How to Convince Your Boss to Let You Work Remotely

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Written by  April 24, 2018

Showing your employer that you can get the job done from any location takes planning, communication and commitment.

Two years ago, I worked as a copywriter in a travel office, where I dreamt of living abroad. I’d always envisioned a life overseas, unbound to a specific location, but I loved my job.

So when I announced my decision to leave, I presented an option to my boss—I could continue working remotely for the company. I’d do the same job, with a few changes. I went from being a full-time employee to an independent contractor.

Moving abroad can be daunting, even without the pressure of finding a new job. So why not keep the job you have when you move? Thankfully, many professions require only a laptop and a good WiFi connection. According to a report from Global Workplace analytics and FlexJobs, around 3.9 million Americans already work from home at least half of the time. Telecommuting has increased by 115 per cent in the last decade—and a number that’s only set to grow.

Assuming that your job can be done completely on a computer, remote work may be an option for you. But how can you convince your boss to let you work from anywhere in world?

Establish yourself as a competent employee

Before you pop the question to your boss, make sure to develop a solid relationship with your company. I worked for my employer in-office for three years, which allowed me to become familiar with their core values and day-to-day operations.

During this period, you’ll also form relationships with your coworkers and your boss. You’ll learn their personalities and the best ways to communicate with each of them. Cultivate a bond so they know you as a reliable, communicative member of staff. Your boss will need to know that they can trust and count on you.

When Sam Schaible decided to join Remote Year—a program where remote workers travel together through 12 countries in 12 months—she had been working as marketing manager for Cannonball Productions, an event management company, for about a year and a half. Since one of her co-workers had already worked remotely, she suspected that her boss would respond positively to her proposal.

“I have a pretty close relationship with [my boss] and felt confident that I was trustworthy and responsible enough to take on this challenge,” says Schaible. “Thankfully, she has the same confidence in my abilities and agreed.”

If no precedent has ever been set and your boss is nervous, you can also demonstrate your abilities through a working holiday. Serving as a trial period, this will subtly show your CEO that you can handle the responsibility.

Emmi Buck, director of communications of Essential Oxygen, a company that creates oral hygiene products, first spent 10 days working remotely from Washington on a trip to visit family. “This was a great way to prove there were no aspects of my job that actually physically required me to be in the office,” she says. She now works remotely full-time.

Anticipate your employer’s questions

Once you are confident of your relationship, write a proposal to show your employer. Anticipate your boss’s expectations and concerns. Outline your responsibilities and provide a logistical breakdown of how you’ll accomplish them.

“It was a great way to prove there were no aspects of my job that actually physically required me to be in the office.”

When I decided to talk to my boss, I wrote up a list of my duties, a schedule for the next three months and a general strategy of how I would continue to work and communicate with my coworkers. Schaible took a similar tack by presenting her boss with a business plan.

“I outlined how each part of my role would be upheld or if it would need to change,” she says. “I laid out solutions for potential issues that could arise while working remotely and schedules for various time zones. We had a very open conversation about how the whole process would work.”

That open conversation and preparation led to her boss, Kate Levenstien, agreeing to the arrangement. “We both knew it was going to be an experiment and we were going to have to be flexible in order to make it work,” says Levenstien.

Make your case

When you’re ready to take the leap, schedule a meeting with your boss. Don’t just leave them a memo—you’ll want a lot of time to hash things out. Wait for the perfect time to pitch; for instance, after you’ve finished a big project or you’re due for a promotion.

As you make your proposal, stress the benefits. Remind them that working remotely will be a boon, not a burden, to the company. Cite stats that help your case: According to one survey by TINYPulse, an overwhelming 91 per cent of teleworkers say they're more productive when working remotely, and in general more engaged and loyal.

Chances are that your boss will have concerns, so have answers ready. Could you deliver progress reports? Absolutely. Would you visit in person every few months? Be open to this idea, and make a suggestion that will fit both you and them. Your plan should anticipate and answer all their questions before they even ask them. Emphasize email, video-conferencing and chat networks. Make their job simpler, not harder.

Keep the relationship strong

Once you get the go-ahead, you’ll need a few weeks to transition, and it’s up to you to make it as seamless as possible. Ideally, ease into it slowly—work in the office four days a week, then remotely for one day.

Organization and clear communication are the keys to success. “I use my Google calendar for everything, down to a coffee date, so that my coworkers know what my availability is like daily,” says Schaible. “It's important to communicate clearly and often with co-workers to ensure that we all stay on track despite the distance.”

Be candid with your boss and communicate regularly. Answer their emails promptly. Be available for chats or video conferences, and deliver reports on time. If necessary, invest in tools to make your life easier—whether it’s a laptop upgrade, a camera or headphones.

Try to schedule an office visit every so often. Remote work can be isolating. Chat and video can only go so far, and you might grow distant with your team. There’s nothing like face-to-face communication to keep yourself in the loop.

However, the true key to a successful transition is self-discipline. As a remote worker, you hold yourself accountable. Treat your new work style as a business, because for your boss, it’s business as usual.

This article was originally published in Verge's March 2018 digital edition.

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Published in Work Abroad
Wailana Kalama

Wailana Kalama is a freelance travel copywriter based in Stockholm. She's travelled through 40 countries and lived in six. Read more at waikalama.com and follow her on twitter at @whylana.

Website: www.waikalama.com

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