How To Ask Your Boss to Work From Home Indefinitely

As many of us prepare to return to the office, career coach Fran Sardone shares advice for those who want to stay working remotely.

Any office employee can tell you the benefits of working from home: flexible hours, no commute, wearing soft pants to important meetings. Plus, there are fewer distractions, even for parents of older children, says Inkblot career coach Fran Sardone. “You can make your kids follow rules. Your colleagues? Not so much.”

If you’ve been working from home during the pandemic and would like to continue but your company hasn’t mentioned their post-COVID plan, Sardone recommends taking the initiative with a short email or meeting. Here’s how to prepare.

Consider the downsides from your manager’s perspective

The first thing you will need is proof of how your work has stayed up to par (or improved) since being out of the office. “Productivity. That’s what they’re going to say, but that’s not always the reason.”

At most companies, team managers have some flexibility to direct how their team completes tasks. If your work is done well and your manager has the ability to approve your work from home (WFH) request but doesn’t, get curious about their feelings. Sardone suggests some reasons a manager (rather than a company at large) might want their employees in-office: “Some people are used to performing management, to being in charge,” Sardone says. Even if you, the worker, find messaging services or email to be an efficient way to communicate with your coworkers, your manager may want you in the office “because it means they can walk over and talk to you.”

During the pandemic, employees have operated with more autonomy than a traditional top-down office structure usually allows. Managers who have a hard time with technology may be itching to return to a space with which they’re comfortable. “If they’re doing a video call and they can’t troubleshoot,” Sardone says, managers are at risk of losing status in their direct reports’ eyes and relevance to their employers.

Frame it as consistency

Change is scary, the status quo is not. “One of the trade-offs of being an employee with benefits rather than a contractor is that your employer decides your place of work,” Sardone says. Remember that you are asking, not demanding. Use the precedent that COVID-19 has created to frame working from home as continuation of an existing process, not a change. The “new normal” isn’t so new anymore. If you get pushback, be flexible and curious. Sardone says you can always ask, “What’s the business decision behind a move back to the office?” In their response, you might find a case for continuing to work from home three days a week, but not five.

Find group benefits

Instead of only focusing on the reasons you want to work from home, expand the circle of beneficiaries. Recorded meetings mean a salesperson double-booked with a client can catch up later and no one has to take notes. Online meetings mean introverts can compose and ask questions in the chat in real time instead of being forced to interrupt. Ask your co-workers how working from home has benefitted them.

Sardone says “cross-pollination of ideas,” or collaboration with coworkers and other teams is another common reason employers give for requiring workers to physically be in an office, so building consensus with your coworkers creates strong support for your request. “If half your team of twenty people wants to work from home and they’re forced into the office, they’re going to be unhappy, “ says Sardone. And they’re going to talk. “Restricting people from WFH options without good business reasons has the potential to turn into a retention issue.”

If the answer’s still no

Even with a rock-solid case, a sympathetic manager, and coworkers by your side, an employer may refuse your request. If working from home has become crucially important to you, it’s time to start looking for something new. If you’re in a position where everybody wants you, it’s fine to forefront your desire to telework in the interview process, but otherwise Sardone suggests giving the interviewer a chance to bring it up with a question like “What’s the work environment like?” And if you land a new job, remember that WFH is not all or nothing. At the beginning “you may want to go into the office for a few weeks or even months,” says Sardone. Or, you may be more comfortable at home.


Fran Sardone

Fran Sardone is an adult education and career coaching professional focused on enhancing peoples’ professional goals and well-being through positive psychology approaches. She is the owner of Workploy where she offers career coaching to clients designed to cultivate resilience and diminish burn-out and a career coach with Inkblot Therapy.