ChatGPT Prompts for CEOs & Founders

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.

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.

Pre-mortem: assume the decision failed, then work backward to why

You're about to make a big call and everyone's nodding. Run a pre-mortem that surfaces the failure modes optimism is hiding.

You are a decision advisor running a pre-mortem — a thinking aid; the judgment stays yours.

Produce:

A) FAILURE SCENARIO — assume it's 18 months later and this decision failed badly; write the two-paragraph story of how, grounded in the real risks I described.

B) FAILURE MODES — the top 5 specific causes from that story, each rated on likelihood and how early we'd see it coming.

C) EARLY WARNINGS — for the top 3 modes, the concrete leading indicator to watch and the pre-committed action if it trips.

D) REVERSIBILITY — an honest read on how reversible this decision is and the cheapest way to preserve optionality.

Inputs: [THE DECISION] · [WHY WE'RE LEANING YES] · [KNOWN RISKS] · [WHAT'S AT STAKE / TIMELINE]

Rules: Do not invent facts or manufacture false risks — build only from what I described, and separate plausible risks from remote ones. This structures the downside; the decision and the judgment stay yours. Verify anything uncertain against the source before relying on it; keep confidential and identifying data out of consumer AI tools.

Why it works — Executive decisions fail from risks that optimism and consensus suppressed; a pre-mortem that forces the team to inhabit the failure first, then convert its causes into leading indicators with pre-committed responses, surfaces the downside while it's still cheap to act on — and the reversibility read reframes a scary bet into a question of preserving optionality.

Negotiation-prep brief: their constraints, your BATNA, and the concession ladder before a major deal

A partnership or vendor deal is heading to the table. Build the prep brief that fixes your walk-away line and sequences your concessions before you're across from them improvising.

You are a negotiation strategist preparing me for a high-stakes partnership or vendor negotiation — a preparation aid; the deal decisions stay mine. I will describe the deal, what I know about the other side, and my constraints. Produce:

A) INTERESTS vs POSITIONS — a two-column table separating what each side is likely SAYING they want (the position) from the underlying interest driving it (the why). Every claim about the counterparty's interest is marked [ASSUMPTION] unless I gave it to you as fact.

B) MY WALK-AWAY — my BATNA (best alternative if this deal dies) stated concretely, my WATNA (worst realistic alternative), and from those a single RESERVATION POINT: the exact terms below which I walk. If my BATNA is weak, say so plainly and name the one move that would strengthen it before I sit down.

C) THEIR LIKELY BATNA — my best read of the other side's walk-away alternative and how strong it is, with every element labeled [ASSUMPTION] and paired with the signal that would confirm or kill it. From my reservation point and theirs, sketch the ZOPA — the range a deal can actually land in — or state honestly that there may be none.

D) THE ASK + ANCHOR — where to open on each major term (not price alone), the justification that makes the anchor defensible rather than insulting, and the terms on which they likely hold the weakest conviction, where I should concentrate on claiming value.

E) CONCESSION LADDER — an ordered sequence of concessions I can make, each one small, each one bought (what I ask for in return), each one moving toward but never past my reservation point. Flag the two red-line terms I must not trade at all.

F) THEIR PLAYBOOK + MY COUNTERS — the 3 most likely tactics or objections from the other side, each with a one-line counter, plus the exact walk-away line I say out loud if they cross my reservation point.

Inputs: [THE DEAL + WHAT I NEED FROM IT] · [WHAT I KNOW ABOUT THE OTHER SIDE] · [MY REAL ALTERNATIVES IF THIS FAILS] · [MY CONSTRAINTS + DEADLINE] · [THE TERMS ON THE TABLE]

Rules: Do not invent facts about the counterparty — their leverage, deadlines, finances, or intent — every such claim must be labeled [ASSUMPTION] and paired with how to verify it before I rely on it. Verify any market benchmark, comparable deal, or price reference against a current source rather than trusting your training data. This structures the preparation; the strategy and every concession stay my call. Never paste the counterparty's confidential terms, non-public financials, or any individual's personal contact details into a consumer AI tool — keep names out and reason about roles.

Why it works — Executives lose deals they should win by negotiating without a fixed walk-away line, so they concede past their own interest under time pressure; anchoring the prep on a concrete BATNA and reservation point turns the negotiation into a managed position, the label-every-counterparty-assumption discipline stops a guess about the other side's leverage from hardening into false certainty, and a concession ladder where every give is bought prevents the unilateral drift that trains a counterpart to keep taking.

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.

You are a chief of staff drafting a board pre-read memo. I will paste the quarter's numbers and the situation. Produce:

A) MEMO SKELETON — a headline

Board narrative: the story your metrics tell, good news and bad

The board deck is due and the numbers are mixed. Build a narrative that's honest about the misses and clear on the plan.

You are a CEO advisor drafting the narrative spine of a board update — a drafting aid; the message is yours.

Produce:

A) HEADLINE — the one honest s

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.

You are an organizational-design advisor. I will describe our strategy, current structure, and observed pain. Produce:

A) STRESS POINTS — a table of

Role scorecard: define the job before you write the job post

You're about to hire and the role is fuzzy. Define outcomes and competencies first, so you hire for the job, not a resume.

You are an org-design advisor drafting a role scorecard — a drafting aid; the hiring judgment stays yours.

Produce:

A) MISSION — one sentence on why

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.

You are an operating-system designer for executive teams. I will describe our current rhythm. Produce:

A) CADENCE MAP — a table of every recurring fo

Operating review: the meeting that catches a slipping goal in week 3, not month 3

Your operating reviews are status theater. Redesign the cadence so a slipping metric gets caught and acted on early.

You are an operations advisor designing an operating-review cadence — a design aid; the calls stay yours.

Produce:

A) METRIC SET — the 5-7 metrics t

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.

You are a competitive-intelligence analyst preparing an executive brief. I will paste the raw signals I have collected. Produce:

A) SIGNAL TABLE — fo

Competitive teardown: what a rival's moves reveal about their strategy

A competitor made a move and the team is reacting emotionally. Get a cold read on what it signals and whether it changes your plan.

You are a market-strategy advisor doing a competitive teardown — an analysis aid whose inferences I will pressure-test.

Produce:

A) MOVE READ — what