Brainstorming

Brainstorming Ideas Into Plans

Purpose

Turn vague ideas into a validated plan or spec through natural, collaborative dialogue.

This is domain-generic: it can be used for product features, websites, backend systems, marketing campaigns, business ideas, content, workflows, or anything else.

Core rules:

• Classify first: ask what type of brainstorming this is (multiple choice).
• One question per message: keep cognitive load low.
• Discovery-first: do not draft solutions until intent and constraints are understood.
• Converge to a deliverable: end with a plan/spec that can be executed.

When to Use

• Any new idea that could branch into multiple directions
• Ambiguous requests (we should…, let’s build…, can we improve…?)
• Planning work that needs clarified goals, scope, trade-offs, and acceptance criteria

Avoid When

• The task is purely mechanical or trivial
• The user provides a complete spec and explicitly wants immediate execution

Inputs That Improve Quality (Optional)

• Constraints: budget, time, team size, deadline
• Existing materials: docs, links, codebase, screenshots, examples
• Success criteria: metrics, target outcomes, definition of done
• Non-goals: what to avoid or explicitly exclude

Step 0: Classification (Required)

Start every brainstorming session by asking a single multiple-choice question:

What are we brainstorming today?

• A) Product / feature (app, SaaS, tool)
• B) Website / UX / UI / design
• C) Engineering / architecture / systems (backend, infra, data)
• D) Bugfix / troubleshooting / quality improvements
• E) Content (blog, video, social, brand)
• F) Marketing / growth / distribution
• G) Business model / pricing / sales
• H) Process / operations / team workflow
• I) Something else (describe in one sentence)

Then ask one follow-up question that is specific to the chosen category.

Rule: until classification is answered, do not assume domain.

The Process

Phase 1: Discovery (One Question at a Time)

Ask one question per message. Prefer multiple choice when possible. Use this ladder in order; skip only if already answered.

1) The Why (Intent and Motivation)

• What problem are we solving, and why now?
• What happens if we do nothing?

2) The Who (Audience / User / Stakeholders)

• Who is this for?
• Who decides what good looks like?

3) The What (Scope)

• What must be true for this to be considered successful?
• What’s in-scope for MVP vs out-of-scope?

Use MoSCoW:

• Must / Should / Could / Won’t (for now)

4) Constraints (Hard Limits)

• Deadline, budget, team capacity
• Tools/stack constraints
• Compliance/legal/privacy constraints
• Brand/tone constraints (for content/marketing)

5) Inputs and Dependencies

• What do we need that we don’t control? (APIs, vendors, approvals, assets)
• What existing systems/content must be reused?

6) Risks and Unknowns

• What are the biggest uncertainties?
• What’s the cost of being wrong?

Unknowns Register rule:

• Any unknown becomes a discovery task with a timebox and decision point.

7) Definition of Done

• What specifically will be delivered?
• How will we validate it worked?

Phase 2: Synthesis (Reflect Back)

Summarize in 150–250 words:

• Problem, audience, MVP scope, constraints, success criteria, open questions Then ask:
• Is this accurate before I propose options?

Phase 3: Explore Approaches (2–3 Options)

Present 2–3 options with trade-offs and a recommendation:

• Option A (Recommended): why it best fits constraints
• Option B: simpler/faster alternative
• Option C: more ambitious/extensible alternative

Each option includes:

• Pros/cons
• Key risks
• Rough effort class (S/M/L) or time range if requested
• What to validate first

Then ask:

• Which option should we proceed with (A/B/C), or should I adjust?

Phase 4: Produce the Deliverable (Incremental Validation)

Once an option is chosen, produce the output in small sections (200–300 words) and ask after each:

• Does this look right so far?

Choose the output type based on the classification:

If A) Product / feature

• Goals and non-goals
• User stories and acceptance criteria
• UX flow (if relevant)
• Data/logic overview
• MVP vs V2
• Rollout and metrics

If B) Website / UX / UI

• Site goals and audience
• Sitemap / IA
• Page-level sections and messaging
• Visual direction and components
• SEO/accessibility basics
• Analytics/events

If C) Engineering / architecture / systems

• Requirements (functional and non-functional)
• Components/services and responsibilities
• Data flow and contracts
• Failure modes and retries
• Security and observability
• Testing and rollout plan

If D) Bugfix / troubleshooting

• Repro and root cause hypotheses
• Fastest validation steps
• Fix options and risk
• Test plan
• Rollback strategy

If E) Content

• Audience and promise
• Angle/hook options
• Outline/script structure
• Examples and CTAs
• Distribution plan

If F) Marketing / growth

• Target segment and channel assumptions
• Positioning and messaging
• Funnel (top to conversion)
• Experiments and metrics
• Timeline and budget assumptions

If G) Business model / pricing / sales

• ICP and value props
• Pricing hypotheses
• Packaging options
• Sales motion and objections
• Metrics and tests

If H) Process / operations / workflow

• Current state and pain points
• Desired outcomes
• Proposed process changes
• Tools and responsibilities
• Rollout and check-ins

If I) Something else

• Ask what output format they want (plan, spec, checklist, outline, roadmap)

Output Handling

Always ask whether the user wants the final deliverable saved to a file. If yes, write a Markdown file and confirm the filename. Default filename: brainstorming-plan.md

Category-Specific Starter Questions (Pick One)

Product / feature

• What user action should this enable that’s currently impossible or painful?

Website / UX / UI

• What is the single most important action you want visitors to take?

Engineering / systems

• What are the top 3 non-functional requirements: latency, cost, reliability, security, or something else?

Bugfix / troubleshooting

• Do we have consistent reproduction steps (Yes/No/Not sure)?

Content

• What platform is this for (YouTube, X, blog, email, TikTok, other)?

Marketing / growth

• Which channel are we prioritizing first (SEO, paid ads, social, partnerships, outbound, other)?

Business model / pricing

• Who is the buyer (end user, team lead, company)?

Process / workflow

• What’s the current workflow step that causes the most friction?

Key Principles

• Classify first (no domain assumptions)
• One question at a time (always)
• Multiple choice preferred (reduce friction)
• Start broad, then narrow
• Explore alternatives (2–3 options)
• YAGNI ruthlessly (MVP-first)
• Incremental validation (section-by-section)
• Make assumptions explicit (and confirm them)
• Stop and clarify whenever uncertainty appears