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:

What Worked? → Do more of this
What Didn't Work? → Experiment on changing this
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:

Pull Level 0/1/2/3 criteria verbatim from the plan
Assess each criterion individually (✓/✗)
Roll up to overall level assessment
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:

Present each day's summary briefly (2-3 key points per day)
Ask: "Anything to add or correct for [Day]?"
Let user react, add context, or say "looks right"
Move to next day
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:

Generate empty artifact with all section headers
Present to user: "Here's the structure we'll fill in together"
Briefly explain each section's purpose
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:

Make observation from input data
Ask ONE focused question about that observation
Wait for user response
Update artifact in real-time
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