The Ultimate Guide to Avoiding Issues & More Effectively Working Remotely

Note: This post was written in collaboration with Matt Bentley, the founder of CanIRank; their team is an entirely remote SaaS startup and SEO agency.
A person working remotely outside with their laptop and iphone.


For many, the idea of breaking free from their cubicle and working at home is a dream come true. Unfortunately, a lot of these same people finally land their remote dream job, only to wonder what they were thinking.

So why does working remotely often fail to live up to our expectations?

There are numerous reasons, and we will get to those in a minute.

Before we dive into the common pitfalls of working remotely and how to avoid being a statistic, let’s tackle specifically what remote work is.

Which Section Do You Want to Read First?

What is Remote Work and What Does Working Remotely Mean?

An image of a computer and multiple people communicating via network.


Remote work has many forms. It can be someone sitting at home on a phone with a headset on, answering calls and providing support. It can also be that Millennial hunched over their laptop in your Starbucks. According to

​”Remote work is a working style that allows professionals to work outside of a traditional office environment. It is based on the concept that work does not need to be done in a specific place to be executed successfully.”

With so many of today’s jobs being digital, working remotely is less and less a rarity. Even in 2016, 43% of workers have worked remotely for at least part of the time. As Google Hangouts (which is owned by Alphabet – the parent company of Google who had 92 billion visits in March 2021), Skype, Slack, and the countless other VOIP services bridge the communication gap, remote work will only become more prevalent. Covid-19, of course, dramatically increased the number of people working remotely, and changed how offices work as well.

This makes being prepared for remote work even more important, from both a manager and employee’s standpoint.

The 7 Pitfalls and Issues with Remote Work for Managers and Workers Alike

An image of a YouTube video of a cat.


When it comes to working remotely, it’s not all laptops at the beach and kittens in your lap.

Because remote work entails working away from the office and physical presences with your team, it has some major pitfalls for both remote workers and managers trying to maintain their team.

Let’s look at the 7 main challenges so we can combat them head on.

1. Poor Communication Kills Trust

This one applies to workers and managers. Too often people go remote and appear to fall completely off the radar. In some cases this can be on the manager, who forgets to check in with their remote workers.

On the other hand, sometimes this is the newly remote employee’s fault, failing to make the extra effort to be a part of the team via Slack, Hangouts, email, etc. It’s easy for managers to let remote workers fall into the, “out of sight, out of mind,” category. Poor communication will only exacerbate that. And with all of the heavy reliance on technology to communicate remotely, don’t forget to prioritize their cybersecurity.

This can even happen where an employee is truly doing great work, but hasn’t kept their team and/or manager in the loop, leaving them to think they are slacking.

Don’t allow this to happen…stay in touch at least once a day, if not more often.

2. Overworking Helps No One

A woman slumped over her laptop, clearly overworked.


This one might be hard to believe, but a lot of remote workers end up overworking themselves. Studies even show that remote workers tend to work more hours than their office-bound counterparts. When you’re at an office, your work stays at the office. When you work from home, your work is right at home with you.

Knowing when to stop can be difficult. This is especially true with smartphones enabling us to respond to emails or knock out micro-tasks from anywhere. Overworking like this can lead to burning out and ultimately result in worse quality work in the long haul.

If you allow yourself to do this regularly, no one wins.

3. Failure to Prioritize

Being a remote worker can be a lot like braving the wilderness; you’re alone in a sense, and it’s up to you to know the way. Now, a great manager will continue to guide you and help ensure you don’t get lost. That being said, there’s still a level of discipline and responsibility required on the employee’s part.

Not to mention the temptation to tune out and watch YouTube until you completely lose track of time can lead to a remote worker being derailed at any point if they’re not careful. ​And it is not empty words cause over a third of people switching to remote work admit to spending more time on social media.

4. Warning: Culture isn’t Remote Friendly

An illustration of a person chained to their desk.


This is a complicated problem that can go beyond the responsibilities of the remote workers’ direct manager.

