mail-follow-up

name

mail-follow-up

description

Use this skill to find threads where the user is waiting on someone else and hasn't heard back, then draft polite nudges to chase a response — via the inkwell CLI. Triggers on "follow up on", "chase", "nudge", "what am I waiting on", "remind people who owe me a reply". Drafts for approval, saved to the Drafts folder — it never sends (Mail.Send is denied by construction, PRD §3.1; the user sends from Outlook). The action counterpart to `mail-executive-summary`'s "waiting on others" section.

Skill: mail-follow-up

Surface conversations where the user sent the last message and hasn't gotten a reply, then draft a brief, polite nudge for each. Draft for approval — never send (there is no send verb; don't simulate one). This is the draft stage of the mail-skill posture.

Procedure

1. Preflight + sync. python3 scripts/preflight.py (relative to this skill's directory; fails clean with instructions), then inkwell sync once.

2. Find what's gone quiet. python3 scripts/find_quiet.py auto-detects the workflow setup: if mail-triage maintains an @Waiting folder it scans the conversations filed there (triage is the single writer of that state — this skill only reads it); otherwise it falls back to scanning recent Sent Items (the user chose not to run triage — that's fine). Force either with --mode waiting|sent; localized mailboxes: add --sent-folder "<localized Sent Items name>". Either way it reports conversations where the user sent the last message, nothing newer arrived, and it's been quiet ≥ --quiet-days 3 business days (adjust if the user gives a window). Each candidate carries quiet_business_days, recipients, a snippet, and has_draft — skip any candidate with has_draft: true; a pending draft in the thread means it was already chased (or a reply is mid-composition). Don't re-nudge the same thread twice in a short window.

3. Filter out what doesn't need chasing. Read the user's last message (inkwell messages show <last_message_id>) — and the thread (inkwell messages --filter '~v <conversation_id>' --all) when the snippet isn't enough. Exclude:

   • Purely informational closers (an FYI, a thank-you, a "sounds good") with no outstanding question, request, or pending answer.
   • Threads the user closed or took ownership of ("I'll handle it").
   • Bulk/automated recipients, newsletters, no-reply addresses.
   • Anything where a reply genuinely isn't expected.

   Only chase a real outstanding ask: an unanswered question, a deliverable owed to the user, or a request awaiting action.

4. Draft a nudge per surviving candidate. You're writing because the user sent the last message and hasn't received a reply; the purpose is to politely check in. Write from the user's perspective. Rules:

   • 1–3 sentences. A check-in, not a new email.
   • Acknowledge you're following up; gently remind the recipient of the outstanding matter. Do NOT repeat the previous email.
   • Polite and friendly. Don't be pushy.
   • Don't mention that you're an AI. Body only. Same language as the thread. Match the user's known style; otherwise short, plainspoken, professional.
   • Natural openers (English): "Just checking in on this", "Wanted to follow up on my previous email", "Circling back on this."
   • Plain text only.

5. Present, confirm, save. Show the list grouped by staleness / importance — each item as "{recipient} — {what's outstanding} — quiet {N} days" plus the drafted nudge. Let the user edit, skip, or approve each. Then save each approved nudge as a reply-all draft on the user's own last message — reply-all is load-bearing: Graph's plain createReply on a self-sent message addresses its sender (the user!); reply-all addresses the original recipients, with the user's own address deduped server-side:

   python3 scripts/save_draft.py <last_message_id> --verb reply-all <<'EOF'
   ...approved nudge...
   EOF
   

   Sanity-check the saved draft's recipients (inkwell messages show <draft-id> --headers) against the candidate's to list before telling the user it's ready.

6. Report. Which threads got a nudge draft ("review and send from Outlook"), which were skipped and why (no outstanding ask / already drafted / automated sender).

Anti-patterns to refuse

• Nudging a thread with no genuine outstanding ask.
• Double-chasing — has_draft: true, or the user nudged recently; the draft sitting unsent in Drafts is the tell.
• Pushy escalation ("this is my third email…") unless the user explicitly asks for a firmer tone.
• Claiming anything was sent. Drafts only; the human sends.
• Chasing from a stale cache silently — sync first, caveat otherwise.