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Facing The Challenges of Virtual Teams: 10 Skills for Managing Remote Organizations Successfully

Managing a remote team successfully requires an attunement to what matters most in communication: understanding the human or humans in front of you.

If you can connect with humans face to face, you can transfer that feeling through the camera and across time zones. Doing so allows communication to flow clearly, commitments to be met, projects to happen with ease, and morale to skyrocket.

The most successful virtual teams have been proving this is possible for decades. 

We rounded up conversations we’ve had on these essential skills to face the challenges of managing virtual teams. Here are 10 skills needed to bridge the distance to the minds and hearts on your team. 

1. Understand the Levels of Listening to Become a More Empathic Listener.

As leaders, you have a choice, first and foremost, in how you process the information that’s coming at you at any given time. It can be helpful to think about the choices available to us in listening as comparable to looking through different lenses. Each lens highlights different elements and colors our perception of what we’re taking in. And different lenses are more appropriate for some situations and less so for others.

“Empathic listening and connection are really about meeting another person on a human level,” notes Reboot coach Andy Crissinger. “They are about suspending my preconceived notions of what’s right, of what might be going on for this person, asking great questions, and listening. Doing so allows new insights to emerge as I allow myself to suspend, at least temporarily, my way of seeing the world and connect with how someone else sees it.” 

Reflect on your own patterns of listening: 

  • What is my go-to mode of listening under normal circumstances? What about when I’m stressed?
  • What mode(s) do I underutilize?
  • How might I shift my listening choices to get different/better results in my life and work?

Encourage your team to take our free email course: Reboot Your Listening.

2. Create Psychological Safety to Build Trust. 

Our best work happens when we’re at ease, not stressed out. Drowning in anxiety and fear about the status of our belonging in our work environment increases our stressors – both internal and external. Creating trust in our organizations requires that we build safe spaces when the collective feels valued, heard, and seen. 

“The best leaders make sure that all members of the team are cared for and know that the leader has their back,” notes Reboot co-founder and coach Ali Schultz. 

Andy Crissinger notes: “One of the most important things a leader can be doing to create psychological safety in the group is actually to model a kind of vulnerability and a kind of humility that from time to time says, “I don’t know.”

Reflect on the culture you have established: 

  • How safe do people feel in my organization? How safe do they feel to say what they need to say? 
  • What do we do to make sure folks feel like they belong? How do we know it’s working? 
  • How have I been complicit in creating the circumstances I say I want to change? 

Most often, we create the conditions we say we don’t want. Even in the most toxic work environment, we have the opportunity to look closely at how we may be contributing to the situation we find ourselves in. Looking closely at what is created in the organization now can help see the behaviors and patterns that are unsupportive and non-generative for the culture you’d like to see. 

Curious about how you’ve been complicit in creating what you say you don’t want? Check out our free email course on exploring your Shadow.

3. Make and Maintain Commitments to Increase Accountability.

Making and keeping commitments is a necessary building block for sustained collaboration and growth within an organization. Coordinated action, the process of requesting and making commitments, requires good hygiene around elements of communication, especially as organizations adapt to working in virtual environments.

“If we can have really clear commitment conversations, and at the same time do so with some grace for the human being that’s behind them, I think we can start to find a bit more of a nice, neutral space where we can still rely on things to get done,” notes Reboot Coach Jeff Riddle. 

We want to know where we’re headed together and who’s doing what and by when. Additional context is always useful in commitment conversations: What am I even committing to? Why am I doing this thing? Why am I saying yes to it? Why am I asking for it? The breakdown of commitments can have a damaging impact on trust, performance, and workplace culture. Good hygiene around communication about commitments and getting clear on what we’re asking, what we’re responding to, what we’re committing to on a very basic level of operating can dramatically shift the way your team works together. 

4. Deliver Better Feedback to Maintain Relational Health.

Feedback can be one of the best ways to maintain relationships and strengthen connections within an organization. Creating an underlying culture that supports the health and safety of an organization through feedback is an extremely valuable leadership tool. 

As Reboot Coach Jen Cody reminds us: “Feedback is an investment in a relationship.”

“We don’t want anonymous feedback frameworks to be the only way that people are giving and receiving feedback from each other,” notes Andy Crissinger. “If you’re doing 360s with anonymous feedback so that you can keep people from having honest conversations with one another, then that’s a problem.” 

Think of some challenging feedback you have to give: 

  • Why is it important to the person you’re giving it to?
  • What is a specific example of the behavior? 
  • What was the impact?
  • What would you like to see instead? 
  • What’s at risk if you don’t deliver this feedback?
  • Write out the feedback you’d like to give.

Sign up you and your team for our workshop on Feedback September 24, 2021.

5. Establish Check-ins as a Meeting Ritual. 

The fundamental unit of doing great work is conversation. Conversations happen easier, clearer, and more harmoniously if we can connect as human beings, look each other in the eye, trust, and feel safe naming what’s up for us. We use a Red-Yellow-Green model for check-ins that can shift the tone of how you relate to folks and hold meetings such as 1-1’s and offsites.

“In this time, especially with the pandemic, having meetings just for check-ins can be a really beneficial way to build resilience and to build understanding in your organization,” asserts Reboot coach Chris VandenBrink. “Having this ability to share, not only what you’ve been doing, but how you’re feeling as you’re doing it, can be incredibly important.”

Often, jumping into an agenda, or trying to get something done without recognizing who’s in the room, where they are emotionally, and what they might be carrying, is a surefire way to have an unproductive meeting. As Andy Crissinger reminds us, “When we assume that the content of [meetings] is all that matters, we’re meeting each other as means to an end, and we really don’t get the best out of our collaboration when we’re interacting in those ways.”

