The Art of Difficult Conversations: 6 Ways to Stay Connected When You Disagree

In this episode of Boomer Banter, we tackle something many of us are exhausted by but can't ignore ... difficult conversations. Not the surface-level small talk, but the real, uncomfortable ones with family members who see the world completely differently, with old friends across the political divide, and especially with ourselves.

Host Wendy Green shares a powerful story from the 1980s about finding common humanity with a coworker on opposite sides of the abortion debate, and offers practical strategies for navigating high-stakes conversations when the relationship matters deeply.

You'll learn:

1. How to set the right intention before a difficult conversation begins
2. Why paraphrasing is one of the most underrated conversation tools
3. When silence might actually be the more loving choice
4. How to have honest conversations with yourself about what you can actually do to make a difference

This isn't about changing minds—it's about choosing connection over avoidance, curiosity over contempt, and showing up with an open heart even when it's hard.

What difficult conversation are you ready to have?

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Connect with Wendy: LinkedIn, Facebook & Instagram or at [email protected]

Resources to help with Difficult Conversations:

Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton & Sheila Heen

Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan & Al Switzler

Braver Angels - organization bringing together people across political divides

Mentioned in this episode:

greenwoodcapital.com

This podcast uses the following third-party services for analysis:

OP3 - https://op3.dev/privacy