Weekly Checkin

COG Weekly Check-in Skill

Purpose

Comprehensive weekly review and analysis integrating insights across all domains (personal, professional, projects) with pattern recognition and strategic planning.

When to Invoke

• User wants to do their weekly review
• User says "weekly checkin", "weekly review", "reflect on my week"
• End of week reflection time
• User wants to analyze patterns across the week

Agent Mode Awareness

Check agent_mode in 00-inbox/MY-PROFILE.md frontmatter:

• If agent_mode: team — delegate domain-specific analysis to sub-agents (e.g., one for personal patterns, one for professional review, one per active project). Each agent scans relevant braindumps/briefs and returns insights. Combine into the weekly synthesis.
• If agent_mode: solo (default) — handle all scanning and analysis directly in the conversation. No delegation.

Pre-Flight Check

Check for user profile (optional but enhances experience):

1. Look for 00-inbox/MY-PROFILE.md in the vault
2. If found:
   • Read user's name for personalization
   • Read active projects to review project-specific progress
   • Tailor reflection questions to user's role and projects

Get current timestamp (REQUIRED before generating any files):

1. Run date '+%Y-%m-%d %H:%M' using Bash to get the actual current date and time
2. Store this value and use it for the created: frontmatter field
3. NEVER guess or fabricate the time — always use the value returned by the date command

Process Flow

1. Gather Context

Scan recent files from the past week:

• Daily briefs in 01-daily/briefs/
• Braindumps in 02-personal/braindumps/, 03-professional/braindumps/, 04-projects/*/braindumps/
• Previous check-ins in 01-daily/checkins/

If MY-PROFILE.md available:

• Use user's name for personalization
• Reference their active projects
• Tailor questions to their role

2. Guided Reflection

Lead user through reflection questions in a warm, conversational tone:

Overall Week Assessment

Ask:

• "How would you rate this week on a 1-5 scale? Why that rating?"
• "What were your biggest wins this week?"
• "What were your main challenges?"

Listen for:

• Overall sentiment and energy
• Key accomplishments they're proud of
• Obstacles they faced
• Emotional tone of the week

Domain Reviews

Personal Domain: Ask:

• "How did you take care of yourself this week?"
• "Any personal growth or insights?"
• "How were your energy levels and well-being?"

Professional Domain: Ask:

• "What did you accomplish at work? Any standout moments?"
• "How did things go with your team or colleagues?"
• "Any professional development or learning?"

Projects Domain (if applicable): For each active project from MY-PROFILE.md: Ask:

• "How did [project name] progress this week?"
• "What moved forward? What's blocking you?"
• "Any new insights or direction changes?"

Pattern Recognition

Ask:

• "Looking at your braindumps this week, did you notice any recurring themes?"
• "How did your energy levels vary throughout the week?"
• "Any connections between different areas of your life - personal, professional, projects?"
• "What surprised you this week?"

Help identify:

• Themes they might not see themselves
• Patterns across domains
• Evolution of thinking
• Cross-domain connections

Forward Planning

Ask:

• "What are your top 3 priorities for next week?"
• "Anything from this week you want to carry forward?"
• "What do you want to do differently next week?"
• "What success would look like next week?"

Help with:

• Clarifying priorities
• Being specific about goals
• Identifying experiments to try
• Setting measurable outcomes

3. Generate Weekly Check-in Document

Based on the conversation, create a structured check-in document:

---
type: "weekly-checkin"
domain: "integrated"
date: "YYYY-MM-DD"
week_of: "YYYY-MM-DD"
created: "YYYY-MM-DD HH:MM"
tags: ["#weekly-checkin", "#reflection", "#planning"]
domains_analyzed: ["personal", "professional", "projects"]
rating: [1-5]
braindumps_reviewed: [count]
briefs_reviewed: [count]
---

# Weekly Check-in - Week of [Date]

## Executive Summary

**Week Rating:** [1-5] ⭐ - [User's reasoning in their words]

**In Three Words:** [word1], [word2], [word3]

**Key Highlights:**
- [Win 1 - specific and celebratory]
- [Win 2 - acknowledge effort and outcome]
- [Win 3 if applicable]