Being able to name your own inner state, or hear yourself name where you are, in a group check-in can have remarkable effects on how present you can be for yourself and others in the meeting. Listening to where others are in their inner states not only helps our nervous systems relax, it fosters a much greater sense of connection among the humans in the room (or virtual room). (See also #1 and #2 above.)

Want to establish connection and community on the team and across timezones? Our guide to creating Peer Groups has useful insights for ways to structure time and engage with each other in safe and authentic ways.

6. Ask Better Questions to Engage Your Team.

Inquiry is an incredibly central and important skill, but it’s often underemphasized or even overlooked in the world of leadership. Adding inquiry as an additional tool in your toolkit can be in service of you, your team, and the work that you’re trying to do together.

“Self-inquiry should actually proceed all of our other outward work as leaders,” Andy Crissinger reminds us. “Inquiry is not just for us to use on other people, it can also be incredibly helpful to get curious about what’s going on for us,” notes Chris VandenBrink.

When our meaning-making process goes unexamined and stays beneath the level of our conscious awareness, we can become trapped in mental models and ways of thinking that are not in service to us. In other words: if we don’t stop to wonder about what’s driving us or our thoughts and ideas, we may be moving blindly through our days, our meetings, our planning sessions. 

Moreover, we might not realize that there’s actually a choice available to us when we feel stuck. Utilizing inquiry by asking open & honest questions can help you understand how you came to have your beliefs about the world can reveal blind spots in your organization.

Download our 28 days of journaling prompts for leaders to help with your own self-inquiry. 

7. Understand How and Where Power Dynamics Exist.

As leaders, we have our work to do personally, especially when it comes to fully grasping the responsibility we have to examine how our power plays out in the organization. As the leader, you are afforded a certain amount of power. The question then becomes: what do you do with it?

“In telling someone how to fix something, if they don’t have a sense of agency, they’re probably not going to be able to resolve it themselves,” notes Reboot co-founder and coach Dan Putt. “And they’ll also continually come back, looking for help, as opposed to being able to fix it for themselves going forward.”


When you think about the power you hold and what dynamics that has in your 1-1s or other meetings, how does that shift how you show up in those meetings? How might that affect the other people in the room? 

The opportunity in any relationship that’s aware of their positions in power dynamics is the experience of being in “power with” versus the feeling of “power over.” This model and way of being is emergent when we operate from the right use of power and lean into generative interactions.

8. Know Where You Are on the Ladder of Inference.

Bringing what’s unexamined into the light of what’s examined can help us communicate and collaborate more effectively, especially during times of difficulty. A tool like the Ladder of Inference can help you slow down just enough to ensure that you’re communicating and collaborating effectively with your virtual team.

“Bringing what’s unexamined into the light of what’s examined can help us communicate and collaborate more effectively during times like these,” Andy Crissinger reminds us. 

As leaders, we’re all coming from different perspectives and operating with shortcuts to our thinking. While these shortcuts can often be helpful, when left unexamined they can limit us to familiar patterns of behavior that limit our choice and ability to be adaptive in remote environments. Recognizing that we have a Ladder of Inference and bringing what’s unexamined into the light can help us communicate and collaborate more effectively across remote environments. 

“When our meaning-making process goes unexamined and stays beneath the level of our conscious awareness, we can become trapped in mental models and ways of thinking that are not in service to us,” notes Chris VandenBrink in this piece on The Importance of Inquiry. “We might not realize that there’s actually a choice available to us when we feel stuck.”

9. Include Inclusivity to Increase Productivity.

Inclusive leadership is not only risky but often uncomfortable. However, all great leaders know discomfort is necessary for individual and organizational growth. True inclusivity requires removing the barriers to belonging in the workplace; when those with whom we work feel a true sense of belonging, trust and productivity increase within an organization.

“Part of our experience of being a leader is to lean into the sharp edges of the places where we might feel guilt and shame, where we feel inadequate, where we feel incompetent and to allow the experience of that means to allow the fullness of our humanity to come forward,” writes Reboot co-founder and CEO, Jerry Colonna.

“To use radical self-inquiry to grow as a leader is incomplete if you are not willing to look at the biases that you have been acculturated with and grown up with,” Jerry Colonna reminds us.

Learning the ways of inclusion is part and parcel of becoming an authentic leader. You can’t have one without the other. Leadership without inclusion is oppression under a different guise. Inclusive leadership is how privilege can be used for good, and how power dynamics can shift from oppressive to free and equal.

Dive into our free email course, Inclusivity: Building Organizations of Belonging.

10. Have Hard Conversations to Manage Conflict and Support Generative Communication.

Conflict in the human realm presents us with many challenges, some we’d rather not face. How we act in the face of conflict tells us something about where we’ve come from and also about what personal obstacles may prevent us from handling conflict with clarity and grace.

“When that impulse to make the conflict go away is applied to inequality and inequity, it exacerbates the harm that has been done to those who might come from a marginalized position relative to others,” notes Jerry Colonna.

Learning to unhook yourself from the ways in which conflict brings out your least-full-self is a big part of growing up and becoming a better human (and better leader). In the process, you attain a greater range of motion in the conversations you face daily without engaging with others from the webs and other emotional places we can get stuck in.

In this blog post, Jerry considers the way in which our unconscious tendencies can inflict damage on our organizations and the people around us. 


We believe strongly that becoming a better human makes you a better leader, and better leaders build more humane organizations. Whether you are just starting out on a team of 2 or managing a virtual team of 50+, in an office, or tied to zoom meetings, these skills are essential to leading humanely. 


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