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In June this year, Jeremy Stoppleman, the CEO of business review website Yelp, announced that within a few short months their 4,400-person organization would be eliminating its hybrid workplace model and would go completely remote.

They’re not the only ones. 

As the BBC recently reported, many other big-name companies are also embracing full remote work models, including Lyft, Airbnb, Spotify, and 3M.

And, while the COVID-19 pandemic has been a catalyst to bring remote work and hybrid workplace models into sharper focus, and has helped accelerate the shift away from traditional office models, remote workplaces have actually existed for decades.

While there are many great benefits to remote work for companies and the people they employ, I know from my own experience previously as a remote manager that there are also many challenges of leading remote employees. 

I’ve led distributed office teams, managed people across different time zones, and experienced firsthand about cultural and demographic diversity. At one point I was managing offices in five different countries and individuals scattered around the world working from home.

During that time, I learned a lot about leading a remote workforce, how individuals respond differently to remote work, and how to create a sense of community and belonging with a distributed team.

In this article, I’ll help you figure out how to manage remote employees more effectively by running through five challenges you’ll face and how you can overcome them. 

These are:

But first up, a little clarification on what we mean by remote working.

Remote Work vs. Work From Home (WFH)

remote work infographic

Remote work and work from home (WFH) are related but different.

When we talk about the challenges of managing remote employees, we’re not just talking about those who work from home. We’re also referring to those who might work in small, remote offices geographically separated from a larger headquarters.

Enterprise service provider VMware offers this great definition of remote work:

Remote work is the practice of employees doing their jobs from a location other than a central office operated by the employer. Such locations could include an employee’s home, a co-working or other shared space, a private office, or any other place outside of the traditional corporate office building or campus.

It’s important to distinguish between work from home and remote work because the approach to managing team members can be very different. 

Working remotely requires special resources, systems, and processes designed specifically to manage multiple team members on a regular basis outside the central office.

Work from home, on the other hand, is often an occasional, unexpected, or impromptu situation. For example, a team member’s child might be sick or their car broke down.

Now that we’ve clarified our terminology, let’s jump into the main challenges of managing a remote workforce.

main challenges infographic

Challenge #1: Trust

Trust is the foundation upon which all successful remote work is built. In my experience, building trust is also one of the biggest challenges of managing remote employees because old-school, traditional thinking is that you can’t ensure productivity if you’re not working in the same office and able to actually see people working.

I’m reminded of an elderly founder and CEO I know who installed security cameras throughout his manufacturing facility so that he could monitor his employees anytime, anywhere.

If he didn’t see someone doing exactly what he thought they should be doing at that moment, he’d call them up and “crack the whip”. Needless to say, “trust” would not be a word I use when describing his company culture!

To effectively lead remote workers, you need to trust that they can be just as successful working from home or remote office as they would be working from corporate HQ and that they are doing the right things for their team and the organization. 

In an interview with Victor Tam, the co-founder of D2C luggage brand Monos, Tam comments on how they approach trust with their people: 

There’s trust in them having the company’s interests in the decisions they’re making and there’s trust in each other; trusting in your teammates to know that they’re also gonna be doing their best work.

Victor tam
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How do you overcome trust issues and build trust with a remote team?

Building trust is not easy and requires time, patience, and persistence. Going into detail on all the ways to build trust is an article in itself, but building trust usually starts with assuming positive intent

The Executive Coaching Network describes how “Assuming positive intent means acting under the assumption that the person with whom you are meeting is trustworthy and a team player – that they share your desire for the best possible outcome for the organization. You “act as if” they are going to behave in an effective and positive way.”

This is a mindset change that’s required to start the cycle of trust with remote team members. If you can assume positive intent, some trusted trust-building activities are:

  1. Create a living trust agreement.
  2. Establish SMART goals and OKRs (objectives and key results) that employees can commit to and follow through on.
  3. Be open and transparent, show vulnerability, and be willing to admit your own mistakes.
  4. Communicate from the highest levels of the organization that you trust your employees, as Airbnb co-founder and CEO Brian Chesky did in his email to employees.  

Challenge #2: Communication

When I was a remote manager, we hired international workers in Germany and Japan so I often started my day early to connect with the German team and then late to meet with people in Japan.

Video conferencing connections could be spotty, language was often a challenge, and it was sometimes difficult for people to keep their schedules and calendars updated to allow for spur-of-the-moment conversations.

Communication can be a big challenge in managing remote employees because of all the different aspects of working remotely that can be impacted by it, such as:

  • Individual communication: how should you connect with people 1:1? What impact do time zones and language have on communication? How do you allow for ad-hoc conversations? 
  • Team communication: how should you organize and lead remote team meetings? How can you communicate organizational (e.g. new HR policies) or team (e.g. new team members) information in a consistent way to everyone?
  • Project management: how do you manage work priorities across team members? How do you ensure effective project management and delivery on commitments?

How do you overcome challenges communicating with remote employees?

There are many aspects to communication, each with their own challenges and ways to overcome them. Here are a few ideas to consider:

  1. Ask your remote team members to ensure their online calendars are up-to-date to make scheduling recurring, one-off, or ad-hoc meetings easier for everyone.
  2. Use the right video conferencing software (e.g. Google Meet) that aligns with how your team works.
  3. Set clear communication guidelines for when and how remote workers should use instant messaging vs. email vs. phone vs. video conference.
  4. Use an appropriate intranet software platform (e.g. Microsoft Teams) that enables effective sharing of work resources and information.
  5. Remove bureaucracy and red tape that results in unnecessary communication.

