Why Leaders Need to Master Conversations That Matter
Have you ever walked away from a conversation feeling deeply connected to the other person? What made it different? Maybe you shared more of yourself than usual, or perhaps you listened with genuine curiosity to understand their perspective. It could be that the space you created for the conversation felt safe and meaningful.
These types of conversations don’t happen all the time, but when they do, they leave a lasting impact. Unfortunately, many leaders either lack the skills to have meaningful conversations or avoid them altogether. Yet, these are the conversations that build trust, connection, and empathy—cornerstones of effective leadership.
Howard Schultz: A Leader Who Made Conversations Count
Howard Schultz, the former CEO of Starbucks, offers an inspiring example of a leader who prioritised conversations that mattered. During the 2008 financial crisis, Starbucks faced tough times, including store closures and layoffs. Instead of sidestepping the discomfort, Schultz leaned into it. He held open forums and town hall meetings with employees—whom Starbucks calls “partners”—to hear their concerns and ideas directly.
In one particularly powerful moment, Schultz travelled to Seattle to meet with laid-off employees. He didn’t just focus on the business aspects of the layoffs; he listened to their personal stories about how the job loss impacted their lives. Schultz shared his own experiences of growing up in a struggling family, demonstrating vulnerability and authenticity.
Through these conversations, Schultz created a culture of connection and empathy. Employees felt heard and valued, even in difficult times. This approach not only reinforced loyalty but also strengthened Starbucks’ core values of human connection and community.
Breaking Leadership Assumptions: Mark’s Story
Last year, I worked with Mark, a leader struggling to engage, motivate, and connect with his team. During our coaching sessions, Mark uncovered a deep-seated belief: leaders shouldn’t share who they are—they’re there to deliver results, not build personal connections. This belief led to disengaged teams, siloed behaviours, and a lack of trust.
Mark decided to challenge this assumption. He focused on creating space for meaningful conversations and practicing vulnerability in his leadership. With feedback from trusted colleagues, he began to make progress. The transformation was remarkable. Mark’s willingness to have conversations that mattered improved his team’s engagement, collaboration, and trust.
The Tech vs. Talk Dilemma
In today’s digital world, connecting seems easier than ever—at least on the surface. We have tools like Yammer for sharing ideas, LinkedIn for professional networking, and virtual meetings to bring global teams together. Yet, our reliance on technology can sometimes create distance rather than connection.
Too often, we default to email or online platforms for communication, turning one-on-one meetings into task-focused check-ins rather than opportunities to build real relationships. While technology enables collaboration, it cannot replace the depth of face-to-face or heart-to-heart conversations.
The Call to Action
Leaders who prioritise conversations that matter create cultures of trust, empathy, and connection. These moments of meaningful dialogue require courage, presence, and vulnerability—but the rewards are immeasurable.
The question is: Are you brave enough to be the leader that has conversations that really matter? What is it time for this week?
Follow us on: LinkedIn Instagram Facebook