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How to Convince Your Boss You Should Work Remotely – A Complete Guide

Working from home changed my life.

I have been able to spend so much more time with my children because I made the change. These are years that I will treasure for ever.

That’s why I want the same for you.

And if you are in a job where it seems unrealistic to even consider the idea of working from home, I want you to think again.

There are a lot of people who successfully alter their work arrangement so that telecommuting becomes a reality.

All without leaving their current job!

In this article I am going to lay out the exact steps so you can do it too.

A Quick Self Quiz

Before you even begin to think about approaching your supervisor with a proposal, you need to think carefully about the role that you do, the business you are in and to some extent the person that you are.

Be honest and ask yourself the following questions:
  • Do you need expensive office equipment to conduct your role?
  • Does your job require regular face-to-face interaction with other colleagues?
  • Is it your job to meet clients and customers at the office on a regular basis?
  • Would your company benefit more from you being in the office rather than working from home?
  • How productive would you realistically be while working from home? Are you easily distracted, or have a tendency to procrastinate when unsupervised?
  • Do you have babies or young toddlers at home? A work from home dad will need help if there’s little ones crawling around too.

If you answered yes to several of those questions, it could be that your current position isn’t ideal for a FULLY remote arrangement.

But all is not lost.

Even a managerial position with lots of client / colleague interaction can make the transition to a partially remote system of work.

Could certain meetings be conducted using applications such as Skype or FaceTime?

If specific equipment is required for your role, could it be purchased for the home? Or used on designated days when you do attend the office?

It is important to realise that many pre-conceived ‘obstacles’ to working remotely can be overcome with the right planning and co-operation from both the employee and the employer.

ACTION POINT: Take the above Self-Quiz. If you answer no to several of those questions your job could be ripe for working remotely. If you answered yes, do not lose heart. Start looking at potential solutions to aspects of your role that require an in-office presence.

A telecommuting proposal for your boss

It’s no good organizing a coffee break with your boss and laying this on him over an informal chat.

The best way to pitch the idea of working remotely is through a carefully thought out, statistics driven written proposal.

Before you begin that however, you need to do the following:

Time to jump in their shoes

At the root of any decision to make a position more flexible, a boss will want the answer to 4 main issues:

  • Can the job be done outside the office?
  • Can it be done better?
  • Will it cost the business any extra?
  • Will this make you a happier, more satisfied worker?

Focus on answering these issues honestly within your pitch.

A professional approach that address these areas of concern (while backed up with data) will help your boss to take your request seriously.

ACTION POINT: Put yourself in your boss’ shoes. As you plan out your proposal you need to consider their perspective. Be aware of their potential concerns as you piece together the details of your request.

Step 1: The opening section

The format should be similar to a business proposal, with clear sections that provide all the information your boss will need to make a decision on whether your position should be done remotely.

The opening page of the proposal should contain the following:


Your brief intro will set out what you want and why it is good for the company.

This section should also state whether you are proposing a trial and/or a partially remote arrangement.

The intro should be only 2 or 3 paragraphs long. Your main points will all be expanded upon within the body of the proposal.


It is worth writing a section with background information.

This should include personal details, brief overview of any (positive) performance reviews, time at the company and any supporting data regarding the company’s current flexible work practices.

Step 2: The Main Details

This section will include all the practicalities involved with you shifting your job to a remote working arrangement.

This will often be the most information-dense segment of your proposal. Try to make this easier on the eye by using bullets or section headers to convey the message clearly.

You should include the following details:

The remote schedule

Are you proposing to work full or part-time from home? If part-time, how would your time in the office be balanced? Make your request clear in this regard, (while allowing space to negotiate should your boss have alternate views).

Tools & Home-Office Environment

Another concern for most bosses is what tools and equipment will be required for you to successfully work from home.

From their perspective they (understandably) want to know how much it is all going to cost.

Also, do you have reliable WIFI and an established home office? Will you need a dedicated phone line, specific industry software or secure access to a company intranet?

Do your research to find out what you will need to work remotely and how they can be accommodated.

Methods of communication

How will you stay connected while working from home? Good communication with your boss, colleagues, and clients is an A1 priority for anyone working remotely.

Carefully map out how you plan to navigate these issues. Will you conduct scheduled meetings and conference calls? Can clients be seen in the office or visited elsewhere?

What tools will you use to keep in successful contact while you are away from the office?

How productivity might be tracked / quantified

Your boss, as far as possible, will want to measure and track the success of you working remotely. Is there anyway your productivity can be quantified?

If so, work out targets that you will aim to achieve under the new work arrangement.

ACTION POINT: Write down the details on how the remote arrangement would work. If partial, what days would you be in the office? What tools and equipment will be required? How will you stay connected with colleagues and clients? How will your productivity be measured?

Step 3: The Benefits to the Company

This section of the proposal will include the benefits to the company.

