Want to Work Remotely? Here’s How to Convince Your Boss

Rob Nightingale 19-10-2016

For many people, working from home is the dream. Imagine you could wave goodbye to the commute and the office politics. Sounds great, right?


But even if you know your work won’t suffer, convincing your boss to let you work from home is rarely easy. Your superiors will think your work will suffer. That your productivity will decrease. That you’ll wash dishes when you should be replying to emails.

When preparing to ask your boss for the chance to work from home then, you’ll need to do some prep work. You’ll have to find some solid ground to at least negotiate a work-from-home trial.

There is a word-for-word script at the bottom of this article to help bring this up with your boss, too.

What’s In It for You?

According to Global Workplace Analytics, over 50% of jobs in the U.S. are “compatible with at least partial telework”. Approximately a quarter of the current workforce telecommutes “at some frequency.”

This is only the beginning. Since 2005, the number of teleworkers in the U.S. How The Internet Has Revitalized Legitimate Work At Home Jobs Is there any truth to the work-from-home stigma? We would like to introduce two examples of today's "online workers" who work exclusively online and you can decide for yourself. Read More has more than doubled, and 80–90% of the workforce want the opportunity to at least partially work from home.

A survey conducted by Microsoft shows why the idea of remote work is so appealing, with the top five benefits given by remote workers being:

Faced with these kind of benefits, working from home seems an obvious choice. But you also need to see this from your boss’ perspective. They will have plenty of reservations, and you need to be armed with the information and tools to put them at ease.

Preparing to Ask

When it comes to working from home, not only are you asking your boss to trust you to focus on work with no-one watching, but also to work with much less guidance than you might previously have received. This all boils down to a worry about productivity.

Writing Keyboard
Image Credit: Anonymous via Flickr

Luckily, plenty of studies have shown these worries to be misplaced. It might be worthwhile sending links to the studies below to your boss if they are particularly worried about a decrease in productivity.

Working From Home vs. Productivity

  • One Stanford study showed working from home to increase productivity by 13%. Of which, “9% was from working more minutes per shift (fewer breaks and sick days) and 4% from more calls per minute (attributed to a quieter and more convenient working environment).
  • A 2015 survey found that 52% of workers were also “less likely to take time off when working remotely—even when sick… Overall, 44% have a more positive attitude and 53% report reduced stress. 51% spend more time with their significant others, adding to the greater job satisfaction.”
  • A 2014 State of Telecommuting PGi report found that 82% of telecommuters experienced less stress, 80% experienced improved morale, 70% saw an increase in productivity, and 69% an improvement in absenteeism.

This doesn’t even begin to touch on the potential savings on overheads (including office supplies and snacks), environmental benefits, and reduced employee turnover.

When Should You Ask?

Timing when you ask your boss about working from home is extremely important. The question should be posed when your boss is in a positive, confident state of mind about your work.

Christopher C. Cook Clock
Image Credit: Clock by Vincent Albanese (Flickr)

As Ramit Sethi points out in his best-selling book I Will Teach You To Be Rich (UK), this would ideally be soon after you’ve received a positive performance review.

Prepping the Practical Proposal

Even if those earlier studies do manage to convince your boss of the potential upsides to working from home, the practicalities can still get in the way of you receiving a thumbs up.

Before you ask about working from home then, you must prepare a plan of how you see this working in real life. The aim is to cause as little inconvenience to your boss as possible. You need to be able to walk into that meeting knowing that you have every angle covered. That you are able to sell the idea of working from home as a benefit to the organization.

It’s best to write this out in a concise document so you can leave it with your boss to review in more detail. This is better than giving a lengthy diatribe of how you’re going to work from home.

Use the list below as a guide to what could be included in this document.

Improvements to Your Workday

Explain current frustrations and bottlenecks to your workflow in the office. You may receive too many distractions when you’re at your desk. Your computer terminal may be too slow. You might be feeling burned out due to your long commute.

Point out how these issues would be resolved if you could at least partially work from home.

