Global Leadership Summit 2018: How to Get Comfortable with Difficult Conversations

joshua-ness--bEZ_OfWu3Y-unsplashSheila Heen said it well at Global Leadership Summit when she said, “Your leadership is defined by your ability to have difficult conversations.” How many times do you shy away from conflict, rationalize away what you want to say, or intentionally avoid the tough talk? You are not alone if you said anything but never. Most people struggle with difficult conversations, but the most respected leaders get comfortable in saying things that need to be said.

Heen describes the types of conversations that challenge us: (1) standing up for oneself, (2) disappointing someone, (3) working across cultures, (4) telling a boss they may be wrong, and (5) helping peers with their self-awareness. When we’re in a difficult conversation, three questions drive the direction of our story are:

  • Who’s right?
  • Who’s fault is it?
  • Why is this person acting this way?

Difficult conversations are challenging, because our identity is at stake, and we may not know what to do with our feelings. How can we approach difficult conversations? Heen suggests shelving those three questions and finding answers to:

  • What is this conversation about? Why do we see this so differently?
  • What did we each contribute to the situation?
  • How can I separate intentions from impact? What impact am I worried about?

As a leadership coach, I frequently work with clients on communication strategies and conflict resolution skills. I encourage people to understand the other person’s worldview and values that drive decision-making. People are not irrational; they make decisions based on what makes sense within their worldview.

About the Author: Sandra Dillon is a professional coach with an extensive background in leadership and business coaching. She works with individuals and businesses as well as designs and facilitates workshops to empower people. She has a passion to help people be the best versions of themselves. You can learn more about Sandra or engage her as your coach by reaching out to her at or by visiting her website at

One thought on “Global Leadership Summit 2018: How to Get Comfortable with Difficult Conversations

  1. Hi there! This blog post could not be written much better!Going through this article reminds me of my previous roommate!He continually kept talking about this. I will forward this information to him.Pretty sure he’s going to have a good read. I appreciate you for sharing!


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