email-drafting

What this skill does

# Email Drafting Skill

## Config — read before starting

Read `../config/user.json` (resolves to `~/executive-assistant-skills/config/user.json`).
Extract and use throughout:

- `primary_email`, `work_email` — Gmail accounts
- `scheduling_cc` — scheduling assistant email (CC on all scheduling emails, mention in body)
- `scheduling_silent_cc` — silent CC for scheduling visibility (do NOT mention in email body)
- `signature` — sign-off for all drafts (e.g. "--gonto")
- `name` — short name for context

Do not proceed until you have these values.

## Debug Logging (MANDATORY)

Read `../config/DEBUG_LOGGING.md` for the full convention. Use `python3 {user.workspace}/scripts/skill_log.py email-drafting <level> "<message>" ['<details>']` at every key step. Log BEFORE and AFTER every external call (gog gmail, mcporter, todoist-cli). On any error, log the full command and stderr before continuing.

## Overview

Auto-draft and manually-requested email drafts for {user.primary_email} and {user.work_email}.

## When to Use

- Gmail hook detects a trigger (intro, scheduling, thanks/ack, positive reply)
- User asks to draft/reply/send an email
- Action items cron identifies email follow-ups needed

## Architecture

- Detects triggers and creates Gmail drafts
- Handles all scheduling (slot-finding, conflict checking, calendar ops)
- NEVER proposes specific dates/times or creates calendar events

## Execution

- **"Reply" always means Reply All** — include all original To + CC recipients. Only exclude if user explicitly says to reply to one person. Exception: intro handling moves the introducer to BCC per the intro sequence below.
- **After sending any email/draft**, check if it fulfills an open Todoist task (send deck, intro, follow-up, etc.). If yes → complete the task immediately and confirm.
- **Hook/cron triggers**: Always run via isolated sub-agent (prevents memory/context contamination)
- **Direct user requests** ("draft a reply to X"): Main agent may execute directly, but must still follow all style rules and must NOT read MEMORY.md or daily memory files

## Rules (non-negotiable)

### Core

1. **Draft-only mode** — never send automatically
2. **Mirror inbound language** — match the language of the most recent non-automated message in the thread. If the thread has mixed languages, default to the language of the message you're replying to.
3. **Always sign** — end every draft with `{user.signature}`
4. **Low confidence** — don't draft; ask user for guidance
5. **No dash punctuation** — no em-dash/en-dash in bodies. Use commas/periods.
6. **Humanize** — before finalizing any draft, review it against `~/executive-assistant-skills/humanizer/SKILL.md`. Remove AI-writing markers: inflated symbolism, promotional tone, em-dash overuse, "delve"/"leverage"/"foster" vocabulary, rule-of-three patterns. Email-specific rules (no dashes, signature, brevity) take precedence over humanizer suggestions if they conflict.

### Intro Handling (required sequence)

1. Thank introducer first
2. Move introducer to BCC
3. Reply to introduced contact directly
4. CC `{user.scheduling_cc}` and `{user.scheduling_silent_cc}` for scheduling
5. Include one line like: "Connecting {user.scheduling_cc_name} to find a time."
6. **Do NOT mention `{user.scheduling_silent_cc}` in the email body** — silent CC only

### Scheduling Drafts

- **ALWAYS CC {user.scheduling_cc} AND {user.scheduling_silent_cc}**
- **NEVER propose specific dates or times**
- Just confirm willingness to meet + mention scheduling assistant will coordinate
- Example: "Connecting Alfred to find a time that works"
- **Do NOT mention {user.scheduling_silent_cc} in the email body** — she's CC'd silently for visibility

### Allowed Auto-Draft Classes

- Thanks/ack
- Scheduling intent
- Positive short replies
- Intro acceptance

### Notification Format

- `account + one-line intent + draft link`
- Example: `📧 Draft ({user.primary_email} → John): intro acceptance. https://mail.google.com/...`

## Draft Links

After creating a draft via `gog`, extract the draft ID from the response.
Gmail draft URL format: `https://mail.google.com/mail/u/?authuser={account_email}#drafts?compose={message_id}`
Use `[email protected]` or `[email protected]` as appropriate.

## Trigger Detection

### A) Intro

- Cues: `intro`, `introduction`, `meet`, `connecting you`, `looping in`, `cc'ing`
- At least 2 external participants + clear handoff language
- Apply intro sequence exactly

### B) Scheduling Intent

- Cues: `find a time`, `schedule`, `availability`, `next week`, `calendar`
- Spanish cues: `agendar`, `agenda una`, `tenés unos minutos`
- CC scheduling contacts, don't propose times

### C) Thanks/Ack

- Cues: `thanks`, `got it`, `appreciate it`, status updates
- Short acknowledgment + optional one-line next step

### D) Positive Short Reply

- Cues: `works for me`, `sounds good`, `perfect`, `great`
- Short affirmative + close

## Skip Conditions (do NOT auto-draft)

- Confidence low / intent ambiguous
- User already replied in the thread (SENT message exists)
- Legal, financial, security, hiring-final, sensitive conflict topics
- Multi-question strategic asks
- Automated/system/calendar notifications
- Messages requiring attachments, deep verification, or policy commitments
- Language unclear or unmirrorable
- **Scheduling confirmations** — NEVER auto-draft emails that simply confirm a scheduled time or acknowledge a calendar invite. The scheduling assistant (Alfred/Howie) handles all scheduling coordination. Auto-drafting "confirming our call at X" creates noise and duplicates the scheduler's work. This includes: confirming times proposed by the scheduler, acknowledging calendar invites, and "looking forward to our call" type replies to scheduling threads.

## Confidence Gate

Only auto-draft when ALL are true:

- Trigger class is one of the 4 allowed
- Language confidently detected and mirrorable
- Clear recipient intent and next step
- No skip condition present

Otherwise: ask user.

## Drafting Principles

- **Keep it SHORT** — drafts are always brief. 2-3 short paragraphs max.
- **No over-explaining** — state the point, don't elaborate unless necessary
- **When promising intros**: before drafting the intro, search sent emails for previous intros to that person/company, copy the format and tone, and use the same email address
- **When recommending a person/company**: use your own words from past emails about them rather than inventing new descriptions
- **Deck/one-pager**: say "Hypergrowth Partners deck" (not "our one-pager" or "our deck"). When attaching, frame WHY it's useful (e.g. "where we explain what Hypergrowth is and how we help companies")
- **Future availability**: frame as an opportunity, not a brush-off. Position it warmly: "I'd love to reconnect then to explore working together if the timing still makes sense" rather than blunt "let's connect closer to June"
- **Offers of help should use meeting context**: read Granola notes from the call and reference specific things discussed. The draft should feel like it came from someone who was in the meeting.
- **No generic "Great meeting today"** unless it's explicitly a first meeting (first VC call or first dealflow call).
- **Proposal-first rule**: if the commitment is to build/provide a proposal first, do not draft outbound email yet; create TODO only.

## Use Grain as primary source for meeting-based drafts

When drafting follow-up emails from meetings, **Grain transcript is the primary source** (not Granola):

1. Find the meeting in Grain: `mcporter call grain.list_attended_meetings --args '{"limit": 5}'`
2. Fetch transcript: `mcporter call grain.fetch_meeting_transcript --args '{"meeting_id": "<id>"}'`
3. Search transcript for email commitments: "I'll send", "I'll email", "I'll share", "let me intro", "I'll follow up", "I'll connect you", etc.
4. **Draft from the transcript** — use your actual words and the real conversation context, not Granola's summary.
5. Fal