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