Boss won’t let you work from home? Here’s what to do next

July 16, 2021

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I'm Tori!

After successfully saving $100,000 at age 25, I quit my corporate job in marketing to fight for your financial rights. I’ve helped over three million badass women make more, spend less, and feel financially confident.


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“Should I quit my job if my boss won’t let me work remotely?”

As August approaches, we’re getting ready for what some experts call “The Great Resignation,” where employees being forced back into the office are deciding to quit rather than give up the option to work remotely from home.

Maybe you’ve already received the dreaded email from HR letting you know when it’s mandatory to come back into the office, or you know it might be coming your way. So what do you do if you’re dreading the idea of going back? You have plenty of options, including negotiating remote work from home as a part of your benefits package.

Here are a few ways to navigate the conversation when you want to continue working from home and a few considerations to keep in mind.

Show your work

One of the biggest hesitations that bosses have in allowing remote work is the fear that employees are just binging their favorite TV shows or just straight up not working during work hours. We’ve all seen the hilarious TikToks of people finding clever ways to make it look like they’re busy at work when really they’re sunning by the pool or getting a few extra snuggles in with their pets.

Overwhelmingly, statistics show us that these fears are not actually based on any fact (despite the tongue-in-cheek TikTok trends). Employees are shown to be more productive and have less stress when they can work from home (47% more productive from home, to be exact).

There are multiple reasons for this–shorter commutes, less money spent on childcare, more time with family after work hours, and less distraction that’s typical in office environments.

When you meet with your boss or HR, bring this information to the table, especially if you have your own data to quantify it.

Do you get more work done at home? 

Feel more creative when you’re in your own space? 

Do you feel sharper and more productive because you’re able to clock an extra hour of sleep you’d otherwise spend commuting?

Put together your argument with as much factual evidence as you can muster. For some extra support, take some printouts of these articles to help back your claim:

Work From Home to Lift Productivity by 5% in Post-Pandemic U.S.

Working from home can benefit employers as much as employees

20 Reasons to Let Your Employees Work from Home

Be willing to meet in the middle

Re-entry anxiety is natural, and for many, the idea of going back to the office is more based in fear than an actual desire to work from home.

Whether you’re anxious about a schedule change or because you have health conditions and are concerned about the vaccination status and additional health considerations and adjustments implemented at your office, there may be a way to meet in the middle with your employer.

A few options you can present to your boss:

  • If you’re concerned about your health, you can ask to wait to return until the majority of the office is fully vaccinated or until you feel more comfortable in large groups. (Note: many people may refuse to disclose their vaccine status, so this may not be an option for every company, this is a great time to ask what your company’s policy will be!).

  • If you need more time to re-establish a routine, asking for a hybrid work schedule may help you ease back into the old groove.

  • If childcare is a concern, you can re-evaluate your compensation plan to ask for a raise to cover the cost of childcare.

  • If you moved during the last year, you might also ask for a re-evaluation of your compensation plan to account for a longer commute or even working from a different office location if there’s a headquarters closer to you.

  • Looking for more travel? Negotiate unlimited vacation, and plan a few digital nomad retreats to scratch the travel itch while still working from the office when you’re home.

Try a little empathy

Not all employers are merciless dictators trying to sap the life out of you for the sake of their bottom line–– they may have never considered the idea of remote work to be valid or don’t have a finger on the pulse of innovation.

Regardless, a little bit of empathy can go a long way in your meetings. Try asking the following questions if you’re getting pushback on working remotely:

  • I’d love to know what your primary concern is with me working from home –– can you tell me a little more?

  • I understand that you’re unsure about having an employee work remotely full time – what additional information about my productivity or work ethic over the last year can I give you?

  • Are you open to a trial work-from-home period with a re-evaluation at the end?

Sometimes, when we think we’re butting up against a wall, we’re really just triggering someone’s fears or even their misunderstandings. Let your boss know that you understand their point of view and make an effort to help walk them through some of that anxiety.

Just in case, start updating your resume

While you’re here with me, can I ask you a pointed question?

Is your hesitation about going back to work in an office really about remote work, or is it about the company environment or culture?

Your answer might be one or the other, or even a little bit of both. The silver lining of the pandemic has been that we’ve had more time than ever to evaluate our current situations (both personal and professional). Being away from a toxic environment in the office may have kept you working with a company for longer than you may have otherwise –– and you may be feeling some fear about reintroducing yourself to that situation.

You can always make a change, and this may be an excellent time to decide if the real difference you need is not just remote work but a new job.

Either way, it never hurts to give your resume and cover letter a little sprucing up. If you’re unsuccessful in obtaining remote-friendly work at your current company, many others are happily taking applications.

P.S. If you are thinking about making an exit, I have a killer job interview package that’s here to help that includes a resume and cover letter template and the Job Interview Overview–– an 11-page guide to finding and landing the job. Learn more about my Job Interview Package here.

The next few months (and let’s be honest, probably years) will bring considerable changes in the job market. The remote vs. in-office debate is just getting started, and there are certainly others on their way.

You owe it to yourself to advocate for your preferred working environment and structure –– so start researching, get prepped, and crush that HR meeting!

More Resources:

The Job Interview Package

Free Workshop: Land the Job

Navigating the Negotiation




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