[AI Synthesis]: There is no perfect answer on whether to raise an issue. Weigh costs of engaging and of not engaging; if you talk, really talk — learn their story, express your views and feelings, and problem-solve together.
Choose whether to raise
- Weigh the pros and cons of raising the tough issue — costs of engaging and costs of not engaging.
- Consider the long-term pain if you avoid, and the potential benefits if you invite a conversation.
- Ask whether the real conflict is inside you; sorting feelings or contribution may mean a change in your behavior is enough.
- If you’re going to talk, really talk.
Three purposes that work
- Learning their story: what information did they see that you missed? What is their reasoning? Intentions? Feelings?
- Expressing your views and feelings: what is important to say about your views, intentions, contributions, feelings, and identity issues — share your story.
- Problem-solving together: can you satisfy both needs? Where needs conflict, work toward a fair way forward.
Actions
- Weigh long-term avoidance pain against benefits of inviting the talk.
- If you raise it, hold three purposes: learn, express, problem-solve — not only deliver a message.
- Ask what information they see, their reasoning, intentions, and feelings.
Sources
| Source | Location | Role |
|---|---|---|
| notes/2026-08-29-difficult-conversations.md | ch7 What’s Your Purpose | highlights |