Overview

Auto-draft and manually-requested email drafts for {user.primaryemail} and {user.workemail}.

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

Steps

1. Read rules and state

• Read {user.workspace}/style/DIGEST_RULES.md for format and rules
• Read state files:
• {user.workspace}/state/scheduling-threads.json — stalled threads (>3 days since proposed)
• {user.workspace}/state/decisions-memory.json — context on people/companies
• {user.workspace}/state/digest-state.json — avoid repeating items

Schema: {"lastRun": "ISO date", "surfacedItems": [{"id": "id|taskid>", "type": "intro|followup|draft|task|calendar", "surfacedAt": "ISO date"}]}. Use consistent IDs: Gmail thread IDs for email items, Todoist task IDs for tasks, calendar event IDs for calendar items. Do NOT use semantic strings like "calendar:golf-mar5" — always use the actual service ID. An item is "repeated" if its ID appeared in the last digest run. Re-surface only if its status changed since then.

Error handling

If any data source (Gmail, Calendar, Todoist, Granola) fails or times out:

• Log the error, note it in the digest as "⚠️ [Source] unavailable — skipped"
• Continue with remaining sources — never halt the entire digest for one failure
• If BOTH Gmail accounts fail, abort and notify: "⚠️ Digest failed — Gmail unreachable"

2. Check Todoist

source {user.workspace}/.env
todoist-cli review

Include: overdue tasks, today's tasks, inbox (needs triage).

Format as "📋 Open Tasks" section: task name, due date, priority.

Highlight overdue first. Skip no-due-date tasks unless in inbox.

3. Check calendar (next 7 days) — BOTH accounts MANDATORY

gog --account {user.primary_email} --no-input calendar list primary --from "<today>T00:00:00-03:00" --to "<today+7>T00:00:00-03:00" --json
gog --account {user.work_email} --no-input calendar list primary --from "<today>T00:00:00-03:00" --to "<today+7>T00:00:00-03:00" --json

Use actual

Scope

• Timezone: {user.timezone}
• Calendars: primary of {user.primaryemail} AND {user.workemail}
• Today's meetings only

Timezone note: Use explicit ART-bounded ISO8601 timestamps for calendar queries, NOT --date. Example: gog calendar list primary --account --from "2026-03-03T00:00:00-03:00" --to "2026-03-04T00:00:00-03:00" --json. The --date flag uses UTC boundaries which misaligns with ART.

• ALL meetings with attendees — both external and internal
• Skip personal/solo events with no attendees (e.g. "Personal Trainer", "Golf", all-day reminders)

Meeting types

External meetings (attendees outside your email domains)

Full research brief (email context, Granola, LinkedIn, company research) — see below.

Internal meetings (all attendees from your email domains: hypergrowthpartners.com, growth.li)

Lighter brief — no LinkedIn/company research needed, but still include:

• Attendee list
• Granola context from previous instances of this recurring meeting
• Recent email threads related to the meeting topic/agenda
• Any open action items from last time
• Format: same structure but skip LinkedIn/company sections

Recurring collaborative meetings (e.g. podcasts, content sessions with external co-hosts)

These are external meetings — give them full briefs. Don't skip recurring meetings just because they're familiar.

Error handling

• If gog calendar fails for one account: continue with the other account, note "⚠️ [account] calendar unavailable" in output.
• If Granola/Grain fails: continue without meeting history, note it per meeting.
• If Wha

Steps

1. Get today's due tasks from Todoist

source {user.workspace}/.env
todoist-cli today --json

Also check overdue tasks:

todoist-cli list --filter "overdue" --json

2. Identify email/ping tasks

Filter for tasks whose content matches outreach intent:

• Keywords: ping, email, follow up, follow-up, send, reach out, text, message, intro, connect, check in, nudge, reply, respond, draft
• Pattern: any task that implies sending a communication to a specific person

Skip tasks that are clearly NOT outreach (e.g. "review doc", "read report", "build proposal").

3. For each outreach task, draft the email

Read and follow ~/executive-assistant-skills/email-drafting/SKILL.md for all drafting rules.

For each task:

1. Identify the recipient: Extract person/company name from task content + description
2. Pull meeting context (if available): If the task description references a meeting name, date, or was created by the action-items cron (check for Granola citation links or meeting metadata in description), retrieve the transcript via Granola/Grain. If no meeting reference exists in the task, skip directly to step 3 — draft from email history and task content alone.

   # Find the meeting in Granola
   mcporter call granola list_meetings --args '{"time_range": "custom", "custom_start": "<meeting-date>", "custom_end": "<meeting-date+1>"}'
   # Query for what was discussed with this person
   mcporter call granola query_granola_meetings --args '{"query": "What did {user.name} discuss with <recipient> and what did he promise or commit to do?", "document_ids": ["<meeting_id>"]}'

Th