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Being Proactive: Asking Your Employer to Make Your Job Virtual

Asking your boss to make your job virtual.

COVID-19 has thrust many onsite employees into remote working roles. Yet not everyone got the same courtesy. Many essential workers or those in states less affected by the pandemic may still have to go into the office. But it doesn’t have to stay that way. Asking your employer to make your job virtual is as far from taboo as ever. Be proactive, use these tips (and these ones), and hopefully, your work-from-home aspirations will become your everyday routine.

Ask Yourself: Why Do You Want to Work From Home?

Before you start asking your employer to make your job virtual, you need to ask yourself why you want to work from home. Working from home isn’t for everyone. It requires discipline, self-motivation, and a division of work and social life. That said, your reasons need to be airtight. You can’t make overarching comments about COVID-19 or wanting to sleep in.

Think about how you work:

  • Can you work without a boss to give you a bit of extra motivation?
  • Do you know what needs to be done without asking anyone?
  • Are you a self-starter? 

If you answered yes to any or all of these questions, you’re probably a solid candidate for virtual employment. Before asking your employer to make your job virtual, have a strong resolve and certainty that you’ll be just as productive—if not more—by working from home.

Ease Yourself Into the Water

One of the saboteurs of virtual work is asking your boss to make your job virtual immediately. Instead of having this viewpoint, consider easing yourself into the telecommuting waters. Ask your boss if he or she will entertain the idea of working from home one or two days a week. Such a work arrangement will make it easier for your boss to digest, as well as give you time to adjust.

Once you’re organized, have a home office, and understand the ins and outs of remote work, you can showcase your productivity as a reason to let you work from home.

Don’t Pry—Make the Possibility of Remote Work a Conversation

The possibility of remote work isn’t a request. It’s a conversation. Convincing someone who hasn’t had remote workers to let you work from home is a daunting request—one that requires careful contemplation.

As a result, you’ll need to make your idea a conversation rather than a demand.

State your need for flexibility and the productivity that results from happier, more balanced workers. If you need to bring out the big guns, highlight this Stanford University study that proves the enhanced productivity of remote workers. Then, show—don’t tell—how your transition will make the company more effective and efficient.

At the end of the day, every employer wants happy employees. But without some valid points as to why you should work from home, most employers won’t hesitate to nip your idea in the bud. Take your idea of remote work and create conversations. Make your idea seem like an adjustment that’s for the betterment of the company—and the bottom line.

Understand That It Won’t Happen Overnight

No matter how grandiose or well-thought-out your plan is, realize that it won’t happen overnight. As much as remote work is gaining popularity, it’s still in its relative infancy. Therefore, not every boss is going to automatically sign off on the idea. In this regard, resolve and patience are coveted virtues.

Make a Plan

Because you’re committing a rare act by asking your employer to make your job virtual, you can’t go into a meeting empty-handed. You need a solid plan to help them understand your intentions. A written “business plan” of your work-from-home ideas is a necessity. Try to include:

  • How working from home will make you more productive
  • How you can interact with your teammates and colleagues
  • Your intended hours of availability
  • Your willingness to work weekends as a trade-off
  • Other negotiations or concessions you’re willing to make

If you cover these aspects within your makeshift plan, you should find that your employer is more willing to accept your request as a serious venture. You might also throw in the idea of lower overhead due to fewer brick-and-mortar expenses, such as heating, cooling, water, and electricity.

With this plan, give your employer a reason to say “why not” instead of just saying “no.”

Try a Practice Run

Before you decide that asking your employer to make your job virtual is a great idea, try a practice run. Obviously, you can’t just ask your employer for a day to work at home out of the blue, but you can work up to it. Before you do, try putting in the time yourself.

This practice run involves accomplishing a task. Whether the task is something for your job or if it’s a hobby is irrelevant. What matters is that you can set, actualize, and achieve goals. If you can accomplish even a personal goal in a strict time frame you set, then you can discuss your results with your boss.

