4 tips for telling your boss you don’t want to return to the office

Consider your manager’s perspective for the best chance of getting what you want.
By Hannah Pitstick

As the pandemic continues to evolve, many leaders are starting to call their teams back into the office and are being met with some resistance. A FlexJobs survey released in April revealed that 58% of respondents would quit if they weren't allowed to continue working remotely, and a survey by VitalSmarts found that 58% of respondents are anxious about having those return-to-the-office conversations.  

"Obviously, anxiety is the dominant feeling a lot of people are having, and a large source of that anxiety is anticipating conversations that can be uncomfortable," said Joseph Grenny, author of Crucial Conversations and Utah-based co-founder of VitalSmarts, a company that offers courses in communication, performance, and leadership.

If you have decided you want to continue working remotely for the foreseeable future, you might be bracing for a potentially uncomfortable conversation with your boss. To ensure that discussion goes as smoothly as possible, aim to tailor your approach to your manager, focus on the positive, and remain open to creative compromise.

Tailor your pitch to your boss. Before approaching your manager with your request, take a moment to figure out which tactics will be most effective, given what you know about them.

"For example, if your boss is an urgent person, explain to them that because you won't have commuting time, you can actually be more responsive," said Liz Kislik, a New York state-based management consultant and executive coach. "Think about the things that worry them or make them tense, and determine how your request will actually make it better for them."

Also consider how your boss likes to be pitched in general, whether that's a one-page memo, a PowerPoint presentation, a phone call, or a data-heavy approach, and organize your request in their preferred format. When you're ready to present your pitch, Grenny suggests "bursting the balloon" by sending them an email or text message telling them you want to discuss the return to the office.

"A lot of people want to keep mystery about what the topic is, but I think you can reduce anxiety for both you and your boss by saying, 'Hey, I've gotten messages from you talking about returning to the office, and I'd like to discuss that,'" he said.

He also recommends having the actual conversation either in person or over video chat so you can see each other's body language and reduce the risk of miscommunications.

Establish psychological safety. Grenny argues the first few minutes of the conversation should be used to establish psychological safety by reassuring your manager that you respect their point of view and understand the difficult position they're in. 

"Start off with reassuring them that you understand and care about their problems, interests, and concerns, within which you can share spirited disagreement with each other," Grenny said. "If the other person truly believes you care about their interests, they're far less defensive about exploring alternatives with you."

He recommends saying something along the lines of, "I understand that you have to manage the entire team and have a responsibility to create the best workplace culture, and at the end of the day, you're going to need to make some difficult decisions."

He added that it's important to strip any inflammatory or judgmental language from what you're sharing. Don't use phrases like, "You're being unreasonable," "This is controlling," or "Why don't you trust us." Instead, focus on affirming their values, the outcomes they're after, and present possibilities that could satisfy both of you.  

Focus on the positives and outline the benefits to your boss. Conversations around returning to the office have a tendency to be on the negative side, so it's important to focus on the positive by emphasizing the benefits of remote work for your boss and the organization as well as yourself, according to Washington D.C.-based Michael Gellman, CPA, CGMA, co-founder at Sustainability Education 4 Nonprofits.

"Flip the conversation from the negative to the positive and remember that you can talk about the negatives by highlighting the positives," Gellman said.

For example, you could point out that the time you save by skipping the commute allows you to tackle assignments first thing in the morning, or perhaps your home office setup offers the uninterrupted solitude necessary to complete focused work. Whatever you do, avoid blurting out all your own needs upfront or just complaining about returning to the office.

"It's much more effective to start by outlining the benefits to the organization and your boss as well as yourself," Gellman said.

Be open to a creative compromise. Grenny argues that part of what makes a crucial conversation degenerate is when you believe there are only two options: theirs or yours.

"There are always creative alternatives," he said. "In this case, it's usually not between either a complete return to the workplace or a complete work from home. As long as you talk about objectives before tactics, methods, and a specific agreement, then there's often a lot of room for creativity around what that looks like."

Perhaps you find a way to work remotely as much as possible but agree to come into the office for important meetings. Or maybe you designate one or two days a week for in-person collaborative work and devote the other days to solitary work. Gellman and Kislik both recommend trying a phase-in approach or trial period so you and your boss can experience what it will actually be like for you to work remotely and then adjust based on what you learn.

"That way you learn for yourself what the pace of your day would be like and how it would really work," Kislik said. "Because if we've learned anything from COVID, it's that our plans are useful because it means we've thought about a situation, but they very rarely work out 100%."

Hannah Pitstick is a freelance writer based in North Carolina. To comment on this article or to suggest an idea for another article, contact Drew Adamek, a JofA senior editor, at

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