proposal plan ready is much more effective than casually asking your manager to work remotely — as it shows that you have put a lot of effort into it.

Here’s what your proposal should include:

  1. Explain why you want to work remotely and the specific nature of your request.
  2. Highlight your office work track record in a way that shows you are capable of handling the responsibilities that come with remote work. Include your qualifications, experience, performance, and any other factors that show you in a positive light. 
  3. During the COVID 19 pandemic, almost everyone worked from home, even if it was only for a short while. Remind your employer of how well you worked during this period. If you achieved increased productivity levels, mention that as well. 
  4. Outline the actual schedule you plan to follow while working remotely. Include your intended work hours. You’ll need to figure out whether you’ll be working at regular office hours or at odd times. 
  5. Explain how you plan to keep in contact with all necessary parties, including clients, managers, and team members. Questions to answer include:
  • How often will you reach out to your team members, clients, etc.?
  • What method of communication will you use, and what software will you require?
  • How do you plan to stay consistent with communication?
  • Will you meet in person or have a Zoom meeting?
  1. Outline the benefits that you anticipate working remotely will have for your organization. Include at least three unique advantages, as mentioned later on in the article. Focus on highlighting the benefits for employers in particular. 
  2. Discuss possible costs associated, along with remote work software that may be needed to monitor your performance.
remote work challenges

Step 3 – Recognize the challenges and provide solutions 

Account for potential problems that may arise and anticipate any objections your employer may have beforehand. 

Telecommuting will present unique challenges that working in an office does not. 

For example, if you share your living space with friends or family, they can distract you while you’re trying to work.  

Consider all the potential issues that could come up when working remotely and the solutions you can to implement to overcome them. This ensures you have effectively planned for the move to remote work.

Let’s a look at some of the challenges :

A. Communication issues

One of the concerns your manager is likely to raise is possible communication issues. 

Remember, you’re giving up face-to-face access to your colleagues, in-person brainstorming sessions, coffee breaks, etc. With a remote work arrangement, you’ll no longer be able to walk over to your colleague’s desk for a chat. 

Your employer may express concern about a lack of employee engagement due to this lack of in-person communication. 

Bridge the communication gap by offering solutions such as live chat and video calls. A video conferencing solution like Zoom and an instant messaging solution like Slack are just two ways to ensure remote worker communication doesn’t suffer.

Check out our article on the best remote team communication tools.

B. Coping with distractions at home 

When working from home, a considerable number of distractions arise just from being with your family – even more so if there are children or pets around. 

One solution to this problem may be to create a workspace where there are fewer distractions, such as a home office.

Other solutions to consider include:

  • Posting a work schedule so your family knows when you shouldn’t be disturbed. 
  • Playing background music to provide ambient sounds that can help you focus. 
  • Breaking up work throughout the day when you have fewer interruptions, such as when the children go to school.
  • Consider hiring someone part-time to assist with childcare or ask for the assistance of a family member.
  • Consider a co working space or coffee shop closer to your home that you could use for a few hours each day (in a post-COVID scenario). 

C. Staying motivated in an isolated environment 

As a remote worker, you’ll be working in an environment where no one is motivating you to take your daily tasks more seriously. 

Additionally, your manager can’t supervise every aspect of your workday and manage your time as they would in a traditional work environment.

With a remote position, you’ll always need to motivate yourself and manage your work under time constraints. 

This may be a particular concern for your manager, who may be used to an office environment where they can watch over employees to ensure they get their tasks done.

Suggest the introduction of productivity management solutions such as Time Doctor so that your manager can track remote workforce productivity. 

Explain to your manager that the tool helps both you (as the remote employee) and them – as they get clarity on what you’re doing during working hours.

With Time Doctor you can:

  • Track time when you’re either offline or online.
  • Easily create and assign projects and tasks. 
  • Categorize websites or apps, like YouTube, Facebook, as productive or unproductive.
  • Receive daily and weekly reports about web and app usage, hours tracked, active summary, and more.
  • Utilize the Android app to monitor time usage on the go.

Step 4 – Arrange a meeting with your manager

Once you have completed the previous steps, it’s time to set up a meeting with your manager to present your request. Here are a few smart tips to help you approach this meeting better:

  1. Make your request either in-person or on a video conference call rather than over the phone, email, or live chat. 
  2. Present your employer or manager with the proposal you’ve developed, as well as personally detailing the main points from your proposal. 
  3. During the discussion, remain as professional as possible. Answer any questions your employer has confidently, and be willing to hear their point of view. 
  4. If your employer sounds interested but doesn’t fully commit, suggest a trial run. Ask them to allow you to work remotely for a limited time and meet again after the trial period to discuss if you can continue with it. This test run will give you both a chance to iron out all issues that could pop-up when you work from home permanently. 
  5. You can also encourage them to develop a remote work policy if the company doesn’t already have one in place. This is simply a document that clearly details what you can or can’t do while working from home.
  6. In the event that your manager needs more time to consider your request, determine a specific time to follow up. This will ensure your proposal discussion keeps moving forward and isn’t forgotten.

What are the key benefits of working remotely?

Here are a few perks of remote work you and your boss can take advantage of:

1. Increases flexibility while promoting productivity

One of the key benefits of remote work is that it provides flexibility to work the way you want.

For example, if you’re an early bird, you can start your workday at 5 am and accomplish more tasks. If you’re a night owl, a remote job allows you to work when you’re most productive — which would be after sunset.

According to a study,  American Express employees were 43% more productive when they were allowed to work from home.

Additionally, not having to travel to the office each day frees up more time. Employees can use that time to either work more or do the things they love.

2. Saves time and money 

According to Global Workplace Analytics, if employees work remotely half the time, it would result in over $700 billion in savings for companies in the United States. 

This would save the average business around $11,000 annually. Additionally, employees who work from home would save between $2k-$7k annually. 

How is this possible?

Employers, even more than employees, benefit from the cost-savings of remote working. Companies save on office space rental, utilities, office supplies, and consumables like coffee, etc. 

Meanwhile, employees save on commuting costs and other expenses related to going to the office. For example, when you’re working from home, you can save a lot of money by not having to buy lunch and coffee every day. 

3. Increases job satisfaction and employee retention

A 2017 study revealed 74% of North American office workers indicated they would change jobs based on the company’s work-from-home policy. 

This study proves that employees are willing to search for jobs that allow them to work from home. Employees highly value workplace flexibility, and as a result, experience more job satisfaction when they are allowed to work remotely. 

Why is flexible working so important to employees? 

Flexible work arrangements give employees the time they need for themselves, to fulfill personal commitments, etc. 

Greater flexibility can also lead to a better work-life balance, boosting job satisfaction. This has a positive effect on employee retention rates. 

To find out more about the advantages of working remotely, check out our article on Important Remote Work Statistics.

Wrapping up

Since the COVID-19 pandemic, remote work has skyrocketed in popularity as it allows companies to operate with employees working from their homes.  

However, it’s continued to be seen in a favorable light even after businesses began resuming in-office operations. This clearly shows that remote work offers several advantages.

It’s up to you to ensure your employer recognizes the many benefits for them as well, such as saving money and having a more efficient and productive workforce.

Follow the steps mentioned in this guide and you can surely increase the chances of getting your employer to approve your remote work proposal.

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