laptop on bed

Virtual difficult conversations can be accomplished well with careful forethought about how the tools of the platform help or hinder.

It’s 2:05 pm. Everyone on the team has finally managed to log onto the virtual meeting space. Casey is sitting on a folding chair with a laptop on his bed because his teenage son is using the family’s desktop computer for a virtual class. Casey is working in his bedroom because he needs a little privacy: he plans to talk about problems his team is having with scheduling remote phone monitoring during the COVID-19 crisis.

As the meeting slowly progresses, Casey switches to the "gallery view" and sees that six peoples' screens are blacked out. Two screens show only a telephone number. He also notices an indicator by the "chat" icon. Casey checks the chat feature and sees there's a side conversation going on that seems to have little to do with the issue the speaker is talking about. Then he notices the host is on mute talking to someone off-screen.

The meeting seems to be off the rails and Casey hasn’t even raised the issue of scheduling phone hours more equitably. He is not sure he can even raise the issue in this environment. [Note: this scenario is fictional.]

Difficult subjects make for difficult meetings in the best of times. As the COVID-19 crisis requires continued social distancing over the coming weeks and even months, difficult meetings will happen in new ways. The technology tools (e.g., Microsoft Teams, or Zoom) that enable everything from large training events to small group collaborations add a unique set of challenges to communications, potentially turning already difficult conversations into impossible ones.

Although you may have used a digital platform such as Zoom successfully in different meetings already, the way you set up and gather for difficult conversations in the virtual realm requires additional thought and planning. Three principles will help you lead or participate effectively in a difficult discussion online: 1) Invite with intent, 2) Unpack the dialogue parts, and 3) Listen to learn.

Invite with Intent

"Without awareness and adaptation, difficult virtual conversations will go off the rails even if we say the 'right' things."

When I was in college, I took a class in broadcast journalism. As part of the class, we read the news for the college’s small radio station. Before our first broadcast, our professor recorded us reading the news in a studio so we could hear how we would sound on the air.

As I read for the recording, I was sure I was clear and articulate. I thought I paced myself well. But when I listened to the recording, I was shocked to hear a flat, monotone-sounding person using my voice. I learned that what may seem perfectly fine in “normal” circumstances easily falls short in a virtual environment (in this case, radio).

Having a meeting over a digital platform such as Zoom creates a similar dynamic. What works with minimal reflection in a face-to-face workplace — such as choosing a common place to gather, figuring out where to sit (if the group sits at all), what to do to "warm up," how to take breaks, and how to close the meeting — all change once the group "goes digital." And those changes only compound the existing challenges we face in conducting difficult conversations.

As you experience the common disconnect that comes from the illusion that a virtual gathering is just a “normal” meeting on video screens, consider people who experience vision or hearing loss as adults. Although day-to-day tasks must still be accomplished, they learn to complete them in ways most of us never have to think about. They give up nearly automatic processes (e.g., reading), focus on overarching goals (e.g., learning something new) and develop strategies to achieve those goals with different tools (e.g., listening to an audiobook).

In a similar fashion, when entering a difficult conversation in the virtual realm, you have to become aware of and dig deep into your core interests for the meeting. With a clear understanding of your interests, you can consider tools and adaptations to meet them with the other participants. Without awareness and adaptation, difficult virtual conversations will go off the rails even if we say the "right" things.

As the host of a difficult discussion seeking to “invite with intent,” start with the basics. Develop and share expectations with virtual attendees regarding the use of the features of the platform and your expectations for the meeting. A virtual platform’s default settings will not fit all meeting goals. And in-person context will not provide clues as it does in a non-virtual workplace. Also, when determining the agenda, be prepared for a virtual “technology friction” that sloooooows down all virtual meetings.

To clarify and streamline expectations, you may want to create and share a virtual meeting guide with fellow participants beforehand. Employing a standard "how we will gather" template for all your virtual meetings helps decrease anxiety by enhancing predictability. If you are not the host, and you believe the stakes may be high, ask what standards will be in effect regarding basic technology considerations (recording, camera use, chats, etc.).

Let’s walk through a couple of representative issues: camera use and chats. For some difficult meetings, you may have an interest in enhancing trust and developing a shared sense of purpose. In that case, you will want everyone to be able to see everyone else’s faces. To "invite with intent," consider a norm that participants should leave cameras on unless bandwidth limitations cause a problem or the participant needs to move unexpectedly. Turning off the camera makes it easier to "hide" and multitask, which may be okay in some virtual meetings but it generally doesn’t work for difficult conversations because of the heightened need for trust-building.

Even with a "cameras on" norm, if participants default to a one-at-a-time "speaker view," they will not be able to see each other for most of the time. In that case, invite participants to switch to a "gallery view." And if the meeting is larger than nine or ten people, even with a "gallery view" the host and most participants will not be able to see each other without scrolling. In that case, be clear about how individuals may join the conversation or be invited to join, so no participants feel marginalized and their perspectives lost.

Similarly, norms regarding one-on-one or group conversations via your platform’s direct messaging function may help resolve side issues quickly but can aggravate shared investment in the process if the conversation is difficult. Strike a balance carefully. When appropriate, consider turning off the feature beforehand.

