Leadership & Management

13 minute read

5 Challenges of Managing Remote Employees (and How to Overcome Them)

Kat Boogaard

Kat Boogaard

Perhaps you lead the charge on a team that always works virtually. Or, maybe you unexpectedly found yourself at the helm of a team who typically worked side-by-side, but now needs to navigate the murky waters of working from home full- or part-time. 

Either way, you’re learning this lesson firsthand: there are a lot of challenges in managing remote employees. Hey, leading a team is never easy, but managing remote teams adds a few new layers of complexity.

Everybody is looking to you for guidance, reassurance, and support, and you want to do this whole remote work thing right.

We’re here for you! We connected with other remote managers and workers to get the lowdown on the different challenges of leading remotely, as well as what steps you can take to overcome them. Trust us—you’ve got this. 


Challenge #1: Keeping everybody on the same page

We all know that communication is key for a successful team, but it becomes a pretty big hurdle when everybody isn’t sharing the same workspace. It’s not as easy to drop by someone’s desk with a quick question or share a brief update in passing. 

Buffer’s 2020 State of Remote Work found that communication and collaboration were the biggest struggles for people who were working remotely—even ahead of loneliness. 

“One major challenge is communicating effectively among a remote team,” explains Hassan Osman, a Director at Cisco Systems who has also authored several books about working remotely, including Influencing Virtual Teams. “Given the lack of face-to-face interaction and heavy reliance on technology, the intent of what someone wants to communicate might be misconstrued.” 

How you can overcome this challenge: 

  • Use a collaborative work management platform: Look for a tool that will centralize all of your communication and collaboration. From Trello or Asana to Basecamp or Wrike, there are plenty of options out there, and they’ll make it far easier for your team to stay in the loop and gain visibility into what’s happening across the organization. 
  • Keep up with your regular team meetings: You might not be able to indulge in shared pastries during your Monday morning stand-up anymore, but that doesn’t mean that meeting should fall off the calendar entirely. Use a conferencing solution (like Zoom or Google Meet) to gather your team together and continue to provide important updates, deadlines, and details. 
  • Find the best communication tool for the job: Of course, a lot of your work from home communication is going to happen digitally, and it’s easy to rely on only instant messages or emails (which goes a long way in explaining why 83% of remote workers feel overwhelmed by email). However, there are times when a quick phone call or video chat will be far more effective and efficient. Remind your team to consistently evaluate which method is best for their specific message, and then encourage them to communicate accordingly. Don’t fall into the trap of always defaulting to written mediums. 
  • When in doubt, over communicate: Really, when it comes to leading your remote team, there’s no such thing as too much communication. “Oftentimes employees can feel out of the loop when they aren't directly engaging with peers and managers in the office. We don't realize how much is conveyed during quick lunchroom catch-ups, body language, or post-meeting walks back to the department,” says Kristy Wallace, CEO of Ellevate Network. "Especially during times of uncertainty, strong leaders should look to over communicate with teams about the state of the business, priorities, and updates."

Challenge #2: Tracking productivity

In a typical office environment, it’s pretty straightforward to keep an eye on what your employees are working on. You can just peek out from your office and see them all cranking away at their desks.

But, when it comes to the challenges of managing virtual teams, most leaders admit that they struggle with ensuring that their team remains efficient and productive. 

“One of the biggest challenges I faced early on was keeping track and monitoring the productivity of my employees,” explains Anh Trinh, CEO and Managing Editor of GeekWithLaptop, which has an entirely remote team.

Here’s the good news: even if you aren’t able to keep a watchful eye on their every move, working remotely can actually boost your team’s performance. Research from Stanford found a 13% improvement in performance for teams who were working from home. 

How you can overcome this challenge: 

  • Use a time tracking solution: If you’re truly worried about the hours and energy your team is sinking into their tasks, you can implement a time tracking tool. “I was able to solve this problem by using software like Hubstaff to track and monitor the work of my employees,” Trinh adds. Not only will it help you ensure they’re making effective use of their hours, but it will also empower your employees to understand where their time is going—and how they might be able to eliminate distractions or boost their own productivity. 
  • Focus on goals and results, rather than hours worked: Ask yourself this: does it really matter what hours your remote team is working? Or, are you more concerned about whether or not they’re getting the job done? Switching to a more results-oriented culture can help to ease your own anxieties, while also showing your team members that you trust them to do their work. “We solved this problem by focusing on goals instead of the time spent working,” shares CEO and Co-founder of Hoppier, Cassy Aite. “As long as the goals are met, we don’t check up on anyone to see if they’re working.”
  • Have regular one-on-ones to check in and converse with direct reports:Routine check-ins are a must for managers who want to make sure that remote employees are staying on track,” advises Hilary Bird, a Digital Marketing Manager who works remotely for Render Pilots. “And a check-in should cover more than just task updates. A manager should also help remind, initiate, or facilitate conversations that need to happen between remote employees.”


Challenge #3: Employee development

You probably already know that your employees (whether they’re remote or not) care a lot about their growth and advancement. 

