Ask a Boss: How Do I Ask to Work From Home?

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Dear Boss,

I’d like your advice on talking points when asking my boss about the ability to work from home once a week. I work on a very small team at a very large company. There are usually just three of us from my department in the office on a given day. My boss travels frequently, and is probably in the office only 50 percent of the time. I have one junior colleague, and often the two of us are the only ones on our team here.

As a whole, my company is very supportive of working from home. However, the official policy states that it’s up to each department on what their team does, and my boss is generally not for it. My job functions do not require me to be in the office, and on the occasions that I do work from home (sick, home maintenance, weather, etc.) I am just as productive, if not more, than I am in the office. I don’t have any really compelling reasons to NEED to work from home, I just enjoy the quiet and comfort of getting to be in my house.

I’ve asked him a few times about my working from home on a regular schedule, as many of our colleagues on other teams do, but each time he brushes my question off rather than answer it. On the rare instance that I do NEED to be home, he gives a begrudging okay, and asks why I don’t just take PTO instead. I think he doubts the ability to put in a full day of work at home because he has a family and many pets and household duties that (admittedly) really distract him, whereas I live alone and can actually focus on work. I also suspect that he worries my junior colleague will then ask for the same privilege on the basis that I was given it. For the record, I’m a high-performing, reliable, long-term employee. I have gotten great reviews, and other than the stated reasons above, I can think of no reasons that my boss wouldn’t trust me.

What can I say to him to convince him to let me give it a shot?

Your boss is one of the old-school contingent who still believe “working from home” means “doing laundry and playing with the cat.” It’s odd that that mindset is still as prevalent as it is, since it’s pretty easy for a manager to know if someone is slacking off when they’re working from home because they, you know, stop producing work. But for managers without a lot of experience managing remote workers — or managers who’ve had bad experiences with colleagues who drop off the grid while allegedly working from home — it can be scary shift to make.

That doesn’t mean you can’t try to convince him to let you give it a shot … just go in prepared for the possibility that in the end, he might not budge. But since you’re a high-performing, long-time employee and you’re in a company that generally supports people working from home, you’re pretty well positioned to extract a yes if a yes is at all possible.

The typical advice about trying to convince your boss to let you work from home is to talk about how it would benefit your employer — you can be more productive, work when you would otherwise be commuting, yadda yadda yadda. And there’s definitely value to approaching it that way. But really, if you have a decent boss, it’s also okay to say that you’d like to work from home because, well, you’d like to work from home. Offering people the ability to at least occasionally work remotely has become a way to retain good employees, and decent bosses get that — or at least they should if you spell it out for them.

Because your boss has brushed you off when you’ve tried to raise this in the past, I’d try scheduling a meeting specifically to talk about this. Or even better, if you happen to have any kind of performance conversation coming up, like a formal evaluation, asking for it right after getting a great review could be particularly effective timing.

When you bring it up, say something like this: “I know that the company as a whole supports working from home, but it’s not something we’ve embraced in our department. I’d like to formally ask to work from home one day a week. I think I’ve proven my work ethic and my reliability, and I’d of course commit to ensuring that my productivity doesn’t suffer on those days. In fact, when I’ve occasionally worked from home in the past, I’ve actually been more productive because I’ve been able to focus without interruptions. My sense is that you’re not the biggest fan of remote work, but it’s something that would be a significant boost to my satisfaction here.” You could even add, “and is something that I could see keeping me here longer.”

In doing this, be sure to preemptively address all the things your boss might be worried about. For example, talk about the specifics of your home office (it’s quiet and fully equipped for work!). And in particular, explain that you’ll go out of your way to be highly accessible — that you’ll respond to phone calls and emails promptly and you’ll be reachable on a chat program if your office uses one, so people can get immediate access to you if they need it.

If he still seems skeptical, try pulling out this trick: Ask for him for a limited-time experiment rather than a permanent change. It’s much, much harder for a manager to say no to a trial run, since you’re explicitly saying that if it proves not to work as well as you anticipate, you’ll end the experiment. That’s reassuring to someone who on some level believes that your work will suffer if he okays a permanent switch.

You could frame it this way: “Would you be willing to let me try it as a short-term experiment and then revisit how it’s going after a month? I could work from home once a week for the next four weeks, and at the end of that period we could talk about how it went. If it turns out that I was less productive — which I don’t think will be the case, but I know you’re concerned about it — or that it caused other problems, we could end it at that point. But it would be a lower-stakes way of testing it out and seeing how it goes.”

If he tells you that, as you suspect, he’s worried that okaying it for you means that he’d have to okay it for your junior colleague as well, you could say, “I think we could explain that I earned it through seniority and she’d understand that.” That’s a pretty normal thing — people often get different privileges based on seniority, work quality, tenure, or all kinds of other legitimate differences. (Or hell, if you really want to push it, you could advocate that he let her experiment with it too, if that makes sense for her and her role.)

And then of course, if your boss does let you try it, go out of your way to be visibly productive. Communicate with him frequently during the day when you’re working from home, be clearly available on any office-chat programs, and send him obvious work product if you can. Make it clear that you are in fact working, and you’ll up your chances of being able to keep doing it.

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Ask a Boss: How Do I Ask to Work From Home?