Executive Digest

Schema: {"lastRun": "ISO date", "surfacedItems": [{"id": "<thread_id|task_id>", "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 ISO8601 dates with ART timezone offset (-03:00). Relative dates like 'today' and '+7 days' are not supported by gog. CRITICAL: You MUST run BOTH commands and merge ALL events from both calendars into a single timeline. Events live on different calendars — showing only one gives an incomplete picture. Deduplicate by time+title if the same event appears on both. Look for OOO, travel, vacation blocks, back-to-back conflicts, and double-bookings across calendars.

RSVP check: For each upcoming meeting with external attendees, check the attendees[].responseStatus field. If NO attendee (other than Gonto) has accepted, flag it in the digest and suggest pinging them to confirm attendance. Frame as: "⚠️ [Meeting] — nobody accepted yet. Ping [names] to confirm?"

4. Check Gmail for pending items — BOTH accounts

Universal rule (applies to ALL sub-steps below): Before surfacing ANY email item, check the FULL thread for replies from Gonto's team (Gonto, Alfred/Howie, or Giulia — see team-handled threads check in §4a). If ANY team member already replied → skip the item. If a draft exists for an already-replied thread → delete the draft silently (gog gmail drafts delete <draftId> --force). This prevents surfacing stale items.

Use gog --account {email} --no-input gmail search "query" --json for all searches. Run each query against BOTH accounts.

4a. Pending intros and follow-ups

• Recent intros not actioned: subject:(intro OR introduction OR connecting) newer_than:7d
• Follow-ups from others: (following up OR checking in OR circling back) newer_than:7d
• Drafts awaiting send

Team-handled threads (MANDATORY check): Before flagging ANY intro, follow-up, or email item as "pending" or "no reply", check the FULL thread for replies from Gonto's team. ANY reply from the following people counts as the item being handled:

• Gonto himself ([email protected], [email protected])
• Alfred/Howie — scheduling assistant ([email protected], [email protected])
• Giulia ([email protected], [email protected])

gog --account {user.work_email} --no-input gmail thread get <threadId>

Scan ALL messages in the thread. If ANY message is from any of the above addresses, the item is handled — do NOT surface it.

Previously resolved items (MANDATORY check): Before surfacing ANY item, check {user.workspace}/state/digest-state.json for the resolvedItems array. If the item's ID (thread ID, task ID, or item key) appears in resolvedItems, do NOT re-surface it. When the user tells you an item is "done" or "already handled", immediately add its ID to the resolvedItems array in the state file.

Schema for resolvedItems: "resolvedItems": [{"id": "<threadId|taskId|itemKey>", "resolvedAt": "ISO date", "note": "brief reason"}]

Draft hygiene (MANDATORY):

• For each draft candidate, check if a matching message (same thread/subject intent) was already sent from that account.
• If already sent, delete the stale draft and exclude it from digest output.
• Only report drafts that still require a send/edit decision.

Stale draft auto-cleanup (MANDATORY):

• For EVERY draft found, fetch the full thread (gog --account <email> --no-input gmail thread get <threadId> --json) and check if Gonto already replied manually (sent message in the same thread AFTER the draft was created).
• Fallback if gmail thread get returns empty {}: This is a known gog CLI issue for some threads. Use gog --account <email> --no-input gmail search "in:sent thread:<threadId>" --json instead to check for sent replies in that thread. If search also fails, use the original search result snippets + metadata to make a best-effort determination.
• If Gonto already replied in the thread → delete the draft automatically (gmail drafts delete <draftId> --force) and do NOT surface it in the digest.
• This catches cases where auto-drafted replies become stale because Gonto replied on his own.

4b. Unanswered emails from known contacts

Search BOTH Gmail accounts for recent inbound emails (last 7 days) from real people (not newsletters, automated, or system notifications) that have NO reply.

• If no reply exists after 24-48h, surface it as needing a decision (reply, ignore, or delegate)
• Prioritize: known contacts > first-time senders, VIPs always surface
• Frame as: "[Name] emailed about [topic] — reply, ignore, or delegate?"