A good podcast for optimizing your internal comms: How to improve business operations through internal communications.

Related read: 10 Best Remote Working Software for Distributed Teams

Challenge #3: Community and Belonging

One of the biggest challenges of managing remote employees is replicating the same feelings of community and belonging that can exist in physical office workplaces. 

With a remote workforce, it’s more difficult to engage with people informally over lunch in the break room or by stopping for a chat in the hallway. These types of relationship-building activities are important to creating and sustaining your company culture

Some of the best employee feedback I’ve received was from a casual conversation over coffee or during a walk outside. 

Remote work also makes culture-building activities like events and celebrations more challenging. These are extremely important parts of fostering a strong sense of community and belonging within your organization.

Related read: 10 Best Virtual Event Platforms for Digital Engagement

How do you overcome the challenges of fostering a sense of community and belonging with remote workers?

The best way to answer this question is to look at how some big-name companies are addressing it, particularly since creating a sense of belonging can often become more challenging as the organization grows.

The musical folks at Spotify talk about the importance of belonging as part of their “Work From Anywhere” program:

“We want everyone who works here to feel like they belong, whether they spend the majority of their time at home or in the office. We’ve adapted how we carry out our work in this area, shifting the focus from in-person events to virtual experiences that create opportunities for community and belonging and celebrate different cultural moments throughout the year.”

In a recent announcement, ride-sharing company Lyft talks about how they support their remote employees with a fully flexible workplace:

“Our expense policies will support travel to and from team gatherings roughly once a quarter. While physical attendance is optional, we expect many team members will look forward to the opportunity to collaborate, brainstorm, and celebrate in person for these moments and more.”

Here are some more ideas for fostering a sense of belonging and community within your remote workforce:

  • Video broadcast all-hands or town hall meetings, and actively solicit questions and feedback from remote employees through virtual Q&A
  • Support in-person attendance wherever possible at company events, celebrations, all-hands meetings, etc.
  • Create employee feedback mechanisms specifically for remote workers that enable them to share their thoughts anytime, anywhere.

Challenge #4: Productivity

The classic objection to remote work—an objection I’ve heard myself from people I’ve worked for in the past—is, “How do I know if my employees are doing their jobs when I can’t see them?”. 

Concerns around productivity and perceptions that people aren’t really working from home, instead lounging in their infinity pools (another real-life example), can be a challenge that you face when either considering a remote work program or managing remote employees. 

How do you overcome the challenge of managing remote employee productivity?

In his email to employees about remote work, Airbnb co-founder and CEO, Brian Chesky, had this to say:

"To pull off this level of flexibility, we need ample structure and coordination. Without it, things would become a free-for-all. The backbone of how we operate will continue to be our single company calendar with our multi-year roadmap. It’s centered around two major product releases each year—a May release and a November release. Even though not everyone directly works on these product releases, we’re organizing our entire calendar around them to maintain company-wide alignment. Our collaboration sessions, off-sites, social events, and breaks will be planned in advance and designed around this calendar."

Embedded in these comments are some great ideas on how to ensure productivity, effective coordination, and positive collaboration with remote employees, including:

  • Implement the CRA model of leadership to help remote workers rally around a clear vision and purpose that drives specific goals and deliverables.
  • Have a single shared calendar and other virtual collaboration tools to maintain alignment between remote teams.
  • Conduct regular 1:1 check-ins with your people that provide you with visibility into each other’s activities, but without micromanaging. To help, check out my guide to 1:1 meetings with template.

Related read: Best Employee Management Systems

Challenge #5: Cultural Diversity

Last, but certainly not least, on the list of challenges of managing remote employees is cultural diversity.

Employer of record services have made bringing international employees into the organization easier, but a good amount of work remains to be done for them feel as though they're a valued part of culture.

How do you overcome managing cultural differences of diverse remote employees?

I’ve experienced the challenges of managing employees from different cultures, from a team of people in Japan to a 62-year-old baby boomer working from his home in Oregon. 

Like their cultures, each challenge is unique and different, but can be overcome using some general leadership principles.

  • Be curious, sensitive, and open to learning when it comes to new cultures and different ways of doing things.
  • Adjust your communication style to accommodate different cultures, particularly when it comes to providing employee feedback or giving direction.
  • Conduct cross-cultural training to help remote team members to better understand each other.
  • Avoid stereotypes and assumptions, such as assuming that all baby boomers are scared of technology or that all Asians are good with numbers.

Further reading

The above are the five challenges I encountered when managing remote employees.

There are others to be aware of as well, including how to handle compensation and recognition, career development, and training.

Some further resources to help you manage teams in a remote and/or hybrid world:

By Mike Gibbons

Mike has extensive experience in sales, marketing, and product strategy; organizational and team development; and business growth and operations. He's held various senior leadership positions in the technology industry, and in 2016 participated as a lead member of the deal team responsible for the sale of Point Grey Research to FLIR Systems for USD$256M. Mike is guided by his deeply-held beliefs in connection, curiosity, humour, empathy, and honesty. Since leaving the corporate world in 2018, he's provide fractional executive and growth and strategic planning advisory services that have helped several early stage companies mature, grow responsibly, and live true to their values.