Deep Discovery

A self-dialogue framework. 100 sequential questions, each building on the last answer, that exhaustively explores a topic before any commitment. Output is a synthesis: top issues, top strengths, recommended changes, honest bottom line.

When to use

• Before committing to a design, architecture, plan, or migration.
• Before approving a non-trivial patch, branch, or pull request.
• Before publishing a product, business plan, go-to-market motion, or pricing model.
• Before deploying a trading strategy, financial system, or anything with money at risk.
• Before publishing a skill, plugin, MCP server, or agent integration.
• During debugging when you need to exhaustively explore root causes.
• Whenever the user asks to "poke holes", "stress test", "find weaknesses", or "vet" something.

Skip this skill for: trivial fixes, well-understood routine work, anything where the answer fits in one sentence.

Required structure

Every run produces a deliverable in this shape:

Topic: [what we're exploring]
Mode: [evaluation | exploration | comparison]
Domain pattern: [software architecture | code review | skill/plugin creation | business/product | trading/financial | general]
Questions asked: 100

Top 10 critical issues found
Top 10 strengths
Recommended changes (with rationale)
Revised proposal (if the original needs significant changes)
Honest bottom line: one paragraph, no sugar-coating

Workflow

1. Preflight. Identify topic, available context, focus, and starting point. If any are too ambiguous to run a useful interrogation, ask at most three clarifying questions before starting.

2. Pick the mode:

   • Evaluation — an existing design, architecture, strategy, or plan exists; interrogate that specific proposal.
   • Exploration — starting from scratch; the questions build toward a complete proposal.
   • Comparison — choosing between 2-3 options; run a full pass per option, then compare.

3. Pick the domain pattern. Open references/question-patterns.md (the index), then load only the closest matching pattern file:

   • Software architecture / system design → references/software-architecture.md
   • Patch / branch / pull request review → references/code-review.md
   • Agent skill / plugin / MCP server / integration → references/skill-and-plugin-creation.md
   • Business / product / go-to-market → references/business-product.md
   • Trading / financial / market strategy → references/trading-financial.md
   • Doesn't fit cleanly or spans multiple → references/general-pattern.md

4. Run the 100 questions. Q1 is always: "What is the goal, and how do we get there?" Each subsequent question MUST build on the previous answer. Progression:

   Phase	Questions	Focus
   Foundation	Q1-Q10	Goal, constraints, assumptions, what makes this unique
   Mechanics	Q11-Q30	How it works, components, data flow, dependencies
   Stress testing	Q31-Q50	Edge cases, failure modes, what breaks first
   Competitive / alternatives	Q51-Q65	What exists, what's different, what's the real edge
   Feasibility	Q66-Q80	Can this actually be built/done, what are the blockers
   Refinement	Q81-Q90	Improvements, optimizations, what was missed
   Synthesis	Q91-Q100	Final architecture, honest assessment, actionable output

5. Synthesize. The final 10 questions must produce the deliverable structure above. Do NOT dump the full 100 Q&A unless the user explicitly asks — summarize the insights.

6. Present the deliverable. Top issues, top strengths, recommended changes, revised proposal (if needed), honest bottom line.

See assets/examples/full-example.md for a complete worked run.

Available resources

• references/question-patterns.md — domain router; read first to choose the right pattern file.
• references/software-architecture.md — system / API / data / infra design.
• references/code-review.md — patch / branch / pull request review.
• references/skill-and-plugin-creation.md — agent skill / plugin / MCP server / integration audit.
• references/business-product.md — business strategy, product, go-to-market, pricing.
• references/trading-financial.md — trading systems, financial strategies, market edges.
• references/general-pattern.md — universal fallback when no domain pattern fits cleanly.
• assets/examples/full-example.md — full worked run on a sample proposal.

Top gotchas (always inline — do not skip)

• Do not skip questions to "save time". A 30-question pass is not a deep discovery — it's a regular review. The value comes from sustained pressure past Q50, where the obvious problems have been surfaced and you have to dig for the non-obvious ones. Run all 100.
• Each question must build on the previous answer. No random jumps. If Q23 reveals a critical flaw, Q24 should explore that flaw, not pivot to a different topic. Track the thread.
• Be brutally honest. Surface problems instead of hiding them. "This actually looks fine" at Q50 means you are not pushing hard enough. There is always something at Q50.
• Challenge assumptions explicitly. Around Q50, circle back to Q1-Q10 assumptions and ask "Is that actually true?" The early answers were guesses; the middle questions tested them; the late questions verify them.
• Go concrete, not abstract. "How does authentication work?" beats "What about security?" "How much latency under 100x load?" beats "Is latency a concern?" Vague questions get vague answers.
• Follow the pain. When an answer reveals a problem, spend 3-5 questions digging into it before moving on. The first crack in a design is usually the surface of a deeper issue.
• Do not dump the 100 Q&A in the final response. The user wants the synthesis. Keep the raw questions internal unless the user asks for them.
• Match the deliverable to the domain. A code-review run produces approve/request-changes verdicts with file references. A trading run produces P&L projections and risk assessment. A business run produces a revised go-to-market and existential risks. Don't deliver the wrong shape.
• Comparison mode runs a full 100-question pass per option. Not 50 each, not 33-each-and-shared. Each option deserves the full interrogation, then compare findings.
• Stop after Q100. The final 10 are synthesis, not "let's keep going". If the run wants to extend past 100, that means earlier questions were not focused enough — start a fresh discovery on the new sub-topic instead.
• Generic fallback is for genuine cross-domain cases. Do not default to general-pattern.md because you can't decide. Re-read the index in question-patterns.md and pick the closest deliverable shape.

What you DO

1. Read the user's topic carefully and ask at most 3 clarifying questions if needed.
2. Pick mode (evaluation / exploration / comparison) and the closest domain pattern.
3. Open references/question-patterns.md first to route, then load only the matching pattern file.
4. Start with Q1: "What is the goal, and how do we get there?"
5. Make each subsequent question build on the previous answer.
6. Spend 3-5 questions on every revealed problem before moving on.
7. Around Q50, circle back and re-test the Q1-Q10 assumptions.
8. Use concrete numbers, scenarios, and named components — not abstractions.
9. Run all 100 questions. No shortcuts.
10. Produce the deliverable in the required structure: top issues, top strengths, recommended changes, revised proposal (if needed), honest bottom line.
11. Keep the raw 100 Q&A internal; surface only the synthesis unless the user asks for the full transcript.

What you do NOT do

• Do not abbreviate the run below 100 questions unless the user explicitly asks for a shorter version.
• Do not jump randomly between topics. Each question builds on the last answer.
• Do not soften findings to be diplomatic. The value of this skill is brutal honesty.
• Do not dump the full 100 Q&A into the user's chat by default.
• Do not invent constraints or facts. If you don't know, ask in preflight or flag the gap in the synthesis.
• Do not skip the assumption-revisit pass around Q50. That is where most missed flaws hide.
• Do not preload all reference files. Pick the closest pattern via the router and load only that one.
• Do not deliver a generic shape. A code-review deliverable should look like a code review, a business-strategy deliverable should look like a business strategy.
• Do not extend past Q100 to keep the run going. If new sub-questions need exploring, propose a fresh discovery on that sub-topic.
• Do not run discovery on trivial tasks. Reserve it for pre-commitment, high-cost, or hard-to-reverse decisions.