Not ready to give up working from home? Here's how to ask your boss.

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Not ready to give up working from home? Here's how to ask your boss.

WFH doesn't have to end if you play your cards right.

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Not ready to give up working from home? Here's how to ask your boss.

As the world continues to return to some semblance of normality, more and more employers are now insisting that their workforce resume showing up in person to the workplace.

For some folks, a return to the workplace is great news and the opportunity to finally get out of the house is cause for celebration. I know quite a few people who have been working from their kitchen table that can’t wait to get back into an office.

For other folks...the prospect of returning to in-person-work is rather disturbing news.

Before the pandemic even started I remember hearing frequent conversations amongst colleagues regarding remote work and how it was starting to become more widely accepted amongst employers. Although it was starting to become more common, it was still rare enough to be considered some form of exotic luxury reserved only for those who were fortunate enough to have found a diamond in the rough.

“You get to work from home?!"

For the better part of 18 months while the world was shut down, a lot of the workforce was working from home out of necessity, not luxury. But now that the necessity seems to be winding down (we hope), what happens to those of us who have grown to love working from home? Is remote work a benefit worth fighting for and if so—is it a fight that you can win? You might have more power than you think.

The job market is seeing a trend of employees who are quitting rather than giving up remote work. As a result, there are a number of top employers who are adapting to that trend and offering permanent remote roles in a bid to stay competitive in the market. Tech giants like Facebook, Twitter, Zillow, Dropbox, Square and more have all committed to switching to remote models in order to attract top talent.

If you work for a company that is insisting that you return to in-person work, what are your options?

Build your case

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If your company is dead set on dragging you back into the office, you’ll need to clearly demonstrate why you want to work from home, and why that’s a positive thing for them.

For instance, remote employees will often end up working more hours than they would if they were coming into the office. That trend can come with its own brand of issues by way of burn out, but the consensus among remote workers that I’ve spoken to is that they don’t mind occasionally working more hours, because of the amount of time they’re saving on a commute.

Ray in Portland says:

“Between getting ready in the morning and my round-trip commute, that’s about an extra 3 hours on my day that I don’t enjoy and I’m not getting paid for. When I'm working from home I’m so much more open to putting in time on nights and weekends when necessary because I don’t feel like my free time is so scarce anymore. Remote work is essentially handing me back 15 hours of my life per week that I use to exercise, meal prep, and spend time with my family. That extra time makes me a healthier person, which in turn makes me a better employee.”

If you're the type of person who is happier and more productive working remotely, be sure to explain that. It's important that your superiors understand how allowing you to work remotely benefits them.

Mention any specific projects you’ve been able to deliver since you began working remotely and elaborate on how remote work either didn’t slow you down—or better yet, how it actively helped you to be more productive. Even better if you have numbers or visuals to support your point.

This is a request, not a demand

At the end of the day, you are making a request of your employer and you should frame the conversation accordingly. Regardless of how much you feel you deserve this or how much more productive you feel you would be, this isn’t about emotion. It’s about business.

Threatening to quit, or giving an ultimatum regarding finding a new job is not only inappropriate, but in my opinion makes you less likely to get a favorable outcome. Calmly explaining your concerns and laying out your case regarding how this would benefit the company is the right way to go.

Bringing it up

Unless you're in sales, it can be very difficult to ask for something you want. Especially when you know it's a touchy subject.

Broaching the topic could look something like this:

"I know that the company is angling toward a return to in-person work, but I feel like I'm a much more valuable asset to the company when I'm working remotely and I would like an opportunity to discuss why."

If you've done a good job of building your case as we discussed above, you should already have talking points as to why it's in the company's best interest to allow you to continue to work remotely.

Anticipate objections

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Many employers are hesitant to let people work remotely due to some legitimate concerns. I’ll admit, I’ve had coworkers and subordinates that I do not think are well suited for remote work, and their performance absolutely suffered as a result. So if you’re going to ask to work remotely, you should be prepared to address some common objections.

If we say yes to you, we have to say yes to everyone

This is a common and understandable response but when it comes to compensation and benefit packages, it's simply not valid in most work environments.

In most scenarios, different employees have different compensation packages based on their skill level, talent, and portfolio of results. Some people are making more money than others. Some people get perks and benefits that others do not because their performance warrants it.

What this objection is really saying is that "we don't want to have tough conversations with some people regarding why they aren't allowed to work remotely while others are allowed to."

Your response could be something like:

"While I do understand why working from home isn't a fit for everyone, I do feel like my track record and performance warrants remote work to be a part of my benefit package."

If you're still met with resistance here, skip ahead to our "negotiation" section below. If this is the company's firm policy and they're not budging—skip ahead to the "final word" section.