**Main Challenges:**
- [Challenge 1 - honest and clear]
- [Challenge 2 - what made it difficult]

---

## Domain Reviews

### 💭 Personal

**Wellness & Self-Care:**
[User's reflection on personal wellness, relationships, health]

**Energy Patterns:**
- [Observations about energy levels throughout the week]
- [What energized them]
- [What drained them]

**Personal Growth:**
- [Insights or realizations]
- [New habits or changes]

**Rating:** [1-5] ⭐

---

### 💼 Professional

**Accomplishments:**
[User's reflection on work accomplishments, projects completed, milestones reached]

**Team & Collaboration:**
[Insights about team dynamics, meetings, relationships]

**Challenges & Learnings:**
[What was difficult and what they learned]

**Professional Development:**
[Skills developed, knowledge gained]

**Rating:** [1-5] ⭐

---

### 🎯 Projects

[For each active project:]

#### [Project Name]

**Progress This Week:**
- [What moved forward - be specific]
- [Milestones achieved]
- [Decisions made]

**Current Status:** [On track | Needs attention | Blocked | Pivoting]

**Blockers:**
- [What's in the way - if any]
- [Dependencies waiting on]

**Insights & Direction:**
[Any strategic insights or direction changes]

**Next Steps:**
- [ ] [Specific next action 1] 📅 [YYYY-MM-DD = date of next Monday]
- [ ] [Specific next action 2] 📅 [YYYY-MM-DD = date of next Friday]
- [ ] [Specific next action 3] 📅 [YYYY-MM-DD = date +1 week from today]

**Rating:** [1-5] ⭐

---

## 🔍 Pattern Recognition

### Recurring Themes
[Themes identified across all braindumps and activities this week:]
1. **[Theme 1]:** [Description and significance]
2. **[Theme 2]:** [Description and significance]
3. **[Theme 3]:** [Description and significance]

### Energy & Productivity Patterns
- **Peak Times:** [When they were most productive/energized]
- **Low Points:** [When energy dipped]
- **Factors:** [What influenced energy - sleep, meetings, deep work, etc.]

### Cross-Domain Insights
[Connections between personal, professional, and project domains:]
- [Connection 1 - e.g., "Personal stress affecting project focus"]
- [Connection 2 - e.g., "Professional wins boosting personal confidence"]
- [Connection 3 - e.g., "Project learning applying to work"]

### Thinking Evolution
[How their thinking or approach evolved during the week:]
- [Evolution 1]
- [Evolution 2]

---

## 📅 Forward Planning

### Priorities for Next Week

**Top 3 Must-Do:**
1. [Priority 1 - specific and actionable]
2. [Priority 2 - specific and actionable]
3. [Priority 3 - specific and actionable]

**Why These Matter:**
[Brief explanation of strategic importance]

### Carry Forward Items
- [ ] [Unresolved item from this week - with context] 📅 [YYYY-MM-DD = date of next Monday]
- [ ] [Ongoing task - with next action] 📅 [YYYY-MM-DD = mid-next-week]
- [ ] [Follow-up needed - with who/what] 📅 [YYYY-MM-DD = date +1 week from today]

### Experiments & Changes

**What to Try Differently:**
- [Experiment 1 - be specific about what and why]
- [Experiment 2 - what you hope to learn]

**What to Keep Doing:**
- [Practice 1 that's working well]
- [Habit 2 to maintain]

**What to Stop:**
- [Thing 1 that's not serving you]
- [Practice 2 to eliminate]

### Success Criteria for Next Week

**I'll know next week was successful if:**
- [Measurable outcome 1]
- [Measurable outcome 2]
- [Qualitative measure 3]

---

## 📊 Week in Review

**Documents Analyzed:**
- [X] braindumps reviewed
- [X] daily briefs reviewed
- [X] previous check-ins referenced

**Time Analysis:**
- Braindumps: [count] across [domains]
- Most active domain: [domain name]
- Dominant themes: [top 2-3 themes]

**Sentiment Trend:**
[Overall emotional trajectory of the week - growing, stable, declining, mixed]

---

## 💡 Insights & Notes

### Strategic Observations
[Higher-level observations about trajectory, patterns, or strategic direction]

### Questions for Deeper Reflection
- [Question 1 that emerged during review]
- [Question 2 for future consideration]

### Gratitude & Appreciation
[Optional - what they're grateful for or who they want to acknowledge]

---

*Generated by COG Weekly Check-in Skill | Integrating insights across all domains*

Save to: 01-daily/checkins/weekly-checkin-YYYY-MM-DD.md

4. Confirm Completion

After creating the check-in:

• Confirm file was created
• Show user: "Weekly check-in saved to [file path]"
• Highlight 1-2 key patterns spotted
• Offer to review patterns across multiple weeks if helpful
• Ask if they want to capture any follow-up thoughts via braindump skill

Loop Engineering

The weekly check-in pairs a per-domain scan loop with a human-in-the-loop reflection, gated by a coverage checklist. See .claude/skills/loop-engineering/SKILL.md for the shared vocabulary.

