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The Challenges of Managing Remote Employees

‍Photo by junaida279 on Pixabay

In today’s rapidly evolving work environment, remote work has become increasingly prevalent. Many companies, including big names like Yelp, Lyft, Airbnb, and Spotify, have embraced full remote work models. While the COVID-19 pandemic has accelerated this shift, remote workplaces have actually been in existence for decades.

Managing remote employees comes with its own set of challenges. As someone who has led distributed office teams and managed individuals across different time zones and cultural backgrounds, I understand the complexities that come with leading a remote workforce. In this article, we will explore the five main challenges of managing remote employees and discuss strategies to overcome them.

Remote Work vs. Work From Home (WFH)

Before we delve into the challenges of managing remote employees, let’s clarify the difference between remote work and work from home (WFH). Remote work refers to employees doing their jobs from a location other than a central office operated by the employer. This could include an employee’s home, a co-working space, or any other place outside of the traditional corporate office building or campus. On the other hand, WFH typically refers to employees working from their homes on an occasional or impromptu basis.

It’s important to distinguish between these two terms because managing remote employees requires specific resources, systems, and processes designed for regular remote work. Now that we have clarified our terminology, let’s explore the main challenges of managing a remote workforce.

Challenge #1: Trust

Trust is the foundation of successful remote work. However, building trust can be one of the biggest challenges when managing remote employees. Traditional thinking often assumes that productivity can only be ensured when employees are physically present in the same office. To effectively lead remote workers, you need to trust that they can be just as successful working remotely as they would be in a traditional office setting.

Assuming positive intent is a mindset shift that helps build trust with remote team members. This means acting under the assumption that the person you are working with is trustworthy and a team player. To build trust, consider the following strategies:

  1. Create a living trust agreement that outlines expectations and responsibilities.
  2. Establish SMART goals and objectives that employees can commit to and follow through on.
  3. Foster open and transparent communication, showing vulnerability and admitting mistakes.
  4. Communicate from the highest levels of the organization that you trust your employees.

Challenge #2: Communication

Effective communication is crucial when managing remote employees. With team members spread across different locations and time zones, communication can become challenging. It’s important to address various aspects of communication, such as individual communication, team communication, and project management.

To overcome these communication challenges, consider the following strategies:

  1. Ask remote team members to keep their online calendars up-to-date for easy scheduling.
  2. Use video conferencing software that aligns with your team’s needs.
  3. Establish clear communication guidelines for different communication channels.
  4. Utilize an intranet software platform for effective sharing of work resources and information.
  5. Streamline communication processes and remove unnecessary bureaucracy.

Challenge #3: Community and Belonging

Creating a sense of community and belonging can be more challenging in a remote work environment compared to a physical office setting. Informal interactions that occur naturally in an office, such as lunch breaks or hallway conversations, are more difficult to replicate remotely.

To foster a sense of community and belonging among remote employees, consider the following strategies:

  1. Conduct video broadcast all-hands or town hall meetings and actively engage remote employees.
  2. Support in-person attendance at company events whenever possible.
  3. Create specific feedback mechanisms for remote workers to share their thoughts.
  4. Celebrate cultural moments throughout the year to promote inclusivity and belonging.

Challenge #4: Productivity

One common objection to remote work is the concern about employee productivity. It can be challenging for managers to gauge productivity when they can’t physically see employees working. To overcome this challenge, it’s important to establish structures and coordination that provide clarity and maintain alignment.

To ensure remote employee productivity, consider the following strategies:

  1. Implement a clear vision and purpose with specific goals and deliverables.
  2. Maintain a shared calendar and virtual collaboration tools for alignment.
  3. Conduct regular check-ins with remote employees to provide visibility without micromanaging.

Challenge #5: Cultural Diversity

Managing cultural diversity among remote employees can present unique challenges. Cultural diversity includes differences between groups from different regions or locations, as well as generational differences. It’s crucial to be curious, sensitive, and open to learning about different cultures and adjust communication styles accordingly.

To effectively manage cultural diversity among remote employees, consider the following strategies:

  1. Foster a culture of curiosity and learning about different cultures.
  2. Adapt communication styles to accommodate different cultural backgrounds.
  3. Provide cross-cultural training to promote understanding among remote team members.
  4. Avoid stereotypes and assumptions about different cultures.


Managing remote employees comes with its own set of challenges, but with the right strategies and mindset, these challenges can be overcome. Building trust, establishing effective communication channels, fostering a sense of community and belonging, ensuring productivity, and managing cultural diversity are key areas to focus on. By addressing these challenges head-on, you can successfully lead a remote workforce and reap the benefits of remote work.

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