How to Ask to Work Remotely Permanently

When Diane Levitt decided she wanted to move across the country in the summer of 2021, she knew that asking her employer if she could go permanently remote was a big “ask.” But she also knew that if she didn’t ask, it would mean leaving her job and having to look for another one. She decided to move forward and her boss, surprise!

These days, it is more common than ever to request to work from home on a permanent basis. According to both parties, the key difference in whether you get a yes or no depends on how and when.

Be prepared to compromise by submitting your idea in writing

Levitt was Cornell Tech’s senior director for K-12 Education. She had to plan and strategize in order to move permanently from New York to California, while still keeping the same job.

“I gave everyone plenty of time, including myself,” she says. “I went in with it well thought out.” She drafted a proposal and had her colleagues and friends help her workshop it. “So, I had a plan that was very well thought out. It wasn’t just: ‘I don’t want to come into work anymore.’”

Bruce Tulgan (author of It’s the art of being indispensable at workRainmakerThinking, Inc., is a Connecticut-based management training company. According to him, work-from home requests are serious business. “The very act of putting your requests into a proposal format will cause you to consider those requests more carefully. And the more carefully you consider your requests, the more you are able to show your boss the benefits of what you are proposing to do, the more likely it is that you will be able to earn more—and better—rewards.”

Levitt says that flexibility is equally important as a well-planned proposal. “You cannot go in rigid. It is important to be flexible. I think that is key, because your employer needs to feel that they are still a priority for you.”

Due to the public facing nature of Levitt’s job, being flexible meant offering one week a month in person as a compromise. “I created a solution that really covered the bases, and that made it easier for them to say yes.” Having a schedule that met her needs and her employer’s helped her to fall in love with her job again, she says.

Timing your request is important

In Levitt’s case, she had been with Cornell for a decade, so she had a track record and was known for being good at her job. It can be difficult for new employees to obtain an agreement from their employers. But it doesn’t have to be if the approach is a solid one, says Scott Gerber, co-founder and Partner of Vrge Strategies, a boutique technology public affairs firm based in Washington, D.C. The current tight labor market, one of the toughest Gerber has ever seen, also helps on the “ask” side. Gerber was pleased to have found an exceptional candidate for the last position that he had filled. She told Gerber that after a successful interview she wanted to move to Bend, Oregon and wondered if this position was still available.

“My business partner and I discussed it, and it didn’t really take long. It was a brief conversation,” says Gerber. “We basically said, ‘Of course, it’s okay. We’ve learned to work from our homes and from spots all around the country so, as long as you are a responsible part of the team and accessible, we don’t see a problem with it.’”

Gerber states that conceding to the remote post represented a shift in thinking. Vrge used to be completely present in person prior the outbreak. “In that decision, we went from being a Washington-based organization to work-from-wherever organization even as we still try to find ways to bring the team together.”

An annual tradition has been to have the whole company attend the Washington Nationals’ Opening Day. It meant that the new employee had to fly out in order for her to join. “I think that’s the hardest part,” says Gerber. “How do you maintain your workplace culture in this hybrid and/or remote environment? It’s hard. You can do some of it over Zoom, but we believe some of it has to happen in person, and it’s really up to us to create those opportunities to get together in a way that makes sense for everyone.”

Gerber was impressed by the manner in which the candidate answered her question. “I think timing is critical. This was in the exploratory stage of the project, which was full of transparency. It wasn’t a surprise at the end,” he says. “It gave us the time and the space to figure out if it made sense for us as a workplace. I thought she handled it extraordinarily well: with a lot of transparency, a lot of integrity, and a lot of upfront openness to discussion.”

Gerber says he appreciated that she didn’t present the request as an ultimatum. However, even if Gerber had presented it as an ultimatum in this climate, both Gerbers and their partner likely would still have to contemplate the matter. “But nobody wants to be leveraged to make decisions that they’re not comfortable with. In this environment, you might have to make decisions you’re not comfortable with, but it doesn’t quite feel right.”

Know your negotiating power

In some cases, ultimatums can work—when done right. Nikita Hurley moved with her family to Colorado from Southern California. She assumed that she would have to leave her position as procurement manager at the University of Southern California. This was the same as it had been up to the time of pandemic. She began looking for another job, and she found one at a remote office in Colorado. Hurley loved her USC job and wanted to let her boss know that the reason she had decided to leave was due the relocation. “When I gave notice, I told her that I was really sorry to be leaving, and that if I could stay, I would want that.”

In a matter of minutes, Hurley was approved by her boss to work remotely. “I had decided for myself that I needed to have something lined up before I had that conversation so that the conversation could be much more candid than me making a demand of the company,” says Hurley.

So, in her case, the “ask” didn’t really end up being an ask at all. However, she believes it is for her and her boss. She feels more productive working from home. This is something not many remote workers experience. “I’m available a lot more, whether it’s early in the morning or later in the day. I will respond to any questions that may arise. I’m able to address it. When I was going into the office before, I was a ‘clock in, clock out’ kind of person. When I went home at the end of the day, I didn’t check in for my own mental health. Now I feel like I’m a lot more like checked into what’s going on, even later in the evening.”

Chris Tritschler believed that he had to present an ultimatum. Tritschler, the purchaser of a Richmond lumberyard in California, had never considered remote work. “We shuffle a lot of papers in our work, literal papers,” he said. As it was always, the only way to do this is in person. The pandemic struck, and Tritschler began to work from home. It was then that it became clear that the time had come to go home.

“I quickly realized I didn’t want to and didn’t need to be in the office anymore,’ he says. So, for him, it wasn’t an ask but rather a tell. “I gave them a number of options,” he says: he could leave right away, help find a replacement, help train the replacement before leaving, or keep his job but only if he could do it remotely.

His employer wasn’t happy, he says—but the company also didn’t want to lose the 15 years of knowledge and skills Tritschler had acquired, he says. “They certainly tried to convince me to come to the office,” he says. “But I was pretty firm in my approach. And there is the reality for the employer that your people are not replaceable right now.”

As the first in his company to do it, Tritschler has already “coached” a colleague on what to say when he asks to go fully remote.

“You have to show that you are capable of doing your stuff. You can’t show that you are weak in some areas. You just have to find solutions and figure out ways to solve all your stuff,” he told him.

Tritschler and his wife Adrienne (who also moved completely at Slack recently) left San Francisco Bay Area in June to head for Bozeman. Their eight-year old daughter was with them. Tritschler claims that his employer is supportive of Tritschler’s move since they now know that he can work from any location.

“It’s everything I hoped it would be,” he says.

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