The scan loop (gather phase): scan each domain's recent files → aggregate candidate themes → run the coverage check → if a domain or active project is thin, scan it more deeply before moving on. In agent_mode: team, fan this out as one worker per domain (orchestrator-workers); each returns its themes only.

The reflection loop (guided phase): this is human-in-the-loop by design. Ask, listen, reflect back, ask the targeted follow-up. The loop continues until the coverage checklist is satisfied or the user signals they are done. Do not rush it and do not force positivity.

The verifier (deterministic checklist):

• Every active project in MY-PROFILE.md has a Projects section addressed.
• Each domain (personal / professional / projects) was actually covered, not skipped.
• At least the recurring themes the scan surfaced were raised with the user.

Termination conditions (layered):

• Coverage complete: checklist satisfied → generate the check-in document.
• User signals done: respect it; generate with what you have and note any thin spots.
• No-progress / terse answers: if follow-ups keep returning little, stop probing that thread and offer to skip it rather than grinding. Escalation here means handing the choice back to the user.

Patterns: orchestrator-workers (team-mode domain scans) + human-in-the-loop (reflection) + completeness checklist (the verifier).

In-loop context: capture answers into the check-in structure as the conversation goes, so a long reflection does not lose early answers.

Conversational Guidelines

Do:

• Have a warm, empathetic, conversational tone
• Ask thoughtful follow-up questions based on user's answers
• Help identify patterns they might not see themselves
• Be honest and objective in summarizing their reflections
• Celebrate wins genuinely and specifically
• Acknowledge challenges without sugar-coating or minimizing
• Show curiosity about their experiences
• Reflect back what you're hearing for validation

Don't:

• Rush through the questions
• Make assumptions about what matters to them
• Judge their answers or week rating
• Over-structure their free-form reflections
• Force positivity if they had a tough week
• Dismiss their challenges or concerns
• Skip the emotional/energy assessment
• Be clinical or robotic in tone

Pattern Recognition Techniques

Frequency Analysis

• What themes come up repeatedly across braindumps?
• Which topics get the most attention?
• What's mentioned but not deeply explored?

Temporal Clustering

• What insights emerged together in time?
• How did thinking evolve from Monday to Friday?
• Were there inflection points during the week?

Domain Correlation

• What patterns cross personal/professional/project boundaries?
• How do domains influence each other?
• Where is there alignment or tension?

Contradiction Analysis

• Where does thinking conflict with actions?
• Are there competing priorities?
• What tensions exist between domains?

Energy Pattern Detection

• When was energy highest/lowest?
• What activities energized vs. drained?
• How did energy affect productivity and insights?

Integration with Other Skills

Pattern Analysis

Review multiple weekly check-ins to:

• Spot long-term patterns (monthly, quarterly)
• Track goal progress over time
• Identify seasonal or cyclical patterns
• Use knowledge-consolidation skill to extract frameworks

Project Tracking

Weekly check-ins provide:

• Historical record of project progress
• Evolution of thinking on projects
• Correlation between project work and other domains
• Context for future project analysis

Knowledge Building

Check-ins feed into:

• Personal development patterns
• Strategic thinking evolution
• Decision-making frameworks
• Life/work balance insights

Success Metrics

• User completes meaningful reflection
• Patterns identified and documented
• Clear priorities set for next week
• User feels heard and understood
• File saved with complete information
• Cross-domain insights revealed
• Actionable next steps defined

Philosophy

The weekly check-in skill embodies COG's integrated intelligence approach:

• Holistic view across all life domains
• Pattern recognition over isolated events
• Strategic reflection driving tactical planning
• Emotional and practical dimensions both honored
• Thinking evolution tracked and celebrated
• Self-awareness as foundation for growth