Whether you’re giving tough feedback, addressing a conflict or expressing a difference in opinion, difficult conversations are inevitable in the workplace. The ability to have these conversations quickly, effectively and authentically often separates good organizations from great ones.

Even under normal circumstances, difficult conversations are … well … difficult. They’re tricky and uncomfortable. When they happen virtually, the challenge is compounded further.

That challenge isn’t going away, because remote work isn’t going away. In a summer 2020 PwC survey of almost 700 chief executives, 78% agreed that remote collaboration is here for the long term. According to a Gartner survey from the same time period, 82% of company leaders plan to allow employees to work remotely at least part time after the COVID-19 pandemic, and 47% will allow employees to do so full time.

Having difficult virtual conversations, then, has become an essential tool in the modern leader’s toolbox, and learning and development (L&D) professionals must ensure that their leaders have developed this capacity.

To that end, here are four tips for having difficult remote conversations:

1. Make Sure the Tech Is There

The first question to ask is whether employees are set up with the requisite technology for seamless virtual conversations. Do they have adequate home computers, Wi-Fi connections and headsets? Have they been trained on how to use videoconferencing software?

These questions may occur as an afterthought for many people. What does tech support have to do with the substance of a difficult conversation?

A lot, actually.

Difficult conversations require a high degree of presence, and presence is all but impossible with the distraction of lagging bandwidth, broken connections or otherwise finnicky technology. You can’t stay focused on “What really matters to this person in this conversation?” when “Will the Wi-Fi hold up?” is occupying your headspace.

2. Difficult Conversations Can’t Be the Only Conversations

In an in-person setting, plenty of spontaneous run-ins occur during the course of the day. The casual, “low-temperature” quality of these interactions help to offset the intense, “high-temperature” quality of an occasional difficult conversation. It’s part of the natural ebb and flow of a workplace environment.

When colleagues work remotely, on the other hand, they may only interact directly with one another when a specific need arises — often, when something has gone wrong and needs to be worked out. It’s easy to see how a mood of resignation and resentment could result from a few consecutive conversations of this variety.

That’s why it’s critical to intentionally manufacture casual interactions to “break up” the difficult ones. You might create casual interaction explicitly by, for example, hosting regular (weekly or monthly) team culture calls to boost morale authentically. Or, you might do so more implicitly by, for example, taking the time to “up the volume” on gratitude and acknowledgement for colleagues (and personally track whether you reach each colleague or team at least once per month).

3. Don’t Avoid People

Another consequence of the elimination of casual run-ins is that it has become easier than ever to hide. In an in-person work setting, one can only duck out of the hallway so many times. In a virtual setting, someone with a knack for conflict avoidance might successfully stay off the radar for days, weeks or even months.

The issue is that the longer people avoid a difficult conversation, the more each party fills in the gaps with false assumptions, narratives and rationalizations. They are likely to minimize the importance of the issue or blow it entirely out of proportion. The only way to head off that unhealthy cycle is to act quickly and have the conversation as soon as possible.

Doing so requires leaning into conflict when it shows up — which is not necessarily what leaders are wired for or accustomed to doing. Especially when collaborating from a distance, it also means reducing one’s tolerance for missing communication. Given the human tendency to focus on what is in front of us, it’s a good idea to set up a structure, such as weekly phone or email touchpoints, to ensure that learning how your team is doing occurs on a regular basis.

4. These Days, Assume a Mitigating Circumstance

We are living in extraordinary times. The pandemic has upended the world as we know it and affected all of us in some way. It’s important to keep this context in mind when the need for a difficult conversation arises.

There is a strong tendency to keep the “human” out of work, and remote work often supports this misguided approach. However, we can only compartmentalize our selves for so long. Moods seep out. Feelings announce themselves. Learning to embrace them creates a more productive and fulfilling workplace in the long run.

This reality doesn’t mean we should pry when speaking with colleagues. It doesn’t mean we should put people on the spot at the beginning of every conversation (“What’s the matter? Come on! You can tell me!”). But it does mean we should remain open and curious about what’s really going on in our colleagues’ lives and proceed with empathy as we embark on a difficult work-related conversation.

This fourth tip is especially important for feedback conversations and performance reviews. The source of the low performance may be rooted in a circumstance that has nothing to with the task or project at hand.

Modern technology is a wonder. During a world-changing public health crisis, it has enabled us to continue to work and collaborate safely. Emerging technologies will only expand that capacity. But, for the time being, we need to make a few adjustments to ensure our virtual conversations are imbued with the authentic presence and connection that we took for granted with in-person conversation. As difficult conversations inevitably arise, it’s important to provide our colleagues with the skills and training to have them powerfully, from a distance.

Share