Home Is Where the Work Is: How to Convince Your Boss to Let You Be Remote

Travers Korch

by Travers Korch

5 min read
Home Is Where the Work Is: How to Convince Your Boss to Let You Be Remote
Guides Careers Future of Work Inspiration
Asking a manager for work-from-home time may seem daunting, but it doesn't have to be—if you arm yourself with the right questions and assurances beforeh

By now, you’ve probably gotten used to not needing permission to DJ the office speakers all morning. Or starting your day by settling into your favorite chair, instead of standing with a herd of strangers on the train to your workplace.

For workers from traditional 9-to-5 jobs, these small pleasures of working from home have now become a daily routine. So, what happens when your boss expects you to return to the office? Why not ask your company what’s possible before resigning yourself to previous restrictions on your commute, your time, and your physical environment?

It may seem like a daunting conversation, depending on personal dynamics and your organization, but it’s easier than you might think, and you’ll be joining a growing trend. Even before the coronavirus pandemic sent workers home in droves, an Upwork study projected that, by 2028, 73 percent of all teams will have remote workers. The number of people working remotely—and liking it—has been increasing for more than a decade, according to FlexJobs and Global Workplace Analytics data.

You can facilitate this conversation—and increase the likelihood that you’ll get what you’re asking for—if you keep a few recommendations in mind.

Decide If Working from Home Is Really for You


Remember that many of your coworkers might decide to return to the office, a Zapier blog post from June says. So make sure you’ll be OK working remotely even after many other employees return to a somewhat “normal” working environment. WFH means no midday lunch or coffee runs with coworkers. It means missing out on impromptu office conversations or impromptu after-work social gatherings. And it also could mean feeling a bit isolated when your coworkers are at the office every day. Coworkers could forget to loop you in on spur-of-the-moment decisions or meetings. Whether it’s fair or not, it will likely be up to you to maintain the connections and make sure colleagues and managers keep you informed. Make sure you’re comfortable taking on that responsibility.

Make a Plan

Enter the conversation armed with knowledge, confidence, and a strategy to show that working from home—for a day, for two days, or full-time—will benefit everyone involved. Gather the supporting evidence, the Zapier blog post advises.

Identify with your boss the key performance indicators (KPIs) that could improve amid fewer distractions and no commute time, or reference the growing evidence touting remote work as a boon for productivity and efficiency. Make sure you and your supervisor agree on how you’ll track and measure these KPIs. Include a commitment to regular progress checks in the office, as well as increased accessibility online, which will help bolster your reputation as someone who’s continuing to contribute to your company’s success.

Determine How Working from Home Will Benefit Your Company (and Your Boss)

While no one would question that staying up late to binge on Netflix because you don’t have to wake up early to sit in a sweaty carpool is a great reason to work from home, please don’t say that. Position your proposal through the lens of what’s best for your boss—and, by extension, your company—not least because it will presumably continue to pay you to do your job remotely.

Try to show how increased flexibility would do more than maintain the status quo. Will you be accessible earlier or later in the day than you otherwise might be? Will improved concentration in the solitude of your home office allow you to make progress on projects? Be ready to defend your manager’s potential concerns about at-home distractions like kids, pets, chores, or Netflix. And note that some companies have strict policies about “no childcare” during working hours—you might want to check with your HR department to see if a remote-work policy exists.

Note that you’re not being negative if you anticipate hesitancies or questions from your boss or coworkers. Think about how your boss and teammates think about work. What are their personalities like? Show that you’ve thought about the best way team members can reach you with a question, how you will clearly communicate and maintain a schedule, and how you’ll stay connected to office events.

Always Demonstrate Cultural Fit

Even though you’re not in the office, you still represent your company. Remember to stay professional and meet the company’s cultural goals and standards. This means not showing up to Zoom meetings in your pajamas. It also means turning on the video and staying engaged. You may still be able to take those midday walks or do the quick yoga sessions you’ve become accustomed to—but you’ll need to discuss with your boss and coworkers how to communicate that you’re stepping away, and for how long. Simply put, you want to match the professionalism of the office and not be a burden on your boss or coworkers.

Keep an Open Mind

Your boss may be taking a risk in granting your request or might need to justify the decision to a superior, so keep an open mind as you work toward an agreement. You may be able to start with only one work-from-home day, but if that day is successful, week after week, it could lead to more WFH time for you.

Also, be flexible. If your company is about to enter a busy season, offer to go in to the office. And if you need to attend particularly important in-person meetings, make an effort to be there.

What to Do If She Says “No”


Some companies might be ready to be back in the office and not willing to introduce more flexibility. That doesn’t mean that you should give up on your goal. On the contrary, try to identify the root(s) of your employer’s resistance to your request, and then ask for a follow-up meeting to revisit the topic. In the interim, do whatever you can to alleviate your company’s concerns about the validity of your request.

If your manager still declines your proposal, start working from home. No, really—find a few hours here and there on evenings or weekends when you can get your work done and put together a case for how that environment benefits your productivity. Diligently track any headway you make on mutually identified KPIs and be prepared to present in a future one-on-one just how efficient you can be out of the office.

Just a Question Away

Although many companies will keep working remotely, some are returning to the office. Assuming the COVID-19 outbreak doesn’t last forever, more eventually will follow suit. Either way, a candid discussion about the positive impact remote work can have on your productivity, as well as careful attention to your employer’s concerns, can go a long way toward shifting company policy. And sometimes, all you have to do is ask.

Action Items:

  • Identify one or two KPIs to highlight, and become confident explaining why a remote working arrangement will make them more achievable.
  • Jot down a handful of talking points to practice with a friend or family member.
  • Schedule a time to ask for your work-from-home day.

If you’ve found you enjoy remote work, you’re not alone. The majority of current teleworkers plan to stay remote for the rest of their careers. Good luck as you approach this conversation with your manager—although you shouldn’t need it if you prepare really well.


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