design-retrospective

Design Retrospective

A retrospective is not a post-mortem. Post-mortems examine failures. Retrospectives examine the whole process — wins, misses, surprises, and taste evolution. This skill runs after a project ships and turns hindsight into foresight for the next one.

When to Use

• After verification-before-shipping passes and the project is declared complete
• When the user says "let's reflect" or "what did we learn?"
• At natural project milestones (end of a major phase, end of a sprint)
• When restarting work on a project after a break — retrospect on what came before

Process

Step 1: Gather Evidence

Before reflecting, assemble the full record:

1. Read design-state.md — the decisions log, handoff chain, and open questions
2. Read the taste profile — what was known at the start vs now
3. Review user overrides — every correction, redirect, and override from the handoff chain
4. Review critique findings — what the design-critic and accessibility-reviewer flagged
5. Review fix rounds — how many, what was fixed, what kept coming back
6. Check the original brief — compare what was asked for vs what was delivered

Step 2: Evaluate What Worked

For each major design decision that survived to shipping:

### What Worked

| Decision | Why It Worked | Evidence |
|----------|--------------|----------|
| [Decision from state log] | [Why this was the right call] | [User approved, critic passed, no fix rounds needed] |
| ... | ... | ... |

Look for:

• Decisions that sailed through critique without issues
• Choices the user explicitly praised
• Patterns that emerged naturally and felt right
• Accessibility approaches that enhanced rather than constrained the design
• Moments that revealed something characteristic about how the user designs (to note in the record — not to apply later)

Step 3: Evaluate What Didn't Work

For decisions that required rework, debate, or user correction:

### What Didn't Work

| Decision | What Went Wrong | Root Cause | Fix Rounds |
|----------|----------------|------------|------------|
| [Original decision] | [What happened] | [Why it happened — misread brief? ignored taste? wrong assumption?] | [How many iterations to fix] |
| ... | ... | ... | ... |

Look for:

• Decisions the user overrode — what signal did we miss?
• Findings that came back in multiple fix rounds — why wasn't it caught earlier?
• Accessibility issues that should have been caught in design, not review
• Moments where agents converged on a direction too quickly (a debate might have helped)
• Taste profile mismatches — did we apply an old preference to a new context?

Step 4: Process Evaluation

Evaluate the workflow itself, not just the output:

### Process Assessment

**Pipeline efficiency:**
- Agents dispatched: [X of 10]
- Agents skipped: [list and why]
- Fix rounds: [count] — [were they necessary or preventable?]
- Mode used: [direct/auto/mixed] — [did the mode serve the project?]

**Handoff quality:**
- Were handoff messages specific enough?
- Did any agent miss context from the previous agent?
- Were there gaps where information was lost between agents?

**Debate moments:**
- Were there decisions that should have been debated but weren't?
- Were debates held that didn't need to be?
- Did debate outcomes hold, or were they revisited?

**User engagement:**
- How often did the user override or redirect?
- Were overrides concentrated in one area? (signals a systematic gap)
- Did the user switch from auto to direct? (signals the system missed something)

Step 5: Design Debt Review

Review the Design Debt Register from design-state.md:

### Design Debt

**Register status:**
- Total items created: [count]
- Resolved: [count] ([percentage])
- Accepted: [count] — [were these the right trade-offs?]
- Still Open: [count] — [should any escalate?]
- Escalated during project: [count]

**Debt patterns:**
- Most affected persona: [name] — [X items affect them]
- Most common source: [design-critic/accessibility-reviewer]
- Average age of open items: [duration]

**Debt health:**
- [ ] Are we resolving debt faster than we create it?
- [ ] Are the same types of issues recurring? (signals a systemic problem)
- [ ] Did any accepted debt turn out to matter more than expected?

Step 6: Taste Evolution

Note what this project revealed about how the user designs, to add to the observational record. This is describing the user's habits, not setting rules for future work:

### What this project revealed (observations for the record)

**Recurring decisions reinforced:**
- [Observation] — now seen in [N] projects, per [evidence]

**New habits or inclinations noticed:**
- [Observation] — first seen here, per [evidence]

**Things the user moved away from:**
- [Observation] — corrected/reversed because [reason]

**Surprises:**
- [What was characteristic or unexpected about how they decided] — e.g. chose [X] over [Y]

_(All recorded as descriptions of how the user designs — never as preferences to apply to future work.)_

Step 7: Carry-Forward Items

What should the next project know?

### Carry Forward

**For the next project:**
- [Lesson learned that applies broadly]
- [Process improvement to try]
- [Taste insight to remember]

**For specific agents:**
| Agent | Lesson |
|-------|--------|
| **design-lead** | [e.g., "User prefers to see colour options before committing — show swatches, not descriptions"] |
| **design-strategist** | [e.g., "Spend more time on the navigation model early — it affected everything downstream"] |
| **content-writer** | [e.g., "User reads everything — content quality matters more than expected"] |
| ... | ... |

**Open questions for next time:**
- [Unresolved question that might be relevant in future projects]

Step 8: Write the Retrospective

Compile everything into a single document:

# Design Retrospective: [Project Name]

**Date:** [YYYY-MM-DD]
**Duration:** [How long the project ran]
**Mode:** [direct/auto/mixed]
**Agents used:** [X of 10]

## Summary
[3-5 sentences: what was built, what worked, what was hard, what we learned]

## What Worked
[From Step 2]

## What Didn't Work
[From Step 3]

## Process Assessment
[From Step 4]

## Design Debt
[From Step 5]

## Taste Evolution
[From Step 6]

## Carry Forward
[From Step 7]

Save to: [project-root]/design-retrospective.md

Step 9: Add to the Design Record

After the retrospective is written:

1. Invoke design-memory to add this project's observations to the record
2. Record them as descriptions of how the user designs (habits, inclinations), with evidence — never as preferences to apply to future work
3. Update the project history in the record

Step 10: Present to User

Show the retrospective to the user as a summary:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
  DESIGN RETROSPECTIVE: [Project Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

  WINS:
  • [Top 2-3 things that worked well]

  MISSES:
  • [Top 2-3 things that needed rework]

  TASTE LEARNED:
  • [Key taste insights from this project]

  DESIGN DEBT:
  • Open: [count] | Resolved: [count] | Accepted: [count]
  • Most affected: [persona]

  CARRY FORWARD:
  • [Top 2-3 lessons for next time]

  EFFICIENCY:
  • Fix rounds: [count]
  • User overrides: [count]
  • Agents used: [X of 10]

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
  Your taste profile has been updated.
  Next project starts smarter.
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Integration

• Called by: using-designpowers (after project completion or on user request)
• Reads from: design-state.md (including Design Debt Register), taste profile, critique documents, verification results
• Writes to: [project-root]/design-retrospective.md
• Calls: design-memory (to update taste profile with learnings)
• Pairs with: design-memory, verification-before-shipping, designpowers-critique

Anti-Patterns

Pattern	Why It Fails
Skipping retrospective because the project "went fine"	Even smooth projects teach you something. "Why did this go well?" is as valuable as "why did this go wrong?"
Blaming agents for wrong decisions	Agents are tools. If the output was wrong, the question is what context they were missing, not what they did wrong
Only looking at what failed	Wins are data too. Understanding what worked is how you replicate it
Not adding observations to the design record	Each project should leave the user a richer mirror of how they design. The record isn't applied to future work, but it's only honest if it's kept current
Running retrospective in auto mode	Retrospectives need user reflection. Always run in direct mode with pauses for user input