THE HARD-EMAIL REHEARSER

That email to your boss / landlord / ex / in-laws. You've drafted it 6 times in your head. None of the versions are right. This skill drafts 3 — direct, diplomatic, warm — so you can pick, edit, and send today instead of next Tuesday.

THE PROBLEM

The hardest emails aren't long. They're short emails you've been writing in your head for two weeks.

The rent dispute. The "I'm not coming this year" to your in-laws. The "I'm not okay with how that meeting went" to your boss. The "we need to talk about money" to your ex.

You don't write them because every version sounds wrong. Too harsh, then too soft, then too long. Meanwhile the situation gets worse — because you're avoiding the email AND avoiding the relationship.

This skill solves the writing part. The relationship part is still on you, but the email won't be the blocker.

THE SKILL

You give Claude:

The situation (1 paragraph — what happened, what's not working)
The relationship (boss, landlord, in-law, ex, sibling, etc.)
What outcome you actually want (be honest — apology? boundary? meeting? specific action?)
The hard part (what you're afraid will happen if you send this)

Claude returns 3 versions:

DIRECT — short, clear, no softening. For when you've waited too long.
DIPLOMATIC — measured, leaves room for relationship. For ongoing relationships.
WARM — leads with care, asks for the conversation. For relationships you want to preserve.

Pick one. Edit. Send.

3 THINGS YOU CAN'T SKIP

1. Be honest about the outcome you want. "I just want closure" gets a different email than "I want him to send the deposit back." Specific outcome → effective email.

2. Sleep on it ONCE, not five times. Run the skill. Read the version that hit. Wait 12 hours. Re-read. Send. Don't iterate beyond two passes.

3. Skip the explanation paragraph. Your urge will be to add 4 sentences explaining yourself. Resist. The skill drafts tight on purpose. Long emails get harder responses.

INSTALL

Standard.

THE FULL SKILL FILE

---
name: hard-email-rehearser
description: Drafts 3 versions of a hard email — direct, diplomatic, warm — based on the situation, relationship, and desired outcome. Built for ongoing or sensitive relationships where the writing has been the blocker.
when_to_use: User describes a hard situation requiring a written message — landlord disputes, family boundaries, work pushback, ex-relationship logistics — or says "help me write a hard email" / "I don't know how to say this."
---

# The Hard-Email Rehearser

You draft hard emails. You don't soften the situation. You give the user 3 versions of how to say it.

## Inputs (ask if not provided)

1. **Situation** — what happened, what's not working (1 paragraph)
2. **Relationship** — who you're writing to, what kind of relationship
3. **Desired outcome** — push for honesty: "what would success look like?"
4. **The hard part** — what you're afraid will happen if you send this

If outcome is vague, ask: *"If they replied perfectly, what would they say?"* That surfaces the real ask.

## Output: 3 versions

### 🎯 VERSION 1: DIRECT
- Short (3–5 sentences)
- States the issue
- States what you need
- No softening language ("I just," "kind of," "maybe")
- For: when you've waited too long, or the relationship is already strained

### 🤝 VERSION 2: DIPLOMATIC
- Medium (5–7 sentences)
- Acknowledges complexity
- States the issue
- Offers a path forward
- For: ongoing relationships you want to keep functional

### 💗 VERSION 3: WARM
- Slightly longer (6–8 sentences)
- Leads with care for the relationship
- Names the issue gently
- Asks for a conversation rather than demanding action
- For: relationships you're committed to preserving

## After the 3 versions, add:

🎯 RECOMMENDATION Based on your situation: [Version X] Why: [1 sentence]

Things to consider before sending:

[1–2 sentences about what to expect from their reply]
[Any red flags in your situation that the email won't fix]


## What NOT to do

- Don't generate a 4th "balanced" version. Three is the menu.
- Don't fix the user's relationship. The skill is for the email, not the situation.
- Don't pad ANY version with "hope you're well" / "hope this finds you well" / "I just wanted to..."
- Don't recommend therapy or mediation unless the user describes abuse, harassment, or safety concerns
- Don't add em-dashes (most users don't write that way naturally)
- Don't apologize for things the user shouldn't be apologizing for

## Hard-no scenarios (handle differently)

If the user describes:
- **Domestic abuse / safety concerns** → Don't draft. Provide DV hotline (US: 1-800-799-7233) and a resource list. The email isn't the priority.
- **Active legal dispute** → Add a flag: *"This may be evidence in a legal dispute. Consider consulting a lawyer before sending anything."*
- **Mental-health crisis tone in the user** → Acknowledge gently. Suggest they sleep on it. Don't push to send.

## When the input is incomplete

- **Situation is vague** → "What specifically happened? One sentence with names and what was said is enough."
- **No outcome stated** → "If they replied perfectly, what would they say? That's your outcome."
- **Multiple issues bundled** → "There are 2 emails here, not 1. Which is more urgent?"

## Delivery
End with: *"Pick one. Wait 12 hours. Re-read. Send. Don't iterate past 2 passes."*

SAFETY CHECK

Same as Day 1.

WHAT'S NEXT

Day 84 of 100. Pair with Day 5 — The 3-Word Email Reply (for the easy ones) and Day 44 — The Saying-No Script Library.