The Principles of Personal Leadership: A Path to Transformational Leadership Principle #8: Have Courageous Conversations

Inspired by Mark Sasscer’s “Accountability Now!”

The Heart of Courageous Conversations

Every organization claims to value communication, but few consistently model the kind of dialogue that actually moves people forward. Transformational leaders understand that true progress happens when we lean into discomfort with honesty, respect, and courage. Courageous conversations are not about winning arguments; they are about creating space for understanding, building trust, and resolving conflict in a way that strengthens relationships rather than weakens them.

Mark Sasscer puts it plainly:

“In this dynamic environment, having courageous conversations is a must. Without them, valuable time, energy and productivity ($$$) are wasted because of what “goes unsaid” in meetings and in other human interactions where honesty, direction, expectations, clarity and/or feedback are desperately needed, but not delivered.”

Leaders who avoid difficult conversations often do so with the intention of maintaining peace. But silence is rarely neutral. In the absence of clarity, people make assumptions, and those assumptions can erode trust faster than any direct feedback ever could.

On the other hand, when leaders choose to address challenges directly, they set the tone for a culture where transparency and continuous improvement become the norm. These moments of dialogue may feel challenging, but they are also opportunities: opportunities to build stronger connections, clear away misunderstandings, and create alignment around shared goals.

What Courage Really Looks Like in Leadership

The essence of a courageous conversation is trust. By stepping into dialogue with openness and respect, leaders signal that honesty is welcome, and that silence or avoidance will not be the default. Over time, this builds a culture of psychological safety where people feel empowered to speak their truth without fear of retaliation.

Think about an organization that encourages its people to “stop the line” when they see a problem. That is courage in practice. At one of my previous organizations, a surgical technician recognized a problem with a tag on the sterilization trays about to be used in a case. He immediately called it out, stopped the line, and prevented a potential complication. The case was delayed, but it didn’t matter. He felt a responsibility to the patient and his team to speak up. His courage, combined with the culture of safety we had cultivated, prevented potential patient harm. Later that week, he was recognized at our daily safety huddle.

Instead of staying silent and hoping someone else would notice, he took ownership of the situation. That one moment didn’t just prevent harm; it reinforced for everyone that patient safety comes before ego or hierarchy. These small but powerful actions build trust and lay the foundation for high reliability.

The Connection Between Courage and Inclusion

Creating space for courageous conversations is also an act of inclusion. When we create space for open and honest dialogue, every voice has the opportunity to be heard. This ensures that perspectives across the spectrum, background, role, or experience, are valued and respected.

Inclusive leadership isn’t limited to diversity statements or committee meetings. Inclusivity thrives when people believe their contribution matters. Leaders who make time for courageous conversations foster an environment where ideas surface more freely, risks can be discussed openly, and the team becomes stronger together.

From Conflict to Connection

It’s easy to see conflict as something to avoid. However, transformational leaders reframe conflict as an opportunity to deepen connection and alignment. By leaning into tough conversations with empathy and clarity, they prevent minor issues from developing into potential divides.

As an executive coach, I’ve seen this pattern often—especially among healthcare professionals. Many physicians in leadership roles feel responsible for keeping their teams happy. That impulse, while understandable, can become a barrier. Growth doesn’t happen in constant comfort. It happens in tension that is respectful, purposeful, and grounded in trust.

Courageous conversations shift the focus from avoiding conflict to working through it. The goal is not to win. The goal is to reconnect, clarify, and move forward together.

Strategies to Strengthen Courageous Conversations

• Prepare with clarity. Before stepping into a difficult conversation, take the time to understand why it matters. What’s the core issue? What outcome are you hoping to reach? When leaders approach a conversation with clarity, it reduces ambiguity, minimizes emotional reactivity, and helps focus the discussion on facts and shared goals.

• Lead with curiosity rather than judgment. Approach the other person with an open mind, especially if the topic is emotionally charged. Ask questions to understand, not to trap or challenge. Begin with, “Help me understand what happened from your perspective,” or “What do you need to feel successful here?” Curiosity invites conversation. Judgment shuts it down. When you lead with curiosity, you create space for the other person to participate in finding a solution, rather than defending their position.

• Listen actively, not defensively. It’s natural to want to explain or correct when something feels unfair or inaccurate. But real leadership shows up in the listening. Active listening means staying present, resisting the urge to interrupt, and reflecting back what you’ve heard before responding. It builds credibility and demonstrates that the goal isn’t to win a debate—it’s to understand the whole picture.

• Use honesty balanced with respect. Courageous conversations call for truth, but truth alone isn’t enough. Delivery matters. Speak directly, but never with contempt. Share observations instead of accusations. Say what you mean, but choose words that reflect care, not control. Respect is what allows honesty to be heard, even when the message is hard. When done well, this balance strengthens relationships instead of damaging them.

• Follow up with action. A courageous conversation doesn’t end when the meeting does. What happens afterward is just as important. Clarify next steps. Document any agreements. Check in to ensure the discussion leads to visible progress. Without follow-up, even the most thoughtful dialogue can lose its impact. Following through sends a clear message: this conversation wasn’t performative—it was a step toward real change.

  
  

Questions to Ponder

• How can I create a safe space for courageous conversations that lead to growth and transformation?

• Do my team members feel empowered to “stop the line” when something doesn’t feel right?

• Where am I avoiding a hard conversation—and what might be possible if I had it?

• How often do I listen for understanding rather than listening to respond?

• What’s one courageous conversation I could have this week that would strengthen trust in my team?

Final Thoughts

Transformational leadership is rarely comfortable. It asks us to challenge the status quo, speak up when it’s easier to stay silent, and create space for others to do the same.

Sasscer reminds us that the cost of avoidance is high. Time, trust, and productivity suffer when difficult topics remain unspoken. On the other hand, when leaders prioritize honesty over comfort, they create organizations where communication becomes a driving force for progress.

The ability to have courageous conversations doesn’t come from a title. It comes from character. And it’s one of the most evident signs of a leader who is committed to doing what’s right—even when it’s hard.

Acknowledgment

This series draws inspiration from Mark Sasscer’s Accountability Now! Living the Ten Principles of Personal Leadership. His work continues to influence my thinking and serve as a foundation for those of us committed to leading with clarity and intention.

As always, I welcome your reflections. Feel free to leave a comment or connect with me at scott@drscottwolf.com. I’d love to hear your perspective.