Having a culture that’s accomodating to remote workers is essential to that person’s success. This includes keeping the remote worker in the loop on office policy changes or projects as well as communicating to your in-office team that it’s expected that go out of their way to support remote workers. Ask them to put themselves in the shoes of the other.

It’s also wise to make sure the remote worker has an ally in the office that can relay daily happenings. This will keep the worker informed, and also make them feel like a part of the team.  52% of remote workers  surveyed said they feel they’re treated differently or left out compared to their in-office comrades. An in-office contact can help prevent this.

If you’re in a management position, check in with your remote workers and see how they’re feeling. If they’re feeling left out or like they aren’t a part of the team, a few small changes will make a world of difference.

If you are considering a remote position, ask what percentage of their workforce is remote, and if it is a very low percentage, consider yourself warned that you may be fighting an uphill battle with most of your co-workers not being understanding of the challenges of remote work if you take the job.

5. Inferior Project Coordination

A lack of communication can lead to a bunch of independently functioning remote workers. When you’ve got a project being tackled by numerous people, this can quickly turn into a mess. This type of issue really manifests when someone is waiting on a deliverable from a worker that’s actually working on something else entirely.

As a manager, make sure you’re stressing the importance of communicating where projects are at. A project management tool like Basecamp or Mavenlink can make this process a breeze. Don’t rule out other more traditional communication tools such as an online fax app. While it may be an older method, it is often a more secure and convenient one than email to send sensitive, confidential documents.

As a remote worker, make sure you’re communicating with your team and clearly stating what you’re working on.

6. Good Work Isn’t Automatically Recognized

Michael Scott of the Office ignores what's happening around him


 Many managers are stuck in a dated in-office mindset because, for most, that is all they know. Sometimes great work often goes unnoticed or unrewarded, as the employee isn’t in-office, turning in work.

Pay close attention to the work your remote workers are doing and take a moment to give great work a shout-out on Slack or Skype or whatever platform you’re using. A little praise can go a long way, especially with remote workers. This will motivate them to continue doing great work and remind them they’re a part of the team, even if they’re not right there in the office.

7. Remote Workers Feel Stuck

Oftentimes remote workers feel as if they’ll never move up or be considered for a promotion. This can be a result of not talking to your remote workers about their overall goals or aspirations within the company.

This once again stems from poor communication and not having a plan on the manager’s part.

Notice a trend?

9 Steps for Leaders & Employees: How to More Effectively Work Remotely

A graphic depicting a man successfully working with his remote team


Let’s get something out of the way: not everyone is cut out for remote work. It takes a great deal of discipline and a certain personality. But, if you’re remote work material or curious about trying it out, there are some steps you can take to better your odds of success.

Managers of remote workers, we’ve got you covered too!

8. Collaborate (and Listen)

As a remote worker, look for any chance you can find to link up with your teammates and collaborate. This could be a quick brainstorming session via Slack about a project you’re stuck on, or it could be a social you host online every other week.

Collaborating has never been easier for remote workers. Take advantage of the many tools available to you and work with your teammates. This will help you feel like a part of the team, build camaraderie, and make things more fun!

9. Be a Self-Starter

A woman working remotely, sipping her coffee at her laptop


Initiative is a key component to success in remote work. In an office it’s easy for your manager to see if you’re falling behind or simply not working. A remote environment requires you be the one taking the reins and starting tasks with little direction.

If you don’t enjoy managing yourself to a large extent, remote work may not be the thing for you.

10. Improve Your Writing Skills

 When you’re remote, a ton of your communication is through writing. Focus on improving your written-communication skills, as clear and concise writing can reduce the likelihood anyone misinterprets your instructions or updates.

This also applies to management. If you’re sending instructions to your team, make sure you’re using clear language that leaves no room for misinterpretation. Muddled instructions can result in questions, or worse, questions not being asked. There’s nothing worse than checking on a project a week in, only to see it’s being taken in the wrong direction.

