Adversarial Board

Adversarial Board

Description

Simulate a 5-person board of advisors who stress-test ideas from different angles before you commit.

Trigger

"Debate this", "what am I missing", "challenge this", "poke holes in", any major decision (hiring, pricing, launches, pivots), or when the user sounds too certain too fast.

Process

1. Understand the proposal — Restate the user's idea in one sentence to confirm alignment.
2. Run 5 personas sequentially:
   • The Skeptic — What evidence is missing? What's the base rate of this working? Where's the survivorship bias?
   • The Optimist — What's the best-case scenario? What tailwinds exist that the user isn't leveraging?
   • The Operator — Can this actually be executed? What breaks at scale? What's the hidden operational cost?
   • The Customer — Would anyone pay for this? What does the user's actual audience want vs. what's being built?
   • The Competitor — If a rival saw this plan, what would they do? What's the moat? How fast can this be copied?
3. Check context:
   • secondBrain.search for related past decisions or market data
   • web_search if the topic needs current market context
4. Synthesize — Identify the 2-3 critiques that actually change the calculus (ignore noise).
5. Recommend — Proceed / modify / kill, with the specific modifications if applicable.

Output

• Proposal restated (1 line)
• 5 persona critiques (2-3 sentences each, labeled)
• Synthesis: "The real risks are..." (2-3 bullets)
• Verdict: proceed / modify / kill
• If modify: specific changes recommended

Examples

1. "I want to launch a $297/mo SaaS next month" — Skeptic questions market validation, Optimist notes the pricing confidence, Operator flags support load, Customer asks about willingness-to-pay research, Competitor identifies 3 alternatives. Verdict: modify — run 10 customer interviews first.
2. "Should I quit my job to go full-time on this?" — Each persona weighs in on runway, traction, opportunity cost, market timing, competitive landscape. Verdict: modify — get to $5k MRR first.

Failure Modes

• Personas agree too much — If all 5 say the same thing, the idea is either obviously good or the framing is too narrow. Push the Skeptic harder.
• User gets defensive — This skill is adversarial by design. Remind: "This is stress-testing, not criticism."
• Low-stakes decisions — Don't run a 5-persona board for "should I use Tailwind or vanilla CSS." Reserve for decisions with real consequences.
• Missing market data — If the Competitor persona can't find real alternatives via web_search, flag that the market may not exist yet (which is itself a risk).