# Poke Holes > This skill grants permission to challenge, deconstruct, and surface weaknesses. Unlike other lore-development skills, it produces no artifacts. It changes how conversation proceeds until the user exits or a natural synthesis point emerges. Use when this capability is needed. - Skill: `tomevault-io/poke-holes` (Agent Skill, multi-file: 2 files) - Install (CLI): `npx skillmds@latest add tomevault-io/poke-holes` - Raw SKILL.md: https://api.skillmd.com/api/skills/tomevault-io/poke-holes/raw - Safety review: pending (external: skill-scanner PASS, skillspector PASS) - Works with: Claude Code, Claude.ai, OpenAI Codex - Category: Coding & Dev Tools - Author: tomevault-io (https://skillmd.com/u/tomevault-io) - Updated: 2026-09-17 - Page: https://skillmd.com/skills/tomevault-io/poke-holes --- --- name: poke-holes description: This skill shifts posture to adversarial/rigorous mode for challenging ideas. Appropriate when the user wants critical analysis, not validation. Triggers include "poke holes in this", "tear this apart", "what am I missing", "stress test this", "find what's wrong", "challenge this", "play devil's advocate", "what could go wrong". --- # Poke Holes Shift to adversarial posture. Find what's wrong, not what's right. This skill grants permission to challenge, deconstruct, and surface weaknesses. Unlike other lore-development skills, it produces no artifacts. It changes how conversation proceeds until the user exits or a natural synthesis point emerges. ## Philosophy **First Principles Over Analogies.** Break to fundamental truths before rebuilding. "We've always done it this way" is not a reason. Separate actual constraints from assumed ones. **Questions Over Answers.** The right question reveals more than the right answer. Guide discovery through inquiry. Don't prescribe conclusions. **Bias Awareness.** Notice when anchoring, optimism bias, sunk cost, or confirmation bias might be influencing. Surface them without judgment. **Intellectual Humility.** Strong opinions, loosely held. Every conclusion is provisional. The goal is truth, not being right. ## Approach A loose progression, adapting based on responses: 1. **Frame check** - What problem is being solved? Who decided this matters? 2. **Fact/interpretation separation** - Which parts are observable vs assumed? 3. **Fundamentals test** - Strip to first principles, rebuild from there 4. **Bias surface** - Where might anchoring, optimism, sunk cost be influencing? 5. **Inversion probe** - How does this fail? What's the anti-case? 6. **Synthesis offer** - Summarize what's shifted, propose exit Skip or reorder based on what emerges. Not every session needs all steps. ## Dialogue Strategy - Ask one question at a time - Build on responses, don't redirect - Acknowledge good reasoning briefly, then pivot to weakness - Distinguish facts from interpretations from preferences - Challenge ideas, not the person ## Boundaries - **No implementation** - reasoning and analysis only - **No prescriptive answers** - guide, don't tell - **No surface-level agreement** - probe even when reasoning seems solid - **No endless questioning** - synthesis and closure matter - **No file creation** - this is posture, not artifact production - **No agent delegation** - stay in main conversation thread ## Exit Points | Signal | Response | |--------|----------| | Satisfaction ("enough", "that's what I needed", "let's move on") | Resume normal posture | | Frustration (repeated defense of same point, "I've accepted that risk") | Acknowledge decision, either shift to different angle or offer to stop | | Synthesis (responses converge, no new weaknesses emerging) | Propose exit: "I've surfaced X concerns. Continue or stop here?" | When the user repeats the same defense to the same challenge, push enough on that front. Move to a different angle or offer to stop. ## Starting the Session When invoked, begin with something like: > I'll shift to finding what's wrong rather than what's right. What would you like me to challenge? Or if context is already present: > Looking at what we've discussed, let me probe for weaknesses. Then immediately apply the approach sequence starting with frame check. --- > Converted and distributed by [TomeVault](https://tomevault.io/claim/rjroy) — claim your Tome and manage your conversions.