Embrace Uncomfortable Conversations and Lead through Listening

One of the most common questions we get from clients working through diversity, equity, and inclusion initiatives is, “How can we help our leaders and managers navigate difficult conversations with employees?” The misconception behind the question is that managers must have deep expertise on subjects such as racism, bias, trauma or any related topic, in order to effectively facilitate a productive conversation. The simple truth, though difficult to swallow, is that learning to lead through listening is the only essential skill needed.

Let’s face it. Difficult conversations in the workplace are not new. They are awkward and plain uncomfortable. Yet, empathetic listening, especially during difficult times and situations, will always make the difference between success and failure. This is such a simple concept that most people dismiss it. 

A New Perspective on Leading through Listening

Effective listeners are bridge builders—the kind of leaders who are able to connect with employees at a deep level. They remember to avoid the following listening pitfalls:

  • Listening in order to have a chance to respond and debate. 
  • Listening to insert their own story. 
  • Listening only to hear what they want to hear. 
  • Listening to catch something they can later use against the person sharing.
  • Listening with contempt or judgment.

These so-called forms of listening are not effective. They are destructive, create mistrust, and fracture relationships. They signal that we aren’t showing up to the conversation with an authentic desire to understand and to learn.

Building your listening skills is one of the greatest investments you will make as a leader, especially if you want to build trust with your team.

How do Bridge Builder Leaders Listen?

They listen not only with their ears, but also with their eyes, their mind, and an open heart—with undivided attention and respect. This empathetic type of listening communicates deep concern and respect. 

If you are ready to elevate your leadership effectiveness to the next level, especially during difficult times, I invite you to exercise your listening muscles. You can begin by practicing the following strategies, starting today:

  • Show up with an empty slate, no agenda.
  • Listen with your eyes: Make eye contact. Be fully present.
  • Listen with your body: Lean in, nod, and affirm.
  • Listen with your heart: Withhold judgment. Assume ignorance and/or positive intentions.
  • Paraphrase or clarify when you don’t understand: “I’m not sure what you mean by that.” “What I hear you saying is . . . Help me understand . . .”
  • Embrace silence. Silence can be one of the most powerful elements of a conversation, opening doors to vulnerability and intimacy.
  • Resist the temptation to hijack the conversation. Avoid steering the conversation with your own story, advice or leading questions.

Patrick Lencioni puts it best: “Smart people tend to know what is happening in a group situation and how to deal with others in the most effective way. They ask good questions, listen to what others are saying, and stay engaged in conversations intently.”

When you embrace uncomfortable conversations by leading through listening, the smart person is you. 


This article is adapted from the book Bridge Builders: How Superb Communicators Get What They Want in Business and in Life by Maria Keckler

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