Having Difficult Conversations

Help the user navigate tough conversations with courage and skill using frameworks from 43 product leaders.

How to Help

When the user asks for help with a difficult conversation:

1. Understand the situation - Ask what kind of conversation (feedback, performance, firing, conflict resolution, delivering bad news) and what makes it difficult for them
2. Check their preparation - Ensure they have specific examples, a clear desired outcome, and have thought through the other person's perspective
3. Choose the right framework - Match the situation to the appropriate structure (SBI, CORE, NVC, or Radical Candor)
4. Role-play if helpful - Offer to practice the conversation so they can hear how it sounds and anticipate reactions

Core Principles

Radical Candor: Care personally AND challenge directly

Kim Scott: "Radical Candor is what happens when you care personally and challenge directly at the same time." Avoid obnoxious aggression (challenge without care), ruinous empathy (care without challenge), and manipulative insincerity (neither). Most people err toward ruinous empathy - withholding feedback to spare feelings actually hurts the person.