How To Lead a Remote Team Effectively

Leadership in any context is challenging. When you start crossing language barriers, cultural boundaries, and time-zones, mixed in with a wide-variety of skills sets and experience, it’s an entirely new level of challenge.

Technology has made it easier than ever for organizations and businesses to build and leverage teams compromised of people scattered all over the place. These teams fall under different names: “remote,” “distributed,” or in academia, “geographically dispersed.” Call them what you like, employees and teams that don’t share the same physical space have existed for a long time (think multi-national corporations) and have become increasingly common for all kinds of organizations.

I have one friend who lives tucked away on the edge of a National Forest in Idaho and works for Heroku (he previously lived on the road with his family for a year-and-a-half, traveling the western U.S. while working remotely).
A former co-worker now runs his online business and lives on a boat with his family, currently in the Bahamas for the next several months.
A local friend does software development for a mobile app that lets you check out digital books and audiobooks with your library card.

This trend will only continue to be more prevalent in the coming years and in increasingly diverse industries.

(Others have made much more compelling arguments for why remote working makes sense than I could. A few examples are below, if you’re so inclined. Otherwise, let’s assume you’re on board with the concept of remote teams.)

(Also, check out the book Remote by Jason Fried)

If we accept that remote teams will become more and more common, two immediate questions arise:

What are the unique challenges remote teams face?
What kind of leadership does it take to lead remote teams well?

I spent four years working for a mobile app with roughly twenty-five team members (at the time I left). Partially remote, about half of us worked in the central office, with the other half being spread out across several states (and one in France). We also leveraged the time and talents of over 400 volunteers from dozens of countries, working in more than a thirty languages and providing user support, translation, and software development. Leadership in any context is challenging. When you start crossing language barriers, cultural boundaries, and time-zones, mixed in with a wide-variety of skills sets and experience, it’s an entirely new level of challenge.

As part of a master’s program, I recently took a look at what research suggests about leading remote teams — what the core challenges are, what strategies are effective, and what type of leaders succeed most often in these environments.

The research confirmed what my experience suggested, pointing to the fact that leadership challenges in a remote team aren’t necessarily unique — but they are presented in ways that can be disorienting, time-consuming, and complex in ways not common in traditional work environments.

Pulling together the practical and the theoretical, here are the four main challenges I see remote teams facing today:

The Challenges

Communication:

  • Not sharing a physical space makes communication more challenging, time-consuming, and prone to formality. The loss of spontaneous and informal communication is especially challenging. And without non-verbals (which are muted even on a video call), interpreting meaning and intent can be perilous.

Norms:

  • Without a shared context for team building and the work to be done, teams often struggle to figure out what “normal” is going to be. How to prioritize projects, how to approach decision-making and conflict resolution, asking for time off, formality of documentation and paperwork, and even understanding what the ultimate goal or purpose of the work will be can be distinct challenges. What’s normal or expected is often left poorly defined and unclear in remote teams, in part because of the inherent diversity of background or culture.

Cultural Differences:

  • Culture differences always exist, even if everyone is in the same country or state. Every one on your team is coming from another organization that had it’s own culture. Now they’ve joined your team and have to figure out how they need to adapt to fit into your culture. True in any organization, but more challenging in a remote environment.
  • Personal experience colors what each person sees and expects, so differences have to be acknowledged and understood before they can be adjusted. Still, these personal differences have to be explored in step with any broader cultural expectations. Communication patterns, leadership styles, and problem-solving strategies can differ widely between countries. Plus, each person is a nuanced representative of their culture, not an exact representative, which means you can’t rely on stereotypes and broad assumptions. Multiply the challenge factor as national and skill-set diversity increases.

Leadership Impact

  • Many who are leading a remote team for the first time find their default style falls flat or isn’t as effective as it usually would be. Leading a remote team takes almost everyone out of their comfort zone, at least initially. The impact of how a leader leads is magnified in remote environments, for better or worse.
Chargify is a 100% remote team, with around 30 employees in about 17 states and four countries.

How Do Effective Leaders Respond to These Challenges?

Looking at academic research from the past ten years, and seeing it through the lens of experience, several recommendations for remote team leaders rise to the top. The principles below will help anyone leading a remote team, but keep in mind that every organization or team is unique and will require you to tailor your approach in your specific context.