11. Schedule EVERYTHING

A screenshot of a schedule being filled out on Asana


Whether you’re an employee or a manager, having every single task scheduled out is essential. Without using Trello, Asana, Clockspot, or any other project management system, it’s really easy for things to devolve into chaos.

Assign every step of every task to someone and make sure there’s a due date on it. Then check up on it. Self-accountability is huge in remote work, and nothing keeps people on task and accountable like looming due dates that both worker and manager have agreed to.

12. Use the Pomodoro Tec hnique

Staying focused when you’re working from home is no walk in the park. With so many potential distractions around you, pumping out quality work can be difficult.

The CanIRank team has had some great success with the Pomodoro Technique. This involves doing 25-minute sprints, during which time you avoid all distractions. This means no emails, texts, coffee breaks, or cat videos. After the sprint you take a few minutes off to unwind, chat on Slack, etc. Then you sprint again.

It’s a really simple technique which is why it works. You’d be amazed at how much you can accomplish in those 25 minutes.

13. Pick the Job that Best Fits You

A screenshot of Indeed showing varying remote jobs


Even if you’re the perfect candidate for remote work, it’s possible you’re the wrong candidate for a particular remote job.

Like any other position, finding the right remote work is key to succeeding. If you love the idea of working from home but loathe phone calls, you probably want to avoid a telecommuting sales job. On the flip side, if you love talking but hate research, you probably shouldn’t take that remote marketing job.

Make sure to ask a lot of probing questions of the hiring manager or HR person to determine if a fit…

14. Pick the Right Candidate for Remote Work

Similar to previous one, as a manager it’s important that you don’t grant remote status to anyone who asks. Think about the strengths and weaknesses of the person requesting remote work before you let them run home with their laptop.

Some people can be stellar employees in the office but horrible at home. On the other hand, some people thrive in a home office environment and might perform better than when in the office. It can sting to let a great employee work from home when you love having them in the office, but sometimes it can mean the difference between that person leaving the company or staying on. For brand new hires, don’t forget to consider whether they are a fit for your company’s values before you consider them a fit for remote working.

15. Separate Work from Home Life

A picture of a fully-furnished home office.


When you work from home it’s easy to feel like you live at work. If you can’t afford to rent an office space or convert a room into an office, make sure you’re mentally separating your home life and work life.

A lot of the CanIRank members regularly work from beaches, coffee shops, or from their backyards to simply “get away.” This simple change in setting can not only make home feel less like your workplace, but also give you some new creative juices.

And who doesn’t love working from a coffee shop (as long as you have good headphones)?

One bottomless mug, please.

16. Relax and Have Fun

Whether you’re an employee or a manager, it’s true that we need to get work done. That’s what we get paid for, but don’t forget to have fun!

We’re living in a time when you can work from home, the beach, the moon – you name it. Embrace the tech that makes this possible, enjoy that you’re free from a cubicle, and have fun engaging with your team.

Make weekly socials a thing, or turn Tuesday into a “Bizarre Article of the Week” day. Host polls about who would win a fight, “Darth Vader or the Michelin Man.” Ask your team what kind of activities they’d like to throw into the week to keep things interesting and ensure everyone is taking a break.

Get everyone involved!

Advancing Your Remote-Friendly Workplace

A man working remotely from his couch using a laptop


Whether you’re the remote worker or the manager of a remote team, you’re a part of the future workplace. The era of being confined to a cubicle 100% of the time is coming to a close, and for the better. Workers are happier and more productive, and businesses are saving money on renting out expensive office space that isn’t really necessary anymore.

If you’re in a leadership role and unsure how to go about handling the shift to having a remote team, check out these other remote work tips or contact me for assistance on effectively leading your team through this transition.

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Hi, I’m Miles Anthony Smith, founder of Why Stuff Sucks™, a lead generation/nurturing focused digital marketing agency.

I live for the business results we get for our clients, and love coaching others to level up their digital marketing and leadership skills. Cheers!