Leading Remotely

Make the most of your distributed workforce.

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(Re)Learn to Lead

(Re)Learn to Lead is a limited article series that distills wisdom from prominent experts on the future of leadership in a changing world. The article series will help you evaluate your leadership skills, know what you need to learn, and get ready for the changing demands of today's workplace.
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Image courtesy of Ken Orvidas/theispot.com

Editor’s note: This article is part of a new MIT SMR series about how leadership is evolving in a digital world.

Shortly after the turn of the century, I left Wall Street to work from home.

My husband had finished his Ph.D., and his best job opportunity was in Boston, not New York City. Well established in my career as an investment analyst, with an Institutional Investor ranking, I wanted to continue to work for Merrill Lynch and was able to persuade my boss to let me work from our new home in Boston.

This doesn’t sound especially exotic today, but it definitely was then. Relatively few people were working remotely; fewer still were working for large, fast-paced, team-collaborative companies that way. The technology was available, of course, but compared with the tools of today, it was primitive. A tech specialist from Merrill Lynch had to come to my home and spend a full day getting me set up.

These days, the organizational challenges are more difficult than the technical ones. And now that I run my own company, with employees in more than five states and the possibility of expanding internationally, I’m thinking about these issues not just as an individual contributor but also as a manager.

For my firm, home base is Lexington, Virginia, but only 15% of us are colocated, so most of our work is done remotely. We’re certainly not alone. A 2018 study found that 70% of professionals globally are telecommuting at least once a week; 53% work remotely half the week or more.1 Swiss office service provider IWG, sponsor of the study, clarified that the numbers refer to full-time employees — not freelancers and the self-employed. Add these other types of workers, hired on a temporary, part-time, or contract basis as critical contributors to many business teams, and the number of remote employees balloons.

We shouldn’t expect this trend to slow, much less reverse. Leaders must evolve strategies for managing both people and technology in an increasingly distributed workforce.

The Challenges

Leading remotely involves grappling with problems in several key areas:

Communication. When a company has employees all over the country or world, it’s understood that time differences can add a layer of complexity to the logistics of everyday communication. However, there are more subtle, and oftentimes more important, complications to consider when managing remote employees.

For one thing, when time zones don’t match up, less information can be transmitted in a given period, which means we as managers need to be aware of how this might affect the pace of project development. For another, in text-based communications like email or instant messaging, we’re unable to convey as much meaning as we can through vocal tone and cadence, facial expressions, and physical gestures — tools we normally take for granted in face-to-face conversations. Even our more robust methods of communicating virtually, like audio or video chats, don’t give us a broad view of body language.

As a result of those fundamental differences, miscommunication will almost certainly be more common among remote colleagues than in a traditional office. Our words alone rarely transmit as much meaning or information as we think we’re conveying. We must continually strive to make all communication as clear and consistent as possible.

But we also need to be patient with our employees and ourselves when miscommunications do occur. I recently hired a new assistant to help with research. She’s capable and has a lot of potential to grow in her role, but every week I cause a misunderstanding because I’ve assumed she understood my feelings and intentions behind sending a certain email, for instance, or I’ve failed to give her enough information about how to send a package. I need to remember that distance can make the onboarding process even more difficult than usual. As we both go through this transition, I try to stay aware of these dynamics, provide clear guidance up-front for each project, give immediate feedback on tasks as my new hire completes them, and praise her for the things she’s doing well. Despite the awkwardness of this adjustment period, she’s told me that the “hands-off” nature of the onboarding has helped her grow immensely. Because she can’t simply go to the next cubicle over to ask for help, she’s forced to problem solve on her own.

Finally, we all have different comfort levels with technology and our preferred modes and styles of communication. It takes time to understand the idiosyncrasies of each employee, not just new hires, and to reconcile those quirks with our own. Some employees may prefer email, some texts, some phone calls, and others video calls. If we don’t invest the effort to meet them where they are and speak their language, then we miss out on opportunities to connect with employees on a deeper level.

Project management. Having good systems and people in place to handle project management is essential for any organization — but it’s even more crucial for remote groups, especially given the communication challenges I’ve just described. For my own company, I’ve found tools such as Slack (which separates communications by topic so that employees can stay informed about the projects concerning them) and Asana (which allows us to share quick and efficient status updates on each of our projects) to be indispensable.