Employees just aren’t as productive when they aren’t in the office

As we mentioned above, the evidence suggests that a lot of employees work longer hours and are more productive from home—but there’s also undoubtedly a lot of slackers out there. I know a number of people who use remote work as an opportunity to fly under the radar and do as little as possible. So how do we address that?

There are a number of options for productivity tracking software that can help to monitor employee’s performance by taking periodic or continuous recordings of your employee's screen. Some of these programs also allow you the ability to login for a live view of what employees are doing in real time.

This is admittedly an extreme option—but if your employer is staunchly opposed to letting you work remotely, volunteering to let them monitor your productivity could potentially put those concerns at ease.

There are too many distractions for you at home

It might be difficult to make a case for yourself to work remotely if every time you get on a video call there is chaos unfolding behind you, or you are constantly needing to excuse yourself to deal with distractions.

Having a designated workspace that is free of interference will make it easier for your boss to say yes to potentially letting you work remotely.

If you’re in a cramped space and that isn’t in the cards, investing in a noise cancelling microphone and a room divider to use as your backdrop can go a long way.

Suggested article: 7 tips for working from home and staying productive

You don’t have proper equipment

If your company’s office has state of the art computers, 40 inch monitors and lighting-fast wifi, but you’re working off a bean bag on a 13 inch MacBook from 2015 that takes 2 minutes just to load TMZ, this is something you’ll need to address.

If purchasing your own technology is out of the question, you should at least be prepared for this objection and request to borrow the appropriate equipment that will put you on a level playing field.

You are not effective as a manager if you’re not on site

Managing a team remotely can undoubtedly be challenging. There is something to be said for sitting 10 feet from your teammates and having your finger on the pulse of what’s happening at all times. But there’s also ways to adapt to the distance.

What’s referred to as a “stand-up meeting” is a perfect way to make sure that you’re maintaining order from afar and it can be held via telephone or video call. Stand-up meetings are usually held in person and on foot so that a team can give updates on projects that have been finished, are in progress, or are about to start. You can also quickly review people’s daily objectives and give them an opportunity to communicate any obstacles that are in the way of them completing their objectives. You can have these meetings as frequently as necessary, with some people opting to go once a week, while other teams managing more detailed projects might need to meet every morning.

Some might argue that the stand-up meeting is a form of micromanagement and you should just trust people to “do what they need to do”. In my experience, that type of approach leads to inefficiency, confusion, poor performance, and bad morale.

Each employee will require their own level of supervision depending on their personality type, and some will need a lot more attention than others. It’s important to remember that just because you thrive in an environment with little/no supervision does not mean everyone else does too. Making sure that everyone is on the same page with each other and the department’s goals is paramount to success.

If necessary, you can also institute an employee activity monitor that was mentioned above to ensure everyone is staying on task.

Having a plan for how you’ll be able to manage a team remotely will help your case when you bring this up to your superiors.

Dealing with no

Even after you share your data and state your case, there’s still a chance your employer might say no. If that’s the case you might be able to persuade them to compromise.

Inquire about a hybrid model

No, not like a Prius.

Hybrid working environments where employees are in the office a few days a week and then remote the other days are becoming more commonplace. Although it may not be your ideal outcome, it is a reasonable compromise.

Negotiate

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We saved this option for last because it definitely won't be your preferred method, but depending on how important remote work is to you, it might be worth considering monetary negotiations in exchange for the ability to work from home.

That is to say...you could offer to give your employer money back from your salary in order to remain remote. This is obviously only to be used as a last ditch effort, but it could also be the key to any of your employer's objections.

This might sound like a radical idea, but let's do some math. Take a look at the following:

  • How many hours do you spend commuting per week?
  • How much are you paying in gas for your weekly commute?
  • How much are you paying per year in car maintenance? For example, oil changes, tires, repairs and overall deprecation.
  • Are you hitting Starbucks on the way to work?
  • Are you going out to lunch a few times a week?
  • Do you frequently eat dinner out because you’re too feel burnt out to cook and clean up the mess?
  • Are you buying dress clothes to wear to the office?

When you really start to examine the expenses you're paying out of pocket to go to work in person, giving a few bucks back in order to maintain your sanity might be more than worth it.

A final word

If all of your requests have been denied and that’s a deal breaker for you, it might be time to quietly dust off your resume and brush up on your interview skills and check out our guide for finding digital nomad jobs.

Did you have to go back to the office after working from home? If not, what was your strategy for staying remote? Let us know in the comments!

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Sean Barela
Sean is a writer and entrepreneur that has a passion for all things personal finance. When he's not writing about finance, you can find him at the nearest steakhouse.

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