Ask LH: How Can I Convince My Boss To Let Me Work From Home?

Dear Lifehacker, I know that the latest trend is to have workers come into the office instead of working from home, but I still think I can be productive at home. My coworkers agree with me, and we’d like to convince our boss to let us try it one day a week. How can we talk him into it? Sincerely, Cubicle Prisoner

Dear Cubicle Prisoner,

If you want to work from home, don’t give up hope just because a few companies have been backtracking on their own telecommuting policies. In the case of Yahoo and Best Buy, the decision to end remote work programs was either for reasons specific to those companies or because both companies are in dire straits. For example, they’re taking out poor corporate performance on easy targets, or they’re trying to make the work environment inhospitable enough that those workers either quit or get laid off, saving the company money.

Whatever the reasons at Yahoo and Best Buy, don’t assume that this is a global trend. More companies than ever before allow their workers to telecommute at least part of the work week or on occasion when it’s necessary (during inclement weather, sickness or injury, for example), or let them work from their home offices because they want the talent that the whole world offers without forcing them to relocate and possibly losing them to a company that won’t. With that in mind, you and your coworkers can put together a compelling case for your boss to let you work from home. Here’s how.

Make Sure Your Job Is the Type that Can Be Done Remotely

It sounds like you’ve already determined that your job is the type that can be done from home, but it’s important to make absolutely sure of this first. Ask yourself some of these questions:

  • Are there special tools only available on your office network or physically present in your office that you need every day?
  • Do you have the right equipment (printer, decent phone reception, a landline, fast internet) and a proper workspace at home?
  • Do you have secure remote access (VPN, remote desktop) to your office network for files, network shares or other information that’s only traditionally available at the office and isn’t accessible over the web?
  • Do you have a computer you can work from at home, like an office-issued laptop or a solid desktop loaded with the OS, tools and utilities you’ll need for your job?

Once you’re sure you have a home office and the equipment you need to get your job done, you should also make sure that you have the type of work that can be measured by results, not just by how many hours your butt is in a chair, being lorded over by a manager. If your boss or your company measures your performance by the work you do and the time required to do it, not just by how many hours you put into the office, you’ll have a better chance at convincing your boss to let you work from home. Picture: C Jill Reed/Flickr

Unfortunately, many managers just don’t believe they can properly manage or gauge someone’s productivity if they can’t physically see the person to see what they’re doing, so even having a completely connected job and the ideal home office won’t help you there. Similarly, some jobs that require shift work or need you to be physically present (retail, customer service jobs or physical labour, for example) won’t be as easy to do from a remote location.

Start with Special Circumstances

Before you ask your boss to approve letting you work from home two days a week or more, be ready to make compromises. You may have to do this on a trial basis to make sure it works out well for you and other people in your department who may want to take advantage of the program. You may also need to lower your expectations and agree to do it only in cases of inclement weather, special projects that require serious focus or extraordinary circumstances. If that’s the case, negotiate and give it a whirl: being able to work from home when the weather is bad or when you have a lot of reports to crank out and need a little peace and quiet is better than not being able to work from home at all.

Over time, as you prove that you can be productive and trusted to do your job without your boss’s eyes watching you (this works best if you already have a boss that trusts you), it won’t be an issue to make working remotely a more regular affair.

Learn to Be a Master Communicator and Check In/Follow Up

When I was a manager in a job that allowed me to work from home some of the time, I had to learn to follow up as regularly as possible. Keeping those lines of communication open is probably the most important way you’ll make sure your working-from-home experiment will be a success with everyone involved. Here are a few tips:

  • Ask your boss how you should best communicate with them while you’re at home. The answer may vary from person to person, but one thing that many managers fear when their employees start working from home is that they won’t be able to communicate with them effectively, or they already have communication problems, and distance makes it more difficult to make sure they’re making progress. Head all of those concerns off at the pass by asking your boss ahead how to address them, and make resulting fixes part of your telework plan. Picture: Irish Typepad/Flickr
  • Set aside time at the beginning and the end of the day to check in with your boss, if that’s what he or she wants. A quick phone call will suffice just to replace a normal beginning and end of day chat to see what’s going on and what you’ve accomplished that day.
  • Use video chat and IM to keep lines of communication open while you work. It doesn’t take much time to start a Google Hangout, make a Skype call, or even send a quick IM to see how things are going. Again, you should be focused on your work, but video chat is a great way to get a little face time and prove that yes, you’re up, at the keys and not just lounging on the couch with your laptop while you watch TV. IM is a great way to chat quickly without being too distracting.