Know How to Answer Potential Questions from Your Employer

When you finally get a chance to pop the question to your boss, you must anticipate questions from them as well. These questions could span a wide gauntlet. But the more you’re prepared for the interrogation, the better your chances of success when asking your employer to make your job virtual.

Some common questions you might receive are:

  • How will you define work hours?
  • Where you will be working to ensure productivity?
  • How will you communicate with other members of your team?
  • How will you resolve conflicts?

If you take the time to research these answers or discover what works best for you, your potential work-from-home situation might just improve.

Be Proactive

Being proactive and assertive go hand-in-hand with a successful remote job request. If you’re the first to provide satisfactory answers for the pros of remote work, or you’re always the first to grab extra assignments, you might have a bit more leeway when you ask your boss to work remotely.

Subsequently, the more proactive you are, the better your chances of gaining or sustaining a remote work schedule.

The Let’s Go Green! Argument

So you might not have to cheer “let’s go green!” but the idea that you can improve the well-being of the planet by working at home is a brilliant idea. Your employer will probably think so as well. Without a commute, you’re cutting carbon emissions. Furthermore, you’re saving your employer money on their energy and water bills.

These are the types of statements you should make in support of your virtual work aspirations. Obviously, a bit of tact in the conversation will go a long way. Don’t force the issue. But if you’re honest and direct about going green, your employer may follow suit. After all, what type of employer wouldn’t want to help save the planet?

Gather Some Relevant Evidence About Remote Work

Just like a courtroom attorney, you should have some sort of evidence ready to sway your boss. The 2019 year-end report from Virtual Vocations should give you a starting point. In this report, you can see how remote jobs have continued to grow in popularity, as well as the top jobs and states for virtual employment. In addition, documents such as The State of Remote Work from Owl Labs can help solidify your argument when asking your employer to make your job virtual.

Ask at the Right Time

“Time is an illusion. Timing is an art.” – Stefan Edmund, author

Although you might feel the urge to ask your boss about switching to a virtual job, timing is everything. If you pop the question at an inopportune time, you might accidentally derail or delay your chance for remote work. Don’t ask your boss following the loss of a client or poor quarterly earnings. Instead, ask about remote work when you’re at your peak. Start by opening up the conversation early and maintain constant communication.

Then, put forth your virtual work plans after a major career victory. Maybe you closed a profitable deal or you finished a project on budget and ahead of schedule. The idea is that you want the best examples of your work front and center and on your boss’s mind.

Discuss Remote Work the Right Way

The world has become a digital place. After all, that’s how you’re getting the opportunity to work from home. However, you should avoid asking about virtual work via text or email. While these popular communication methods are ideal for quick questions, instructions, and social interactions, they’re far too impersonal to ask for a life-altering transition to remote work.

If possible, set up a meeting in person that revolves around your boss’s schedule. They can name the place and the time, and you can bring your convincing A-game. Don’t drop the question at first. Instead, phrase the topic of conversation as a discussion of your work roles and functions. By doing so, you won’t come off as confrontational or abrasive.

Consider Other Options

Some employers are still skeptical of remote work. But that doesn’t mean you shouldn’t ask about remote work. Nevertheless, if your employer is unwilling to change or consider remote work, you may want to consider employment elsewhere. Obviously, you’ll need to weigh the pros and cons of remote work compared to other aspects of your work. At the end of the day, trust your gut to make the right decision.

Although working from home is becoming the “new normal,” asking your employer to make your job virtual is a daunting task. It requires tact, experience, and dedication to workplace productivity. But if you follow these tips, you just might become another person who successfully lobbied for a telecommuting job. Not everyone gets such an opportunity, so you may as well make the most of it. Impress. Become a leader. And you might just find a perpetual spot in the world of virtual employment.


Do you have any tips for asking your employer to make your job virtual? Connect with Virtual Vocations on FacebookTwitter, and LinkedIn to tell us. We’d love to hear from you!

iStock Image: izusek


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