10 Mistakes To Avoid When Transitioning to Remote Work

Working remotely is not only a great way to create work-life balance - it’s the springboard to make a major career move. Employees who have successfully made the transition from in-person to remote worker may find that they are not only more productive, but that they are seen as leaders on their teams and within their organizations. Some remote workers even transition out of full-time employment and launch their own businesses or take on clients as freelancers.

That being said, the remote work transition isn’t always easy. For some people, having a conversation with their boss about working remotely is just as nerve-wracking as asking for a raise. For others, the discussion is easy, but they’re worried about maintaining their success and position within their company as remote employees. As a company that has spent the past 8 years helping people to work as effectively on the road as they do in an office, we’ve seen it all, from those who excel when offered flexibility to the people that have made critical errors while navigating their remote journey.

Your next opportunity and dream life is waiting for you:

• Don’t have a remote job yet? Look for your next remote job opportunity on this remote job board with fully vetted remote work opportunities and companies.

• Already have a remote job? Take your job on the road and explore the world while working remotely as part of a remote work and travel program along with a community of professionals just like you.

Common Mistakes That People Make When Asking to Work Remotely

If just the thought of asking your boss for something outside of the norm makes you squirm, this is going to be a significant growth moment for you. Asking your manager to work remotely doesn’t have to be a scary concept, but it does require a bit of ground work and sincere preparation before you jump into the who, what, when, where, why, and how. 

Here are a few common mistakes that people make when they’re asking to work remotely - and how you can avoid them:

Going in Unprepared

This is not a conversation that should be taken lightly. First, consider your manager’s personality and demeanor. Do you have a good rapport with the person who will ultimately make the decision on whether or not you can work remotely or will you have to take your case to someone you don’t have a relationship with? No matter the situation, you need to do some major preparation beforehand to demonstrate that you’ve thought through the situation thoughtfully. We suggest building a business case to share with your employer, one that outlines why you are interested in working remotely, what you think it could do for your performance (and the company’s), and how you will measure your own progress and success. In addition to creating a presentation, be prepared to answer any of your manager’s questions. 

Trust us, they will have more than a few. Here are some you can expect:

• Why should we let you work remotely when others do not?

• Will this set a precedent?

• How do you think your position can be done remotely?

• How will this affect your team members?

Mull these questions over and have thoughtful, well-researched answers before setting up time to chat with your boss.

Focusing on Personal Benefits instead of Professional Benefits

Working remotely has its personal benefits (flexibility and location-independence to name a few), but, as much as your manager cares about your wellbeing, he or she is more concerned, and rightfully so, with how you working outside of the office will affect the company’s bottom line. 

Come to the meeting with as many benefits to the organization as you can think of. Here are a few that we would suggest:

• Remote workers are more productive

• Companies who employ remote workers save money

• Remote work results in global understanding - and fresh ideas

If you can relate these benefits to specific actions and results within your company, your conversation has the chance to be even more successful. Your boss will appreciate that you took the time to dig deep into what can make your company better, and you’ll have a better understanding of what you can do as an employee to make a difference.

Going Big, then Going Home

There’s a saying that goes something like this: “‘No’ is just a request for more information.” As someone who is looking to work remotely, it’s clear that you’re not deterred by a few closed doors. 

Be prepared - your first conversation may result in just that.

The best way to avoid an instant “no”? Start with a baby step. We’ve seen now full-time remote employees get to where they are by asking to work remotely one day a week. This small request tends to be a great jumping-off point for a larger ask later on. Managers have the opportunity to engage in a trial run, and employees can focus on finding out what works for them (and what doesn’t) as a remote employee.

Not Taking Time for Self-Reflection

This is the easiest mistake to make and the one that should be avoided at all costs. Before engaging in a remote work conversation with your employer, take some time to self-reflect. Do you think that you can be an effective worker when you’re not in a traditional office environment? Do you have access to a workspace that will allow you to be productive? Are you more motivated by in-person collaboration or solo deep work time? 

If you are harboring any doubts about your ability to be an efficient remote employee - be honest with yourself! Remote work is not a perfect fit for everyone. Consider what is holding you back from affirmatively answering the questions above, and set goals that will help you work toward putting yourself in a position where you could become a successful remote worker.

