Retrospective (Base Framework)

Core insight: The retrospective process is the same at any time scale. What changes is the inputs and the time horizon framing.

The Three Questions

Every retrospective answers these three questions:

1. What Worked? → Do more of this
2. What Didn't Work? → Experiment on changing this
3. How Do We Improve the Retro Process? → Meta-improvement loop

That's it. Everything else is structure to support these questions.

Time Scale as Parameter

Scale	Inputs	Horizon	Output
Daily	Raw observations	1 day	Daily summary
Weekly	Daily summaries	7 days	Weekly retro
Monthly	Weekly retros	4 weeks	Monthly retro
Quarterly	Monthly retros	3 months	Quarterly retro
Yearly	Quarterly retros	12 months	Yearly retro

Fractal pattern: Each level compresses the previous level's outputs into inputs for the next.

Process

1. Establish Boundaries

# Verify current date
TZ='America/New_York' date '+%A, %B %d, %Y - %I:%M %p %Z'

Confirm the period being reviewed:

• Daily: "Reviewing [Date]. Correct?"
• Weekly: "Reviewing [Start] - [End]. Correct?"
• Monthly: "Reviewing [Month Year]. Correct?"
• Quarterly: "Reviewing Q[X] [Year]. Correct?"
• Yearly: "Reviewing [Year]. Correct?"

2. Load Context

Load inputs appropriate to scale:

• Daily: Load today's notes/logs
• Weekly: Load daily summaries for the week
• Monthly: Load weekly retros for the month
• Quarterly: Load monthly retros for the quarter
• Yearly: Load quarterly retros for the year

Also load:

• Previous period's retro (for comparison)
• Current goals/plans at that scale
• Relevant project documents

If inputs missing: Note gaps, proceed with available data.

Load Level Criteria from Plan

When a plan document exists for the period being reviewed:

1. Pull Level 0/1/2/3 criteria verbatim from the plan
2. Assess each criterion individually (✓/✗)
3. Roll up to overall level assessment
4. This is the primary success measure - Success Metrics table is secondary detail

3. Day-by-Day Review (Default for Weekly+)

When to use: Weekly or longer retrospectives with daily summaries available. This is the default approach for weekly retros - it's valuable enough to do every time.

Purpose: Before synthesizing patterns, walk through each day briefly. This surfaces details that might otherwise get lost and helps the user reconnect with the full week.

Process:

1. Present each day's summary briefly (2-3 key points per day)
2. Ask: "Anything to add or correct for [Day]?"
3. Let user react, add context, or say "looks right"
4. Move to next day
5. After walkthrough, create empty framework doc

Why this helps:

• Surfaces forgotten details ("Oh right, Tuesday was rough")
• Catches summary gaps or errors
• Warms up memory before synthesis
• Low effort (reactions, not generation)
• Produces condensed timeline for final doc

Keep it light: This is orientation, not analysis. Save synthesis for the main sections.

4. Show Empty Framework First

CRITICAL: Create structure-only artifact and explain it to user before filling anything.

Process:

1. Generate empty artifact with all section headers
2. Present to user: "Here's the structure we'll fill in together"
3. Briefly explain each section's purpose
4. Then proceed to fill ONE SECTION AT A TIME

Why this matters:

• User sees the whole picture before diving in
• Reduces cognitive load (knows what's coming)
• Enables reactions over generation

Filename template:

[Scale]-Retro-[Date-Range].md

Examples:

• Daily-Summary-2025-12-05.md
• Weekly-Retro-2025-12-01-to-07.md
• Monthly-Retro-2025-12.md
• Quarterly-Retro-2025-Q4.md
• Yearly-Retro-2025.md

5. Framework Structure

# [Scale] Retro: [Theme/Title]

**Period:** [Date range]
**Context:** [Brief context line]

---

## TL;DR - [Period] Summary

**Format: Bulleted list for easy scanning**
- Major pattern 1
- Major pattern 2
- Key discovery
- Primary challenge
- Overall trajectory

---

## Day-by-Day Timeline (Weekly+)

**Include for weekly or longer retros. Condensed reference from day-by-day review.**

| Day | Date | Context Tag | Key Events |
|-----|------|-------------|------------|
| Mon | [Date] | [tag] | [1-2 key events] |
| Tue | [Date] | [tag] | [1-2 key events] |
| ... | ... | ... | ... |

