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How to Convince Your Boss to Let You Keep Working Remotely Post-COVID

by Elizabeth Alterman

When COVID-19 first forced non-essential employees to work from home, the shift may have been jarring if you’ve never telecommuted (and maybe even if you have, just not during a pandemic).

But the experience may have led you to recognize the appeal of the virtual office. And it’s easy to see why. Working remotely offers a range of benefits, from enjoying a more comfortable environment to saving time and money by skipping the commute. Or maybe you’ve long dreamed of working from home, but didn’t feel you could ask because it wasn’t common at your company or in your industry.

If you’ve realized over the last few months that you prefer working remotely and want to stick to it in the long term, you’re not the only one. Nor are you alone if factors like childcare options or safety concerns mean you want to keep at it for the medium term. And you may have a good chance now to make it happen.

For many, this period has allowed them the unique opportunity to show their managers that they have the ability to work responsibly and efficiently outside the confines of the office. Some bosses, however, may still be on the fence about allowing employees to remain at home.

Here are eight steps you can take—starting right now—to help you make it happen.

1. Track Your Productivity

As you gear up to request a more permanent WFH arrangement, the silver lining of the pandemic and mandatory work-from-home orders is that you probably won’t have to go through a trial run first.

“Under ordinary circumstances you might have had to convince an employer to provide you with the opportunity to illustrate that you can be just as productive at home, if not more productive, than if you were required to report to the office,” says Lori Rassas, executive coach and author of The Perpetual Paycheck. “Now, most of us have been granted an audition. Take advantage of this opportunity to see what works best for you and to educate your employer, who might not have had much experience with remote workers, about the benefits of [a] work-from-home arrangement.”

That means collecting evidence from the time you’ve spent working from home already that will help you build a case for continuing to do so later. Tracking tangible data around your productivity and deliverables—using tools like RescueTime—and then presenting your boss with statistics and examples can go a long way toward convincing them that this arrangement can be good for both sides. For example, if you’re in customer service and you’ve taken more calls or resolved more issues, let your boss know. “Highlight how much more productive you have been from home,” says Henley Griffin, career coach at SAHM Jobs Center.

Of course, living and working through a pandemic brings inherent stress, especially if you’re juggling your job with childcare and other responsibilities. Given that, it’s understandable if you didn’t hit the ground running or have had some bumps in the road. But if you’ve been able to make it work despite all of these additional factors, it can be all the more impressive and hint at what you’ll be capable of in post-pandemic times.

2. Collect Your Work-From-Home Wins

Don’t be shy about putting together a list to showcase your accomplishments while working from home. Because the first half of 2020 was particularly stressful due to the pandemic, your achievements and the ways in which you supported your team—and your manager—during this time may carry more weight.

Create a one-page document to compile your wins and list out the reasons you’d be a more impressive employee if you were allowed to remain working from home, recommends career coach and success strategist Carlota Zimmerman. Ask yourself these questions to see what you can highlight:

  • Which projects have you completed on time (or early)?

  • How many new clients have you wooed and won?

  • Have you kept your team under budget?

  • How much money have you saved the company?

  • Did you successfully transition a process to a totally virtual environment?

  • What kind of positive feedback have you gotten from colleagues, managers, leaders, and clients during this time?

Amanda Augustine, a career and resume expert, recommends creating a “brag book” and updating it frequently. Some people may choose to record their accomplishments in a Google document or an app like Evernote, which can be updated from any mobile device. No matter how you capture it, “all of this information will help you demonstrate how effective you can be to the company while continuing to work from home,” Augustine says.

3. Be Responsive and Present

Again, if your company hasn’t started transitioning back to the office yet, use this time to help you make your case later. When they’re evaluating your request, your boss and company will surely look back at your behavior during the mandatory work-from-home period as proof that could help—or hurt—you.

Just because you’re not physically in the office, that doesn’t mean your presence isn’t expected. Being online and quick to respond to emails and meeting invitations shows that you’re available and on top of things.

It's easy to get into your own little bubble when working from home, but that’s something that you should try to avoid, notes Griffin, as this can weaken your case for working remotely. With this in mind, stay on top of emails and be ready to hop on a call or join a meeting during the hours you’re “at work,” the way you would if you were in the office.

“If your employer doesn't offer it, then suggest setting up a company Slack, Skype chat, or other way to stay connected,” Griffin adds. “This helps working from home feel a bit more normal—and keeps in you that ‘work’ mindset—since you can easily talk with coworkers and the boss.”

4. Take Into Account Any Post-Pandemic Changes to Your Role

Before you propose a permanent work-from-home schedule to your manager, level with yourself to determine if working remotely full time is truly possible once your company heads back to the office, or if you’ll need to adjust your proposal to meet the needs of your job, Augustine says. Consider the following:

  • Which of your responsibilities, if any, had to be put on hold during COVID-19 because they proved to be too difficult or unrealistic to perform while working from home?