Unpack the Dialogue Parts

""In much of the current 'everyone at home together' virtual working world, a person may transition instantly from a 'home' issue into a virtual meeting with no opportunities to read the emotional temperature of other participants."

According to authors Douglas Stone, Bruce Patton and Sheila Heen, discussions become "difficult" for three reasons: 1) we fail to understand the range of different perceptions we and others have about a situation; 2) we don’t address motivating emotions; and 3) we don’t consider identity issues that may be at stake. See Difficult Conversations: How To Discuss What Matters Most. If you have "invited with intention," you are prepared to use or work around your platform’s features to mitigate these potential friction points.

In short, be mindful of the three simultaneous "conversations" that go on in every difficult conversation (differing perceptions, emotions, and identity) and to structure your virtual meeting to allow these issues to b addressed effectively.


To get ahead of gaps in perception that may derail a virtual gathering, the meeting host may want to use the virtual platform’s polling feature or standalone website to seek input about one or more key considerations. Various websites such as “” offer this feature free to small groups.

Inviting the participants to consider their perceptions and to see each others’ responses live can provide valuable insights in real-time. It can also help focus participants on joint problem-solving over the mischaracterization of intent that usually flows from unexamined differences in perception and available facts.


In preparing for the emotional component of difficult conversations, remember that most in-person meetings naturally include time before and after a meeting to see and hear other participants informally — even outside the meeting time. This helps participants transition and gather emotional clues about what is going on with others.

In much of the current "everyone at home together" virtual working world, a person may transition instantly from a "home" issue (e.g., a child’s unexpected school problem) right into a virtual meeting with no opportunities to read the emotional temperature of other participants. This abruptness and emotional disconnect can aggravate and even generate conflict.

Consequently, consider including a "gathering time" at the start of or before a meeting for participants to ease transitions and experience each others’ emotional cues. Not everyone needs to talk, but everyone should be encouraged to be there if possible.

Once a meeting starts, emotional cues will remain hard to receive. If the subject matter may generate deep-rooted emotions, you may want to schedule breakout sessions or request they be scheduled in advance. These can be framed as "check-in" opportunities. The size and dynamic of the overall gathering will determine how mid-meeting check-ins will be accomplished and who will participate, but the principle is to acknowledge that emotions are understandably part of the discussion and have a place.

Another option for plumbing the emotional responses of participants is to create a live "word cloud" poll where participants share one word or phrase they feel about an issue. To allow more free expression, consider offering anonymity with ground rules (e.g., entries must be framed as an implicit "I feel" statement).


Identity issues are generally the hardest to address in difficult conversations. Identity in a difficult conversation is a person’s ideas about who they are at a base level (e.g., competent, worthy of respect, considerate, effective). The virtual environment doesn’t change that dynamic. In the current mass telework world of the COVID-19 crisis, some offices, organizations and even industries have employees experiencing fewer opportunities to feel their contributions are needed and valued.

Thankfully, many of the tools discussed above — live anonymous polling, building in explicit transition processes, scheduling breakout meetings — can also work to flesh out identity issues during virtual meetings. Much depends on the size of the group and the existing dynamics.

However, perhaps the best way to address identity issues may be to look for them in yourself and to acknowledge them bravely. If you feel unexpectedly off balance or unsettled by an issue, consider what identity issues in yourself may be prompting the feeling. It may be insecurity about your continued value to the organization. Or, it may be a desire to be seen as competent in this rapidly changing work environment.

If you find identity issues at stake for yourself, look for opportunities to share those concerns and invite others to do the same, when possible. Modeling vulnerability well builds stronger teams.

Listen to Learn

Acknowledge that virtual meetings make it hard to be heard and understood and build in a process to compensate

Virtual meetings generate more communications friction than in-person meetings. It's a rare meeting where at least one participant’s connection doesn’t freeze or there is not some confusion about who should be talking. Despite the fact that communication friction is an inevitable feature of virtual meetings, our human need to feel heard and understood persists unabated.

To make matters worse, the human tendency to plan what we are going to say when our "turn" comes up instead of listening becomes even more pronounced in virtual meetings due to communication friction. One way to work through this tendency is to have an agenda that includes explicit structures and facilitated activities for expressing ideas and feeling heard (e.g., Casey's desire to talk about remote phone monitoring in the situation above).

For example, you might have a "listen to learn" item immediately following the meeting's opening. The "listen to learn" session could begin with a short block of time for each person to share one observation about an issue or issues. After two people speak, the next person would be invited to identify one difference or commonality between the previous two speakers and then share her own observation. The process would continue until each person has had an opportunity to compare and share.

Your "listen to learn" session could take many other forms. The key is to openly acknowledge that virtual meetings make it hard to be heard and understood and that you would like to build in a process to compensate, giving group members a fair opportunity to accomplish these essential steps. If it would make it easier to "sell" the group on the idea, just blame the limitations of technology.

Digging into Difficult, Virtually

In summary, difficult conversations will be a part of our "brave new world" during the COVID-19 crisis whether we prepare for them or not. Virtual difficult conversations can be accomplished well with careful forethought about how the tools of the platform help or hinder core goals, by giving attention to the constituent parts of the difficult conversation, and by ensuring that participants have ample means to express themselves and to feel heard through a predetermined structure.

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