Being available and regularly in touch will be your strongest tool in making sure that both your boss and everyone else who’s stuck at the office while you’re home are all happy with the idea of you working from home, even if they’re not. Plus, being open to these options helps build the kind of trust that’s essential to telecommuting. It’s unfortunate that so many offices still lack the kind of basic trust that their employees will do their work even if they’re not sitting at their assigned desks, but it really is the biggest obstacle to telework in most companies.

Make Your Time at Home Really Worth Your While

It almost goes without saying, but the best way to convince your company to let you work from home periodically is to really do great work when you have the opportunity to work from home. You don’t have to commute, so use your commuting time to clean up your inbox instead of doing it during the day, or get a headstart on your work. You don’t have to commute home either, so use that time to follow up with your boss and fill them in on what you accomplished while you were telecommuting. Picture: Logan Ingalls

Remember, it’s not just your productivity that matters when you’re in the office. The productivity of your coworkers and the way you all rely on each other as a team can be compromised when people are out and working remotely — it may be more comfortable to be at home, but it can be difficult for others to swing by your desk and ask you a quick question about something you’re working on or get your input on something. The same applies to your boss. Even the sense of team that your department or coworkers may share will take a hit when you’re not around.

Being open and available at home will alleviate a lot of this, so use that to your advantage. I used to have my desk phone routed to my mobile phone so people calling me at work would get me at home, and I would frequently sit on IM and video chat ready for incoming connections in case anyone wanted to chat while I was busy working. And make sure you take advantage of your situation by doing great work. Then, no one can dispute that working from home works for you.

Don’t Forget the Small Stuff

There are a few things you won’t want to forget when you’re working from home that are important to making sure you have a professional appearance and atmosphere in your home office. For example:

  • Dress like you’re working. You don’t have to go full business casual (although we’ve mentioned this before as one way to stay productive while working from home), but a video conference while you’re wearing PJs and clearly have bed head isn’t going to go over well with everyone who had to make the commute into the office that day. Also, don’t forget to put on pants: I’ve been on a video conference with someone who wore a nice shirt, but when they had to get up to pick up something, we all saw he was in his boxers. Picture: Brett Selvitelle/Flickr
  • Clean up your home office. Again, it doesn’t have to be spotless, but it should look like a place where you get work done, especially if you’re going to be on camera. Appearances are important when you’re telecommuting.
  • Keep out the distractions. Both for yourself and for anyone you may be on a conference call or video chat with. Your pets, kids and family should understand that when you’re working you need to be productive, so they should only interrupt you if they have to. Don’t get us wrong, a sleeping dog or a purring cat in the office with you can be great, but a dog that insists on playing, or a cat sleeping on your keyboard, is a productivity killer. Know where to draw the line.
  • Don’t forget to take breaks and disconnect. Working from home is great, but it can be tough on the whole work/life line. Do what you can to keep your boundaries intact, and remember to take breaks — just because you’re working from home doesn’t mean you should take lunch at your computer or work late into the evening.

For more suggestions like these, check out our guide to staying motivated while working from home. It covers a lot of the concerns that will likely come up once you get started working remotely, after you’ve convinced your boss to let you try it.

Make Your Case by Citing All the Possibilities

Once you’ve been through all of these options and you have a plan with your boss, make sure they’re aware of all of the ways working from home periodically will benefit you and your coworkers. Set up a rotating schedule for everyone who’s interested. Make sure you have the technologies on hand to facilitate remote work. If you don’t, see if there are free, hands-off options that won’t require a lot of support and effort from your company’s IT staff (making it easy on them if the tools aren’t already in place can make a world of difference). Finally, commit to following up and checking in as if you were in the office so no one has to wonder how to get a hold of you or what you’re working on. Picture: Andrew Bowden/Flickr

It helps to already be a rock star at your office and be an indispensable employee — if you are, your boss or company will be more likely to loosen your leash a bit, because you have a track record of good performance. If you’re not, you might want to work on that before asking for an additional benefit. Even so, it sounds like you have a group of people willing to make this work, so that could be even more helpful.

Just remember that telecommuting — especially when new at an office — will likely be treated as a privilege, not a right, so you’ll have to work to maintain it. If you need more help convincing your boss, we asked you the same question a few years ago, and the stories there can help you as well. Good luck!


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