Negotiation Skills

Making the Pitch to Work Remotely: Best Practices to Boost Your Odds of Success

work from home; work remotely

Gig, remote, or contract work is on the rise according to many reports.

Yet some employees already in traditional jobs find it daunting to consider how they might raise the issue of working remotely.

What are some best practices here? How should you make the pitch for working remotely?

How to Work Remotely 

Andy Abramson is CEO of Comunicano, Inc., a remote agency he’s operated for more than 25 years.

When it comes to how to work remotely, Abramson says that knowledge workers are best positioned. “Knowledge workers are the biggest category of workers who can most easily work remotely,” he says. “People who write or code are ideal to have working remotely as long as they have a means to communicate with colleagues. Publicists, analysts, and consultants are also good at remote work, but the tools for them need to be in place to succeed.”

“Asking to work from home shouldn’t be an issue these days,” says Abramson. “Better broadband connectivity, the use of smartphones and tablets, and simply better tools that allow people to work remotely these days have made it easier to accomplish.”

Yet, while technology is prevalent and working from home is technically possible, other barriers may get in the way. Most notably, some managers’ continued concerns about their own ability to effectively manage remote workers and pervasive concerns that employees working remotely may be less productive and more prone to personal distractions.

Also read: 7 Questions to Ask Yourself Before Making a Hard Descision at Work

Making the Pitch

Recognizing the perspective of your employer/manager and what’s important to them is critical in making the pitch for working remotely. Considering the technical necessities outlined by Abramson is a good starting point. In addition, though, it’s important to consider some of the soft skills that become particularly important in an “out-of-sight” working relationship.

Being a valued contributor definitely helps, as Kathy Kristof well knows. Kristof made her pitch to work remotely almost 30 years ago which working at the LA Times. “I set up a home office at my own expense, I volunteered to work while on maternity leave to establish that I could do it effectively and I made it clear that this was the only way I could come back to work,” she says.  Since that time, Kristof has also worked from home for Kiplinger, CBS News and others and is not the editor of, “the Consumer Reports of the gig economy,” she says. “We research, review and rate the only platforms that allow you to make money.”

Janet Matta is a career strategy consultant and runs a consulting company on remote working. The first step in making a pitch, says Matta, is to “observe, consider, and research your company’s culture around remote work”:

  • Do other people work remotely?
  • Are those other people doing work similar to yours?
  • What are the existing policies around remote work?

Consider objections, advises Matta. “Often, concerns around remote working center on fears about reduced integration with company culture, lack of communication, and trust,” she says. “Companies that do not already have a remote working culture may fear that remote workers are less productive because their work is less visible.” Think also, she advises, “about your company culture and what might be important to your leadership.” Consider how you can address these concerns and make this part of your pitch.

In crafting your case, Matta advises, included these elements:

  • Be specific about what you are asking for (Fully remote work? Working one day a week remotely? Working remotely on an as-needed basis?)
  • Share the expected benefits and value to the organization
  • Talk about any existing successes with working remotely if you’ve had them
  • Be sure to anticipate and address objections

Importantly, your pitch should focus on what’s in it for the company and not what’s in it for you.

Also read: 10 Things Smart People do to Enhance Their Reputation at Work

Taking the Employer Perspective

Tara Lopez is benefits manager at Konnect Agency. From an HR perspective, she says, this is how the company handles requests to work remotely. (Hint: these are the points to consider and address in your pitch to ensure you’re addressing company concerns thoroughly.)

  • Does a work-from-home (WHH) program fit the company culture?
  • Is the team ready for a WFH program?
  • Is the organization set up for a successful WFH program?
  • What tech items will need to be in place to ensure employee success?
  • How will a WFH program affect the organizational goals?
  • How will teams, managers, executives and clients by impacted?
  • What are the potential issues that might emerge?
  • What are the potential gains?

Finally, Matta suggests, consider proposing a pilot, rather than asking for an immediate and permanent change. During the pilot make sure to check in and identify, up front, how you will evaluate success.

Once you get the green light, here are some important points to help you boost the potential for success.

Making it Work

Making a remote relationship work requires above all, communication. Here, say Kristof and others, the onus is really on the person wanting to maintain the remote relationship. She recommends:

  • Send your boss an email every morning when you start work, telling him or her what you’re up to that day and whether you’ll be out of the office at any point during the day.
  • Make yourself available for in-person meetings, if possible, especially if working on group projects.
  • In addition to managing your boss, you will need to manage your friends and family. They may “think that you have time to socialize because you’re at home” Kristof warns. “Be clear. Home is your office; you have office hours; socializing during office hours is not possible.”

Bottom line: communicate, communicate, communicate. “You don’t have the luxury of being able to walk down the hall—or be seen in your office pulling your hair out over a project that’s not going as planned,” Kristof says. “You will need to keep everyone up to date on what you’re doing so they know when you’re hitting snags and why.

Looking for More Help with Working from Home?
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About the Author

Lin Grensing-Pophal is a freelance business journalist and content marketer with a wide range of writing credits for various business and trade publications. In addition to freelance writing for trade journals and publications, Grensing-Pophal does content marketing for Fortune 500 companies, small businesses and individuals on a wide range of subjects, from human resource management and employee relations, to marketing, technology, healthcare industry trends and more.