In fact, one study conducted by the Society for Human Resource Management, found that 30% of employees consider career development opportunities for learning and personal growth very important. 

But, especially if you’re just making the transition to an entirely remote team, it’s easy to let employee development slide to the back burner—or off the stove entirely. You’re all so caught up in trying to make it through your daily tasks, something like remote training doesn’t even cross your mind. 

How you can overcome this challenge:

  • Connect with your employees about goals and career ambitions: We’ve already mentioned the importance of hosting regular one-on-one meetings with your remote employees. Occasionally during those conversations (at least once a quarter), make sure that you’re also asking them about their career goals, skills they’d like to refine, and whatever other objectives are on their mind. You can’t support them if you don’t know what they’d like to achieve, but oftentimes you need to be the one to bring this topic up—especially when you consider that 78% of employees feel uncomfortable talking about career growth and salary. 
  • Offer opportunities for continued learning: Just because you’re not in the same office doesn’t mean you can’t be learning. Find innovative ways to continue fostering your team’s knowledge from afar, whether it’s hosting a video seminar, starting a book club, or giving them access to online courses that they can complete in their own time (GoSkills is great for this, by the way). You’ll prove that you’re invested in their skills and growth. And, as an added bonus, you’ll have a more informed and knowledgeable team.

Want to start boosting your team’s learning? Check out the GoSkills LMS right now. 

Challenge #4: You find yourself micromanaging

Remember when we talked about the fact that it’s tougher to keep a close eye on what your team is working on when you’re not all together in the same office? Well, that can add fuel to your urge to micromanage.

You feel as if you can’t trust your team to get their work done appropriately, so you continue to stick your nose into every piece of the process. 

While you might think that you’re helping, be forewarned that this tactic will only backfire. 69% of employees have reportedly considered changing jobs just because they were micromanaged. 

How you can overcome this challenge: 

  • Provide clear instructions and expectations: When you’re managing a remote team, there’s no room to be vague. “This challenge can be overcome as long as the remote manager sends out projects with clear instructions on what's expected, when it is expected by, and any other relevant commentary,” shares David with DollarSanity. “Then, let the remote workers get their job done as they see fit. It's not necessary to manage the process A-Z—you simply have to trust your employees. Likely you'll find that they perform better if you're not constantly interjecting or asking for updates.”
  • Regularly solicit feedback from your team members: Not sure if you’re getting too involved? There’s one simple way to find out: ask your team for their input. It’s a great way to find out what’s going well and what you could be doing better. Plus, it will engage your team and prove to them that you truly value their suggestions and opinions. 


Challenge #5: Promoting a sense of belonging

Whether your team is remote or not, employee engagement matters. In fact, 71% of managers feel that employee engagement is one of the most crucial factors in overall company success. Yet, keeping engagement levels high is a struggle when your team is virtual. 

“Remote workers are in danger of developing ‘out of sight, out of mind’ mindset, and they can quickly become less engaged, which can cost a company precious time and money,” explains Luka Arezina, Co-founder of DataProt. “Employees, on the other hand, are at risk of decreased job satisfaction levels, which can endanger overall life quality.”

Plus, remote employees run the risk of becoming totally disconnected from the broader vision and work of your company, as well as other teams they aren’t interacting with regularly. 

“Going fully remote can exacerbate the distance between teams or departments that don’t need to work together daily, causing people to feel out of sync and possibly undervalued,” says Quincy Smith with Ampjar.

How you can overcome this challenge: 

  • Leave time for small talk at the beginning and end of meetings: You lose a lot of the natural watercooler or coffee pot chatter that happens in the office when your team is working virtually. But, in order to keep them connected, it’s important for your team members to have time to catch up about lighthearted subjects. Reserve some time at the start or end of your team meetings when people can just casually catch up. Always being strictly business leaves almost no wiggle room for your employees to bond. 
  • Institute a fun remote tradition: Just because you aren’t in the office together doesn’t mean you can’t have any fun. Start a tradition that your team can participate in together, such as sharing a photo within a theme every Friday on Slack or collaboratively building a team-wide playlist. These sorts of activities might seem inconsequential, but they can actually go a long way in solidifying relationships and fostering your culture. 
Venngage Infographic Maker

Yes, you can overcome the challenges of managing remote employees

Leadership is never easy, but managers who need to oversee remote teams (whether that’s their permanent status or something they’ve been unexpectedly thrown into during, say, a worldwide pandemic) face some additional hurdles.

You feel a lot of pressure to be a strong leader and set a confident, encouraging example for your team. Rest assured, you can do this! Refer back to the virtual team challenges and solutions we’ve outlined here, and you’ll have a ton of strategies in your back pocket to help you keep your team focused, productive, and positive—regardless of what’s happening in the world. 

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Kat Boogaard

Kat Boogaard

Kat is a writer specializing in career, self-development, and productivity topics. When she escapes her computer, she enjoys reading, hiking, golfing, and dishing out tips for prospective freelancers on her website.