How To Get Your Boss To Let You Work Remotely

June 08, 2017

Josh Li

Digital Marketer at Institute of Code

Imagine being able to work from home, or better yet, in an entirely different country! Working with your laptop on a balcony, sipping coffee and munching on fresh fruit in sunny Greece would be the dream. But does it sound too good to be true?

​Not really!

Remote working is rapidly growing; according to some research, 62% of the US workforce already work remotely to some degree, with millennials, who are set to make up 75% of the workforce by 2020, driving this change. Faster internet, better communication and collaboration technologies, and the cloud are all making remote work more streamlined than ever.

It might be a lot easier than you think to travel and work remotely.

Imagine being able to work from home, or better yet, in an entirely different country! Working with your laptop on a balcony, sipping coffee and munching on fresh fruit in sunny Greece would be the dream. But does it sound too good to be true?

​Not really!

Remote working is rapidly growing; according to some research, 62% of the US workforce already work remotely to some degree, with millennials, who are set to make up 75% of the workforce by 2020, driving this change. Faster internet, better communication and collaboration technologies, and the cloud are all making remote work more streamlined than ever.

Sounds great, you say, but my boss will never let me do that. Working from another desk is already hard enough, let alone from another country!

But remote working benefits so much more than just you. Research is already proving that people who work from home are a lot more productive than those who remain in the office. Companies also save on the huge overheads that keeping large office spaces require, as stationary, furniture and technology costs all add up. It’s also a great way to reduce a company’s carbon footprint; not only do companies save energy, but employees also don’t have to make the commute to and from the office, potentially taking a car off the roads.

Having said that, it’s important to remember what benefits you also benefits your company. Remote workers are happier, heavier and more balanced in life, helping them love their jobs.

So aside from talking about all the benefit, how can you talk your boss into letting you work remotely? Here are 5 steps you should try that should at least put you on the right track.

1. Look at your role and performance

One step is to take a look around your office right now and think about whether you could take it all with you in a laptop. If you’re a surgeon, for example, you might be out of luck; remote surgery using the arrow keys on your laptop is not quite here yet!

If you have a lot of documents lying around, consider whether you can upload it all to a cloud server. Work regularly in close contact with your team? See if you can shift your work online as well, by using Google Documents, inVision or other collaborative platforms. Hook your team up too to project management software, such as Asana or Trello, and messaging platforms such as Slack, so everyone can keep updated with your work. It’s a good idea to migrate onto these platforms early to make sure your team adapts to the software before you leave, rather than having everyone trying to adapt just as you’re going.

Another slightly more awkward part is to look at your own performance. If you’ve been lagging behind, then let’s be real, your boss isn’t going to let you off the hook. In order for management to feel comfortable with you not being around, you need to have shown a proclivity for independence, proactiveness and ownership of your work, which are traits you’ll carry outside the office.

2. Communicate the value of your time

Your time is valuable to the company - you just need to communicate it.

If you’re able to quantify your worth the company, i.e. by summing up how much revenue you generate the company through your work, you’ll be able to leverage that when you negotiate for remote work. Let your boss know how much you currently get done, then posit how much more you could get done at home, with no distractions and no time wasted commuting to and from the office. It’s all about how you sell it!

3. Take a trial run

Often, managers just need to be warmed up to an idea. Just as many companies won’t try to sell you software without at least giving you a free trial, you’ll have a much easier time convincing your boss if you can prove to them the arrangement can work.

Start slow. Try asking your boss for one-day a week remote, and to trial the arrangement for a month. Make sure you communicate with your boss at all times, making sure they’re up-to-date. At first, they might want to micro-manage you, but that’s because they’re trying to adjust too. If things go well, then step it up to several days a week, or one week a month, and before you know it, you’ll be spending more time at home than at the office!

Don’t see your boss letting you go at all? Tim Ferris, the author of the 4-Hour Work Week, suggests pulling a sickie. But instead of curling up in bed with your blinds closed, sunglasses on, and a ‘No Loud Noises’ sign on your bedroom door (like what you do on your other ‘sick’ days), try to smash out as much work as you can. That way, you can come into work the next day and tell your boss something along the lines of, ‘I was really sick yesterday, but I knew we had a lot of work, so look at what I got done, even though I was sick’. This proves to your boss you can at least be independent and proactive, which is a good start for negotiations!

4. Set up a remote desktop

Sometimes, companies are reluctant to allow their employees to work remotely because of the sensitive information they possess. Other times, it’s because the office has technology that isn’t usually available in homes. That’s where being proactive comes into play! Make sure you do your research and figure out if using remote desktop services, or security software, such as LastPass, can solve these problems. A remote desktop service might allow you to access your work computer from home, giving access to things only available at work, whilst security software will give you secure access to systems without actually having to type in passwords.

When it does come to working remotely, exercise caution and common sense. Try working in an office, not in a cafe where people can overhear sensitive phone calls, or see information on your screen. Don’t boast to your friends about working at home by sending them selfies with your work in the background - people have been fired for less than that! The key is to be extra mindful because you aren’t always going to be in such a controlled environment.

5. Promise Transparency

In the end, the most important thing is transparency. Your boss will appreciate it if you’re transparent about why you want to work remotely, and how you plan to spend your days. Let them know how they can contact you, and be open to how flexible they want you to be. After all, deadlines are deadlines, even if you’re working at 10 pm on a Friday night, or through the weekend!

While you are working remotely, make sure you’re transparent about your work, your hours, and your progress. You need to not only hold yourself accountable, but also your team accountable, and vice versa. At risk of sounding like a relationship counsellor, you all need to communicate!

Those are 5 steps you can take to convince your boss to work remotely. One of the biggest fears holding people back from living a life more in line with what they dream of is fear of oppression. However, if you actually reach out and ask for what you want, you might be pleasantly surprised. With remote work and its well-documented benefits, it might be a lot easier than you think!


Written by: Josh Li

Digital Marketer at Institute of Code