
delicate-conversation-scripts
by Coowoolf
105 Product Management Skills extracted from Lenny's Podcast - For use with Claude Code / Cursor / Windsurf
SKILL.md
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
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