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Convince Your Employer to Let You Work From Home

The dos and don'ts of getting past the "on-site only" job requirement

You’ve spotted an opening on the job board for the perfect full-time or freelance gig, but the position is based miles away. What do you do—apply anyway?

Although most media professionals can do the majority (if not all) of today’s work from a home office simply with a decent Internet connection and a working phone, not every company is open to flexible working solutions. If a listing explicitly states “on-site only” and you don’t live within commuting distance, warns John Poore, a director of staffing services who works with Facebook, don’t even waste your time applying, as those companies may have had bad experiences with remote employees. “You’ll spend more of your time on their objections,” he says.

Yet, with a little research and a positive attitude, it is possible to convince a hiring manager that you’re the right person for the job, regardless of your location. Here are some dos and don’ts to help you get past that “in-house” mentality.

DO: Assess your own candidacy

Taking time to see if you’re a match for the position is important, because then you can build your elevator pitch around it. “For the best candidate, companies will become flexible,” Poore notes.

But that entails proving you are the best, so it’s important to consider a few things before pressing forward: Are you set up to work from home with regard to equipment, space, privacy and self-motivation? Do you have systems in place to track time spent on projects? If you’re trying to convince an employer to embrace a new arrangement, the onus is on you to prove that you’re worth it. So, arm yourself with evidence to rebuff any possible objections.

DON’T: Pitch working off-site off the bat

Caroline Ceniza-Levine, a career expert based in New York City, says expressing your desire to work remotely in a cover letter is a huge no-no. “It is potentially a turn-off because it requires the employer to accommodate you,” she says. “Now, it might not be hard to accommodate you, but until you know more about the job and company, you don’t know that so it’s presumptuous on your part.”

Instead, concentrate on impressing the hiring manager with a strong resume highlighting your skills and experience first. Once you’ve secured an initial interview, then you can present your case. “Get the employer to want you, and then figure out all the details to make off-site work good for both of you,” says Ceniza-Levine.

DO: Devise a practical plan

The best time to negotiate is when the employer is interested. Ceniza-Levine advises media professionals put themselves in the employer’s shoes and come up with a logistical plan on how telecommuting will work. “How you will communicate with the team, do you need any special equipment or access, how you still stay connected to the office culture…” she notes.

Let the company know during that first interview that you want a flexible work option. If you wait until a second or third interview, the company could feel like they’ve been misled, Poore adds.

“When you think about the ability to work remotely, it’s all built on trust,” he notes. So, once you make that connection, let the person know upfront that you are interested in flexible work and demonstrate that you can save the company time and money by doing so.

DON’T: Make it all about you

When pitching your proposal, be open to what will work best for the company as well. A good idea is to ask if other employees have flexible working arrangements and how they operate. You may be able to state that you can emulate an already-successful model, so the company doesn’t feel like it’s creating a new platform just for you.

Another tip is seeing how your potential superiors like to communicate. If they prefer conference calls to email, offer to accommodate their preference. They may want a daily check-in via Skype, email or IM, or require that you be available for in-person meetings. You want to show that you’re open to developing the working relationship and that your plan is just a starting point that can be fine-tuned if necessary.

“Build your strategy around what makes it easy for your manager and colleagues,” says Ceniza-Levine. “This is what keeps resentments at bay… when people don’t have to accommodate your off-site work habits, they won’t mind.”

Poore says that offering to discount your rate is another appealing approach for many companies. “You have to be willing to have a trade off as well,” he adds.

DO: Offer to put in face time, if you can

Again, an ability to come into the office when you’re needed can really help you land the gig. Many companies want to see and interact with the people they’re paying. After they know who you are, they may be able to offer a virtual work option.

That’s worked for Alisha Miranda, a freelance writer and social media manager who has telecommuted from her home in Brooklyn with teams in Manhattan. One strategy she has used to convince clients that she can be a valuable member of a team is by offering to attend monthly meetings in person or via conference calls. In her case, most of her clients have been close enough to make an occasional meeting doable.

She has successfully interviewed for full-time positions in the past and persuaded the company to take her on in a freelance, telecommuting capacity. “It’s about proving yourself as a valuable asset and negotiating shorter-term gigs,” she says.

DON’T: Get too comfortable

We talked about sweetening the deal and building trust; a great way to do so during your pitch is to offer a two-week trial period. Give the company the option to reconvene later to determine the long-term potential of your flexible work agreement, Poore says.

But make sure to put the agreement—and any metrics that will gauge your success—in writing. You can come back in two weeks and say things are going great, but the employer may want to see a list of projects completed, the time it took and how you saved them time and money. So, include quantifiable results in any reports you create on your progress. And if the employer says it’s not working out, stop the sales pitch right there. You don’t want to beg for work or be an inconvenience.

DO: Have strong references handy

Poore says that another way to get the gig is to demonstrate that a flexible arrangement has worked for you (and other organizations) in the past. The best way to do that is to get previous clients to highlight your competencies and your ability to work under little direction. “Once that first project is under the belt, it makes it easier to do that again,” Poore adds.

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