How to ask your boss if you can work remotely

How to ask your boss if you can work remotely

It’s a big ask, but if you want to make your newfound freedom permanent, it’s one you have to make.

COVID-19 has taught you how to be a remote worker. Maybe you were a bit apprehensive at first. You didn’t know if you’d be as productive. But holy lord, you’ve seen the light. You can’t imagine going back to an office, which means you need to come to an understanding with your employer. More specifically: you need to know how to ask your boss if you can work remotely.

Depending on how laid back your company is, this could be an easy conversation or a difficult one. But if you’re intent on keeping this newfound freedom intact, it’s one you’ll need to have.

Bring the facts

Working from home leads to increased productivity. The studies are there to back it. Your own experience likely confirms it. You avoid the office noise. You avoid the chit-chat. You’re able to get more stuff done. What’s wild is that we knew this even before COVID-19 struck. But some companies were so intent on hovering — often under the guise of “maintaining a company culture” — that they preferred to take that productivity L.

In 2013, a landmark study by Stanford University’s Nicholas Bloom found that working from home boosted productivity by 13%. A University of Oxford research paper in 2019 revealed that happy staff closed more sales.


Now the rules of the game have changed. You’ve worked from home for a year and a half. You’ve shown it can be done. All your boss needs is for you to put it in terms he or she can understand. When you work remotely, you’re a work machine. When you’re in the office, not so much. And Stanford frickin’ University agrees.

Offer some examples

Maybe your boss isn’t convinced that remote work is long-term viable. Everyone’s done it because they’ve had to, they might say. It works now, but when the world goes back to normal, the concept will no longer fit.

Tell that to Basecamp’s Jason Fried, who’s operated a fully remote company for the better part of two decades and has succeeded despite having all of his employees scattered around the world.

Fried pretty much despises the idea of working in an office. In fact, one of his big pleas to companies during the pandemic was not to take their office traditions virtual. He didn’t even want people to feel like they were in an office while remote. (As you can imagine, Fried wasn’t all that thrilled about the rise of apps like Zoom.)

Yet Basecamp has over 6 million paying customers and one of the happiest workforces on the planet. The company and everyone who works in it manages to get stuff done. And that was true long before we had this whole COVID thing to worry about.

Basecamp isn’t the only all-remote company by the way. You probably use the products or services of another business that’s made the leap. There’s also:

  • Automattic (WordPress!)
  • GitHub
  • Harvest
  • Zapier
  • MailerLite (where my newsletter is hosted)
  • GoDaddy
  • ConvertKit
  • Shopify
  • Trello

And I’m leaving out a ton. The point is, lots of pretty darn successful companies are completely remote and manage to roll on just fine.

You want to know how to ask your boss if you can work remotely? You broach the topic and you bring examples of others who’ve made it work.

Play some hardball

It’s no secret that talent is driving the job market right now. Lots of people are quitting in order to find a new gig or to enter the world of independent work. If you have skills that lend themselves to remote work, there’s a good chance they’re in demand somewhere. That somewhere could let you work from home if your current employer isn’t too keen on the idea.

You can pop the remote work question before you ever start looking elsewhere. The answer you receive should give you some idea of how open your boss is to letting you leave the office behind.

If you get the sense that your employer just isn’t going to budge and will want you back in the office once COVID-19 mercifully disappears or chills out, you can start to scope out new opportunities. From there, you can either use an offer to negotiate with your current boss — like, “If I can’t be fully remote, I’m afraid I have no choice but to submit my notice” — or simply take that other offer and work in a place that gives you the freedom you crave.

How did you ask your boss if you could work remotely?

For those of you who’ve pulled it off — how did you seal the deal with your employer? How did you get permission to be a full-time worker after initially working in an office? I’d love to know what kind of approach you took and what served as the silver persuasion bullet. Feel free to leave a comment and let me know.

For everyone else: good luck to you! I hope you get what you’re after — and that you’re tenacious enough to seek it out if you fall short the first time.

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