Difficult remote conversations: How to keep your cool

Tough conversations are happening remotely right now: Leaders need to use emotional intelligence to stay calm and focus on making difficult conversations as healthy as possible
258 readers like this.
soft skills email etiquette

Think about the last time you faced a difficult conversation at work. Perhaps you needed to tell a manager that their team wasn’t hitting its performance targets. Or maybe an employee had to be reprimanded for disrespectful or irresponsible behavior. It’s possible that you’ve even had to terminate someone. These conversations can be tense and stressful for everyone involved, which is why leaders need to be prepared to hold them effectively.

Tough conversations can bring out the worst in otherwise good leaders. Because they expect awkwardness or even confrontation, defense mechanisms spring up preemptively: they cajole, threaten, or yell at employees instead of approaching the situation with a cool head. But self-awareness and self-management are two of the most fundamental traits of emotionally intelligent leaders, and they’re skills that can be developed over time.

[ Do your employees feel psychologically safe? Read Crisis leadership: How to give people psychological safety. ]

When communication norms are being challenged, it's even more important that leaders stay calm.

In our current climate, many of these tough conversations are now happening remotely, with leaders and their direct reports meeting through a video call. All the strategies we’ll cover here can be implemented in this environment as well. When communication norms are being challenged, it’s even more important that leaders stay calm and focus on making difficult conversations as healthy as possible.

Remote conversations: Context is crucial

Employees should never feel like they’re being asked to do something strenuous for arbitrary reasons – or worse, for no reason at all. “Because I say so” might work with children, but it’ll never be acceptable to your colleagues. That’s why it’s essential to give employees the context for your decisions.

"Because I say so" might work with children, but it will never be acceptable to your colleagues.

CEOs should always remember that employees generally don’t have access to the same information they do. While it may be obvious to C-suite executives that specific timelines and targets need to be met for product launches, major announcements, etc., the leadership team still needs to give employees and managers all the relevant information about long-term goals, constraints, and anything else that will help them understand why they’re being asked to do certain tasks.

Context increases empathy because it makes employees feel like collaborators and partners rather than cogs who are just being ordered around. By explaining why employees’ contributions are so vital to the task at hand, you won’t just reduce the chance of pushback – you’ll show employees that they’re valued members of a team. If your team is new to working remotely, communicating this context becomes increasingly important. Don’t doubt the effectiveness of your all-hands meetings, and try offering office hours via video so employees can drop in to ask questions face-to-face as they come up.

Great leaders show empathy

Just as leaders should work to generate empathy among managers and employees, they should also be empathetic themselves. It isn’t enough to merely explain why a job needs to be done – it’s also necessary to take employees’ concerns seriously and try to look at things from their point of view.

For example, if you need an employee to focus on a different task than the one they are working on, you could say, “I really appreciate the work you’re putting in on this project and I know you’ve made some serious headway, but we really need you on something new we’re starting up this month.” This ensures that the employee feels seen and their accomplishments aren’t being taken for granted.

Empathy leads to mutual respect. When members of the C-suite and other leaders make a genuine attempt to understand what their employees are experiencing, employees will take notice.

Here are three foundational ways to show empathy, whether you’re meeting in person or virtually:

  • Attune your affect: Reflect the emotion of the person you’re speaking with. If they’re sad, look sad as well. This demonstrates visually that you understand what they’re going through.
  • Repeat back emotion words: If someone says they’re frustrated, annoyed, sad, etc. you can demonstrate your understanding by repeating those emotion words back. For example, “I hear you saying you’re frustrated.” Go deeper by asking a question that demonstrates interest in their emotional experience. “I hear you saying you’re frustrated – can you tell me more about that?”
  • Don’t turn it around and make it about you: Whatever the situation, don’t take the topic and use it to tell a story about yourself. For example, a direct report says they’re overwhelmed and need help. Instead of attuning your affect and repeating back emotion words, you launch into a story about how you’ve mastered prioritization and it’s easy. This ignores the legitimacy of your direct report’s feelings and can make it seem like you don’t care about their situation.

Take ownership of difficult conversations

Leaders should accept as much responsibility as possible, especially when it comes to difficult conversations.

Leaders should accept as much responsibility as possible, especially when it comes to difficult conversations.

A leader should never be a passive observer. For example, when you say something like, “I’ve been hearing that you aren’t cooperating with your team members,” you instantly create resentment and hostility. Instead, try to determine what’s actually going on between your employees – this requires that you approach discussions with each employee with an open mind and without judgment. If some sort of admonishment is necessary, the reasoning shouldn’t be attributed to someone else.

Here’s a helpful way to think about this dynamic: Leaders should deliver “I” messages instead of “you” messages. Let’s say an employee turns out to be a bad fit for a team – instead of telling the employee “You did X, Y, and Z, which is why we have to transfer you,” a good leader should hold themselves accountable: “I thought this arrangement would make sense, but it looks like we should reconsider.” Instead of heaping disproportionate blame on the employee, this will create a healthy dialog.

When it comes to communicating context, speaking with empathy, and taking ownership while working remotely, focus on building a structure that allows people to connect virtually so they can socialize with intention. Fortunately, things like affect, tone of voice, and body language are captured in a video call. You’re still building trust and connection, even if you can’t meet in person. Making time for socializing and building trust through video calls makes it easier to have difficult conversations remotely because you’ve continued to build the foundation of your relationship.


While difficult conversations are inevitable at any company, leaders who hold themselves accountable, provide context, and show empathy might just find that these conversations are opportunities for growth.

[ IT leaders in our community are sharing advice on navigating this crisis. Read also: How to lead in the age of newly remote teams and Crisis leadership: How to overcome anxiety. ]

Cameron Yarbrough is the Co-founder + CEO of Torch, a company that provides the industry's first end-to-end suite of leadership learning and development platform for executives, employees and HR leaders.