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How to Ask Your Boss to Let You Work from Home

Out-of-office time can mean peak productivity, but asking for flexibility is harder than you think

Beth Castle
Managing Editor, InHerSight

Woman working from home

Beth Castle is the managing editor at InHerSight. Based in Durham, she writes about women in the workforce as well as Southern travel, tourism, arts and culture, and food. 

It seems like everyone wants to work from home these days. Remote or telecommuting jobs are in high demand, and flexible work hours rank as one of the top-four things women want from their employers

The American workforce has become so freaking lazy, right? We can’t even go into the office anymore.

Um, no. We’re more driven than ever. (Hence burnout.)

In fact, employees who work from home are about 13 percent more productive than their counterparts. They work more hours and they’re less distracted because they’re not surrounded by gossipy coworkers or other distractions. 

That could be you! (Not the gossipy part, the work from home part.) But in order to work from home effectively, you have to lay the proper groundwork for a successful relationship with your coworkers, boss, and workflow. 

Let’s take a look at whether working from home is right for you, how you can talk to your boss about it, and how you can actually get things done when you’re away from the office.

Is working from home right for you?

For some jobs, working from home is simply not an option. If you work in construction, food service, or other industries that require you to be present and, likely, on your feet, then you have to be at work to do your work. No question.

But if you’re an office worker with a laptop, you have more flexibility—sort of. There are a few factors to keep in mind when weighing how often you can work from home or whether working from home is right for you at all.

  1. Do you have a lot of meetings? Yes, you can call into meetings these days, but you don’t want every interaction with your coworkers or business partners to be remote. In real life, facetime is still a valuable part of our work lives. You’ll be more engaged in the meeting, you’ll form stronger relationships with your cohort, and you’ll speak up more often if you’re physically in the room.

  2. Do you supervise someone? Just as face time is important for building relationships with coworkers, it’s also important for managing people. You’re more likely to understand what’s affecting your direct reports’ workflow, both inside and outside work, if you have a presence in the office.
  3. Is there technology in the office that you need to do your job? Again, you can connect to a VPN remotely. But if you don’t have a work laptop, you might not be able to access certain programs from home. That doesn’t mean you can’t work from home ever, but you’ll need to be strategic about what you do when you’re in the office versus when you’re at home.  

  4. Do you lose focus easily? Working from home takes focus and drive. If those are two of your top qualities, great! Keep those yoga pants on. But if you need to be around other people working to do you job, which is totally a valid feeling, go into work.

  5. Are you a good communicator? It’s much easier to explain a misunderstanding or request when you’re in the office. You can talk things through and read your coworkers’ body language. Still, if you excel at communicating your needs and wants in advance, over email, or on the phone, then you’ll probably be a good candidate for working from home.

How to ask to work from home

You’ve decided working from home is a-okay. That’s awesome. Now you have to talk to your boss about it. Even if you have a solid relationship with your manager, asking to change your schedule can be a stressful and complicated conversation. You might not feel like you’re affecting others by working from home, but having team members outside the office changes the work dynamic. You want to go into the conversation ready to present your case and prepared to compromise.

Like asking for flexible work hours, you’ll need to consider these questions:

  1. What will be your communication plan? This includes updates on the status of your projects as well as when you’ll be in and out of the office, and how coworkers can reach you if they need to talk to you when you’re out.

  2. How do you plan to reach your goals? This is fairly straightforward, but important in reassuring your boss that you’re not just watching Netflix at home. Point out how productive workers are at home (just grab those stats up above!), and share what projects you think would be completed more effectively away from office distractions.

  3. Do you need any extra equipment at home to carry out your responsibilities? Think of that technology question above. Do you need a work computer? What about access to certain servers? If you can’t access your work materials, it’s going to be hard for you to sell your case.

  4. What support will you need from your boss? You might need to switch your weekly in-person meetings to a different day, or you might want to schedule a quick call every morning to check in. Be prepared to ask your boss to make those changes. Similarly, you’ll want your boss’ support in communicating to coworkers why you’re not in the office as often.

Once you have solid answers to these questions, you need to schedule a meeting with your boss. You should drive the conversation here because you’re the one who wants to negotiate. Expect your boss to have feedback on the plan you present, and be willing to make changes to accommodate your company’s needs or policies. 

If your boss is hesitant, you can always suggest a trial period for you working from home. Give specific dates you’d like to test, and schedule a follow-up meeting where you can work out the kinks of your out-of-office time.

How to actually be productive when working from home

You did it! You’re officially a remote worker—at least part of the time. The hardest part of working from home (asking) is behind you. And yet, you still have quite a bit of work to do to make sure your at-home work environment is conducive to productivity.

These are a few factors to consider when setting up your ideal space:

  1. Your environment: Loud or quiet? Alone or in a crowd? Couch or kitchen table? Working from home looks different for everyone. Based on your work style, you might end up in a coffee shop, on your back porch, or curled up in bed. Choose whatever you think will be most productive.

  2. Your attire: If you’re still in bed hammering out emails, disregard. You’re one of the lucky few who can work from home without dressing for the day. For most of us, it’s important to have a clear divide between home and work, so showering and dressing (even in sweatpants) can make a big difference in your mindset.

  3. Your schedule: A routine can help you stay productive and focused. Do what you’d do on a normal workday—go to the gym, get dressed, and start checking your emails. Oh, and make sure to set a time when you’ll be, for sure, logging off. Working from home doesn’t mean you’re always available. You do you.
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