having-difficult-conversations

Generate conversation packs with briefs, talk tracks, and objection handling.

5|Updated Jan 19, 2026
One-click install
npx skills add https://github.com/oldwinter/skills --skill having-difficult-conversations
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: having-difficult-conversations
Source: https://github.com/oldwinter/skills/tree/main/lenny-skills/leadership-skills/having-difficult-conversations
Command: npx skills add https://github.com/oldwinter/skills --skill having-difficult-conversations

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes references (resource) components.

What problem does it solve?

This Skill helps managers and leaders prepare for and conduct difficult conversations, ensuring clarity, respect, and constructive outcomes, especially in high-stakes situations like performance issues or terminations.

Core Features & Use Cases

  • Conversation Planning: Develop a structured approach including briefs, talk tracks, and objection handling.
  • Delivery Guidance: Provides scripts and strategies for clear, direct, and empathetic communication.
  • Follow-up: Assists in creating documentation and planning next steps to ensure accountability and progress.
  • Use Case: A manager needs to deliver critical performance feedback to a direct report. This Skill helps them craft a clear message, anticipate reactions, and plan a supportive follow-up conversation.

Quick Start

Prepare a difficult conversation about performance feedback for a direct report.

Frequently Asked Questions about having-difficult-conversations

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I prepare for a difficult conversation about performance feedback?

Prepare for performance feedback by generating a comprehensive conversation pack that includes briefs, talk tracks, objection handling plans, and follow-up notes. This approach ensures clear, direct, and empathetic communication while preserving dignity in high-stakes interactions.

What is the best way to handle objections during a termination conversation?

Handle termination objections by using a pre-built objection handling plan that anticipates reactions and provides clear, direct scripts. This structured strategy helps managers preserve dignity while maintaining clarity and constructive outcomes in high-stakes interactions.

Can I use this approach for denying a promotion to a direct report?

Yes, you can use this approach for promotion denials. It facilitates the preparation and execution of difficult conversations by generating tailored talk tracks and delivery guidance that ensure clarity, respect, and constructive outcomes for leadership interactions.

Do I need prior management experience to use these conversation planning tools?

No prior management experience is required to use these conversation planning tools. They deliver comprehensive conversation packs with structured briefs and delivery scripts, guiding managers through clear, direct, and empathetic communication in high-stakes situations.

How does Radical Candor apply to delivering critical performance feedback?

Radical Candor applies to delivering critical performance feedback by guiding managers to communicate clearly and directly while maintaining empathy. The generated talk tracks and delivery scripts adhere to these principles to preserve dignity in high-stakes interactions.