Connection Issues

Your boss might be worried about you not having a reliable or fast enough internet connection at home. Run an internet speed test using a site like SpeedTest or to make sure your home network is up to scratch 9 Quick Ways to Instantly Speed up Your Home PC Network If you have a wired or wireless home network, chances are you'll be looking for ways to optimise it so that it is running as fast as possible. Read More .

If your Wi-Fi goes down for any reason, be sure to have an Ethernet cable that you can plug directly into your computer as these can be more reliable (and faster). Finally, reassure your boss that if there are any serious connection issues, you can still make it into the office at short notice if needed.

Access to Software and Company Data

It’s likely that any job that can be done from home will require access to certain software applications. Be sure you can access all of these from home. If you have a company laptop, this should be easy enough. If you’re planning to use a personal computer, you’ll have to figure out a way to access each piece of software securely.

If you need to access company data on a company server, you might already have access to a VPN connection What A VPN Tunnel Is & How To Set One Up Read More . If not, your IT department might be able to help you out.

Constant Communication

Another worry for your boss will be that you are not open to communication as much as you would be in the office.

Ease their worry be explaining that you will be available just as you would be in the office, whether that’s via phone, Email, Skype, Google Hangouts, or your company’s current communication tool (which may be something like Slack or one of its alternatives The 7 Best Free Slack Alternatives for Team Communication Slack is excellent, but it isn't the right tool for every team. Here are the best Slack alternatives your team should consider. Read More ). If needed, you could also suggest one of these collaboration tools for remote workers The 6 Best Free Online Collaboration Tools for Working From Home Online collaboration with clients and teams can be complicated. Use these reliable free tools when working from home. Read More .

Performance Reviews

To help your boss keep an eye on the work you’re actually completing at home, suggesting a regular performance review can be helpful. This will be a way for you to explain what you’ve done each day/week, any problems you’re having, and any breakthroughs you’ve made.

If you’re not already doing something similar at work, introduce something simple. This could be as obvious as sending a regular email or spreadsheet (at the end of each day or week), keeping your boss up to date on your progress. Or you could send a plan each Friday covering your goals for the coming week.

Asking to Work From Home

To quote Ramit Sethi’s book, I Will Teach You To Be Rich, after a positive performance review, you could say to your boss something like:

I’d love to provide even more value to the company in the future. But lately, I’ve been getting burnt out from the commute. It would make a world of difference if I could work from home a day or two each week.

Question Marks
Image Credit: Valerie Everett via Flickr

If your boss simply responds “sorry we don’t do that here”, you have the chance to turn this into an opportunity for the organization.

I understand that Acme Co. hasn’t done it in the past. But this could be a great opportunity for the company. We have the technology to make everything possible. If it works out, we can find candidates in other states for XYZ role that we’ve had a hard time filling. And given my track record here, testing it out with me on a small scale is low risk. If it doesn’t work out, we can always go back to the old way. So what do you think?

Sethi advices you to keep schtum after this point, and wait for a reply. I, however, would recommend you also mention that you’ve made sure it’s completely achievable, and that you can send over a document (which we covered above), explaining everything, if your boss wishes.

Hopefully, your boss will agree to a trial. And if that trial goes well, and you start to see the benefits mentioned elsewhere in this article, you’ll be in a great position to request to work from home more regularly.

If it still doesn’t work out, and for some reason you really need to work from home, there are plenty of work at home jobs 20 Micro Jobs to Help You Make Money in Your Free Time Online opportunities to earn additional income are everywhere. It can be difficult to sniff out the legit companies from the scams. Below are 20 legit opportunities to easily make some extra income in your free... Read More you could turn your hand to. LinkedIn has some pretty useful features to help you work from home Working Remotely Is The Future! This Is How LinkedIn Can Help You A remote or telecommute job is the holy grail of job searching. Leverage the resources on LinkedIn to find your dream job. Read More , too.

If you were able to convince your boss to allow you to work from home, how would that change your life? Would you have the self-discipline to make it work? Why Self-Discipline Is the Best Productivity Hack You Need What is the secret to get deep work done? Is it motivation or is it discipline? If you cannot focus and finish your work, here are some habit tips which will help you accomplish more. Read More

Explore more about: Freelance, Productivity.

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