Agent-Skills.md

Agent Skills: Delicate Conversation Scripts

Use when delivering difficult feedback (performance issues, firing, promotion denial), when managers avoid necessary conversations due to fear, or when needing structured scripts for high-stakes communication

UncategorizedID: coowoolf/insighthunt-skills/delicate-conversation-scripts

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coowoolf/insighthunt-skills
Coowoolf
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pnpm dlx add-skill https://github.com/Coowoolf/insighthunt-skills/tree/HEAD/team-leadership/delicate-conversation-scripts

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team-leadership/delicate-conversation-scripts/SKILL.md

Skill Metadata

Name
delicate-conversation-scripts
Description
Use when delivering difficult feedback (performance issues, firing, promotion denial), when managers avoid necessary conversations due to fear, or when needing structured scripts for high-stakes communication

Delicate Conversation Scripts

Overview

A structured approach to delivering difficult feedback that relies on observable facts rather than judgment, reducing defensiveness and clarifying expectations.

Core principle: Your job is to drive results, not make employees happy. But doing it well preserves the relationship AND improves performance.

The Six-Step Script

┌─────────────────────────────────────────────────────────────────┐
│  1. NEUTRAL OPENING                                             │
│     "I want to chat with you about [Topic]..."                  │
├─────────────────────────────────────────────────────────────────┤
│  2. OBSERVABLE EVIDENCE                                         │
│     "What I am hearing/observing is [Specific Fact]..."         │
│     NOT: "You're not a team player"                             │
│     YES: "In the last 3 meetings, you interrupted others 7x"    │
├─────────────────────────────────────────────────────────────────┤
│  3. SHARED REALITY                                              │
│     "We both know that to be successful here [Expectation]..."  │
├─────────────────────────────────────────────────────────────────┤
│  4. THE STAKES                                                  │
│     "If this doesn't change, [Consequence]..."                  │
├─────────────────────────────────────────────────────────────────┤
│  5. THE PAUSE                                                   │
│     Check for reaction/defensiveness.                           │
│     "I notice you're getting emotional..."                      │
├─────────────────────────────────────────────────────────────────┤
│  6. THE FUTURE                                                  │
│     "I want to help you succeed by [Next Steps]..."             │
└─────────────────────────────────────────────────────────────────┘

Key Principles

| Principle | Good | Bad | |-----------|------|-----| | Evidence | Observable facts/data | Judgments/feelings | | Framing | Career goals link | Personal attack | | Mindset | Help them improve | Vent your frustration | | Reaction | Hold the line | Back down |

Handling Emotional Reactions

When they get defensive/emotional:

  • "I notice you're getting a little emotional..."
  • "We can take a break if needed, but ultimately we need to have this conversation."
  • Hold the line—don't back down just because it's uncomfortable.

Common Mistakes

  • Vague to be "nice": Specifics are kinder in the long run
  • Personality focus: Critique behavior, not character
  • Backing down: When emotional reaction happens, persist

Example Application

Manager telling employee she's not getting promoted:

  • ✗ "You're just not ready"
  • ✓ "The skills we need for this role are X, Y, Z. My observation is you're strong in X but need development in Y and Z. I want to help you build those skills for the future."

Source: Alisa Cohn (Executive Coach, Top Startup Coach) via Lenny's Podcast