Design Thinking

Design Thinking Skill

A structured, iterative framework for human-centered problem solving. Use this to move from "what should we build?" to "here's why we're building this, for whom, and how we'll validate it" — before writing code.

Commands

Stage 1: Empathize

Goal: Understand the real humans who will use this thing.

Process

1. Identify the user(s). Ask:

   • Who are the primary users? (Be specific — "busy professionals learning Korean" not "users")
   • What's their context? (Device, time of day, emotional state, environment)
   • What are they trying to accomplish? (Job-to-be-done, not feature request)

2. Map pain points. For each user type, identify:

   • Current frustrations (what's broken or missing today?)
   • Workarounds they use (reveals unmet needs)
   • Emotional friction (confusion, anxiety, boredom, overwhelm)

3. Build an empathy map. Output as a structured artifact:

EMPATHY MAP: [User Type]
--------------------------
THINKS: What occupies their mind? What matters to them?
FEELS:  What emotions drive their behavior? What worries them?
SAYS:   What do they tell others about this problem?
DOES:   What actions do they take? What workarounds exist?
PAIN:   Frustrations, obstacles, risks they face
GAIN:   What would success look like for them?

4. Contextual factors. Consider:
   • Technical literacy level
   • Language/cultural context (critical for multilingual projects)
   • Accessibility needs
   • Frequency of use (daily vs. occasional)

Output

Deliver: 1-3 empathy maps + a pain point priority list ranked by severity and frequency.

Stage 2: Define

Goal: Turn empathy insights into a crisp, actionable problem statement.

Process

1. Synthesize insights from Stage 1 into themes. Group related pain points.

2. Write a "How Might We" (HMW) statement:

How might we [action/change]
for [specific user]
so that [desired outcome]
without [key constraint to respect]?

Good example:

How might we help busy professionals maintain daily Korean practice so that they build lasting habits without requiring more than 10 minutes per session?

Bad example:

How might we make the app better? (too vague)

3. Define success criteria. What does "solved" look like?

   • User behavior change (measurable)
   • Business metric impact
   • Emotional outcome ("feels confident" → measured via NPS/survey)

4. Scope check. Is this:

   • Too broad? → Split into sub-problems
   • Too narrow? → Zoom out to the real need
   • Already solved elsewhere? → Study existing solutions first

Output

Deliver: HMW statement + 3-5 measurable success criteria + scope assessment.

Stage 3: Ideate

Goal: Generate diverse solutions before converging on the best approach.

Process

1. Diverge first. Generate 8-12 ideas without judgment. Use these prompts:

   • "What if we had unlimited budget?"
   • "What if the user could only use this on mobile?"
   • "What would the competitor's version look like?"
   • "What's the simplest possible version?"
   • "What if we removed [core assumption]?"
   • "How would [analogous industry] solve this?"

2. Challenge assumptions. List 3-5 assumptions baked into the current thinking. For each, ask: "What if this isn't true?"

3. Prioritize using Impact/Effort matrix:

HIGH IMPACT
    |
    |  Quick Wins    |  Big Bets
    |  (DO FIRST)    |  (PLAN)
    |________________|________________
    |                |
    |  Fill-ins      |  Money Pits
    |  (MAYBE)       |  (AVOID)
    |
    LOW IMPACT -----------> HIGH EFFORT

4. Select 2-3 candidates to prototype. For each, note:
   • Why this idea (link back to HMW)
   • Key risk/assumption to validate
   • Minimum viable version

Output

Deliver: Idea list + assumption challenges + prioritization matrix + 2-3 selected candidates with rationale.

Stage 4: Prototype

Goal: Make ideas tangible enough to test, with minimum effort.

Process

1. Choose fidelity level based on what you're validating:

2. For UI/UX prototypes, describe:

   • Page/screen layout (what appears where)
   • User flow (step-by-step interaction sequence)
   • Key states (empty, loading, error, success, edge cases)
   • Content hierarchy (what's most important visually)

3. For system/architecture prototypes, describe:

   • Data flow diagram
   • API contract (endpoints, request/response shapes)
   • State management approach
   • Integration points with existing systems

4. For dashboard prototypes, describe:

   • What questions does this dashboard answer?
   • What are the 3-5 most important metrics? (link to user goals from Stage 1)
   • What actions can the user take from this view?
   • What's the information hierarchy? (glanceable summary → drill-down detail)

5. Build constraints into the prototype:

   • Must be testable in under 30 minutes
   • Must reveal whether the key assumption (from Stage 3) is valid
   • Must be throwaway — don't over-invest

Output

Deliver: Prototype artifact (spec, wireframe, code, or schema) + what assumption it tests + how to test it.

Stage 5: Test

Goal: Validate with real users (or realistic proxies) and decide next steps.

Process

1. Define the test. For each prototype:

TEST PLAN
---------
Hypothesis: [What we believe will happen]
Method:     [How we'll test — user session, A/B, analytics, survey]
Audience:   [Who we're testing with — be specific]
Duration:   [How long the test runs]
Success:    [Quantitative threshold — e.g., "70% complete the flow in < 2 min"]
Failure:    [What result means we pivot]

2. Identify what to observe:

   • Task completion (can they do it?)
   • Time on task (is it efficient?)
   • Error rate (where do they get stuck?)
   • Emotional response (do they feel confident/frustrated?)
   • Unprompted feedback (what do they say without being asked?)

3. Create feedback capture framework:

   • What worked? (Keep)
   • What was confusing? (Fix)
   • What was missing? (Add)
   • What was unnecessary? (Remove)

4. Decision framework after testing:

Output

Deliver: Test plan + observation checklist + decision framework + recommended next action.

Audit Mode (/dt audit)

Review an existing feature, page, or system against design thinking principles:

1. User alignment — Is it clear who this is for and what problem it solves?
2. Problem-solution fit — Does the solution actually address the stated problem?
3. Assumption exposure — What untested assumptions are baked in?
4. Feedback loops — Is there a way to know if it's working? (Analytics, user feedback)
5. Iteration history — Has this been tested and refined, or shipped once and forgotten?

Output a scorecard:

DT AUDIT: [Feature/Page Name]
==============================
User Clarity:        [1-5] — Do we know who this is for?
Problem Definition:  [1-5] — Is the problem clearly stated?
Solution Fit:        [1-5] — Does the solution match the problem?
Validation:          [1-5] — Has this been tested with users?
Iteration:           [1-5] — Has it been refined based on feedback?
-------------------------------
SCORE:               [X/25]
TOP RECOMMENDATION:  [One actionable next step]

Integration with Existing Workflow

• Before GSD phases: Run /dt define to sharpen the problem before creating a roadmap
• Before new features: Run /dt empathize + /dt define to validate you're solving the right problem
• Dashboard design: Run /dt empathize to surface what metrics users actually need
• Architecture decisions: Run /dt full to consider the human impact of technical choices
• Multilingual projects: Empathy maps should be created per-language audience (cultural context matters)
• Post-launch: Run /dt audit on shipped features to identify iteration opportunities

Principles

1. Users first, technology second. The question is never "what can we build?" — it's "what should we build?"
2. Diverge before converging. Generate many ideas before picking one. Premature convergence kills innovation.
3. Make it tangible. Abstract discussions waste time. Prototypes — even rough ones — accelerate decisions.
4. Test assumptions, not egos. The goal of testing is to learn, not to prove you were right.
5. Iterate, don't perfect. Ship, learn, improve. A shipped 80% solution teaches more than an unshipped 100% solution.