  • Were the expectations lowered for certain projects while everyone was sheltering at home? If so, do you anticipate those expectations to change once things resume some form of normalcy?

  • Are you managing a team that will be expected to return to the office? If so, will your team require your presence on-site?

  • Is your home office truly conducive for performing your job well, or have you merely been making it work the best you can since the lockdown began? For instance, is your internet connection or phone service spotty?

If you find that any of these could impact your chances of working from home, consider how to address them, as your manager will likely want answers before making a decision.

5. Start Talking About It Early

Once you’ve realized that you’d prefer to work from home, start the conversation sooner rather than later. But keep in mind the old adage that timing is everything. “It's wise to think of everything that’s going on in the business,” says Ben Taylor, founder of Home Working Club, an advice site for home-based workers. “Raising something like this when there’s a project deadline approaching and everybody’s stressed is obviously not a good idea. But suggesting it when you’ve just done a great job of something and you’re in the bosses’ good books is a good idea.”

Since there’s no hard and fast rule, it’s best to use your intuition on this, but if there’s a formal plan for reopening you may need to take that into account too and ensure your request is considered as part of the process, Taylor adds.

It’s better to start laying the groundwork or doing a little digging sooner rather than later. When you have your next one-on-one meeting with your manager, ask about the company’s timeframe for reopening, if you haven’t already been told. Then, ask if the organization is open to allowing employees to continue working remotely in either a full- or part-time capacity.

While you don’t need to launch into your request quite yet, you can also start planting the seed with your manager by letting them know how productive and focused you’ve found yourself to be while working remotely. Use this informal chat as a way to assess your manager’s response and then tailor your proposal in a way that overcomes possible objections and offers compromises that work for both of you.

6. Approach Your Manager

Once you have a sense of your organization’s overall policy on remote work, your next step should be to broach your specific request directly with your manager. Whenever you decide to bring it up, try to have the conversation over video instead of a phone call. This will allow you to observe your manager’s body language and help you gauge whether your proposal is being well-received.

What do you actually say? Taylor suggests getting right to the point by saying, “As you know, I’ve now been working remotely for x weeks, and in that time I’ve….” and then list some very specific examples of how you’ve performed and excelled.

Discuss what you and your team have accomplished during this challenging time while working from home. For example: “We launched the new mobile customer portal on time and under budget,” Or, “I’ve rolled out the new newsletter, which has already increased site traffic by 15%, securing 30% more media coverage year-over-year.”

Then be direct by saying, “I’d like to continue working from home on a regular basis once the office reopens.” If you sense hesitation on your manager’s part, show some flexibility by adding, “Of course, I’m happy to meet in the office whenever a face-to-face meeting is necessary. Are you open to such an arrangement?”

“I’d suggest following up the meeting with something in writing, which could be anything from a summary of the points discussed to a full and detailed proposal,” Taylor says.

7. Make It About Them

Just like when you’re asking for any other workplace benefit, the key to success is to make the request about your employer instead of about you, recommends Rassas. “The idea is to figure out what you want, and present it in a way that benefits the employer,” she says. As an example, Rassas shares that she once had a client who informed her she was going to ask for a flexible schedule, including multiple work-from-home days, so she could spend more time with her family. But Rassas helped her successfully reframe the request so she could lean on how it would help the company rather than how it would benefit her personally. “When I learned that the employee had a lengthy commute to and from work each day, I suggested she focus on the fact that with the elimination of her commute, she would be more readily available for early morning meetings, which was appealing to the employer because the company had clients in different time zones,” Rassas says. “This had the potential to be a win-win situation.”

8. Offer a Compromise or a Trial Period

If parts of your role can be executed more smoothly when they are performed from the office, consider proposing an arrangement that would allow you to work remotely most of the time and only come into the office a couple of times a week to handle those responsibilities. “With so much attention focused on social distancing and spreading out, a recommendation centering around reducing employee traffic at the office...could also be a way to compel your employer to seriously consider your request,” Rassas says.

If office space previously was at a premium, or your employer is considering downsizing to a smaller facility due to the pandemic-related economic downturn, the thought of fewer workers on-site on any given day may appeal to management.

Another way to make it easier for your boss to say yes? Starting with something temporary that will give them an opportunity to see how it goes before they commit to anything permanent. “Suggestions of doing things on a trial basis are always good—perhaps starting with just a couple of days per week, or trialing the idea for a set period with an agreement to review afterwards,” Taylor says. Make sure you’re open to feedback and ready to make adjustments, if necessary.

“There’s probably never been a better time to propose home working arrangements,” Taylor says. “Employees who’ve already shown themselves to be completely effective throughout the pandemic will likely find their bosses need a very solid argument as to why the arrangements cannot continue, at least in some form. The genie is very much out of the bottle.”


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