**Context Tag:** Optional column for domain-specific state tracking (defined in personal extension).

---

## Plan vs Actual (Weekly+ When Plan Exists)

**Include for weekly, monthly, quarterly, yearly retros when a plan document exists.**

### Theme Assessment
**Planned theme:** [From plan]
**Did it hold?** [Yes/Partially/No + evidence]

### Success Metrics

| Area | Target | Actual | Assessment |
|------|--------|--------|------------|
| [Priority 1] | [Goal] | [Result] | ✓ Met / ◐ Partial / ✗ Below |
| [Priority 2] | [Goal] | [Result] | ✓ Met / ◐ Partial / ✗ Below |

### Level Assessment (from [Period] Plan)

**Level 0 (Foundation):** [✓ Met / ◐ Partial / ✗ Not met]
- [Criterion 1 from plan] [✓/✗]
- [Criterion 2 from plan] [✓/✗]

**Level 1 (Base):** [✓ Met / ◐ Partial / ✗ Not met]
- [Criterion 1 from plan] [✓/✗]
- [Criterion 2 from plan] [✓/✗]

**Level 2 (Target):** [✓ Met / ◐ Partial / ✗ Not met]
- [Criterion 1 from plan] [✓/✗]

**Level 3 (Reach):** [✓ Met / ◐ Partial / ✗ Not met] (if applicable)
- [Criterion 1 from plan] [✓/✗]

### Venn Diagram

**Planned Only:**
- [Things planned but didn't happen]

**Both:**
- [Things that happened as planned]

**Actual Only:**
- [Things that happened but weren't in the plan]

---

## What Worked (Want More Of)

[Fill conversationally through observations → reactions]

---

## What Didn't Work (+ Experiments to Try)

**Format: Challenge → Proposed experiments**

### Challenge 1: [Issue]
**Why problematic:** [Impact]
**Experiments to try:**
- **Next [shorter period]:** [Immediate test]
- **Next [current period]:** [Medium-term experiment]
- **Longer timeframe:** [Deferred approach]

---

## Progress Tracking

**Compare against relevant intervals:**

### Last [Period]
**Previous:** [Summary]
**Current:** [Summary]
**Trajectory:** [Better/Stable/Declining + evidence]

### Longer Timeframe (if data available)
**Then:** [State]
**Now:** [State]
**Arc:** [What shifted]

---

## [Scale]-Retro (Improve This Process)

[Meta observations about the retrospective itself]
- What worked about this retro format?
- What was awkward or missing?
- Skill updates needed?

---

## Gratitude

[Positive closing anchor - peak-end rule]

What are you grateful for from this [period]?

6. Fill ONE QUESTION AT A TIME

⚠️ CRITICAL: Ask one question, wait for response, update artifact, then move to next.

Pattern per section:

1. Make observation from input data
2. Ask ONE focused question about that observation
3. Wait for user response
4. Update artifact in real-time
5. Confirm before moving to next section

Lead with observations, not open questions:

• ✅ "I noticed [pattern]. Want more of that?"
• ✅ "[Challenge] kept coming up. What experiment addresses it?"
• ❌ "What was most significant?" (requires generation from scratch)
• ❌ Asking multiple questions at once

Pacing by section:

• "What Worked" → flows fast (observation → agreement)
• "What Didn't Work" → needs depth (experiments develop interactively)
• "Retro-Retro" → one question about process
• "Gratitude" → save for last (positive anchor)

7. Save and Archive

Save to: /mnt/user-data/outputs/[filename]

Remind user: "Click 'add to project' to save permanently."

Archive previous level's inputs:

• After weekly retro → archive daily summaries
• After monthly retro → archive weekly retros
• Keeps context lean, preserves history locally

Core Principles

Same questions, any scale: The three questions work whether you're reviewing a day or a year.

Inputs compress to outputs: Each retro compresses its inputs into a summary that becomes input for the next level.

Observations → Reactions: Humans react better than they generate from scratch.

Experiments over judgments: "What didn't work + what to try" beats "what failed."

Peak-end rule: End with gratitude regardless of period difficulty.

Meta-improvement: The retro process itself should improve over time.

Edge Cases

First retro at a scale:

• Skip comparisons (no previous data)
• Focus on establishing baseline patterns

Missing inputs:

• Proceed with available data
• Note gaps for future improvement

Combined scales:

• Can do weekly + monthly in same session if context allows
• Natural flow: weekly insights → monthly synthesis

Flexibility

Structure is guide, not prescription:

• Skip sections if not relevant
• Add domain-specific sections
• Adapt length to complexity
• Focus on signal over noise