Establish Norms Early

  • Because remote teams don’t share a physical space, it’s easy to leave a lot of questions and expectations unanswered. Explicitly establish meeting practices (when, where, how, why). Promote question-asking as essential to every interaction. Have an all-hands conversation, as early as possible, to explore what the “norm” will be for expressing disagreement and resolving conflict. Especially as cultural differences increase, it will be important not to impose the leader’s preferences on everyone else, but instead to establish a third way that integrates input and buy-in from everyone. Ultimately, the lack of spontaneous conversations and informal learning that happens in a shared space means you need to over-communicate the vision and culture you are looking to establish.

Limited Communication Channels Doesn’t Have to Mean Limited Communication

  • You don’t have a water cool or lunchroom and you can’t grab drinks after work, but that doesn’t have to mean your team has to be less informed or connected. In fact, research shows that having a limited range of communication methods doesn’t mean overall communication effectiveness will decline. What does have an negative impact? Infrequent, vague, unpredictable communication. That’s true in any environment, even more so when you can’t see the people you are working with. Make it clear that communication is a priority by establishing a rhythm of communication, formal and informal, that fosters personal connection and clarifies goals, progress, feedback, and success.

Build Trust and Connection With Each Person

  • As the leader of a remote team, you become a sort of proxy for the entire team and organization. Each person will look to you for inspiration, guidance, clarity, confirmation, and much more than you might expect. Again, the loss of shared space changes where people look to make sense of the chaos that comes with doing meaningful, collaborative work. You can eliminate some of the chaos team members feel right from the start by establishing a personal connection even before work begins. Don’t overdo it, but attune to each person and make an appropriate connection that moves your interactions from transactional to relational.

Monitor Progress Toward Goals

  • People want to know that they are winning. And having a sense of progress toward success is highly motivating. Use technology to create a digital dashboard of sorts that makes it clear where the team stands at any given moment. What’s working? What’s not working? What’s the next step? Clarity on the mission progress is especially key for remote teams that have a lot of blind spots on what everyone else is doing.
An example of a digital dashboard, used to keep everyone on a remote team up-to-speed on support ticket metrics.

Leadership Style Matters

  • Leaders who just want to get stuff done (i.e. “transactional leaders”) make remote work harder for individuals and the team. Leaders who demonstrate inspirational or transformational leadership qualities (evoke enthusiasm, loyalty, and trust; leverage positive emotions; demonstrate empathy and active listening) are much more effective and successful. In fact, research shows that inspirational and transformational leaders can actually be more effective in a remote environment as compared to a traditional face-to-face environment.
  • As a leader, if you think leading a remote team sounds easier because you don’t have to deal with “all the personal stuff,” you’re likely going to face a frustrating uphill battle with your team. You should also look for opportunities to empower “informal leaders,” those on the team that rise up to support, encourage, and develop the team through their own relational connection. Because you will likely have less interaction with each person, great leaders understand that informal leaders play an important role filling in gaps you won’t be able to fill singlehandedly.

While working with a remote team brings complex human challenges to the forefront, it also creates unique opportunities to draw upon the best talent and resources, regardless of geography. Remote teams can accomplishing meaningful, highly successful work when leaders are intentional to meet the needs of the team and foster a culture that creates personal connections, clarity, consistency, and shared success.


Maybe I’ll write more later about my specific experiences leading and being led in a remote environment.

Lastly, though, is a list of digital tools teams can use to lead remote teams well. I’ve used many of these, there are many more out there, and there are always more being developed. Understand what you are trying to accomplish and only use tools that move you toward that goal. Leave a comment and let me know what tools you have used or would recommend.

  • Basecamp — full service platform for planning, conversations, and more
  • Slack— communication platform with plenty of integrations
  • 15 Five— weekly check-in platform to increase dialogue and transparency
  • Jell— daily stand-up platform with ability to track progress and goals
  • SproutMark— regular check-in platform to increase dialogue
  • iDoneThis — daily tool to share progress and increase transparency
  • Know Your Company— designed to help mid-sized teams stay connected

I’m a leadership and organizational development coach and consultant. I offer leadership coaching, emotional intelligence assessments, team training, and more. Get more info at www.adambouse.co and let’s pick up a conversation.