4c. Promised follow-ups not yet executed

Scan for commitments made but not yet completed:

• From SENT mail (last 14 days): Look for promises like "I'll intro you", "I'll send the deck", "let me connect you with", "I'll follow up with" — then check if the intro/email was actually sent
• From Todoist: Check open tasks tagged with follow-up intent (intros, send deck, ping someone) that are overdue or due today
• From Granola/Grain (last 7 days): Query recent meetings for action items assigned to you that haven't been completed:

  mcporter call granola query_granola_meetings --args '{"query": "What are all of {user.name} personal action items and commitments from the last 7 days? Only things they need to do."}'
  

  Cross-check each item against: (a) sent emails — was the intro/follow-up actually sent? (b) Todoist — is there already an open task for it? (c) calendar — was the meeting/call already scheduled? Surface anything that fell through the cracks — promised but not yet actioned.
• Frame as: "Promised [action] to [person] on [date] — still pending"

⚠️ MANDATORY sent-mail verification for EVERY promised follow-up (no exceptions): Before surfacing ANY item from this section, you MUST search SENT mail on BOTH accounts for evidence it was already fulfilled:

gog --account {user.primary_email} --no-input gmail search "to:<person_or_company> in:sent newer_than:14d" --json
gog --account {user.work_email} --no-input gmail search "to:<person_or_company> in:sent newer_than:14d" --json

Also search by name/company if email address is unknown. Check the thread content — a sent reply in the same thread as the commitment means it was fulfilled. If you find a sent email that addresses the commitment → do NOT surface it. Log: python3 {user.workspace}/scripts/skill_log.py exec-digest DEBUG "Follow-up already sent" '{"person": "<name>", "thread": "<id>"}'

This is the #1 source of false positives in the digest. Never skip this check.

Additional checks (per DIGEST_RULES.md)

For sections not explicitly covered above, follow {user.workspace}/style/DIGEST_RULES.md:

• OOO conflict detection (§2)
• Action-required non-urgent emails — billing, contracts, renewals (§7)
• Decision memory integration — read and apply {user.workspace}/state/decisions-memory.json for context on people/companies

5. Compile and send

• Format per {user.workspace}/style/DIGEST_RULES.md
• If items exist → send via WhatsApp to {user.whatsapp}
• Also send to Chief of Staff: Send the full digest as a single Slack DM to {user.chief_of_staff.name} (DM channel: {user.chief_of_staff.slack_dm_channel}). Use the Slack API (chat.postMessage) with the bot token. Prefix with "📋 Executive Digest — <date>".
• Update {user.workspace}/state/digest-state.json with items surfaced
• Nothing needs attention:
  • Cron context: NO_REPLY (don't send anything)
  • User asked for digest: Send "Nothing needs attention today ✅"

Overview

Generates a daily executive digest summarizing everything needing attention: stalled scheduling, pending intros, unanswered emails, promised follow-ups, open Todoist tasks, and upcoming calendar events, delivered via WhatsApp and Slack.

Prerequisites

• gog CLI configured with both Gmail/Calendar accounts
• todoist-cli installed with valid API token in workspace .env
• mcporter with Granola MCP connection for meeting commitment lookup
• Slack bot token for Chief of Staff DM delivery
• WhatsApp delivery endpoint configured in user.json
• State files: scheduling-threads.json, decisions-memory.json, digest-state.json

Instructions

See the Steps section above (Steps 1 through 5) for the full execution workflow.

Output

• WhatsApp message with categorized digest (tasks, calendar, pending intros, unanswered emails, promised follow-ups)
• Slack DM to Chief of Staff with the same digest content
• Updated digest-state.json tracking surfaced items to avoid repetition

Error Handling

See the Error handling subsection under Step 1 above. Individual data source failures are logged and noted in the digest; the entire digest only aborts if both Gmail accounts are unreachable.

Examples

# The skill checks Todoist, both calendars, Gmail threads, and Granola commitments.
# Example WhatsApp digest excerpt:
# "3 overdue tasks, 2 pending intros, 1 unanswered email from Sarah Chen,
#  5 meetings this week (2 external, 3 internal)"

Resources

• Todoist REST API
• Gmail API
• Google Calendar API
• Slack API - chat.postMessage