How to Tell Your Boss You Want to Work Remotely Forever (and Get the Answer You Want)

published May 5, 2021
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Credit: Lula Poggi

For many people, being well into year two of the pandemic means they’ve spent more than a year getting used to working from home. Sure, people worked from home before the pandemic, but millions more people suddenly found themselves scrambling to put together workstations after years of commuting and traditional office life. 

While remote work definitely required some adjusting — no more in-person lunches with coworkers or impromptu deskside brainstorm sessions — your WFH routine probably feels familiar by now, and honestly? Now that more and more workplaces are announcing a return to in-person, you might find yourself not-so-excited about ditching the no-commute, hard-pants-optional set-up. As long as your job description doesn’t require in-person duties, shifting to a permanent remote role might be a possibility. But before you pitch the idea to your boss, take a look at the big picture. 

According to telework expert Christine C. Durst, co-founder of the virtual job search site Rat Race Rebellion, your manager might be sympathetic to your needs. Ultimately, though, your supervisor and the company you work for as a whole have their own goals, and switching to a full-time remote-friendly system might not be one of them. “Though it may sound cold, if a company starts making decisions based on ‘feelings’ instead of earnings, profits may suffer and jobs may be put at risk — including yours,” says Durst.

Vicki Salemi, a career expert at Monster, says whether your supervisor goes for the pitch depends on factors like your job description, your company’s policies, and your boss or department’s culture. One surefire clue your ask might be worthwhile? “If you already have people on your team working full-time remote, then it may be an easier decision from your boss to continue having you work remote than if you would be the only one,” she says.

If you’re ready to start the conversation about working from home forever, here’s how to boost your chances — and how to deal if your boss says “no” or “not yet.”

Plan a formal time to talk.

The first thing to know: Even if you have a great relationship with your boss, asking to shift your role to fully remote isn’t a casual conversation topic. Resist the urge to discuss the change via Slack or email and instead, schedule a video or phone meeting. “Don’t just casually spring this on your boss,” says career success strategist Carlota Zimmerman, J.D. “Request a meeting with her, and show up with a plan explaining what it is you want, why it’s beneficial first and foremost to the company, and how it will help you be an even better employee.” 

Don’t schedule the meeting without any details, either. Melissa Smith, a remote work consultant and the founder of the Association of Virtual Assistants, says it’s a good idea to give your employer a heads up about the meeting topic. “If your employer has not had time to prepare or worse, feels blindsided, you are already at a disadvantage,” she says. Either message your boss asking to discuss working remotely during the meeting, or include information in the meeting invite. This isn’t your pitch, however, so keep details short and sweet.

Come with data to prove your case.

Once you get a time and date on the calendar, it’s time to build a case that convinces your boss the switch will be worthwhile for your department and the company as a whole. Zahria Little, a career coach and executive recruiting manager at JMJ Phillip Executive Search, suggests thinking about your upsell for working remotely as a job interview. Just like you came ready to list your accomplishments and capabilities when you applied for your role, prepare to flaunt your WFH successes.

“Collect data and research how productive you’ve been since working from home, and present that information to your boss,” Little says. “Talk about how you’ve been able to consistently meet KPIs and metrics since working from home, and why you’d like to continue that long-term.”

Share your plans for future success.

Your past successes help to paint a picture of whether you’ll do well working remotely on an ongoing basis, but it’s also your job to illustrate how you’ll do a stellar job moving forward. The goal is to help your manager envision both how you’ll continue making important contributions to your company, and how you’ll function on a daily basis. “You are the one who wants to enact changes, you are the one who needs to come to this meeting with concrete ideas and solutions,” says Zimmerman. 

For example: Career coach Maureen Crawford Hentz says while there are very few actual job descriptions that actually require people to be on site, your boss may be concerned about how you’ll engage with the team (your manager included) on an ongoing basis. In your meeting, describe how you’ll make it easy for your boss to stay abreast of how you’re handling your work and how you’ll interact with other employees. 

“What the business wants is to ensure availability for informal drop-ins, which can be virtual,” says Hentz. “Talk about your availability and times when you both reached out to colleagues and were reached out to.”

It’s also a good idea to outline how this plan will continue to make life easier for your boss, too. “Do you have a plan to make it easy for your boss to keep an eye on you, and easily know what, at any given time you’re working on? This is a great time to tell her,” says Zimmerman. “During the past year of working remotely, have you and your team created a great method of communication thus making the office almost irrelevant? Speak up and share!”

Be flexible (and patient).

Keep in mind the decision may not be totally up to your direct supervisor. Salemi says your company may have specific policies about working from home, or your boss may need approval from leadership — so try to be patient in the process. “Be diligent about following up, set reminders on your calendar and send follow up emails,” she says.

If your supervisor is hesitant, you have a few options. Salemi says you can ask for a short-term trial period, clearly outlining deliverables ahead of time that you’ll monitor during the trial. You can also compromise, Zimmerman notes, for a part-time WFH setup — for example, three days a week from home and two in the office. 

You can also revisit the topic later if your boss isn’t sure now is the best time.“Ask [your boss] what kind of progress she needs to see to seriously consider your request and ask if you both can meet again in three to six months to discuss said progress,” Zimmerman says.

If it’s clear the final answer is “no” after your trial period or six-month progress meeting, try not to be discouraged. A “no” can be tough to hear, especially if you know you function and perform better when you work from home — but the good news is, you’ll have a chance to recalibrate your work life to better align with all the lessons you learned about yourself during the pandemic, even if that means exploring new job opportunities with a different company whose culture might allow you the work-from-home setup you’ve been looking for.