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By Mallika Mitra
June 16, 2020
Calum Heath for Money

Just because you can start going back to the office doesn’t mean you want to — or that you necessarily have to.

Across the country, states are loosening up the restrictions they implemented to slow the spread of the coronavirus. If your office hasn’t opened back up yet, there’s a chance it will soon.

Some companies have taken the leap to a permanent work-from-home model. Twitter and Square led the tech industry in this change, telling employees in May that they can continue to work from home after the pandemic. Shopify and Upwork followed suit.

“Office centricity is over,” Shopify CEO Tobi Lutke tweeted.

Maybe working from home will become the new normal — but for now, these companies are the exceptions, not the rule. So if you want a commute-free work life, you'll likely have to ask for it.

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The good news is, navigating that conversation with your boss is "more opportune now than any time in history,” says negotiation expert Ted Leonhardt. Here's how to do it.

Know what you’re talking about

Knowledge is power — so gather as much of it as you can before setting up a meeting with your supervisor.

Stay on top of the messages your executives are putting out, Leonhardt says. If your company issues a press release with a line about how upper management is trying to cut costs, think about how having you work remotely might help them save money. If they seem concerned about productivity, consider how you can prove that you’ve been doing more in less time since leaving the office. Maybe your workday can start earlier because you don't have to commute, or you have fewer distractions in your home office.

You might also try reaching out to coworkers and trusted mentors at the company to see if you can gather intel on management’s plan to come back to work.

“Understand what the company's overall strategy is in the world,” Leonhardt says. “Align your desire to work from home with company goals.”

Write a proposal – whether or not you plan to send it

Mapping out exactly what you want to say ahead of time is a good move, even if you don’t plan on sharing what you write with your boss, says Lynn Berger, a career counselor and coach.

In this proposal, document all of the best work you’ve done while telecommuting, with specifics about how efficient you've been, she says.

Follow that with a few lines about your plan for the future, and how it will have a positive impact on the company — whether that's tied to your lack of a commute, fewer office expenses, or otherwise.

“You want to emphasize the win-win,” Berger says.

You don't have to share the actual written proposal with your boss, but it could be a good idea if your company relies heavily on documentation.

At the very least, it’s good to review all the great things you’ve recently done before broaching the topic with your boss, as it “preloads your frontal lobe with a sense of accomplishment” and “makes you feel good and worthy,” Leonhardt says.

Suggest a trial period

Consider asking for a three-month trial of working from home while the rest of the office opens.

Keep the focus on performance and productivity when suggesting the trial, says Paul Wolfe, senior vice president of human resources at Indeed. Offer to set milestones or OKRs (objectives and key results) that will keep you on track as you’re working remotely, he adds.

You also can offer to dip your toes in with a trial of two or three days a week. But avoid asking to work from home Monday and Friday out of the gate, Wolfe cautions.

“A boss might think you just want to take it easy on the days before and after the weekend,” he says.

Get some (digital) face time

Leonhardt once had a client who was up for a job at a big university, he says. The school flew her out for an interview, and she spent an entire weekend meeting potential colleagues. She got an offer, but promptly had it rescinded — all because of an email.

This client, Leonhardt says, sent a note outlining 10 questions she had about the offer, which, to the university, sounded like 10 demands. His advice? Next time, discuss it in a phone call.

Negotiating is uncomfortable, so it’s common for people to put it off, or put it in an email. But this is "a delicate issue and you need to be able to see their reactions,” he says.

“You're not pitching them,” Leonhardt adds. “What you’re doing is having a conversation about how you can make this work for both of you.”

You know you can work from home — after all, you've been doing it successfully for months. Hopefully your boss does too.

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