Five Tips for Talking to Your Boss About Relocating

In the past few months, high-profile companies such as Shopify and Twitter have made returning to the office optional. So if you can do your job anywhere, do you want to stay where you are? Or is now the time to move to Hawaii? “We have been artificially asking everyone to live in one location,” says Raj Choudhury, an associate professor at Harvard Business School who studies remote work.

Before you get a tattoo that says “work is something I do, not someplace I go,” talk to your manager, who might not endorse your relocation plans. Here’s how to handle the conversation.

Do your homework. “Preparation is the most important phase,” says negotiation expert Parker Ellen, an assistant professor of management at Northeastern University’s D’Amore-McKim School of Business. Can your job be done remotely and effectively? What about post-pandemic? Write down your—and your boss’s—interests and motivations. Anticipate questions, fears, and goals. Prepare flexible solutions.

Think about your career. Will working remotely slow your advancement? Pre-pandemic it probably would have. “From my experience, yes, there is a higher risk of career stagnancy in remote workers than in their office counterparts,” says Laurel Farrer, founder of the Remote Work Association. Particularly at companies with bustling headquarters that value face time, remote workers are second-class citizens and may see the axe swing their way when layoffs come. It’s hard to say how the new normal will change that; either way, plan to make a significant effort—using regular Zoom one-on-ones, perhaps—to keep your managers informed.

Have all the answers. Write an action plan. “Make it easy for them to comply with the request,” Ellen says. Your proposal should include the benefits to the company—details like the hours you’ll work, any state licensing issues, and, most pivotal, who will foot travel expenses to headquarters and to visit clients.

Be a good salesperson. Start with the benefits to your boss, then your team, then your company. Choudhury says these include real estate savings, increased productivity, and future recruiting benefits (for hiring remote workers). “For the company, the economy, and the work force, it’s a great thing,” he says.

Get into the nitty-gritty. A “yes” is not enough. “The discussion is really about wages,” Choudhury says. Be prepared to discuss local costs of living and how much of a pay cut you’d be willing take. You will also need clear flows of information (e.g., a daily meeting, shared databases), set a schedule that’s reasonable for both your time zone and your boss’s, and agree on advancement and socializing opportunities. Don’t underestimate how important the virtual water cooler or regular in-person office visits will become.

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