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Work Remotely – How To Convince Your Boss

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Working from home and you will save your company money. You will be more productive and valuable to your employer. Except your boss probably doesn’t think so.

Most bosses are resistant to change and many believe  tele-work is code for doing very little work. That’s okay. That’s maybe why you’re reading this.

Working at your home office comes with all manner of personal benefits. There’s the freedom, improved work-life balance, and a chance to work from anywhere. This article will give you strategies to make remote working a reality.

WFH (Working from Home) – Let’s First Demystify Stereotypes

We Don’t Work Remote From Beaches

Stereotypes do not work in your favour. Picture a woman in bikini, lying back on a palm tree, with a Macbook at her lap. Or a man sunning himself on the beach with cocktail and computer. Nobody works online from the beach, but that’s the image portrayed by wannabe digital nomads and most websites promoting the benefits of working virtually.

Let’s move the conversation forward.  Being part of a distributed remote team means you can work from anywhere. And just about the last place you want to work is the beach. Screen glare is a disaster, sand wrecks your machine, the Wi-Fi is sketchy, and seriously, working at the beach is more antisocial than working out at the beach.

Nor Noisy Coffee Shops

Stereotypes suggest that online work means doing less work. The reality is that you will do more work, just from a different place. Not a beach. Probably not anywhere that looks very exotic. Most probably, you will complete remote work tasks at a desk, just like you do now. But what about all the keyboard warriors filling up Starbucks?

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Working Remote is Not a New Thing

Remember, working at home is also considered telework. So is working anywhere that’s not the office, including any business trips you have taken. Bosses and employees are often resistant because the stereotypes create an entirely new concept, based on working from anywhere (i.e. somewhere exotic).

Remote work is not new. In terms of what you do for the company, is it exactly the same as working from home. It is functional, not glamorous. And that’s something both you and your boss need to understand.

digital nomad

Can You Work from Your Home Office?

It’s good to know your starting point. Most jobs do not need your physical presence and they can be performed virtually. As a general rule, if you’re working from a computer you can take that work anywhere. Chances are that you fall into one of four categories.

  1. Remote work can be done as a freelancer – freelancing means working for yourself. Work for yourself and you can telecommute. You may face restrictions over timezone and availability, but in general, freelancing is tailor-made for remote working.
  2. Work as part of a remote team – the next easiest scenario is working as part of a remote team. Many start-ups and small businesses operate on this model, without a physical base. These businesses actively recruit remote workers. is a good resource for finding remote start-up jobs. is the largest platform for remote jobs.
  3. Request to telework at your current job – it’s often easier to take your work somewhere else than to find new work. In today’s business climate, a lot of businesses are open to remote working and have a policy in place. Maybe your colleague did it? Perhaps it’s been discussed before? Keep reading for a selection of strategies to make it a reality.
  4. “My employer doesn’t have a work remote policy” – unfortunately, many people believe that remote work is impossible, because their employer would never agree. This is usually because they have no policy. Or they’re backwards, like Yahoo who banned remote working in 2013. Think positive, as pandemics like Coronavirus force every business to reassess how they operate and how they can be more efficient.

digital nomad
Think From Your Employer’s Perspective

This isn’t the place to get all excited about your benefits. To convince a boss you need to face the stereotypes head on. If you ask for a flexible working arrangement, here is a selection of what your employer may be thinking.

  • You will be doing less work (remote workers are considered lazy, remember).
  • You will not be available when required (your physical presence is expected, even though you can give instructions over a video call).
  • Micro-management will more challenging (some bosses like to have a clear eye on you).
  • You will need to attend meetings and network together (even though meetings are generally more efficient when they’re done from home, via video conferencing.

They think this way because they have always worked this way. So something needs to change.

Position the Benefits for Your Employer, Not For You

Crucially, you need to make the benefits of remote work relevant to your boss. Your boss is also annoyed by daily commuting, internal politics, and the generally depressing mood hanging throughout the office. If they have to put up with the office on every single work day, why can you escape?

Boasting about working from an exotically named island isn’t going to convince your boss, so save the personal benefits for later. Start with how remote working is going to help them.

The Proven Benefits of Remote Work

Don’t just shout about the benefits. Get scientific and give your boss some evidence using the links below.

Increased Employee Productivity

Staff in office environments waste a lot of time. How many times have you been at work doing nothing? Maybe you were hungover. Maybe you couldn’t get into it. So you play around on the Internet, wander around having conversations with colleagues, and wait until it’s an acceptable time to leave the office.

Employees in offices have to be there. Employees who telecommute are actually getting stuff done, because they have better places to be. That change in perspective massively boosts productivity. Studies have suggested remote working increased employee productivity 35 – 40%.

