How to talk your employer into letting you work remotely

As millennials continue to redefine success and performance metrics, the idea of an office doesn’t just feel outdated, but unnecessary, as nearly every meeting, brainstorm and deliverable can be completed online. This mentality motivates younger generations of professionals to challenge the cubicle environment, arguing that since their jobs don’t require a physical space, why can’t they complete their assignments and pull reports from say, Bali? Or Japan. Or Prague. Or anywhere.

And hey, if you aren’t on a mission to rack up passport stamps or join the digital nomad community, negotiating to work from home a few days a week can help clear your mind and free space for creativity and save on expenses — like childcare or dog walking. While it might seem like a win for an employee, as they country hop while still earning a paycheck, career and executive coach Maggie Mistal explains it’s also a bonus for employers. Especially since they not only save on office space and electricity, but they get the bonus of happy, satisfied workers who achieve a stronger — and more inspired — work and life balance.

“There are many benefits to remote work, including fewer distractions and the ability to get through thought-requiring work quickly and easily. Remote workers also have greater productivity because they spend less time and energy commuting,” she explains. “This creates a stronger feeling of engagement in their job and a commitment to their employer, thanks to an improved quality of life because they can get the work done on a schedule that works for them.”

To get your boss to adopt this trending lifestyle, take it from remote employees who managed to free themselves from that 9-5 tango, to dance on laptop keyboards across the continents:

Consider having a few years of experience first

While strategic account director for Stylus Media Group, Emily Mitnick was presented with the opportunity to travel the world for a year while maintaining her career — it was a dream come true. She knew convincing her boss to adopt her proposal would be a tall order — but one that she felt ready for since she had paid her dues. That’s why she stresses the importance of working for a company or in your industry for a few years will give you tangible proof of your abilities, talents and skill sets. “I worked really hard over my years at Stylus and am really passionate about what we do. I positioned working remotely as a way to develop and grow my role in the organization and also help grow the business,” she shared. Because Mitnick had developed trust and repertoire with her employer, they knew she could deliver the same — and even better — results than she did while logging hours stateside.

Pitch the idea to the person you’re the most comfortable with

It’s inevitable you’ll develop close relationships and friendships with people you burn the midnight oil with, especially when you wade through tough quarters, moody clients and deliverables together. When preparing to ask to work remotely, it can be helpful to gauge the temperature of your company by first going to those you’re most comfortable with, according to brand and marketing strategy consultant, Jordan Rosenbaum. Currently traveling the world while working with a myriad of clients, Rosenbaum first approached the idea of remote work with his former company. To jumpstart the process, he had candid conversations beginning from the bottom up, all of which helped him prep his case. “Definitely start with those you’re closest to in your office so they can help provide feedback and advice that help you better prove your ability to work out of the office,” he explained. While ultimately Rosenbaum’s employer didn’t sign-off on a full-time gig, they did grant him the opportunity to work part-time. The experiencing of bargaining for remote work proved to be invaluable for Rosenbaum, as it prepared him for a freelance career where he’s his greatest proponent.

Come prepared with facts

It pays to be a perfectionist if you want to file reports from a coffee shop in Copenhagen or meet a last-minute deadline in Hanoi, more than 12 hours ahead of your employer. As both Mitnick and Rosenbaum explained, coming armed with a strong argument, facts, statistics and outlines were essential to their propositions. This is your reference guide for detailing the why, the when, the where and most importantly, the how of remote work. “Prior to the meeting, I spent many hours preparing a very detailed business case. I got creative and even built my business case using our own internal Stylus collateral that we use for sales pitches. I work in new business development, so I thought this would be a strategic approach. Throughout the slide deck, I addressed topics about the program I wanted to join, why it mattered to my company, why it mattered to me, why it was a solution to our company and my personal life and more,” Mitnick explained. “I used our own internal Stylus analytics and trend research around ‘The Future of Work’ to support my business case. I essentially positioned the program as a platform to bring our research and trends to life.”

Even if you don’t work in the trend forecasting space like Mitnick, Rosenbaum explains the idea of appealing to millennials is a persuasive stance, too. Because nearly all industries want to entice this tech-focused generation, remote work can help modernize their offerings, making them more attractive to not only potential customers but to prospective employees, too.

Stress your ability to self-motivate

Though sure, the view of a sunset over the islands of Thailand or the cityscape of Kuala Lumpur are more interesting backdrops than a white wall in your office, Mitnick warns sometimes the view can be distracting — and at times — detrimental to work. Employers are aware of this too, and not physically seeing you daily by the coffee pot could make them hyper-conscious of your ability to self-motivate. That’s why Mitnick stresses the importance of demonstrating your dedication. “You need to be a certain type of person to manage it all. When you’re traveling the world — moving every month, learning a new language and adjusting to time zones — it’s a lot to adapt to and work at the same time.”she says. “While Instagram may paint a beautiful picture, the digital remote life is tough! I think if you are convincing your boss to let you go on this adventure, you need to have a valid purpose and have gained the respect and trust within your organization to do so.”

Even with the difficult days though, Mitnick says the experience has proven to be beneficial for her, tenfold. Not only is she happier and more fulfilled, but she says her quality of work has improved. “Working remotely while traveling the globe takes an incredible amount of discipline and motivation. Even so, I’ve never felt more creative or rejuvenated at work and I am doing my absolute best to apply this new energy and perspective to grow our business globally.”

Detail your plan and anticipate questions

If you’re piqued the interest of your manager and they’re considering your proposal, now is the time to get specific. Sitori Holbrook, an audit senior associate at Tanner LLC explains a smart, specific outline was instrumental in convincing her company to let her work remotely. “By presenting a detail plan and thinking though possible contingencies and scenarios they could build their own plan off mine, they didn’t have to figure out for themselves how it would work and it proved I was committed to my goals,” she says. “On a calendar, I detailed my current workload and which clients I thought I would be able to continue to work with remotely, which clients I thought could better transition to staff who would be on site, how that transition would work, and which clients I proposed to fill in the open time on my schedule with.”

Having this outline helped answer lingering questions her company had about her role abroad, and Holbrook added it reassure them that her quality of work wouldn’t change. Even if she takes a day off to visit an elephant sanctuary, she makes up the time on another day, giving her the flexibility to explore and her employer the trust she can always meet deadline, no matter where she is or what comes up. “Before I worked remotely, work was the main focus of my life and I lived my life around my work schedule,” Holbrook added. “Now as much as possible I work round my life schedule. Sure, working on a Saturday can suck, but it’s small price to pay for taking part in once-in-a-lifetime invitations that come up when you’re a nomad. It’s worth it.”