The Disagreeing Advisor

Strategic Decisions

For: CEOs and executives about to commit real money or direction

Decision stress-test: pre-mortem, base rates, and pre-committed tripwires

A big call is hardening into consensus. Stress-test it with the advisor who is paid to disagree — before the money moves.

Copy & paste into your own LLM

You are a skeptical board advisor whose job is to disagree with me productively. I will describe a strategic decision, my rationale, and my data. Produce: A) STEEL-MAN TABLE — my 3 strongest stated reasons, each with the strongest honest counter-argument and the evidence that would settle the disagreement. B) PRE-MORTEM — it is 18 months later and this decision failed: the top 5 causes ranked by likelihood times damage, each with its earliest observable warning indicator. C) BASE RATES — the reference class this decision belongs to and what typically happens in it, explicitly labeled "from general knowledge — verify current figures before relying on this". D) VERDICT — proceed / proceed-with-tripwires / pause, with 3 tripwires (metric + threshold + the pre-committed action when hit). Inputs: [THE DECISION + DEADLINE] · [MY RATIONALE + KEY DATA] · [ALTERNATIVES I CONSIDERED] · [WHAT WOULD MAKE ME WRONG] Rules: Do not invent market data or figures — keep my facts separate from your general knowledge and flag every external claim for verification against current sources. Do not soften the counter-arguments to be agreeable. I will not paste material non-public information or personnel records, and you must not ask for them.

Why it works: Consensus is where companies lose money — human advisors are too polite, too invested, or too far away to object. Pre-committed tripwires convert a bet into a managed position, and the label-your-training-data rule stops the model's stale base rates from masquerading as current market fact.

Useful? 👍 Yes👎 No

Own the Narrative

Board & Investor Comms

For: CEOs, CFOs, and chiefs of staff preparing board materials

Board memo: the pre-read that kills surprises

Board meeting in two weeks. Draft the pre-read that surfaces the hard topic on your terms — before a director does it on theirs.

Useful? 👍 Yes👎 No

The Team Is the Strategy

Org & Talent

For: Executives reviewing structure, roles, and succession

Org design review: structure follows strategy, with a migration plan

The org chart grew by accretion and the strategy changed. Review structure against strategy before the next planning cycle locks it in.

Useful? 👍 Yes👎 No

Run the Machine

Operating Cadence

For: CEOs and COOs redesigning the meeting and metric rhythm

Operating cadence audit: fewer meetings, real decision velocity

The calendar is full and decisions still take three weeks. Audit the operating rhythm — meetings, metrics, decision rights — end to end.

Useful? 👍 Yes👎 No

See Around Corners

Market Intelligence

For: Executives turning competitor noise into a quarterly read

Competitive scan brief: signal-ranked moves and the response option set

Quarterly strategy review. Turn scattered competitor news into a ranked read on what actually threatens you — with response options costed.

Useful? 👍 Yes👎 No

What you did NOT get today (Pro)

Prompt of the Week (Pro)

This week's bonus: a negotiation-prep brief that maps the other side's constraints, your BATNA, and the concession ladder for a major partnership or vendor deal — with every assumption about the counterparty labeled as an assumption.

Which section is most useful to you this week?

One tap — it shapes which prompt leads next week.

What would you like to see more of?