How to convince your boss that you should work from home

Flickr / Alessandro Valli

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.

Thanks,
[Your Name]

If your boss micromanages

He likes knowing what you're doing when, and even though you don't share your computer screen with him (can you imagine!), since you work nearly side by side, he's got a good idea of your day-to-day. He knows that when he throws a new, urgent task your way, you're going to get it done ASAP. And then he figures he can expect you to complete the less timely project, sending it his way for approval as you've been doing since you started working together more than a year ago.

If he's not asking you for daily email updates, then he's sending you a list of what he wants you to get done before the EOD. You've gotten used to it and really like the job, so you've just accepted the fact that your boss is a micromanager, but you know it means your chances of WFH are slim to none. And yet, you're positive that having even one day a month away from the hectic office — and out of his laser gaze — would make you get your work done faster. How could anyone have a hard time accepting that?

Try starting with just one specific day so you don't scare him — the email looks like this:

Hi [Name of Boss],

I was hoping to speak to you about the possibility of working from home on Friday. I've got family coming into town that night, and if I can save myself the commute and get work done during that 90 minutes, I'm confident that would lead to a more productive day. Ideally, I'll even get an early start on [name of project].

Since we typically work so closely together and we wouldn't be able to physically do that on Friday, I thought the next best option would be to email at the end of the day with a list of my works in progress and what I plan to accomplish the following week? That way, if there are any loose ends or anything you want me to tackle first thing on Monday, you can be sure to let me know.

Best,
[Your Name]