Common Mistakes That Remote Workers Make Once They Are Working Remotely

Now that you’re working remotely (congratulations!), it’s important that you live up to the expectations that you set in your initial discussions. Your manager will be looking to you to lead the way and be the example for what a remote worker should be.

Here are the most common mistakes that newly-remote workers make:

Flying Solo

One of the most common pitfalls of remote workers is a feeling of disconnection or loneliness. Though the first thing that you may think of when you picture a remote employee is a person hanging out on their laptop at home, there are many different ways to work remotely that won’t result in inevitable isolation. Many remote employees turn to coworking spaces as a source of community, while others seek out a more immersive experience such as a work and travel program. No matter which way you choose to work remotely, make sure that you build some social opportunities into your daily working style so that you don’t miss out on community.

Overcompensating To Appear Productive

Another issue that many remote workers face is the fact that no one can actually see them working. Though they may be more productive and inspired in their new remote environment, they may feel pressured to make it clear that they are getting a lot done. This can lead to remote employees overworking in order to appear that they are doing just as much work as everyone else. Needless to say, those extra hours do not make for a better experience for you or for your employer. To avoid this overcompensation and potential burnout, stay connected to your team.  Establish a daily habit of updating your team members via email or via an instant message platform like Slack. If you’re available when your team needs you the most, they’ll know that they can rely on you and that you’re doing just as much work as you were in the office.

Not Embracing the Perks of Remote Work

The worst thing that you can do as a remote worker? Not act like one. Now that you finally have the flexibility and balance that you’ve always dreamed of, you need to embrace the opportunity to its fullest. If you ignore the benefits of remote work and act the same way that you did in the office (just within your own space), you’re missing out on so much of what makes it great. Go ahead, take a walk in the middle of the day or go grocery shopping in the morning when the store is less busy. Head to a local cafe to get into the zone or to a city that you’ve always dreamed of visiting in order to get inspired. If you’re self-motivated, it won’t matter where or when you get the job done - as long as you do!

Common Mistakes That Managers Make With Their Remote Teams

Employees aren’t the only ones who need to be intentional during a remote work transition. Managers and team members have a say in how a remote work trial goes as well. Though communication seems to be the common thread between the potential issues, there are specific mistakes that are common enough to call out so that managers and employees alike can keep an eye out for them.

Not Setting Clear Goals and Expectations

The key to a successful remote work agreement is in the setting of clear goals and expectations from the start. Though aspiring remote employees should come to the initial discussion with progress trackers and objectives in mind, it is up to the manager to hold the employee accountable and give them direct feedback if expectations aren’t being met. If there is no way to check-in on progress, remote employees can fall behind and feel like they are floating in a world of their own. As a manager, make sure that you are finding ways to keep remote employees connected to the overall mission and goals of the company and you’ll find that you not only have a more productive employee, but an engaged one as well.

Assuming Remote Employees are Always Available

Another myth surrounding remote work is that employees who work from home (or anywhere else in the world) are always online and available. Because they don’t report to an office during set hours each week, they can sometimes be viewed differently than a traditional employee. Don’t fall into the habit of picturing your remote employees in front of their computers 24/7. Make it a point to establish core hours of availability with your remote workers ahead of time and you’ll never find yourself wondering why you aren’t getting a response at 8pm on a Sunday night.

Relying on Old-School Communication Tools

Email is great and phone calls are fine, but remote teams need other ways to communicate that allow for immediacy and a bit of facetime in order to truly connect. Many remote teams use instant messaging services like Slack to stay in touch throughout the day and keep their communications organized. Other platforms that remote teams rely on for organization are project management tools like Trello and collaboration tools within the Google Suite. 

Finally, if possible, choose video calls over phone calls as your team’s main form of communication. Face-to-face interaction is what helps to build relationships and can prevent the miscommunication that happens so easily over email. If you foster a culture of sharing and openness in your remote team from the beginning, you’ll see that no matter where your employees are, they are capable of collaborating and innovating just as well as an in-office team.

Looking for a remote job that aligns with your professional ambitions while nurturing your love for travel and adventure? 

The Remote Year Job Board opens doors to genuine opportunities that seamlessly blend remote work with the freedom to explore the world. Imagine browsing and applying for positions that empower you to embrace a nomadic lifestyle without compromising on career growth. Search for your next opportunity here.