Executive Assistant - Weekly Leadership Briefing System

Generate automated weekly leadership briefings that synthesize management journal notes, calendar patterns, and strategic priorities into actionable Sunday night briefings.

Purpose

This skill provides a comprehensive weekly briefing system designed to:

• Extract leadership signal from the week's management journal notes
• Analyze next week's calendar for time optimization
• Connect daily work to strategic priorities
• Identify what matters most and where to focus energy
• Track progress against role expectations

How It Works

The system uses three specialized prompts that work together:

1. grove-notes-reflection.md - Extracts lessons and people signals from the last 7 days of management journal notes
2. calendar-analysis.md - Optimizes next week's calendar for impact and alignment
3. weekly-briefing-prep.md - Synthesizes reflection + calendar into one comprehensive briefing

File Structure

.claude/skills/exec-assistant/
├── SKILL.md (this file)
├── prompts/
│   ├── weekly-briefing-prep.md        # Main briefing generation prompt
│   ├── grove-notes-reflection.md      # Weekly notes reflection prompt
│   ├── calendar-analysis.md           # Calendar optimization prompt
│   ├── executive-assistant-prompt.md  # System overview
│   └── zapier-setup-guide.md         # Zapier automation setup
└── briefings-README.md                # Archival documentation

resources/exec-assistant/  (in repo root)
├── priorities.md           # Current leadership priorities (input)
├── expectations.md         # Role performance standards (input)
└── briefings/             # Generated briefings saved here
    ├── 2026-03-02.md
    ├── 2026-02-23.md
    └── ...

Required Inputs

The briefing prompts reference these files from the Knowledge System:

• Management Journal: notes/management-journal/YYYY-MM.md - Monthly working notes with meeting reflections, strategic thoughts, 1:1s
• Priorities: resources/exec-assistant/priorities.md - Current leadership focus areas (updated quarterly)
• Expectations: resources/exec-assistant/expectations.md - Role performance expectations and GPS framework mapping
• Calendar Data: Meeting hours, alignment %, prep/prune lists from Google Calendar

Outputs

Each Sunday night briefing includes:

• THIS WEEK IN ONE SENTENCE: Sharp, tactical summary
• THE MOMENT: 3-4 paragraphs of strategic context
• THREE THINGS THAT MATTER MOST: Concrete strategic moves with people observations
• STATUS: 3-5 key items requiring attention (with momentum tracking)
• FRAMEWORKS WORTH KEEPING: Reusable mental models that emerged
• CONNECTING TO YOUR PRIORITIES: How the week mapped to standing priorities
• WHERE TO SPEND YOUR ENERGY: Inspiring close on 2-3 focus areas

Briefings are saved to: resources/exec-assistant/briefings/YYYY-MM-DD.md

Usage

Option 1: Manual Generation (Current)

1. Extract weekly reflection:

   • Use prompts/grove-notes-reflection.md with last 7 days of notes/management-journal/YYYY-MM.md
   • Produces: lessons, focus items, people signals, quotes

2. Analyze calendar:

   • Use prompts/calendar-analysis.md with next week's calendar
   • Produces: prep priorities, cuts, misalignment, recovery plan

3. Generate briefing:

   • Use prompts/weekly-briefing-prep.md with outputs from steps 1-2
   • Produces: Complete Sunday night briefing (~800-1200 words)

4. Save briefing:

   • Create file: resources/exec-assistant/briefings/YYYY-MM-DD.md (use Sunday date)
   • Commit to git

Option 2: Automated via Zapier (Recommended)

Setup: See prompts/zapier-setup-guide.md for complete Zapier workflow

What it does:

• Every Sunday at 9pm
• Fetches management journal notes from GitHub
• Fetches calendar from Google Calendar
• Generates briefing using Claude API
• Saves to resources/exec-assistant/briefings/YYYY-MM-DD.md on GitHub
• Optionally sends email copy

Requirements:

