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delicate-conversation-scripts

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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

2 stars
1.2k downloads
Updated 1/19/2026

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SKILL.md

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

PrincipleGoodBad
EvidenceObservable facts/dataJudgments/feelings
FramingCareer goals linkPersonal attack
MindsetHelp them improveVent your frustration
ReactionHold the lineBack 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

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AI Quality Score

95/100Analyzed 2/13/2026

An excellent, highly structured resource for leadership communication. It provides concrete scripts, a visual flow (ASCII art), and clear principles. The content is universally applicable and easy to follow.

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Metadata

Licenseunknown
Version-
Updated1/19/2026
PublisherCoowoolf

Tags

ci-cd