Leaning into the discomfort: Managing difficult conversations at work

Sharing critical feedback. Canceling a pet project. Discussing changes your employees may be dreading. Curbing conversations that may not belong in the office. Speaking up when you disagree with others’ decisions. Difficult conversations are inevitable at work. But can they be less uncomfortable and more productive for everyone involved?

A place to start is to recognize their necessity. Research tells us that difficult conversations can be so challenging that many of us postpone or try to avoid them altogether. But avoidance often leads to festering problems and escalating issues. Further, if we attempt to balance being upfront and being nice by withholding information, we fail in both categories. Yet if we move too far in the other direction and pursue brutal honesty, it can feel like a personal attack. Given so many pitfalls, what can we do?

Normalizing difficult conversations and recognizing their importance for growth and improvement are key. These successes are good for our people and our organizations. Employing strategies like active listening, considering the specific ways we engage with our colleagues, and embracing open communication at work are associated with increased organizational productivity.

What Works?

We spoke with communication experts to learn what works for effectively managing difficult conversations.

Professor Amanda McKendree is the Arthur F. and Mary J. O’Neil director of the Fanning Center for Business Communication and a teaching professor of management and organization whose research examines crisis and conflict communication.

Professor Jennifer Cronin is an associate teaching professor of management and organization who teaches interpersonal and organizational communication and studies the benefits of narrative and data storytelling for better decision making.

Professors Cronin and McKendree agree that polarizing times make for more emotionally-charged conversations - even outside of the context of political or other disagreements. Professor McKendree suggests we start by asking ourselves why we are labeling the conversation as difficult:

"Our answer to this question ultimately determines the communication skills and strategies that we employ. Topics that prove most challenging to discuss are those topics that generate disagreement and difference."

In politically-fraught times, these two areas of difficulty can intersect at work. And the tools we use to navigate these conversations can differ depending on the specific context.

Professor McKendree notes,

"You may find that the topic is relatively easy, but particular qualities of your conversation partner contribute to your assessment of the difficult conversation. For example, most of us have experienced working with a difficult colleague. This is a natural aspect of workplace dynamics that requires a careful response. In these moments, we’re called to maintain composure and avoid reacting emotionally or defensively. We’re also challenged to practice active listening skills and being aware of our nonverbal cues. Depending on the past history and relationship with your difficult colleague, you may choose to ignore, engage directly or indirectly, or remove yourself from the encounter."

It can be the topic itself or the parties involved that lead us to characterize conversations as difficult.

"Identifying why we are labeling conversations as difficult also influences how we might approach improving our ability to handle them. For example, for difficult topics, you may first need to educate yourself on the history and various perspectives of those controversial topics. Being able to approach a difficult topic with a more nuanced understanding will enhance your confidence when interacting with your conversation partner. When conversing with a difficult colleague, you may need to hone specific skills in listening, maintaining a sense of calm, and asking questions that might uncover causes of the difficult behavior."

Dr. McKendree concludes:

At the individual level, this requires taking the time to fully assess the situation. Taking a step back to evaluate the various factors of the situation allows us to make informed decisions and purposeful moves. Practicing self- and other- awareness as we consider our own communication styles and the styles of our conversation partners is a powerful skill because we may realize that the situation calls for a communication style that takes us out of our comfort zone. Lastly, assessing the situation offers us insights that inform our communication strategy, whether we choose to engage directly or indirectly, for example.

And reminds us that organizational strategies can help:

"At the organizational level, we can improve our ability to navigate difficult conversations by first gaining buy-in that these skills matter. Relying on employee resource groups or other affinity groups allows business leaders to accept feedback and acknowledge areas for improvement. Business leaders may also be able to identify “champions” for initiatives focused on workplace communication skills development."

Professor Cronin notes that storytelling can be a powerful tool. We can appeal to empathy and finding common ground including by sharing stories of organizational exemplars who successfully managed complexities with tools accessible to all of your employees. Acknowledging alignment with the values of your organization can be a strong compass for these interactions. Professor Cronin:

"Narrative storytelling provides a vehicle to understand and make sense of the human experience. Data gives us facts, but when we couple that with story, meaning is created. We can see the bigger picture and the impact a business problem is having. It’s learning more about the context and the people that are affected that help us to make better decisions and achieve the outcome we desire."