| name | retrospective-base |
| description | Framework for retrospectives at any time scale (daily, weekly, monthly, quarterly, yearly). Trigger with "daily retro", "weekly retro", "monthly retro", etc. Answers three questions - what worked, what didn't, how to improve. Inputs vary by scale - daily uses raw logs, weekly uses daily summaries, monthly uses weekly retros, etc. Fractal compression pattern. |
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
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.
3. 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.mdWeekly-Retro-2025-12-01-to-07.mdMonthly-Retro-2025-12.mdQuarterly-Retro-2025-Q4.mdYearly-Retro-2025.md
4. 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
---
## 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]?
5. 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)
6. 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
