After you've gathered all of the information you need and assessed how remote work will benefit both you and the company, the next step is to present your plan. Rather than simply emailing your proposal, set up an in-person meeting with your boss that's convenient for their schedule.
"If you know Monday morning your boss is always really stressed out then you won't want to talk to them then," says Reynolds.
Once the meeting is scheduled, be as detailed as possible when discussing your request. If they agree to a trial period then you're one step closer to winning them over. If they say no, then Reynolds suggests waiting a few months before following up again.
"During that time, try to keep showing how reliable and productive you will be by working from home," she adds. "For example, if there is a snowstorm and you can't get to the office, use that time to show your boss how working from home can actually boost your productivity."
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