setup-monitoring

If kate-coach SKILL.md is not already loaded in this session, read skills/kate-coach/SKILL.md now — it contains Kate's identity, session context, and file ownership rules.

Watchlist Structure

monitoring/watchlist.md contains five sections:

• Funnel Companies — auto-populated from user/application_history.md; always tracked
• Watchlist — user-defined companies to follow without an active application
• Similar Companies — Kate-suggested, user-approved, with reasoning logged
• Key People — individuals from transcripts, upcoming calls, or explicitly named
• Industry Topics — web search terms for domain news; each has Active/Paused status

Setup Steps

1. Detect the current project folder path — required for Step 6.

2. Check whether monitoring/watchlist.md already exists.

   If it does not exist:

   • Create the monitoring/ folder
   • Copy the watchlist template from skills/kate-coach/references/templates/watchlist_template.md
   • Auto-populate Funnel Companies from user/application_history.md
   • Ask: "Before I set up monitoring, let me confirm what to track. Any companies you want on the watchlist beyond the ones you're already pursuing?" Wait for answer.
   • Ask: "Any specific people I should track — executives at target companies, recruiters, people you'll be interviewing with?" Wait for answer.
   • Suggest 3-4 industry topics based on user/user_profile.md target domains. Ask the user to confirm, trim, or modify before saving.
   • Write the completed watchlist.md.

   If it already exists: confirm with the user whether to keep the current watchlist or update it before proceeding.

3. Run the run-monitoring skill inline to generate the first digest before scheduling. This lets the user validate the output before committing to a weekly run.

4. After the first run, ask: "Does that look right? Too much, too little, anything to change before I set this up to run weekly?"

5. Apply any feedback to watchlist.md.

6. Read the Monitoring Flow in skills/kate-coach/references/flows.md and write monitoring/scheduled_task_prompt.md using this structure, substituting the actual project folder path detected in Step 1:

# Kate Weekly Monitoring — Scheduled Task Prompt
# Generated: [YYYY-MM-DD]
# Re-run setup-monitoring to regenerate this file after updating flows.md.

You are running Kate's weekly monitoring task. This is a headless background job — no user is present.

Project folder: [PROJECT_FOLDER_PATH]

Follow the Monitoring Flow as defined in the kate-coach skill's references/flows.md exactly. The flow file is at: [PROJECT_FOLDER_PATH]/skills/kate-coach/references/flows.md

Steps are defined there in full. Do not deviate from them. Do not interact with the user. Write files and exit.

Key paths:
- Watchlist: [PROJECT_FOLDER_PATH]/monitoring/watchlist.md
- User profile: [PROJECT_FOLDER_PATH]/user/user_profile.md
- Application history: [PROJECT_FOLDER_PATH]/user/application_history.md
- Digest output: [PROJECT_FOLDER_PATH]/monitoring/digest.md
- Digest archive: [PROJECT_FOLDER_PATH]/monitoring/digest_archive/
- Pending suggestions: [PROJECT_FOLDER_PATH]/monitoring/pending_suggestions.md

This file is the single source of truth for the scheduled task. If the monitoring flow in flows.md changes, re-run setup-monitoring to regenerate it.

7. Create the scheduled weekly task pointed at monitoring/scheduled_task_prompt.md. Set it to run weekly (cron: 0 7 * * 1 — Monday mornings at 7am local time, adjustable).

8. Record the scheduled task ID in the monitoring/watchlist.md Scheduled Task Settings section.

9. Confirm: "Monitoring is live. It'll run every Monday morning and have a fresh digest ready when you start your next session after that. You'll see a note at session start if the digest is more than 7 days old."