How to Convince Your Boss to Let You Work From Home Forever

Pete Ryan for Money
Pete Ryan for Money

Nearly two years ago, employees across the country left their offices as headlines warned of a mysterious new virus that had hit the U.S. Now we’re headed into 2022, and COVID-19’s Omicron variant is pushing the return to work back once again.

For some workers, this is welcome news.

A survey conducted by FlexJobs this summer found that 97% of workers want some kind of remote work option, whether it’s a full-time or hybrid situation. Nearly a quarter of respondents said working remotely is so important, they’d even take a 10-20% pay cut to make it happen.

Some companies, like Twitter and Shopify, told employees they could work from home forever during the early days of the pandemic. Others, like Spotify, are giving employees and their managers the flexibility to figure out what works best for them. But some companies are planning on bringing workers back to the office full-time, and things are getting messy fast. Apple, for one, announced intentions to require employees to return to in-person work for at least part of the week, and suffered a barrage of criticism — and employee petitions — as a result.

There’s no way of telling what work will look like in 2022, but if you’ve been loving a commute-free 9 to 5, you might be able to keep it — even if your boss has plans to bring you back.

Here’s how.

Make a business case for staying home

Before you meet with your supervisor, pay attention to the messaging your company is putting out. If your CEO has announced cost cutting, think about how remote work helpz save money. If upper management is concerned about productivity, prove that you’ve been doing more in less time since leaving the office. Maybe your workday starts earlier without a commute, or you have fewer distractions in your home office.

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

Put your thoughts on paper

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.

Write a proposal documenting all of the best work you’ve done while telecommuting, with specifics about how efficient you’ve been. 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,” she says.

Suggest a trial period

Float the idea of working remotely for a three-month trial period while the rest of the office opens back up.

Again, you’ll want to focus your ask around your own performance and productivity, says Paul Wolfe, former vice president of human resources at Indeed. And offer to set milestones and OKRs (objectives and key results) that will keep you on track as you’re working from home.

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

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 [your boss’s] reactions,” Leonhardt 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 successfully — you’ve been doing it for the last two years. With a little convincing, your boss should be able to recognize that too.

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