Rethinking 'Difficult' Conversations and People: A Different Take on Leadership Communication

How often have you heard someone say, “That was a tough conversation,” or “They’re just a difficult person to work with”??

These phrases are so common in the workplace that they feel like undeniable truths. But what if they aren’t? What if these conversations aren’t difficult—just truthful??

And what if the so-called difficult people aren’t actually difficult but struggling within an ineffective structure or under unclear leadership?

It’s time to rethink the labels we casually throw around and ask: Are we avoiding real engagement by calling things “difficult” instead of understanding what’s actually happening?

Conversations Aren’t Difficult—They’re Just Uncomfortable

When we call a conversation “difficult,” what we often mean is:

• This conversation challenges my assumptions.
• It requires accountability or change, and that’s uncomfortable.
• I don’t feel equipped to navigate this conversation effectively.

But honesty, clarity, and feedback aren’t inherently “hard.” They’re just real.

What makes them feel tough is the lack of skill, preparation, or comfort with discomfort. Instead of calling them “difficult conversations,” we should call them “clarifying conversations” because that’s what they are.

When leaders reframe these discussions as opportunities for alignment rather than battles to endure, they shift from avoidance to engagement.

Labels Create Self-Fulfilling Problems

When we label a conversation as “tough,” we go into it with resistance. We anticipate conflict. We brace ourselves. And that mindset shapes the outcome before the conversation even begins.

When we label a person as “difficult,” we subtly justify dismissing their perspective. We stop asking why they’re pushing back. We see them as an obstacle rather than a source of insight.

Instead of defaulting to these labels, try reframing:

• Instead of “tough conversation” → “a necessary discussion for clarity and alignment.”
• Instead of “difficult person” → “someone whose needs or concerns aren’t being heard or addressed.”

The words we choose don’t just describe reality—they shape it.

People Aren’t “Difficult” in a Vacuum—Context Matters

Labeling a teammate as “difficult” is an easy way to dismiss them.

But let’s take a step back. If someone is struggling under one leader but thriving under another, is that person truly difficult—or are they reacting to the environment they’re in?

People are not difficult in isolation. They are shaped by:

• The clarity (or lack thereof) of their roles and expectations.
• The psychological safety of their environment.
• The level of structural and psychological empowerment they experience.
• Whether their input is valued or ignored.

Instead of asking, “Why are they so difficult?” leaders should ask: “What about this environment is creating tension?” or “What am I missing in how I’m leading this person?”

Leaders who shift their focus from blaming individuals to improving structures will see fewer so-called “difficult” people and more engaged, empowered team members.

The Hidden Impact of This Language in Leadership Development

Here’s the irony: The very people who are supposed to help leaders navigate challenges— leadership coaches and other leadership development professionals—are often the ones reinforcing these labels.

When these professionals talk about difficult conversations and difficult people, they unintentionally send a message that:

• Conflict is inherently negative – Rather than something to engage with productively, it’s something to brace for.
• Some people are just problems – Instead of recognizing that people respond to their environments, they reinforce a fixed mindset about others.
• They themselves struggle with these conversations – If even the experts frame these interactions as “hard,” what hope do everyday managers and employees have?

When leadership development professionals reinforce these labels, they aren’t equipping leaders—they’re priming them for avoidance and resistance.?

Instead of teaching leaders to navigate these conversations well, they reinforce the idea that some people and discussions are just inherently problematic.

If leadership professionals truly want to create empowered leaders, they need to examine their own language. Instead of “difficult,” they should emphasize:

• Clarifying conversations → for alignment and understanding.
• Adaptive conversations → for handling change and complexity.
• Engaging conversations → for bringing people into the discussion.

Instead of labeling people as “difficult,” they should ask:

• What about this situation is making collaboration harder?
• What might this person be experiencing that isn’t visible at the surface?
• How can we adjust the structure or expectations to improve engagement?

The Leadership Shift: From Avoidance to Engagement

High-performing teams don’t avoid conversations because they’re “hard.” They learn how to navigate them well.

Great leaders don’t write people off as “difficult.” They seek to understand what’s really happening.

If you want to foster a culture of trust, alignment, and empowerment, it starts with changing how you approach challenges:

• Lean into clarity. Instead of assuming a conversation will be hard, approach it as an opportunity to create understanding.
• Look beyond behavior. If someone is pushing back, assume there’s something worth exploring rather than dismissing them.
• Model engagement. Show your team that tough topics aren’t to be feared, but addressed head-on with respect and transparency.

By shifting our mindset away from difficult and toward truthful, clarifying, and engaging, we don’t just improve workplace culture—we create a foundation where real trust and alignment can thrive.

A Call to Leadership Development Professionals

If you’re in the business of developing leaders, your words matter. When you use fear-based framing like “difficult conversations,” you’re not preparing leaders—you’re preparing them to avoid or mishandle these discussions.

It’s time to shift the narrative. Leaders don’t need help surviving “hard” conversations. They need to learn how to engage in truthful, productive, and empowering discussions. That starts with us.

The Question for Leaders

Next time you catch yourself calling a conversation “tough” or a person “difficult,” ask yourself: Is that actually true? Or is this an opportunity to engage more effectively?

The difference between conflict and clarity often lies in how we choose to see it.

Final Thought

If we want to build better leaders, we need to start by leading better conversations—beginning with the way we think and talk about them.