Raising these points (along with solutions to any cons) will show that you have carefully considered your position, and that there is (hopefully) a strong supporting argument for why you should work from home.

Again, remain as impartial as possible and think about these issues from the perspective of your employer.

Resist any temptation to discuss how working from home will improve your personal life. Frame the benefits in terms of how it will help you do your job better.

Remote work options increase productivity

Scientific research backs up what a lot of those that work from home state; a flexible working arrangement and working under their own terms leads to an increase in productivity.

In statistics compiled by Global Workplace Analytics, remote workers at JD Edwards showed up to 25% higher productivity levels than their office colleagues.

The same study found that home-based American Express employees were 43% more productive than their office based counterparts.

That’s a huge boost in work levels; the argument being that happier employees with more control over their lives and time, work better and more efficiently.

Remote work options reduce turnover

Offering flexible work arrangements is a great way to increase employee retention.

Statistics show that remote workers are a more willing work force that is likely to stick around.

Which of course leads to reduction in the cost of recruiting and training new employees.

Remote work options improve employee morale

Linking to the first point, telecommuters tend to be healthier both physically and emotionally.

Not only does that boost productivity, it also improves employee moral.

According to The Sloan Center on Aging & Work at Boston College, a study of more than 19,000 employees at nine different companies showed that stress and burnout were lower among workers who had workplace flexibility.

Remote work options reduce employee stress

Having the option to work remotely reduces stress.

Not only is the home a more pleasant environment for (most) people to work in, the absence of other work-based distractions (interrupting colleagues, chit-chat, interpersonal issues), make for a noticeably stress reduced day.

And then the biggie for me – the absence of a rush hour commute.

My standard of living now compared to my 10 years of working in London is incomparable. Mainly because I no longer have to suffer the underside of someone’s hot, sweaty armpit being thrust into my face on the tube everyday.

Whether you’re used to dealing with traffic jams or service disruptions, eradicating the commute from your daily existence is a top prerequisite to a stress reduced life (and probably a longer one too).

Remote work options are eco-friendly

Following on from limiting your daily suffering to the whims of rush hour traffic, the remote worker is also reducing carbon emissions by avoiding the commute.

Remote communication tools can also help companies reduce business travel costs and related pollution too.

Home based workers also utilize less electricity, fewer supplies and less waste; your carbon footprint as a remote worker is vastly reduced.

Any company that is looking to emphasis their efforts to be environmentally friendly organization, should adopt flexible work arrangements as par of the course.

Remote work options are cost-effective

It is possible to round up a number of these pros to show that remote work options are actually cost effective for the employer.

  • Higher employee retention reduces the cost of training and recruitment.
  • Better communications can lead to a drop in the cost of business travel.
  • The cost of office space and supplies in your absence is also reduced.
  • Flexible work arrangements also help lower the cost of absenteeism, (you’re a happier worker so there’s less reason to pull a swift sicky because you don’t feel like going in today).

Add that to the increase in productivity from an individual remote worker and you see that the future of a flexible work arrangement is definitely bright, for you and your boss.

ACTION POINT: Write down all the benefits of how you working remotely will benefit the company. Try to frame these benefits in terms of how it will help you do your job better. 

Step 4: Some negatives points to consider

The following are some of the well known negatives to working from home. If you do list these in your proposal, set any negative points in terms of how you will overcome them.

If you decide not to raise any negative issues, ensure you are aware of them all the same. Your boss is likely to mention any obvious ones while discussing your proposal.

Employee isolation

A disadvantages of remote work is that you can lose touch with colleagues on a more interpersonal level. Being unavailable for get-together lunch breaks or after work drinks, can take its toll as far as disconnection goes.

Team productivity can also suffer where remote members are missing from face-to-face meetings, brainstorms and other team activities.

These problems can be alleviated through communication tools and efforts to socialise where you can however.

Measuring productivity

The potential for slacking off is one area bosses not used to flexible work arrangements can find particularly problematic.

Some employers think that the lack of supervision automatically means that an employee will not be as productive as they would be in the office.

If your boss seems like they may fall into that camp, (do they micro-manage? Do they hold luddite sympathies in terms of technology and progress?) you may want to suggest within your proposal that a system of Key Performance Indicators (KPIs) be employed.

How these KPIs are used should be tailored to your unique position within the context of your business, and is something for you and your boss to work out.

The risk of distraction

Remember, working from home is not for everyone; especially if you are reading The Balance Hub as the father of small children.

While I want every dad reading my blog to enjoy flexible work and to see more of their family, that in itself can cause problems.

The risk of distraction is huge, and if you do have sprogs at home you need to be sure that fatherhood will not jeopardise your ability to do your job properly while you work remotely.

ACTION POINT: Consider any negative issues surrounding a shift to working remotely. Write down your solutions and either include them in your proposal, or have them ready for any potential concerns from your boss.

