Multi Perspective Grilling

Multi-Perspective Grilling

You take a target (an idea, a plan, an active strategy, a draft) and run it through a rotating roster of skeptical perspectives. Each perspective has its own posture, set of questions, and failure modes it's looking for. The output is the union of every perspective's pushback, filtered by your judgment for which pushbacks are actually load-bearing.

This is not "give me three opinions". It's a structured grilling where each persona is sharp in a specific direction — the financial-analyst is looking for unit-economics fragility, the historian is looking for "this exact thing failed in 2014 because Y", the contrarian VC is looking for "why isn't a smarter team already doing this." Different personas catch different bugs.

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Inputs

• Target: path to the markdown file or a verbatim text block to grill
• Mode: one of single-pass (run all personas in one prompt, one synthesis), rotating (one persona per scheduled run, output appends), tournament (each persona runs independently, you summarize)
• Persona set: which personas to invoke — defaults to the canonical roster below; agent config can override or extend

Read your agent's config for:

• personas_default: [<list>] — which personas to use when the operator doesn't specify
• personas_<domain>: [<list>] — domain-specific persona overrides (e.g. for financial: [financial-analyst, market-historian, contrarian-vc, compliance-officer]; for perfumery: [perfumer-master, retail-buyer, regulatory-fda, niche-blogger])

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Canonical persona roster

The skill ships with these personas defined. Each is a posture + a set of pressure questions. Domain configs can swap in domain-specific replacements.

Financial Analyst

• Posture: trained to spot unit-economics fragility, hidden customer-acquisition costs, churn assumptions that don't survive contact with reality
• Pressure questions: "What's CAC over LTV at year 1 vs year 3?" "Where does the cost curve bend negative?" "What's the realistic churn at month 6?" "Show me the sensitivity to a 20% price drop."

Market Historian

• Posture: pattern-matches against past attempts in adjacent spaces; default skepticism around "this time it's different"
• Pressure questions: "Who tried this in 2015 / 2008 / 1999, and what killed them?" "What's the analogue from a different industry where the same dynamic played out?" "What did the survivors do that the failures didn't?"

Contrarian VC

• Posture: trained on "why isn't a smarter team already doing this"; looks for the trade you're making with second-order effects
• Pressure questions: "If this is so obvious, why isn't [established player] already shipping it?" "What does the smartest version of this look like, and how does ours compare?" "Where's the hidden trade — what are we giving up that we don't realize?"

Customer

• Posture: lives in the user's chair; asks the questions the user actually asks
• Pressure questions: "Why do I care?" "What did I have to do BEFORE this existed, and is the new thing actually less work?" "Why should I trust you (a 2-person op) over [incumbent]?" "How does this fail me on a Tuesday?"

Compliance/Regulator

• Posture: paid to find the regulatory gotcha; default to "if you have to ask whether this is legal, it isn't yet"
• Pressure questions: "What licenses does this require?" "What's the failure mode if a regulator audits in year 2?" "Where do you cross from editorial to advice to recommendation?" "What disclosures are missing?"

Pessimist Engineer

• Posture: spent 20 years debugging production at scale; assumes the happy path doesn't exist
• Pressure questions: "What breaks at 10x scale?" "What's the SLO and who's on call?" "What's the data-loss exposure?" "What dependencies have we just bet the company on?"

(Domain configs can add: perfumer-master, niche-blogger, regulatory-fda, accessibility-advocate, etc.)

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