The Advisory Board
Convene a multi-perspective AI advisory board — not generic “expert personas” but a structured hierarchy of advisors with different levels of authority, different domains, and genuine disagreement built in — to evaluate any decision, strategy, or challenge from angles your default thinking can’t reach. From Kasimir’s 5-level advisory board architecture discussed in the Oct 30, 2025 AIMM session.
You will simulate a structured advisory board for a specific decision, challenge, or strategy. This is NOT “pretend to be five experts.” It’s an architecture with real hierarchy: advisors at different levels have different types of authority, different information access, and different incentives — and the disagreements between levels are often more valuable than any single advisor’s opinion.
The mechanism: most “multiple persona” prompts fail because the personas agree too easily or disagree superficially. Real advisory boards have structural tensions — the domain expert conflicts with the financial advisor, the strategist conflicts with the operator, the contrarian conflicts with everyone. This architecture preserves those tensions by assigning each advisor a specific role, a specific decision weight, and a specific type of blindness.
THE DECISION/CHALLENGE: $ARGUMENTS
If no decision was provided above, ask me what I need advisory input on.
BOARD COMPOSITION: [WHICH DOMAINS MATTER MOST — e.g., strategy, finance, operations, marketing, technology, industry-specific. Say “you decide” to have me compose the optimal board for this decision] DECISION STAKES: [LOW for tactical decisions, MEDIUM for significant business moves, HIGH for bet-the-company or career-defining decisions. Say “you decide” to have me assess from context]
If “you decide,” assess and compose the board accordingly.
STEP 1 — BOARD COMPOSITION: Assemble 5 advisors across 3 levels:
Level 1 — The Chair (1 advisor):
- The meta-perspective. Doesn’t advocate for a specific answer — manages the process.
- Role: synthesize conflicting advice, identify what the other advisors can’t see because they’re inside their own frames, and make the final recommendation.
- Specific expertise: should match the highest-level challenge (strategic, existential, architectural).
Level 2 — Domain Leads (2 advisors):
- Deep expertise in the two most relevant domains for this decision.
- Role: provide authoritative analysis from their domain. They have strong opinions and they should state them directly.
- Built-in tension: the two Level 2 advisors should naturally disagree on at least one major aspect. If they don’t, one of the domains is wrong for this board.
Level 3 — Specialists (2 advisors):
- One is a tactical operator — focused on execution, feasibility, and “how this actually works in practice.”
- One is a designated contrarian — their job is to find the strongest case AGAINST the emerging consensus. Not devil’s advocacy as performance, but genuine effort to break the argument.
For each advisor, state:
- Their specific domain expertise and what makes them credible
- Their natural bias (every expert has one — naming it makes the advice more useful)
- The one thing they’ll see that no other board member will
- The one thing their perspective systematically misses
STEP 2 — INDIVIDUAL BRIEFINGS: Each advisor independently analyzes the decision. No collaboration yet — isolated analysis prevents groupthink. Each advisor delivers:
- Assessment (2-3 paragraphs): Their analysis from their specific lens
- Recommendation: What they’d advise, stated directly
- Confidence level: How certain they are, and what would change their mind
- Risk flag: The one thing about this decision that concerns them most
Advisors should genuinely disagree where their frameworks predict different outcomes. Forced consensus is a signal of bad board design.
STEP 3 — THE COLLISION: Now bring the advisors into conversation. Identify:
- Points of agreement: Where all advisors converge (these are likely true, but verify — groupthink at scale is still groupthink)
- Sharp disagreements: Where advisors reach opposite conclusions from the same evidence (these are the most valuable — the resolution reveals something none of them saw individually)
- Blind spots: What is NO advisor discussing? What falls between all their domains? (This is often the real risk)
For each sharp disagreement: trace the root cause. Is it different values, different time horizons, different risk tolerances, or different assumptions about the facts? Each root cause requires a different resolution approach.
STEP 4 — THE CHAIR’S SYNTHESIS: The Chair delivers the integrated recommendation:
- What does the weight of evidence suggest?
- Which advisor’s perspective should be weighted most heavily for THIS specific decision, and why?
- What’s the residual risk that no amount of analysis can resolve? (The irreducible uncertainty)
- What decision would they recommend, with what caveats?
The Chair should NOT split the difference. “Do a little of each” is usually the worst possible advice. The Chair picks a direction and explains what’s being traded off.
STEP 5 — DECISION BRIEF: Deliver a structured decision brief:
- Recommended action: One clear recommendation
- Key rationale: The 2-3 strongest reasons, traced to specific advisor analyses
- Primary risk: What could go wrong, and what’s the early warning signal
- Minority report: The strongest dissenting view and why it shouldn’t be dismissed
- Decision triggers: What new information would warrant revisiting this decision
- 90-day check: What should be true in 90 days if this was the right call
STEP 6 — VERIFICATION:
- Are the advisors genuinely different, or are they the same worldview wearing different hats? Test: if I removed the labels, could I tell which advisor said what? If not, the board isn’t diverse enough.
- Did the contrarian find a real weakness, or did they perform dissent without substance? A contrarian who can be easily dismissed isn’t doing their job.
- Does the Chair’s synthesis actually integrate the perspectives, or does it just summarize them? Integration means the recommendation couldn’t have been reached by any single advisor.
- Am I simulating a board, or am I simulating the appearance of one? Test: would a real board of this caliber produce a materially different recommendation? If I think they would, my simulation isn’t sophisticated enough.
Revise what doesn’t hold up.
Source
- 2025-10-30_Mastermind (Kasimir Hedstrom — 5-level advisory board architecture)