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Uncomfortable Conversations Leadership Scorecard
How well do you lead when things get difficult?
This scorecard helps you evaluate your comfort, awareness, and leadership ability in navigating emotionally challenging or culturally charged conversations.
Rate yourself on a scale of 1 (rarely/never) to 5 (always/strongly true) for each statement below. Then review the interpretations at the bottom. Scoring guide below.
Dialogue Skills
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I listen without interrupting, even when I strongly disagree.
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I can reflect back what someone else is saying, even if I don’t agree with their view.
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I ask open-ended questions to understand perspectives, not to argue a point.
Self-Awareness & Bias Recognition
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I actively examine my own cultural or identity-based assumptions.
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I can recognize when my reactions are based on past trauma or unconscious bias.
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I can name and sit with discomfort when faced with opposing values or beliefs.
Handling Conflict & Emotions
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I remain calm and grounded during emotionally charged discussions.
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I have tools to de-escalate conversations that are becoming defensive or hostile.
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I can identify when my silence is avoidance rather than wisdom.
Boundary Critique & Systems Thinking
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I challenge the "default" boundaries or assumptions in systems and conversations.
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I consider how race, gender, or power might influence who gets to speak and be heard.
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I can hold multiple truths or perspectives simultaneously in a discussion.
Appreciative Lens & Relationship Repair
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I approach difficult dialogue with curiosity and appreciation rather than blame.
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I can stay in relationship even after disagreement or discomfort.
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I follow up after hard conversations to repair or strengthen connection.
Scoring Guide
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​60–75: Transformational Leader – You have the mindset, skill, and heart to lead through complexity.
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45–59: Growth-Oriented Leader – You have strong instincts but may benefit from sharpening specific tools.
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30–44: Emerging Leader – You’re aware of the value of uncomfortable conversations but need more structure.
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<30: Reflective Learner – Begin with self-awareness and practice foundational skills.