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Use when confronting a specific counterpart about a breach, violation, or adversarial behavior — situations where trust is already broken and the goal is accountability or resolution, not relationship-building. Not for giving developmental feedback (use feedback-coach) or building trust with new people (use rapport-builder).
How this skill is triggered — by the user, by Claude, or both
Slash command
/dealmaker:difficult-conversationsThe summary Claude sees in its skill listing — used to decide when to auto-load this skill
Difficult conversations are defined by high stakes, opposing opinions, and strong emotions. This skill provides a dual-track approach: a **strategic framework** for deciding whether to engage at all, and a **tactical framework** for restoring safety and reaching a resolution when you do.
Difficult conversations are defined by high stakes, opposing opinions, and strong emotions. This skill provides a dual-track approach: a strategic framework for deciding whether to engage at all, and a tactical framework for restoring safety and reaching a resolution when you do.
Avoid the "Fundamental Attribution Error"—attributing bad behavior to a person's character while ignoring the context. Analyze the conflict through interests rather than positions.
When people move toward "Silence" (withdrawing) or "Violence" (attacking), it is because they don't feel safe. You must step out of the content and restore Mutual Respect and Mutual Purpose before continuing.
Others don't "make you mad." You make yourself mad based on the "story" you tell yourself about their intent. Re-humanize the counterpart by asking: "Why would a reasonable, rational, and decent person act this way?"
Difficult conversations often trip Identity Triggers, making you feel off-balance. Move from an "All-or-Nothing" identity (I am either good or bad) to a "Growth Identity" (I have things to learn).
In difficult conversations, trust but verify. Ensure any agreement includes explicit Implementation and Enforcement mechanisms, especially with unreliable counterparts.
Before speaking, perform a dispassionate cost-benefit analysis:
Define what you really want for yourself, for the counterpart, and for the relationship. Refuse the Fool's Choice (the belief that you must choose between candor and kindness) (Source: Grenny).
Watch for the "S" and "V" signals:
Deliver your most controversial views using the sequence:
If they blow up or clam up, use AMPP:
Use this to fix misunderstandings:
npx claudepluginhub joellewis/skill-library --plugin dealmakerPlans and facilitates high-stakes conversations involving conflict, feedback, performance issues, or sensitive interpersonal topics using Harvard Negotiation and radical candor frameworks.
Guides structured preparation, delivery, and followup for workplace conflicts, performance discussions, challenging feedback, and sensitive topics.
Coaching for multi-party negotiations: salary, sales, collective bargaining, hard 1:1s, recruitment closes, cross-cultural deals. Prepares, coaches live, and debriefs lost outcomes.