Could I Work Remotely At My Current Job?

Many people say, “I want to work remotely”. They dream of a flexible work-life balance and the ability to determine when, where and how they work. There’s just one thing stopping them: their current job. Too often, we look at our current situation and see no way of changing it.  Our jobs have always been done this way, so that’s the way that they have to be done - right? They’re set in their traditional ways, beholden to a strict 9-5 schedule and confined to the four walls of a conventional office. You might love your job, but crave the flexible lifestyle that you know is attainable. Maybe you feel like it’s time to update your resume and begin the search for a new position...

Not so fast! Today, many jobs can be done, if not fully, then at least partially remotely. Thanks to advances in technology, it’s possible to create digital workspaces in ways that would have been thought impossible even twenty years ago. So much of our work can be done online using the Cloud and digital collaboration tools, from anywhere with a great WiFi connection. To determine if you’re capable of doing your current job remotely, there are a few questions that you’ll need to ask yourself.

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Could I Work Remotely At My Current Job?

Take some time to reflect on your current position and your day-to-day activities. Before answering the following questions, create an image in your mind of what your role looks like. Are your days structured or more fluid? Is your calendar filled with meetings or do you have large blocks of time to work? Are you in a casual environment or is it a bit more corporate? Hold this picture in your mind as you run through the questions below. Don’t worry if you can’t answer ‘yes’ to every question - there is some wiggle room here!

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Could you perform your daily tasks solely from a computer or a phone?

For practical purposes, it’s great if you can already confirm that you can do at least 80% of your professional tasks from a computer or phone. Do you spend most of your time working on a computer? Is your work dependent on a great WiFi connection? Do you conduct most of your sales communication over email or phone conversations? Remote work is possible as a result of advances in modern technology. How can you use these tools to get your workload up to 80% digital if it’s not quite there yet.

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Would it be possible for you to participate in meetings via video call?

Are most of your meetings internal with the same group of people? As much as you like to chat with your coworkers in person, is it possible for you to have the same level of collaboration and accomplish the same tasks over a video call? If members of your team are meeting in person, is it possible for them to dial you in for the brainstorm or announcement? To ensure that you’re still an effective team member over a video call, make it a point to stay off of mute and contribute to the conversation often. As a fully-distributed company ourselves, we’ve found that video calls can sometimes be even more intimate than an in-person meeting, as everyone is engaged and focused on the task at hand.

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Are you a self-starter?

This is one of the most important aspects to consider when you’re interested in working remotely. Without your boss a few doors down, it will be your responsibility to ensure that you’re minimizing distractions and being productive throughout the day. Remote workers find that they must bring it upon themselves to determine the tasks that need to get done each day, and set their own priorities when it comes to projects and last-minute requests. A great remote worker will put systems in place to transparently track their progress and pursue their goals with as much passion as they would in a traditional office environment.

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Are you considered a top performer at your company?

The backbone of any successful remote work agreement is the trust between a manager and an employee. Without this mutual understanding, it is difficult for a manager to rely on the employee to do a high-quality job, and vice versa. If it’s apparent that a manager does not have confidence in their employee, it’s difficult for a remote employee to perform without constantly looking over their shoulder.

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That’s why we recommend that you consider your standing in the company before you ask your boss if you can work remotely. Have you been able to repeatedly excel in your role? Does your manager rely on you in high-pressure situations and trust you when there is a lot at stake? If you can reasonably say that you are one of the top performers on your team, or in your entire company, then it’s more likely that remote work could be an option for you. Your performance sends a signal to your managers (and their managers) that you are trustworthy and committed to the success of the company, which means that it will be more reasonable for them to allow you to work with more autonomy.

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Do you thrive when you are pursuing goals that you are passionate about?

A key factor to being a great remote employee is the capacity to set goals and commit yourself to achieving them. You will face the same challenges as a remote worker (if not a few more) as you would if you were working in the corporate office, but now it will be up to you to motivate yourself to solve them and surpass your goals. Think about the last time that you faced a problem and had to solve it on your own. Did you feel a sense of determination or were you paralyzed with fear at the thought of screwing up? Once you are working remotely, you will need to develop a positive mindset in the face of any challenge.

