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Want To Work Remotely? Here’s How To Talk To Your Boss And What To Consider Before You Make The Leap 

Melanie Brooks  |  October 17, 2019

Working in your pajamas might sound like an ideal situation … but think twice. Check out the pros and cons of telecommuting before teeing up a remote work policy at your company. 

Brian Rahill wanted to be there for his family when his kids got home from school, so he built a home-based business to accommodate. Today, his company, class registration software CourseStorm, has a thriving culture of employees who telecommute, or work remotely. “I understood early on the value of being able to work from home,” he says. “We started implementing remote work opportunities as soon as the technology could support it.” 

One of his employees, Becky Willough, who provides tech support and customer service for CourseStorm, says the ability to work from home has been a game-changer for her day-to-day life. Even with no traffic, her commute into the office would be over an hour each way. “Telecommuting is important for me because it suits my personality and work ethic,” she says. 

Today, the majority of U.S. companies — 63% —  have remote workers, according to a 2019 Upwork Study, and according to Gallup’s State of the American Workplace Report, 43% of employees work remotely at least some of the time. We Work Remotely has seen a 700% increase in the number of jobs posted since 2013.  Still, depending on your company or your personality, a remote job isn’t always perfect. 

How To Know If Telecommuting Is Right For You 

“Some jobs are conducive to telecommuting … and some are not,” says Lisa Shuster, president of PeopleWorks, LLC. For jobs that are collaborative in nature, Shuster says research suggests that those types of jobs are better kept in-house. “Innovation and brainstorming is better when done in a group,” she says.

Likewise, if you’re young, living in a new place, or thrive on social interaction, telecommuting might be tough. Donald Asher, career guru and author of “Who Gets Promoted” suggests that workers who are right out of college should take advantage of what they can learn in an office environment. “There’s a lot of advantage to showing your face at the office,” he says. “Recent graduates aren’t getting the socialization from working in high school. They’re waiting until after college to get those soft skills. And by telecommuting, they’re not getting them at all. If a young person doesn’t go into the office, they’re shorting themselves.”

Asher points out that younger people may be prone to more loneliness than older people. “If you’re in a new city working from your apartment and you don’t have any friends yet, [telecommuting] is isolating,” he says. Work gives you a social outlet  — the proverbial “water cooler.” If you’ve ever watched an episode of “The Office” you know what I’m talking about.

On the flipside, employees like Willough, who have the drive to work independently, and are performing jobs that require concentration, are often excellent candidates for work-from-home positions. “If you have a history of being a strong player and meeting your deliverables, there is less of a question of if you’re really doing the work if you’re working remotely,” Shuster says. 

Creating a Plan to Work Remotely

When Willough first applied to CourseStorm, the job she was interested in wasn’t advertised as a remote position. During the interview process, she talked with her now-supervisor about her long commute and her inability to travel more than two hours a day on a permanent basis. “At the time, I thought this conversation was me basically saying, ‘I’m really sorry, but I can’t pursue this job,’” she says. “Much to my surprise, I was offered the position as a remote worker. I was ecstatic!” 

Shuster says that if you’re interested in remote work, negotiation with your supervisor may or may not need to happen. If your job is one that can be done out of the office, she suggests putting together a list of talking points that detail exactly how you’ll stay on top of your work while being offsite. Your list should include things like: 

  • Communication. This is the No. 1 challenge of remote work. How do you plan to attend meetings and stay in contact while off site? (At HerMoney HQ, where we have team members in Florida and California, we love a good Zoom meeting.) 
  • Defined work hours. Since you’re not going into the office, people need to know exactly when you’ll be available for communication.
  • Location and time zone. Where are you going to be doing your work? If it’s in another time zone, how will you work to accommodate the rest of your team?
  • Clearly defined goals, objectives and outcomes. You must ensure ensure that there will be no difference in the level of service you provide when working remotely.
  • Safety considerations. You need to have a safe, secure and ergonomic environment. If you are hurt in any way, it could become a workers comp issue. 
  • Privacy considerations. How are you going to protect records, materials, technology and sensitive information? If you work with confidential information, you need to have a plan.
  • Boundaries. Telecommuting is not a solution for day care. A crying baby, noisy kids or a barking dog can send red flags to your manager. Your remote work location can’t have distractions. 

A Look At The Benefits — For Companies And Employees

For CourseStorm, which is based in a relatively rural part of Maine, offering remote work accommodations broadens their pool of potential employees. “We saw that requiring everyone to work from the office would have held us back,” Rahill says. “We recognized that if we wanted to seek excellence, we’d have to be open to different kinds of working arrangements. Being open to telecommuting has allowed us to hire incredible people, and keep them with us in a competitive job market.” 

Also, while it may be obvious that working remotely will cut down on transportation costs and the stress of commuting to work, it also helps to reduce carbon emissions and overall costs for employees — they can reduce costs on gas, wear and tear on their automobiles, and the number of lunches they buy out every week. 

From a human resources perspective, Shuster thinks the benefits of telecommuting far outweigh the costs. While she says that the missed collaboration can sometimes be a problem, you can’t put a price on employee retention. When employees are happier, more productive and more relaxed when they are working from home, that translates directly into the service they provide to clients, she says. “That literally results in increased revenue, profit and shareholder value.”

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