While digital tools facilitate remote project management and collaboration, they can also make it harder to tell what each person is actually contributing. With onsite employees, managers can simply visit people at their desks to have a better grasp of what they’re doing. But with offsite employees, we need to be proactive in reaching out and teach people how to manage up effectively so they can advocate for themselves. Relying solely on updates via digital tools can lead to under- or over-appreciation in the best-case scenario and misattribution and resentment in the worst. Staying in close contact with people can help avert some of these problems and give leaders a more complete picture of everyone’s contributions.

Talent development and management. In my thinking about how to effectively manage people along what I’ve been calling their “S-curve of learning,”2 I’ve come to appreciate the importance of having some employees who are at the launch point of their curve. Not only do they generate fresh ideas, they also help companies continually disrupt themselves so they can keep innovating in their fields. Despite my belief in this and the benefits shown in research, it’s hard to resist hiring a team of seasoned pros who are at the high end of their curve, who possess a full tool belt of skills, and who have a history of strong performance. It’s especially tempting in a remote setting to seek out people who require little to no training or oversight. I always try to push against this natural bias and make sure I have the proper systems in place to train and mentor new hires in order to cultivate their skills and gain their valuable insights.

However, I also have many employees who are at the high end of their S-curve. For them, I have to make sure I’m constantly taking their temperature and managing their engagement level with novel tasks. This helps maintain productivity and fend off boredom, which can be a greater challenge for offsite employees, given the lack of workplace camaraderie.

IT support and service. Since moving to rural Virginia, I’ve learned the hard way how much we take easy access to high-speed internet for granted. On numerous occasions, I’ve had to reschedule podcast interviews or make the 20-minute drive to my husband’s office to do a webinar because the connection at my own house just wouldn’t cut it. This rude awakening to the non-universality of good internet has led me to reevaluate assumptions that I used to make (and probably continue to make) about the availability and reliability of technology across my business.

As managers, we cannot assume that all of our remote employees will have equal access to reliable technology, internet, and (if they’re contractors) tech support. And even if they do, systems sometimes fail. It’s vital to have a good understanding of everyone’s situation and construct backup plans to use in the event of technical difficulties, which always seem to happen when we least want them to.

Why Bother?

Given the list of challenges, it may be tempting to question whether engaging with remote employees is even worth it. In my experience, it is. The concerns are valid, but over the years, I’ve reaped considerable benefits from having a largely remote staff.

Allowing people to work remotely means that you are not limited to the talent that’s near you geographically. If you’re introduced to a skilled sound engineer on the other side of the country, or if you have an acquaintance who could, with a little bit of training, become a great COO but lives in Singapore, those people can be viable employees or business partners instead of impossible collaborators.

Face-to-face interactions tend to be richer, as well, because more thought goes into planning them when team members aren’t colocated. These encounters can’t happen simply by chance — we have to carefully arrange a time for and understand the purpose behind each in-person meeting. Given all this planning and forethought, I’ve found that my employees are much more likely to be truly engaged in the meeting — offering suggestions and valuable insights and really listening to what I say. Instead of being brushed aside as everyday chatter, the words spoken in these meetings have real power.

There’s an unexpected upside to leading remote employees, too: When colleagues don’t share the same physical space day after day, there’s a distinct lack of workplace drama. I’ve found that this decrease in unnecessary conflict increases productivity and reduces the drain on everyone’s emotional energy. That isn’t to say that brick-and-mortar workplaces can’t be energizing — many are. But without a physical stage for gossip, intergroup antagonism, and the like, such issues are less likely to materialize.

Digital tools make working from home possible and contribute greatly to the flexibility of both organizations and individuals. But remote work is like a genie in the lamp of the digital revolution. Once released, there’s no stuffing it back in. We must learn to lead an increasingly large cadre of workers at home. And yet, if we effectively harness the strengths of this workforce while taking steps to minimize the drawbacks, we managers will find ourselves with an extremely motivated team who is willing to put in the time and effort to make the relationship work.


(Re)Learn to Lead

(Re)Learn to Lead is a limited article series that distills wisdom from prominent experts on the future of leadership in a changing world. The article series will help you evaluate your leadership skills, know what you need to learn, and get ready for the changing demands of today's workplace.
More in this series


1. R. Browne, “70% of People Globally Work Remotely at Least Once a Week, Study Says,” CNBC Make It, May 30, 2018, www.cnbc.com.

2. W. Johnson, “Build an A-Team: Play to Their Strengths and Lead Them Up the Learning Curve” (Boston: Harvard Business Review Press, 2018).

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