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Are you motivated by collaboration or do you need solo time to get into ‘flow’?

Picture yourself doing your best work. What kind of environment are you in? Are you a few hours deep into a particularly stimulating brainstorm session or are you focused on your laptop, typing as fast as possible to get every idea onto the screen before it slips your mind? Does teamwork make your heart light up or do you shine when you’ve completed something on your own? As a remote employee, you can have it both ways thanks to technology. Though a lot of your time will be spent working solo (unless you work at a coworking space!), you can still participate in group think tanks via video call.

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Do you need validation to feel successful?

Much of the work that you’ll do as a remote employee will be done on an individual basis. Perhaps you’ll submit a portion of a project that the greater team has worked to put together, but for the majority of the time, you’ll be flying solo. This means that while you will receive some feedback on your work, you may not get as much one-on-one validation as you are used to in a traditional environment. Your manager is no longer able to offer a quick “great work” as he or she passes by your cubicle, and it may seem like too much effort for them to send you an email to pass along the sentiment. If you do feel like you need validation in order to know whether your work has been successful, consider setting up a monthly video call with your boss to go over your high-level progress and your pain points, in addition to more detailed weekly or bi-weekly check-ins.

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Do you make important decisions without the help of your boss?

This is an integral question to ask yourself if the details of your role frequently require an urgent response. As a remote employee, you may not be able to get in contact with your manager as quickly as you’re used to. Now that you’re not an office away from your boss, will you be able to do your job as effectively? Does your manager need to sign off on the majority of the decisions you make or are you fairly autonomous? Before asking if you can work remotely, observe yourself over the course of a week and see how many times you need to consult your manager in order to tackle the regular duties associated with your role. If you catch yourself needing approval more than once a day, every day, you may want to consider ways in which you can prove yourself trustworthy enough to make more decisions without their direct input.

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Can you handle tough feedback and criticism?

Having a cubicle neighbor to fall back on after receiving tough feedback can be helpful, not necessarily for a shoulder to cry on, but to have someone who can hear you out and assure you that it’s not the end of the world. However, as a remote employee, this interaction may be a bit more difficult.

In addition, because you aren’t sharing the same space with these people, you aren’t always hearing the same message delivered in the same ways. A lot of communication is taking place one on one, so ideas and action items have an opportunity to fall through the cracks. Make it a point to send written follow-ups to each member of a project reiterating what was discussed so that you are all on the same page when it comes to responsibilities and deadlines.

It can also be harder to tell what your manager is feeling about your work when you receive criticism over email or a video call. And, if you work by yourself at home, you might fall into a trap of overthinking the issue. If you have the ability to compartmentalize feedback and keep it separate from self-worth, while implementing the changes that your boss recommended, there’s a good chance that you could be a great remote employee.

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Could you block your schedule one day a week for deep work?

One of the most commonly cited benefits of working remotely is the ability to improve productivity because you are able to design your own day, and steer clear of meetings that have the potential to clog your schedule and keep you from getting in the zone. However, if as a remote employee you still have to fill your schedule with constant meetings and check-ins, you could be held back from that potential productivity boom. Looking at your current day-to-day - would it be possible to move around a few meetings so that you have at least one free day to work on projects that require your full and undivided attention? If so, perhaps that’s the one day a week that you work remotely or simply the one day a week when you can plan on being your most productive self.

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How Do I Start Working Remotely?

Now that you’ve done a lot of self-reflection, take a deep breath. If you ran through the above list without hesitation, smiling as you began to realize that this dream could actually become a reality, we have news for you. You have already taken the first step toward working remotely by doing the research. Dig a little bit deeper into what remote work could look like for you, compile a business case for why it would benefit not only your work, but the company overall, then get ready to talk to your boss.