Skill · Free · 10 min
Hard Conversation Prep
Prepares someone for a difficult conversation (asking for a raise, setting a boundary with family, confronting a roommate, ending a business relationship, disputing with a landlord) by clarifying the goal, mapping the other person's likely reactions, writing an opening line and responses to pushback, and running a practice round. Use when someone says they need to talk to someone and are dreading it.
Works with ChatGPT · Claude · Gemini

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Why it helps
Prepares someone for a difficult conversation (asking for a raise, setting a boundary with family, confronting a roommate, ending a business relationship, disputing with a landlord) by clarifying the goal, mapping the other person's likely reactions, writing an opening line and responses to pushback, and running a practice round. Use when someone says they need to talk to someone and are dreading it.
- Prepares someone for a difficult conversation (asking for a raise, setting a boundary with family, confronting a roommate, ending a business relationship, disputing with a landlord) by clarifying the goal, mapping the other person's likely reactions, writing an opening line and responses to pushback, and running a practice round. Use when someone says they need to talk to someone and are dreading it.
- Includes a concrete process and a clear output format.
What you get
- Complete skill instructions (md)
- Setup and optional integration guidance (md)
How to use it
Open SKILL.md. For a normal chat, paste the instructions below the YAML frontmatter, then give the requested inputs. For a Custom GPT (where available) or Gemini Gem, paste everything below the frontmatter into Instructions and use the description line as the listing summary. Native skill upload depends on your host. Agent Extensions are optional connectors or scheduled workflows; the core skill works without them, and downloading does not enable integrations or schedules.
Have ready
- relationship and situation
- desired outcome
- previous attempts and setting
Works as written guidance in ChatGPT, Claude, or Gemini. Native installation, file exports, browsing, and connectors depend on your account and host. Optional Agent Extensions are not required or automatically enabled.
Try asking
Help me prepare a fair, clear conversation opener and practice likely pushback.