Friday Monday-prep automation -- compile status report, talking points, and risk areas for the weekly leadership meeting

Compile the Monday prep package for your weekly leadership meeting: status report + talking points + risk areas.

Identity

Read ~/Edwin/docs/identity/SOUL.md for your voice. Direct, opinionated, dry. You synthesize -- you don't list raw data. Think like a tech leader briefing the executive team.

Context Loading

Before anything:

Run date "+%A, %B %d, %Y" to get today's date. Confirm it's Friday. If not Friday, note the deviation but proceed.
Read ~/Edwin/memory/conversation-state.md for current context
Read the 2 most recent ~/Edwin/memory/sessions/*-summary.md files for this week's narrative

Data Gathering

Run ALL of these. Missing data is fine -- work with what you have. Do not fabricate tickets, names, or status.

Project Tracker (Linear, JIRA, or equivalent)

Use your project management MCP tools:

Find active projects and teams. Note their IDs.
Get all issues updated this week. For each issue, capture:
- Issue identifier (e.g. PROJ-128)
- Title
- Status (Todo, In Progress, In Review, Done, Cancelled)
- Assignee
- Priority
- Labels
Group issues by status: Shipped (Done this week), In Progress, In Review/QA, Blocked
Check current sprint health (items planned vs completed vs remaining)

If you use multiple project trackers (e.g., Linear + JIRA), repeat for each and merge the results.

Team Status Updates

Read any team status update channels (e.g., Teams, Slack, standup notes):

Check ~/Edwin/data/ for relevant team communication files
Read the most recent entries to get this week's developer/team status updates
Extract: who's working on what, what shipped, what's blocked, what's planned

Email & Calendar Context

Scan this week's email data for messages from leadership, escalations, client issues
Check Monday's calendar -- what meetings are scheduled?
Look for emails from key stakeholders flagging issues

Semantic Memory

memory_search for: "leadership priority", "executive concern", "leadership request" -- surface what leadership has been asking about
memory_search for: "blocker", "risk", "escalation" -- surface open risks
pm_list with filter "due" -- check for overdue/due items that leadership might ask about

Compilation

Write THREE documents:

Document 1: Status Report

Output: ~/Edwin/briefing-book/docs/1. Briefs/Software Dev Status -- Week of YYYY-MM-DD.md

Format (match the established template exactly):

# Software Development Status -- Week of [Monday date]

**Prepared for:** [Leadership] | **From:** [Your name] | **Period:** [Mon] -- [Fri], [Year]

---

## Executive Summary

[3-5 bullet points. Lead with wins (shipped count, key deliverables). Then current state (what's in flight). Then blockers/risks. Be specific with numbers. Leadership wants to see velocity and health, not process detail.]

---

## Key Projects Status

| Project | Health | Notes |
|---------|--------|-------|
| [Project] | [On Track / Watch / At Risk / Starting] | [One-line status] |

[Include all active projects. 4-8 rows.]

---

## Who's Working on What

| Team Member | Current Work |
|-------------|-------------|
| [Name] | [What they shipped + what they're on now. Be specific with ticket numbers.] |

[Include every team member who posted updates this week.]

---

## Risks / Blockers

[2-4 paragraph narrative. What could derail next week? What needs leadership attention? What's blocked on cross-team coordination? QA throughput? Be honest.]

---

## Detail (Appendix)

### Shipped This Week ([count] items)

[List each: ticket number -- description -- assignee. Group by project/tracker.]

### In Review / QA

**In Review ([count])**
[List each with assignee]

**In QA ([count])**
[List each with assignee]

### Added Mid-Sprint ([count])
[List items added after sprint start]

Document 2: Monday Talking Points

Output: ~/Edwin/briefing-book/docs/1. Briefs/Monday Talking Points -- YYYY-MM-DD.md

# Monday Talking Points -- [date]

## Leadership's Likely Questions
[Based on this week's emails, drive-bys, and known concerns -- what will leadership ask about? Prep concise answers.]

## Wins to Lead With
[What looks good? What can you point to as evidence of velocity?]

## Risks to Get Ahead Of
[What bad news is coming? Better to surface it proactively than let leadership discover it.]

## Ask Leadership For
[What do you need from them? Decisions, resources, air cover?]

## Pipeline Status
[What PRDs or initiatives are in the pipeline? Who owes what? What's ready to prioritize?]

Document 3: Leadership Risk Radar

Output: ~/Edwin/briefing-book/docs/1. Briefs/Leadership Risk Radar -- YYYY-MM-DD.md

# Leadership Risk Radar -- [date]

[Short doc. What are the things leadership might escalate? For each:]

## [Risk Name]
- **What:** [the situation]
- **Why leadership cares:** [connect to their known concerns -- growth, client commitments, velocity]
- **Current state:** [facts]
- **Your position:** [what to say if asked]
- **Worst case:** [what happens if this goes sideways]

Publishing

Write all three documents to the briefing book paths above
Publish to Obsidian if configured (e.g., run ~/Edwin/briefing-book/scripts/obsidian-publish)
If the conversation is live (not a scheduled task), notify the user: "Monday prep package ready in the briefing book. Three docs: status report, talking points, leadership risk radar."

Quality Rules

No fabricated data. If you can't find a ticket, don't invent one. If a team member didn't post updates, note the gap.
Ticket numbers must be real. Cross-reference every ticket number against the project tracker data you pulled.
Names must be real. Only use team member names from status updates or issue assignees.
No em dashes. Use -- instead.
Be honest about what you don't know. "Data unavailable" is better than a guess.
Steelman as the executive. After writing the status report, reread it as if you were the executive reading it Monday morning. What questions would they ask? Make sure the report answers them.

monday-prep