Brainstorming & Design

Structured methodology for transforming rough ideas into fully-formed designs through systematic questioning and iterative validation.

Brainstorming & Design

Structured methodology for transforming rough ideas into fully-formed, validated designs through six systematic phases of exploration, refinement, and documentation.

Perfect for developers and architects who need to explore design options methodically before committing to implementation.

Six-Phase Process

Phase Overview

  1. Understanding - Gather purpose, constraints, success criteria
  2. Exploration - Present 2-3 architectural approaches with trade-offs
  3. Design Presentation - Validate design incrementally in digestible sections
  4. Design Documentation - Write findings to docs/plans/YYYY-MM-DD-<topic>-design.md
  5. Worktree Setup - Establish isolated development workspace (optional)
  6. Planning Handoff - Create detailed implementation plan

Phase 1: Understanding

Goal: Gather complete context before proposing solutions

Systematic Questions:

  • What problem are we solving?
  • Who are the users/stakeholders?
  • What are the success criteria?
  • What constraints exist (time, budget, technical)?
  • What's already been tried?
  • What must we preserve?

Use AskUserQuestion Tool:

  • For decisions with 2-4 distinct options
  • When choices are mutually exclusive
  • To ensure explicit user selection

Use Open-Ended Questions:

  • For feedback and validation
  • When gathering context
  • For exploratory discussion

Phase 2: Exploration

Present 2-3 Architectural Approaches:

For Each Approach, Include:

Pros:

  • Key advantages
  • What it does well
  • Alignment with requirements

Cons:

  • Limitations and drawbacks
  • What it doesn't solve
  • Technical debt created

Trade-offs:

  • Performance vs. simplicity
  • Flexibility vs. maintainability
  • Speed-to-market vs. scalability

Example Structure:

MARKDOWN
### Approach A: Microservices Architecture

**Pros:**
- Independent scaling of components
- Technology flexibility per service
- Fault isolation

**Cons:**
- Operational complexity
- Network latency
- Distributed debugging challenges

**Trade-offs:**
- Complexity for scalability
- Dev velocity vs. long-term maintenance

Phase 3: Design Presentation

Incremental Validation:

Present in 200-300 Word Sections:

  • One concept per section
  • Wait for user feedback
  • Adjust based on input
  • Build consensus incrementally

Don't:

  • Dump entire design at once
  • Assume understanding
  • Skip validation points
  • Ignore feedback signals

Validation Checkpoints:

  • After high-level architecture
  • After each major component
  • After integration points
  • Before finalizing

Phase 4: Design Documentation

Create: docs/plans/YYYY-MM-DD-<topic>-design.md

Document Structure:

MARKDOWN
# [Feature/System Name] Design

## Problem Statement
[What we're solving and why]

## Success Criteria
[How we'll know it's working]

## Approach
[Chosen architecture and rationale]

## Components
[Key parts and their responsibilities]

## Trade-offs
[What we're accepting/rejecting and why]

## Implementation Plan
[High-level steps]

## Open Questions
[Unresolved issues to address]

Phase 5: Worktree Setup (Optional)

If Implementing:

Create isolated workspace:

BASH
git worktree add .worktrees/feature-name
cd .worktrees/feature-name

Benefits:

  • Keep main workspace clean
  • Parallel development
  • Easy abandonment if needed
  • Isolated testing

Phase 6: Planning Handoff

Create Implementation Plan:

Detailed Plan Includes:

Tasks Breakdown:

  • Ordered implementation steps
  • Dependencies between tasks
  • Estimated effort
  • Testing strategy

Success Metrics:

  • How to verify each step
  • Integration testing approach
  • Acceptance criteria

Risks:

  • Known challenges
  • Mitigation strategies
  • Fallback options

Decision Flowchart

When to Revisit Phases:

New constraint emerges? → Back to Understanding
Trade-off unacceptable? → Back to Exploration
Design not validating? → Back to Design Presentation
Implementation blocked? → Back to Planning

Iteration is Expected:

  • New information requires revisiting earlier phases
  • User feedback triggers design adjustments
  • Implementation reality tests assumptions

This is normal and healthy—embrace it.

Question Patterns

Understanding Phase

  • "What's the core problem we're solving?"
  • "Who will use this and how?"
  • "What are the non-negotiable requirements?"
  • "What constraints must we work within?"

Exploration Phase

  • "Which of these approaches fits your priorities?"
  • "What trade-offs are you willing to accept?"
  • "Do any of these miss critical requirements?"

Validation Phase

  • "Does this make sense so far?"
  • "Any concerns with this approach?"
  • "What am I missing?"

Common Pitfalls

Avoid:

  • Jumping to solutions before understanding
  • Analysis paralysis (3 options max)
  • Information dumping (validate incrementally)
  • Ignoring constraints (they're real)
  • Skipping documentation (future you needs it)

About This Skill

This skill was created by obra as part of the Superpowers Skills Collection.

Explore the collection for complementary skills on test-driven development, systematic debugging, and git workflows!


Structured methodology for transforming rough ideas into fully-formed designs through systematic questioning and iterative validation.