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Experts weigh in on how to approach your boss about working from home permanently

How to talk to your boss about continuing remote work
Posted at 2:57 PM, Apr 29, 2021
and last updated 2021-04-29 14:57:20-04

CHICAGO — As millions of people continue to get vaccinated, a return to some normalcy looks possible. Right now, companies across the nation are considering a return to the office. But what if you actually prefer to work from home?

Recent studies show many teleworkers don’t ever want to go back to the office.

“So, we know that over a third of the workforce says, 'you know what? I'm good. I want to stay home,’” said Wayne Pernell, a clinical psychologist, performance coach, and bestselling author.

However, wanting to stay home and being allowed to work from home are two very different things, and it could make for a tough conversation when your boss decides it’s time to come back to the office.

“I know that this sounds obvious, but sometimes when we are entering an emotional conversation like this, we can forget to do our work to be kind of grounded and to be clear on what we're asking, said Emily Golden, a master certified career coach and author of The New Golden Rule: The Professional Perfectionist's Guide to Greater Emotional Intelligence, A More Fulfilling Career, and A Better Life.

“Some people are finding 20 extra minutes in the morning to be able to be with their children to do their workout routine. It’s having them show up to work happier. They're more productive, so share that.”

Productivity is measurable. Have practical examples that you can work from home efficiently. Pernell suggests also trying to put yourself in your boss’ shoes.

“What do they need to feel secure in your being able to do that? Do you need me to check in from time to time? Do you need me to check in daily, weekly, monthly? What do you need from me to know that I am being productive, working remotely?” Pernell said of questions to ask yourself.

Pernell says it’s also important to understand it’s a negotiation.

“Business decisions aren't personal. So, if you go, ‘I love staying at home,’ it's whining. Stop it. Don't show up with some emotional plea,” he said. “Show up with the understanding that you staying home, you working remotely, will actually help the other person. Your being remote helps the business.”

Working remotely, experts say, shouldn’t mean being isolated. Using technology to stay connected is key to making your case.

“Being able to have some competence and confidence in being able to use the technology matters,” said Pernell. “We're using Zoom, we're using Slack. We're using various channels of communication that allow us to stay in touch in a moment's notice.”

“We've all been through this incredibly unpredictable, uncertain period of time,” said Golden. “We're heading into the next wave of that, so communication is key.”

But both experts agree, the most important part to this conversation is the willingness to be flexible.

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