Five essential steps for having a difficult conversation

“These days, it seems that there are more and more deal breakers when it comes to deciding whom we’re willing to talk to. But in our tense era of deep divisions, talking to each other—and having difficult conversations—is more important than ever before.”

So begins an essay in the Wall Street Journal by Celeste Headlee, a journalist, radio talk show host and author of the upcoming book, “We Need to Talk.”

Her article—“The right way to have difficult conversations”—outlines much of what we explore in depth in my free workshop. Below are her five main pieces of advice. The last one is, in my experience, the most essential.

  1. Be curious: “Have a genuine willingness to learn something from someone else—even someone with whom you vehemently disagree.”
  2. Listen to understand: “Resist the impulse to constantly decide whether you agree with what someone else is saying. The purpose of listening is to understand, not to determine whether someone else is right or wrong, an ally or an opponent.”
  3. Be respectful: “Show respect at all times. View the other person as a human being and put yourself in their shoes. Empathize.”
  4. Stick with it: “If you’re talking to someone and a taboo subject comes up—whether it’s death, divorce or race—don’t try to change the subject, make a joke or go off on a tangent. Talking through tough issues can be awkward and painful, but try to avoid getting frustrated and walking away.”
  5. End well: “My final piece of advice really applies to all conversations, but it is especially true of difficult ones: End well. You don’t need to have the last word. Take a moment to thank the participants for sharing their thoughts. It can be scary to talk about politics or religion with someone else, so express your gratitude for their time and their openness. If you end the conversation in a friendly and gracious way, you set the groundwork and tone for future conversations.”

Great advice, and none of it’s easy. If it was, we’d all be good at it and the world would be a better place. So if you’d like some tools and processes that can really help, check out my workshop: “Difficult Conversations: The Art and Science of Thinking Together.”

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