Step 5: Suggest a Trial Period

Before concluding your proposal, you may want to include details of how a temporary remote arrangement might work.

Outline a specific amount of time (30 days, 90 days, etc.), alongside some suggested pre-determined accountability measures.

This will make it easier for your boss to jump on board without the pressure of fully committing.

You should ensure that brief details of the trial period are stated in your proposal introduction.

Measuring the productivity of the trial period

You should also suggest ways in which the success of the trial might be measured.

Set goals and timelines for completion of projects as you would normally while working within the office, in order to be able to compare results.

Your goal will then be very clear – get the work done in or ahead of time so that your work-from-home trial run becomes permanent.

ACTION POINT: A trial run is a good way of getting your boss to agree to you working remotely without the pressure of committing to the arrangement. Make sure to include details of this in your proposal, along with duration and productivity goals to be measured.

Step 6: Renegotiations

In support of your proposal to shift to a flexible work arrangement, you might want to discuss areas you would be willing to renegotiate on.

For example, due to the fact you will be saving on commuting costs, or daily lunch fees, you could renegotiate salary and state that you would be willing to resign your next pay increase.

Or maybe you see flexibility in the amount of holiday days you have and reduce your annual amount.

Be creative here, and think about what benefits you would be willing to sacrifice in order for your proposal to be met.

However, this is by no means a compulsory element of your proposal and should only be used in a way you feel comfortable.

ACTION POINT: Think about any benefits, salary or holiday options you would be happy to renegotiate on in order to facilitate the success of your proposal. Either write them down as a section within the document, or have them ready for any face-to-face discussion.

Step 7: Final Sections

Next Steps

Clarity on next steps will help keep your proposal in the mind of your supervisor so that a conclusion can be made.

Rather than demand a specific deadline, just openly suggest a time frame in which the two of you can get together to discuss your request.

Summary/Thank You

The final paragraph can be used to say thank you for taking the time to read the proposal and that you look forward to hearing what your boss has to say on the matter.

ACTION POINT: Pull together everything you have researched and learnt from this article so far. Sit down, and write the damn proposal. A new work / life balance is yours for the taking!

Step 8: Making the Pitch

Once you have finished your proposal and completed all the necessary content, formating and spelling checks it is time to set up a meeting so that you can present the proposal and make your pitch.

Alternatively, you can submit the proposal while asking to arrange a date to go through it.

The important issue is to have the opportunity to go over the proposal with your boss face-to-face.

This way questions can be asked, and concerns can be addressed.

Here are some helpful tips in preparation for this situation:

Pick your time wisely

Avoid seeing your boss 20 minutes before they are due to leave off for the day. They will be more concerned about getting the first available train home, or where they’re meeting friends for a drink rather that your written proposal.

Hopefully you have some incline of your boss’ behaviour patterns. Are they more amenable in the mornings or are you better off catching them after lunch?

Ensure you set up a meeting to present your proposal (don’t just tap on their door and ask if they’ve got a minute), a proper appointment is more professional and will give them notice so you don’t catch them at an inconvenient time.

Be prepared

You should hopefully have all the information in your mind after researching and writing the proposal.

Ensure that you go over it again before walking into the meeting. The details should be fresh in your head and easily recalled.

It is crucial that you consider your position from all angles. You will want a solution for anything that could potentially make working at home a challenge.

If you can cover any concerns your boss might have, you will be well on your way to a new, remote working arrangement.

Be patient and understanding

Your proposal was spot on and the pitch was even better. You feel there are no holes in your request to start working from home.

However, if your boss needs time to mull it over (which is likely the case), take a back seat until its time to discuss the proposal once more.

Hopefully the time span you have set in your ‘next steps’ section will ensure you are not waiting too long.

In the event they decline

In the event your boss refuses point blank, do not get frustrated or angry. Remain professional throughout and take time to rethink your position.

It might be possible to suggest a more limited trial (e.g., one day a week vs. two).

Maybe your boss would be open to you telecommuting for specific tasks (completing reports on a set afternoon during the week); sometimes all it needs is baby steps.

However, if your boss remains unconvinced, do not lose heart. You should take time to consider your future and whether you will ask again or start a remote job search elsewhere.

Boom, you’re in!

But I’d like to end this article on a high note.

After a carefully crafted proposal and a well delivered pitch, your boss is all smiles.

And so are you, because they just said yes!

Now it’s your time to shine.

Nail the work from home productivity like a boss and show how the reduced commute, added flexibility and overall happier lifestyle has made you even better at your job.

With the trial run a complete success you will permanently join the work from home community with all the benefits that this wonderful work life balance provides.

Over to you…

Have you made the transition to a remote arrangement? What did you include in your telecommuting proposal? And what concerns did your boss have? If you have any comments, I’d love to hear from you below.

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