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59. How to Have Difficult Conversations Pt. 1

Episode 59 Show Notes:

The conversations you're avoiding are slowly destroying your most important relationships. The unspoken truths between you and others are creating distance that's eroding trust, building resentment and ultimately costing you success and happiness.

In this first part of a two-part series on how to have these difficult conversations, we explore why difficult conversations are the determining factor in relationship quality, how avoiding them creates more conflict than having them ever could and why the belief that good relationships don't have arguments is dangerously wrong.

Episode Summary: Drawing from years of coaching executives and founders, I address one of the most common leadership challenges: navigating difficult conversations with employees, bosses, business partners and even family. Through the story of a COO whose once-fantastic relationship with her CEO crumbled into resentment because they avoided core conversations, this episode exposes the hidden cost of "keeping the peace." I frame it this way... each unspoken truth is like placing a pillow between you and the other person for each withhold you have, until there's so much distance that just their presence bothers you. The episode challenges the misconception that good relationships don't have arguments, revealing instead that relationships without difficult conversations are superficial masks destined to break. Most importantly, I distinguish between conflict (reactive, emotion-fueled, about being right) and difficult conversations (proactive, understanding-focused, about solving problems together), while exploring the Pygmalion Effect and how our beliefs about others directly impact their performance.

Key Takeaways:

The Cost of Avoidance:

  • Unspoken truths erode trust and accumulate tension
  • Distance grows until you're bothered by the person's mere presence
  • Suppressed truths leak out through frustration, sarcasm, withdrawal and burnout
  • Relationships end not from conflict but from accumulated withholds

The Pillow Metaphor:

  • Each unspoken concern creates a "pillow" between you and the other person
  • Pillows accumulate with every avoided conversation from both sides
  • Eventually so many pillows exist that you can't touch or connect
  • Difficult conversations remove the pillows and restore closeness

Conflict vs Difficult Conversations:

  • Conflict happens when dialogue breaks down (silence or violence)
  • Difficult conversations transform potential conflict into understanding
  • Conflict is "me versus you" while difficult conversations are "us versus the problem"
  • The goal isn't to win but to understand each other and create clarity

The Pygmalion Effect:

  • Your expectations about someone directly impact their performance
  • Teachers given "high potential" students (randomly selected) helped them perform better
  • If you don't believe an employee can improve, don't waste time on feedback
  • Clear is kind - either help them improve or end the relationship

When to Have Difficult Conversations:

  • Any conversation involving money, honesty, emotions or unmet expectations
  • Performance feedback, boundary setting and partnership discussions
  • The moment you notice you're putting "pillows" between you and another person
  • As a regular practice, not just during annual reviews

Episode Highlights: [00:00] Welcome to episode 59 - part one of difficult conversations series [01:30] Tony Robbins quote: relationship quality determines life quality [02:15] Most of us never received training on good relationships [03:00] Defining difficult conversations - high stakes, strong emotions [04:00] Examples: performance feedback, unmet expectations, boundaries [05:00] Why avoiding conversations erodes trust and accumulates tension [06:30] COO and CEO story - from fantastic to leaving the company [08:00] The pillow metaphor explained [10:00] How to know you've created too much distance [11:00] Quality of relationships determined by difficult conversations [12:00] Good relationships aren't conflict-free - that's a misconception [13:30] If you don't talk it out, you'll act it out [14:30] Difference between conflict and difficult conversations [15:30] Brené Brown: "Clear is kind" [16:00] Conflict as me vs you, conversations as us vs problem [17:00] Is it worth the discomfort - assessing belief in the person [18:30] The Pygmalion Effect research explained [20:00] Teacher expectations impacting student performance [21:00] How beliefs about employees affect their success [22:30] If you don't believe in them, have the conversation to end it [23:30] Recap and preview of part two [24:00] First step preview: putting righteousness aside

Memorable Quotes:

"The quality of our relationships determines the quality of our life."

"When we don't address the elephant in the room, when we don't address the truth, the core of what's bothering us, it grows and relationships end."

"If you don't talk it out, you will act it out."

"Clear is kind. When we're clear about our expectations, our thoughts, our feedback, that is demonstrating kindness to the other person."

"Conflict is me versus you. Difficult conversations are us versus the problem."

"The quality of your relationships are determined by the difficult conversations you have."

Resources Mentioned:

  • Episode 28: "The Cost of Being Right"
  • Tony Robbins on relationship quality
  • BrenĂ© Brown's principle "Clear is Kind"
  • The Pygmalion Effect (Rosenthal & Jacobson, 1968)

About This Episode: This episode tackles one of leadership's most critical skills - having difficult conversations. I dismantle the myth that avoiding conflict creates harmony, revealing instead how unspoken truths destroy relationships from the inside out. Through practical examples and psychological insights, you'll understand why the conversations you're avoiding are costing you trust, connection and success. This is essential listening for any leader, entrepreneur or person who wants authentic, lasting relationships.

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Next Episode Preview: In Part Two, I walk through the exact steps for having successful difficult conversations, starting with the crucial first step: putting your righteousness aside and taking full responsibility for your part. Don't miss the framework that will transform how you approach every challenging conversation.