---
name: difficult-conversation-prep
description: Prepare for tough conversations with a script, talking points, and responses to likely pushback. Use this skill when the user says "difficult conversation", "tough conversation", "hard talk", "how do I tell them", "I need to have a conversation about", "prep me for a confrontation", "how to bring up", "negotiate", or any variation of needing to have an uncomfortable or high-stakes conversation.
triggers:
  - difficult conversation
  - tough conversation
  - hard talk
  - how do I tell them
  - prep me for
  - confrontation
  - how to bring up
---

# Difficult Conversation Prep

Prepare for any tough conversation with a clear game plan. Get opening lines, talking points, responses to likely pushback, and a framework so you walk in confident instead of anxious.

## Instructions

### Step 1: Understand the Situation

From the user's request, identify:

- **Who is the conversation with?** — Boss, client, partner, employee, friend, landlord, etc.
- **What is it about?** — Raise, firing, boundary, complaint, breakup, disagreement, feedback, etc.
- **What's the goal?** — What outcome does the user want?
- **What's the relationship?** — Power dynamic, history, how the other person typically reacts
- **What makes it hard?** — Why haven't they had this conversation yet?
- **Any constraints?** — Timing, witnesses, HR involvement, legal considerations?

### Step 2: Build the Prep Guide

```markdown
# Conversation Prep: [Brief Description]

**With:** [Who]
**About:** [What]
**Your Goal:** [Desired outcome]
**Their Likely Goal:** [What they probably want from this conversation]

---

## Before You Start

**Mindset:** [1-2 sentences on the right mental frame. Not "be confident" but specific reframing: "This is not a confrontation. This is you advocating for something you've earned."]

**Timing:** [When and where to have this conversation. Not over text. Not on a Friday at 5pm. Specific advice.]

**What NOT to do:** [1-2 common mistakes people make in this type of conversation]

---

## The Opening

[Write 2-3 opening line options. These are the hardest part. Give them exact words they can use.]

**Option 1 (Direct):**
"[Exact opening line — gets right to it]"

**Option 2 (Softer):**
"[Opening that sets context first, then gets to the point]"

**Option 3 (Question-Led):**
"[Opens with a question that leads naturally to the topic]"

---

## Key Points to Make

[3-5 bullet points. Each one is a specific thing they need to communicate. Written as talking points, not a script — they need to sound like themselves.]

1. **[Point]** — [How to say it naturally. Example phrasing.]
2. **[Point]** — [Phrasing]
3. **[Point]** — [Phrasing]

---

## Likely Pushback & How to Respond

### If they say: "[Likely objection 1]"
**Respond with:** "[Specific response — calm, firm, redirects to your point]"

### If they say: "[Likely objection 2]"
**Respond with:** "[Response]"

### If they say: "[Likely objection 3]"
**Respond with:** "[Response]"

### If they get emotional or defensive:
**Respond with:** "[De-escalation language — acknowledge their feelings without abandoning your position]"

### If they shut down or refuse to engage:
**Respond with:** "[How to keep the door open without forcing it]"

---

## Your Non-Negotiables

Before going in, be clear with yourself:

- **Must have:** [The minimum acceptable outcome]
- **Ideal outcome:** [The best case]
- **Walk-away point:** [When do you end the conversation or escalate?]

---

## How to Close

[2-3 options for ending the conversation well, regardless of outcome]

- **If it goes well:** "[Closing that locks in the agreement and next steps]"
- **If it's unresolved:** "[Closing that keeps the door open: 'I'd like to revisit this on [day]. Can we both think about it?']"
- **If it goes badly:** "[Closing that protects the relationship while maintaining your position]"
```

### Step 3: Writing Rules

- **Give exact words, not advice.** "Be assertive" is useless. "Try saying: 'I need to talk about my compensation. Based on [X], I'm requesting [Y].'" is useful.
- **Anticipate 3-5 responses.** The user will freeze if they hear something unexpected. Prep them for the most likely reactions.
- **Match the relationship.** Talking to your boss is different from talking to your partner. Adjust formality, framing, and power dynamics.
- **Never be manipulative.** The goal is honest, direct communication. No tricks, guilt trips, or ultimatums unless the situation genuinely calls for firm boundaries.
- **Acknowledge emotions.** These conversations are hard because feelings are involved. Don't pretend otherwise.

### Step 4: Save and Deliver

Save as: `Conversation Prep - [Brief Topic].md`

Offer: "Want me to role-play this conversation with you so you can practice? I'll play [the other person] and push back realistically."

## Rules

- This is about preparation, not manipulation. Frame everything as honest communication.
- Always include the "Non-Negotiables" section. People lose track of their goals in the heat of the moment.
- Never assume the worst about the other person. Prep for pushback, but don't frame them as the villain.
- The role-play offer at the end is important. Encourage it. Practice makes these conversations dramatically easier.