Increased Employee Performance: From Time-Based to Task-Based Work

Fixed office environments promote the idea that your work is paid in time. That’s why you get dodgy looks leaving the office at 2pm on a Friday afternoon. Or why some people stay longer in the office to impress their boss.

When you perform distance work, your boss can’t see you. There’s a shift towards getting paid for the work you do, not how much time it takes you. This stronger autonomy is proven to increase performance.

Saving Money on Office Space

It’s pretty simple – the more employees working from home, the less fixed office space that’s required. So your employer saves money. InVision and Automattic are both worth over $1 billion and have zero fixed office space.

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Access to a Wider Talent Pool

A remote worker can be hired from anywhere. An employer isn’t restricted to people who live or want to live close to their office. Whereas a remote team is based on the widest possible talent pool.

Greater Staff Retention

“54% of employees would change jobs for one that offered more flexibility.” Companies that prioritise the remote work revolution are those that will keep their employees longer. You’re probably reading this, ready to jump to another job if it can offer you a remote working solution.

Working from Home – 5 Steps to Convince Your Boss

All of the following strategies can work. Think clearly about who you approach. You will probably need an advocate who can take your argument to the top of the chain and your director.

1. Start Remote Work From Home

In a perfect world you will be booked on a flight tomorrow, ready to work from anywhere. Except, your boss doesn’t want you to work from anywhere. They want you close. They demand reliability and even if they agree to remote working, it’s a long jump from working at home to working from Sri Lanka.

For this to work long term you will need to establish remote systems (see below), so business continues as normal and your absence from the office is no longer a talking point. Small incremental steps are important and are less of a jump for your boss.

The majority of businesses already allow some working from your home office. Maybe you already work from home on occasion. Even if they don’t, working from home is an easier sell than working as part of a permanently suited  distributed work team.

First you need to do some work away from the office.  Then you can make working from home a fixed part of your schedule. Every Monday? Every Wednesday and Thursday morning? It doesn’t matter when. Establish consistency so your boss can’t call you into the office for a meeting, if it’s your working at home day.

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2. Establish Professional Remote Systems

Here’s what your boss is probably thinking – “what happens when we absolutely need you and you’re on the other side of the world? (lounging on a beach while I’m stuck in this hellhole…)

You need to convince your boss that, yes you are still here. And to do that you need to establish efficient systems that bypass a typical office environment. This can be done while you are working from home, so you can showcase how work continues as usual.

Establishing such systems is a major step forward for any employer as these systems can lead towards a remote work policy.

Responsive Communication

Remote workers need to connected socially and informationally to all their colleagues, not just their boss. You need a system that ensures collaboration isn’t siloed, or becomes too infrequent.

Slack is the market leader as a tool for achieving this. But also consider the new features of Google Hangouts and other Slack alternatives.

Availability and Time Tracking

Employers want to know whether they’re getting value. And your boss will want to know whether remote work is a good idea. Time Doctor and Hubstaff are great time tracker tools for remote teams.
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3. Get a Fixed Base on the Same Time Zone

Now it’s time to make the next little jump. Working from home to working from somewhere on a similar time zone. This is obviously preceded by an agreement that you can be working from home, permanently, rather than occasionally.  But there is no fundamental difference between working from home and working from a professional co-working space on a similar time zone. From this more remote base you can expand on the remote systems.

Professional Environment

You’re not working all day from a coffee shop or a beach. Nobody does this! But it’s good to establish some guidelines for your boss and take most of your work to a co-working space.

Presenting the Brand in External Interactions

Image means a lot in business and many employers fear that remote workers can come across as less professional. They think a remote worker is going to dial into an important sales meeting wearing board shorts and singlet. So keep a smart shirt in the office or in your bag, so you can easily switch to a professional look when required.

4. Work at a Distance From Anywhere

Very few employers will immediately agree to a permanent switch from office to remote work. You will have to test the water and prove that it works for them and you. Maybe it will initially be for one or three months. When systems and policy are in place, you will have more opportunity to work from anywhere.

Time zones may still be a factor. You also need to confident of getting solid Wi-Fi. NomadList is a good resource for comparing potential destinations, including a city’s average Wi-Fi speed.

Although you can travel without a plan, you still need a plan for work. Most importantly, arrange your office space before you arrive. Use Coworker to search for coworking spaces, read reviews and make appointments, before you arrive in a city.

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5. If All Else Fails: Coronavirus

Google can send everybody home for a month because many of their staff already work from home. Their systems support remote working so it’s business as usual, even during quarantine.

Many traditional businesses are resistant to change. But if they rely exclusively on fixed office space they will struggle to survive. What about the next virus? Or conflict? Or seismic natural disaster?

Businesses that use distributed work teams (remote first) are more future-proof. They’re more adaptable and can respond efficiently to change. And that’s the argument you can try with your boss.



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