How to Talk to your Boss about Working Remote

Working from home is trending, to say the least. What was initially a response to the COVID-19 pandemic’s shelter-in-place order quickly became a comfortable norm. Local mountain professionals – along with pros from all across the country – began to understand the benefits of remote work. Not only can it boost productivity, but it can often make work-life balance a relative breeze.

Overall, 56 percent of the non-self-employed workforce are in jobs that they could feasibly handle remotely. But if you aren’t in a position that allows for remote work today how do you convince your boss that it’s the bees’ knees? Begin by crafting a compelling value proposition, one that shows exactly why working from home is a smart move. And not just for you, but your employer, too.

Yes, talking to your boss about working remotely is a bit anxiety-inducing. But don’t panic just yet. By following the tips below, you can navigate the conversation like a pro. Here’s how to pull it off.

Do Some Detective Work

Technically, this first step has nothing to do with having a conversation. Instead, it’s all about preparation. After all, you can’t create a standout value proposition if you don’t get a few ducks in a row.

One of the biggest reasons some managers shy away from allowing their employees to work from home, to put it simply, is fear. They worry that their team is going to slack off if they can’t peer over their shoulder to check in on them. So, you need to put their mind at ease. With a little bit of research, that will be much easier (don’t worry, we’ve already done some of the heavy lifting for you, keep reading).

For example, one study showed that employees who worked from home saw their performance increase by 13 percent. That alone is pretty compelling. Additionally, pre-pandemic, 5 million professionals worked from home at least half of the time, showcasing how many people are already hopping on the remote work bandwagon. Plus, telecommuting reduces turnover and makes employees happier. That’s a win-win.

Now, these points alone aren’t enough to convince most bosses to embrace the work from home model. However, metrics like these can help your case. Spend a little time as an amateur detective and dig up the numbers. That way, if your boss expresses concerns about productivity dips or other fears, you can address them with facts. Heck, you may even go so far as to research and suggest the perfect remote work productivity tools for your organization.

Have a Plan Ready

Another pre-meeting-with-your-boss step is to get a plan together. You need to sort out the logistics a bit in advance, or at least understand how they would work. For example, do you need anything special, like a company laptop or VPN? Is your home internet up to the task? Do you have a quiet workspace for meetings? Do you need collaboration or video conferencing software downloaded to your computer?

The more you can figure that out up front, the better off you are. It allows you to address major concerns during your conversation instead of having to pause and get back to your manager.

Additionally, you need to have a plan hashed out for how you’ll handle various aspects of your role. This includes everything from scheduling your tasks to participating in team meetings. You also need to consider how you’ll get deliverables into your boss’s hands, how often you’ll check-in, and anything else that relates to the flow of your day.

If you don’t know where to begin, it’s time for a little imagination. Think about your typical workday. Picture yourself as you move through it, jotting notes about every activity and interaction that usually occurs. Alright, now consider how you would pull most of that off while working from home. If you can figure that out, you can create a plan.

Don’t Do a Drive-By

When you’re ready to present your case, don’t make it a drive-by. This isn’t the kind of conversation you should start in a hallway while your boss is heading to a meeting. If you go that route, you’re probably not going to get a “yes,” at least not then.

Instead, schedule a meeting. Let your boss know that you want to discuss your work arrangements. This isn’t guerrilla warfare, so be upfront (but general) about what you want to talk about.

In most cases, a half-an-hour conversation should be enough to test the waters. After all, even if your boss is game, working from home isn’t something you can usually start the next day. So, keep things high level and get the ball rolling.

It’s Not Just About You

Yes, asking to work from home may technically be about you. But when you talk to your boss, you need to make sure your desires aren’t the sole focus. Instead, talk about how this new approach also benefits them.

Your manager isn’t going to change your work paradigm if they don’t get something out of the arrangement. It doesn’t matter how amazing it is for you; you have to show that it’s awesome for them, too.

During your detective phase, you may have found some statistics that can help in this area. However, you don’t have to stop there.

If there is a potential benefit for the company, roll it around in your head, and see if you can articulate it clearly. For example, does working from home mean you can be available to customers during hours that aren’t well covered now because you’re eliminating your commute? Can the company benefit from having your workspace available for other purposes besides giving you a place to plant yourself every day? Will your boss also feel more productive when some of their staff are working from home?

Be ready to share as much as possible about why this is a great move for your employer and boss. That way, you can make your position more compelling.

Request a Trial Run

If your boss is still hesitant after you’ve presented your value proposition, then see if they are open to a trial run. See if they’ll let you give it a try for two weeks or a month. Then, once that amount of time has passed, you can have a debrief meeting to go over the outcome of the experiment.

Alternatively, you could see if they’d let you work from home just two days a week at first. This approach can also let you both get a feel for the arrangement without as much commitment on the part of your boss. They can dip their toes in the water and see if it’s comfortable. Then, after a few weeks, you can revisit the topic of making working from home your new normal.

In many cases, this approach is effective. With a test period, you’ll get a chance to prove you’re capable of working from home and remaining productive. That’s powerful. It can put your boss’s mind at ease while increasing the odds that they’ll let you telecommute full-time.

At a minimum, the test may open the door to a part-time work-from-home arrangement. That’s a great way to strike a balance between your preferences and your manager’s comfort level. And, who knows, in time, they may think having you work-from-home more isn’t such a bad idea after all.

Lastly, invite your boss to visit us at We’ve got all of the resources handy so your fearless leader can make the switch to a remote workforce feel comfortable, easy, and beneficial.

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If you’re asking yourself, “Why is Walking Mountains talking about remote work?”

The answer is quite simple: we aim to reduce local carbon emissions by 50% by 20305. Telecommuting, compressed workweeks, and other flexible schedule options can reduce you and your business’s carbon footprint. With less commuters on the road, we can improve our communities’ air quality and put ourselves one step closer to achieving our carbon reduction goals. Drive less to do more for Mother Nature.

Resources for Making Remote Work