Increased productivity, employee satisfaction, and reduced overhead have teams around the globe going virtual — but not without overcoming the challenges of managing remote teams first.

While we’re certainly guilty of championing remote work as a remote team ourselves, a number of problems can arise when transitioning from a traditional office setting.

What management tools will we use? Will our days be filled with virtual meetings? Will our company culture suffer?

These are probably just a few of many remote work-related questions you’re asking yourself. We’re here to help.

Our entire Hubstaff team works remotely and has since 2012, so you can rest assured that we won’t sugarcoat it for you. Managing remote workers can be a challenge — but only if you’re not prepared.

That’s why we’ve outlined five remote management challenges you’ll need to conquer.

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Table of contents

  1. Communication
  2. Scheduling
  3. Creating an accepting culture
  4. Building a workspace around trust
  5. Sharing in success

Challenges of managing remote employees

1. Communication

If there’s one remote work challenge you absolutely have to overcome, it’s communication.

Communication is the cause of almost every other management issue. Managers provide direction at every step of a project or business initiative, so they need to be extremely good at communicating the strategy and understanding what’s happening within a team. Similarly, team members need to provide progress updates, understand “the why” behind a project, and handoff work seamlessly to ensure initiatives stay on track.

Efficient, effective communication is the cornerstone of any functioning group — and it is especially crucial for remote teams.

Coordinating virtual team members can be challenging, and communication can be a big stumbling block for many companies successfully navigating remote hiring. In fact, 45.8% of remote managers state that a lack of communication is the biggest challenge to managing remote teams.

When communication falters, a number of problems arise:

  • Work progress suffers
  • Training new hires takes longer
  • Morale worsens
  • Burnout risk increases

Communication issues can be devastating to a company, but there is a solution.

Potential solution: Communication manifesto

Desirable communication varies across different cultures, demographics, and age groups, so it’s important to set some ground rules for how your team plans to communicate.

The best way to do this? Create a communication manifesto.

At Hubstaff, our communication manifesto helps us answer a few basic questions:

  • What communication channel will you prioritize? (Phone calls, video conferencing, email, instant messaging)
  • How do you signal and enforce focus/uninterrupted work time?
  • What hours do you expect employees to be available?

Want to create one of your own? Check out our template.


2. Scheduling

When all of your employees are in the same geographic region, it’s easier to set clear expectations concerning hours worked. However, if your remote employees are located around the globe, coordinating work time can be a lot more difficult.

Scheduling challenges

When managing across different time zones, it can be hard to find any overlap at all. This makes it difficult to know if your team is working. You might ask yourself:

  • Are they logging in for scheduled shifts?
  • Are customer support questions being answered?
  • Are deadlines being met?

Sometimes scheduling challenges become so overwhelming that it’s hard to hold employees to any semblance of a schedule at all. Of course, giving up on scheduling altogether could actually help you in the long run.

Potential solution: Asynchronous work

Asynchronous work is becoming increasingly common amongst remote teams. When time zone and location differences get you down, allow your team to work the hours they want. It’s one of the perks you should take advantage of when it comes to remote work.

Whether you choose to adopt a fully asynchronous schedule or incorporate traditional scheduling techniques, just make sure you communicate effectively. Before making this drastic shift, make sure to outline deadlines, communication ethics, time tracking practices, and other collaboration guidelines.


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3. Creating an accepting culture

Diverse teams are beautiful and powerful. In fact, diverse teams perform 35% better than their competitors.

Making your workplace inclusive becomes increasingly difficult with a remote workforce. Languages, cultural differences, religious beliefs, gender identities, and other factors are difficult to handle on-site but become even more challenging without direct communication.

These differences can impact how employees interact with one another, how they prioritize project tasks, what they deem to be a success, and so on.

Even personality types, work habits, and other psychological factors can lead to management issues.

With so many individuals from unique points of view working together, how can you create a culture where everyone feels welcomed, integral to the company’s success, and encouraged to do their best work?

Potential solution: Virtual and in-person retreats

The best way to embrace your culture is to invest in it. Virtual team building helps your employees strengthen relationships and build chemistry. One of the best ways to do this is a retreat.

Retreats allow remote teams to put work on the back burner and learn more about their teammates — and have a little fun in the process. At Hubstaff, we gather annually for an in-person retreat. In the past, we’ve gone to The Dominican Republic, Portugal, Cancun, and a slew of other places.

Of course, meeting in person can be one of the most common challenges. When other factors keep us from gathering, such as the COVID-19 pandemic, we still make sure to hold a virtual retreat. Virtual retreats help us learn about one another’s cultures, families, and interests. It gives us the chance to gather around a virtual water cooler and discuss important topics like the company roadmap, burnout factors, how we’re approaching work-life balance, and any big challenges we face as individuals or as teams.

When we return to work, an increased sense of community helps us empathize with one another when communicating and collaborating. This is one of the best ways to build trust in a remote team.

4. Building a workspace around trust

Without actually spending time together, both employers and employees may see a diminished sense of trust and cohesion.

Face-to-face interactions and daily communication help us bond. These interactions are less common with a remote team, but that doesn’t mean trust can’t be built in other ways. The true challenge is coming up with ways to establish and foster trust.

Even with the most cohesive and functioning virtual teams, there will simply be less oversight of remote employees. This can manifest in the form of missed deadlines, longer meetings, and micromanagement.

These issues aren’t sustainable. So how can you trust your employees while still ensuring they get their work done correctly and on time?

Potential solution: Employee productivity tracking technology

Measuring productivity can be a challenge. Sadly, 36% of remote managers state that it’s difficult for them to understand what each team member is working on (and when).

Whether you look at website and app usage or keyboard and mouse activity, setting measurable productivity goals is a fair way to set and gauge expectations for each of your employees. Having the right employee productivity app and project management software can help ensure that the right work is getting done on time.

5. Sharing in success

It’s much easier to celebrate your team’s successes when you work in an office. Whether it’s going out to lunch to celebrate a big promotion or grabbing drinks when you meet sales goals, gathering is relatively easy.

It can be a challenge for remote teams to show their appreciation when their team reaches a major accomplishment. Even smaller, day-to-day accomplishments are harder to notice. Simple acts of positive reinforcement go a long way in helping your team build chemistry and do their best work. You’ll be fighting an uphill battle here.

Potential solution: Slack channel

Here at Hubstaff, we were worried about our team’s success going unnoticed. One of the things we’ve done to keep achievements front and center is by creating a Slack channel.

Hubstars Slack channel

Our #Hubstars Slack channel is an opportunity to show gratitude to our fellow teammates and congratulate them on their success — no matter how big or small they may seem.

We’ve created an incentives program within this channel to take it a step further. If your supervisor or another Hubstaff teammate congratulates a team member on their work via the #Hubstars channel, a small bonus will be added to their next paycheck.


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Final thoughts

Well, there you have it. Remote team management certainly comes with its fair share of obstacles. We feel the positive effects of remote work far outweigh the challenges we face.

We all want to have successful, productive workdays. Aiming to create the best possible work environment, remote or otherwise, makes all the difference.

If you’re just starting to manage remote team members, we hope this post helped you find a realistic barometer for the challenges you may face. If you have questions, comments, or concerns, drop us a comment.

If you’ve found solutions of your own you’d like to share, we’re all ears.

This post was originally published September 29, 2017, and updated in April 2022.