How Can Your Boss to Start Letting You Work From Home

It’s happening. One friend after another is remarking on how he or she “worked from home” yesterday or is going to be “working remotely” on Wednesdays this summer. They claim they get so much done, and it’s a great way to mix up the office routine. Making calls is easier and so is zoning out on tasks that require a ton of focus and not a lot of distraction. Suddenly you wonder why you’re not doing this on occasion or even regularly. Wouldn’t your boss be all for it if she knew how much you’d accomplish? How insanely productive you’d be?

But how can you convince someone who thinks this is a foreign concept, best left for contract employees who don’t actually live in the same state as the company? It may not be easy, but with a little finesse and a proven track record, you can make it happen.

Depending on the type of person you’re dealing with and what his or her hesitations are, here are four ways to approach the often tricky subject.

 

If Your Boss Really, Really Likes Face-Time

You have your twice-weekly one-on-ones, and aside from that, your boss prefers striking up a face-to-face conversation to chatting over Slack or on Gchat. He even ignores your headphones when he’s got something to ask you. He values in-office time above all else, liking all team members present when they’re on the office clock. Working remotely isn’t something he cares to do, and so he can’t understand why you’d want to do it either. This type of manager is going to take some convincing, but it’s not a lost cause.

Because he likes in-person communication best, avoid emailing your request and instead initiate a face-to-face discussion. Say, “I wanted to run something by you. I wanted to see if you’d mind if I worked from home on occasion. Maybe every other Thursday to start and then if that goes well, on a weekly basis? I really value our chats about work projects throughout the day the day, so I’d make sure I’m still completely available—email, chat, phone. Let me know how that sounds and if we can test it out.”

By stating your availability and flexibility (starting out slow and then establishing a regular pattern once he sees how well it’s working out), you address his desire to get in touch with you at random and not just over email. It’s unlikely that he’ll start calling you every hour of every day that you work remotely, but giving him the options to get in touch however he prefers should at least put his mind at ease.

 

If Your Boss Is Suspicious

True story: I once had a colleague (not my boss, fortunately) who bluntly told me that she wouldn’t allow her reports to work from home because she didn’t “trust them.” She didn’t think they’d actually work. I shook my head and tried to convince her otherwise; they were adults, after all. Whatever assignments they had to complete, they’d get done—or face the consequences. How could she not realize this?

Unfortunately, I know she’s not the only person to harbor suspicions about what her employees might do should they be given a little freedom every now and again. If this sounds like your boss, you’re probably going to have to be explicit about what you intend to do while you’re at home. Assume that there’ll be lots of regrouping on the subject if it goes into effect. Send an email along these lines:

Hi [Name of Boss],

In the past when the subject of working for home has come up, I know you’ve expressed doubts about it working for your team. I want to do what I can to show you that working from home on occasion would actually enable me to be quite productive, in some ways, more so than being in the office. It’s not something I’d want to do often—I genuinely enjoy being in house—but it is an option that I’d like to take advantage of sometimes.

Would you be open to me giving it a try? I’d be happy to have a couple of check-in calls throughout the day if that’d help. And, since it is a big adjustment, I could also be sure to let you know when I’m going offline, even if it’s for 10 minutes to take the dog for a walk. Let me know what you think.