Life & Work Skills

How to Convince Your Boss to Let You Work Remotely


You’ve decided that you want to work remotely. You dream of skipping the commute, making your well-loved sweatpants your new professional wardrobe, and working all day with your dog curled up beside you.

Yes, you want all of that. But, here’s the thing: you don’t want to leave your current job in order to get it. You’re happy with what you do, you just want to change where you do it.

It’s time to approach your boss about the possibility of working remotely. Yet, every time you even think about starting that conversation, your mouth goes dry and your stomach drops into your shoes.

I get it. Any sort of serious discussion related to changing something about your current role is enough to inspire some nerves.

But, fortunately, there are a few steps you can take to talk to your boss about your desire to work remotely in a way that’s poised and professional — and doesn’t require overly-sweaty palms.


1. Make Sure Your Request is Reasonable

It’s time for a quick reality check. Your dream may be to work remotely, but is that even a feasible possibility for you?

Do you have a position where you could reasonably work from home or elsewhere without tons of hassles or major adjustments on your employer’s end? Or will not being in the office consistently present some issues?

Maybe you work in a highly-regulated field where you can’t even access your email once you leave the premises. Perhaps your position requires that you frequently meet with clients face-to-face in the office.

Whatever those limitations might be, make sure you give them some consideration. This might seem like a disheartening first step, but that’s important information for you to have as you formulate a plan to present to your manager.


2. Set a Meeting With Your Boss

Expressing your desire to work remotely isn’t something that you should do in passing or in line for the coffee maker in the break room. This is a somewhat drastic change to your work arrangement that deserves a designated conversation and full attention.

If you already have a regularly-scheduled one-on-one on your boss’ calendar, that’s a great time to bring up a career goal like this and get that conversation rolling.

If you don’t already have a meeting set, send your boss a short email to schedule some time with them when you can talk through the details of your request.


Source: @rianasingh_


3. Prepare an Actual Plan

Do you know what won’t lead to a productive conversation? Marching into your boss’ office and saying, “So, I’d like to start working remotely…” and then nothing else.

Rather than approaching your manager with a vague request, you need to put in the legwork to figure out some of the logistics ahead of time.

Are you hoping to work remotely full-time or just for a few days each week? Is your goal to jump right in or are you open to a trial period? Is there any equipment or special access you’ll need in order to complete your tasks from a different location? Will you still maintain normal work hours? How can people quickly get in touch with you?

Those are questions that your boss is bound to have, so it’s best to have the answers worked out ahead of time.

You get bonus points if you pull all of that information into a written proposal. It doesn’t need to be anything overly formal. But, having those details documented gives your boss something to review and refer back to — especially if they need a few days to mull over your request.



You need to put in the legwork to figure out some of the logistics ahead of time.



4. Focus on the Benefits to Your Employer

There’s no denying that remote work has plenty of benefits for you. You don’t have to deal with rush hour traffic and you aren’t forced to listen to your colleague clip their fingernails at the next desk over.

Those are just a few of many perks you’ll experience, but those also probably aren’t going to sell your employer on this arrangement.

Remember when you were job hunting and you had to place the majority of your emphasis on the value you would provide to that company, and not the other way around? The same rule applies here.

During your conversation with your boss, you need to shine the spotlight on how you working remotely will lead to positive outcomes for them. Here’s the good news: there’s plenty of research out there that proves how working remotely is good for both employees and employers.

For example, this Stanford University study  shows how remote workers experienced a huge boost in productivity — and saved their employers tons of money as a result.

That’s just one of many studies that boast similar results. So, you really shouldn’t have a problem building a strong case to present to your manager.


Source: @scstockshop


5. Be Patient and Persistent

Of course, this rule won’t apply if you’re in a situation where you need to be able to go remote right away — like maybe you’re moving soon but want to keep your same job. That’s an entirely different story.

But, in those situations when you have the flexibility to wait, you need to be willing to.

Some workplaces will be slower to come around to the idea of remote work, particularly if it’s an industry where that’s not the norm.

Have some patience. Request that your boss keep it in mind, and then revisit that conversation again in a few months or so. This isn’t a change that will happen immediately, so you need to be prepared to wait for a while.

Even if your manager does eventually give the thumbs up on working remotely, be aware that you might need to wade into the remote waters slowly. For example, you might start with a day or two each week, rather than going full-time remote the second you get the go-ahead.

Be encouraged — that’s still a step in the right direction!


This should go without saying, but if and when your boss does let you work remotely, you need to knock things out of the park. This isn’t your excuse to coast.

So, get your work done, remain a communicative and helpful team player, and generally be an impressive employee — otherwise you might just find yourself back in the office (or worse!) in no time.