How To Ask To Work From Home Permanently — And Get What You Want

Here's what to do when you want to convince your boss to let you stay remote post-COVID-19.
Office workers who went remote during COVID-19 shutdowns have leverage right now. But they should be prepared to negotiate.
Alistair Berg via Getty Images
Office workers who went remote during COVID-19 shutdowns have leverage right now. But they should be prepared to negotiate.

Many of us had to make the sudden transition to remote work at the start of the coronavirus pandemic. And a significant number want to keep it that way, even when returning to the office becomes an option. About 1 in 4 workers currently working from home due to the pandemic wants to continue to stay fully remote, according to a March survey of more than 1,000 U.S. workers.

Some people are even willing to stake their jobs on it. Forty-two percent of workers said they will start job hunting if their company ends its remote work policy, according to a Prudential survey of 2,000 adults in the U.S. who’ve been able to work from home during the COVID-19 pandemic.

Some jobs are best done in person, but for office workers who have already proved they can work well from home, now might be a good time to leverage the remote experience to full advantage.

“Working from home used to be seen as a rare and coveted perk. Building the case to work remotely full time with your manager and HR department was always a challenge, and companies routinely balked at these requests,” said Tracy Cote, chief people officer of StockX, an online marketplace. “But now that most office workers have proven that they can work from home and still be at least as productive as they ever were, if not more so, the tables have turned, and companies are much more open to this discussion.... But you still will have to build your proposal, as it’s not an automatic yes in most companies.”

Here’s what to consider when building and presenting your case:

Research your company’s remote policies, if any.

Your company may already have a remote work policy in place. If so, Cote suggested engaging your company’s human resources department to figure out how flexible it would be about a permanent remote request.

Cote said you should ask if remote work is feasible for your role from the company’s perspective. Other questions: “Will they let you move anywhere, or only in places where they already have an established legal entity? Will they adjust your pay based on cost of living for that location?... Will they pay for your travel to and from your home base to any corporate hub for critical meetings, or will this be on your own dime?”

This way, you can get a better sense of what a permanently remote transition would mean for your career development and for you financially.

Before you convince others, be sure this is the best move for you.

Be realistic about the day-to-day challenges you may face if you stay remote, particularly if you are the only one on your team doing so.

“Have you considered the time zone difference, and whether or not that’s realistically going to work for you?” Cote said. “Is your company one that’s likely to forget to recognize and reward remote employees, or will you get the same amount of attention and opportunity that you had in the office?”

Figure out what is most important to the company, and use that language in your request.

Once you’ve done your homework, it’s time to present your case to the decision-makers, such as your boss or department head.

Keep in mind that you should present a business case, not a personal pitch for how you will benefit personally from working from your couch. Lara Hogan, a leadership coach and author of “Resilient Management,” said remote-seeking employees need to figure out what their leaders care about right now. “It’s probably not team health,” she said. “It’s probably about profits, or it’s probably about getting this project out the door.”

This is crucial to making a winning argument for why you should be allowed to work from home long-term. “This is change-management work: understanding what this person cares about and framing the thing I want to see happen in those terms,” Hogan said.

Hogan gave the fictional example of a deadline for a huge company initiative called “Project Zebra” that you keep hearing about in all-hands and team meetings. That’s a sign you need to frame your remote work request around “Project Zebra.”

In this scenario, Hogan said, you could say something like, “When I think about productivity, any kind of change right now to how we all work together is going to affect that deadline... That’s going to create more uncertainty, more unpredictability, [and] we would have to create all of these new norms again. What if we continue to let people to choose where they worked or how they worked until we get ‘Project Zebra’ out the door, and then revisit this conversation?”

Frame it as an experiment, not a forever change.

Saying that you want to work from home “permanently” or “forever” may be a turnoff to leaders who are already skittish about allowing people to work from home any longer than necessary.

“Suggest a trial period ... . This will give your manager comfort that the arrangement can be dialed back if it’s not working out, and they may be more likely to give it a go.”

- Tracy Cote, chief people officer of StockX

It’s helpful to ease bosses into the idea by proposing it as an experiment that could end.

“Suggest a trial period to see how it goes with you working fully remote, even as other members of the team are in the building or working in a hybrid model,” Cote suggested. “This will give your manager comfort that the arrangement can be dialed back if it’s not working out, and they may be more likely to give it a go.”

Hogan noted that it’s important to frame this request as a winnable, doable experiment, and you can do this by gathering data during the trial that makes stakeholders feel good about the decision. The trial period should have a check-in point that is tied to a natural time for reflection, like fourth-quarter planning or end-of-year retrospectives, she said. In this check-in, you can share data that is important to your boss, such as, “In my time remote, we shipped X more work.”

Be prepared to ask more than once.

It’s likely that you will not hear “yes” right away.

“Negotiations like this often take time and are a series of conversations.”

- Nadia De Ala, founder of Real You Leadership

But don’t see this lack of immediate approval as a reason to give up. “Not being flexible with your manager if the response to your request isn’t an immediate ‘yes’ is a mistake, said Toni Frana, a FlexJobs career coach. “It’s important to have a dialogue about your proposed arrangement and to be prepared to negotiate your request.”

Because it can take a while to get your request approved, get the ball rolling now.

“Negotiations like this often take time and are a series of conversations, and your boss likely has to check in with a few other stakeholders,” said Nadia De Ala, founder of Real You Leadership, a group coaching program for women of color. “Set yourself up for success by bringing up the topic sooner than later, and seeing what’s possible and what else your employer might need from you to approve this.”

If the company refuses to give on full-time remote work, ask about other options, such as working from home one to three days a week, De Ala said.

Make sure your performance can address concerns people commonly hold about remote work.

The top two concerns professionals hold about fully remote work are being able to maintain good relationships with colleagues and having decreased productivity, according to an April survey by staffing firm Robert Half.

You can address these concerns through your performance. “Well in advance of making this request, make sure your instant messaging is consistently on during working hours, that you don’t miss meetings and that you respond to emails or calls in a timely manner. If you’ve been doing this consistently, it will be easy to make the point that you will continue to do so,” Cote said.

To make a successful case, De Ala said, employees need to prove that working remotely is mutually beneficial and to show how it is actually in service to employers, their goals and the success they want to achieve.

“Do you have proof that you are actually more successful and impactful in your role while working remote this past year?” she said. “Start collecting that proof and get ready to show it off!”

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