• Zapier Pro account
• Anthropic API key
• GitHub + Google Calendar access
• ~$20/month cost

After the Week: Add Reflections

Annotate each briefing after the week concludes:

---

## End-of-Week Reflection

**What landed:**
- [What actually got focus/traction]

**What shifted:**
- [Unexpected changes or pivots]

**Insights:**
- [Patterns or learnings]

**For next week:**
- [Adjustments or carry-forward items]

Integration with Knowledge System

Reads from:

• notes/management-journal/YYYY-MM.md - Monthly working notes (via /log-meeting, /note)
• resources/exec-assistant/priorities.md - Strategic priorities (updated via /refresh-priorities or manually)
• resources/exec-assistant/expectations.md - Role expectations

Outputs to:

• resources/exec-assistant/briefings/YYYY-MM-DD.md - Weekly briefings

Related commands:

• /log-meeting - Populates management journal with meeting notes
• /note - Adds timestamped reflections to management journal
• /weekly-review - Tactical weekly review (different from strategic briefing)

Principles

The briefing system follows these core principles:

1. Be ruthlessly selective — Most things don't matter, focus on what does
2. Be blunt and opinionated — Challenge misaligned attention
3. Extract meaning, not summaries — Find strategic shifts and trajectory changes
4. Optimize for leadership effectiveness — Connect daily work to impact
5. Track evolution — Use git history to see patterns over time

Best Practices

1. Use Sunday dates: Briefings prepare for the coming week, so use Sunday date that starts the week
2. Add reflections: After the week, annotate with what actually happened
3. Review quarterly: When running /refresh-priorities, review last 3 months of briefings
4. Share selectively: Briefings contain sensitive strategic information
5. Track themes: Use grep/search to find recurring patterns across weeks

Files You Can Share Publicly

Since you plan to share this system publicly, these files contain no PII:

Shareable (system prompts):

• prompts/weekly-briefing-prep.md
• prompts/grove-notes-reflection.md
• prompts/calendar-analysis.md
• prompts/executive-assistant-prompt.md
• prompts/zapier-setup-guide.md
• briefings-README.md
• SKILL.md (this file)

Private (contain work-specific data):

• resources/exec-assistant/priorities.md - Your actual priorities
• resources/exec-assistant/expectations.md - Your role expectations
• resources/exec-assistant/briefings/*.md - Generated briefings

When sharing, you can copy the prompts to a blog post or gist and add example placeholder content for priorities/expectations.

Maintenance

• Update priorities: Quarterly via /refresh-priorities or manual edit
• Update expectations: As role evolves or GPS framework changes
• Archive briefings: Keep all in git (valuable history)
• Review prompts: Iterate based on briefing quality

Getting Started

1. Ensure inputs exist:

   • resources/exec-assistant/priorities.md (your current priorities)
   • resources/exec-assistant/expectations.md (your role expectations)
   • notes/management-journal/YYYY-MM.md (current month's notes)

2. Generate first briefing manually to test:

   • Copy prompts/weekly-briefing-prep.md into a new conversation
   • Add last 7 days of management journal notes
   • Add your priorities.md and expectations.md
   • Review output quality

3. If quality is good, set up Zapier automation:

   • Follow prompts/zapier-setup-guide.md
   • Test thoroughly before activating
   • Monitor first few weeks

4. After each week:

   • Review the briefing
   • Add end-of-week reflections
   • Commit to git

Status

Current State: System designed but not yet activated

• Prompts: Complete and tested
• Zapier workflow: Documented but not implemented
• Briefings generated: None yet (directory empty)

Next Steps:

1. Test manual generation with current priorities/expectations
2. Validate output quality and iterate on prompts
3. Decide whether to implement Zapier automation
4. Generate first few briefings manually
5. Review value before committing to automation

Support

For questions or issues:

• Review prompts/executive-assistant-prompt.md for system overview
• Check prompts/zapier-setup-guide.md for automation setup
• See briefings-README.md for archival best practices