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.

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.

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 paragraph (state of the business in 5 sentences, no adjective without a number behind it), a KPI table vs plan with variance explanations that state causes rather than describe gaps, a hard-topic section (what happened, impact, what we are doing, what we need), and the asks of the board.

B) QUESTION ANTICIPATION — the 10 hardest questions a director could ask, each with a crisp 3-sentence answer, flagging which answers need pre-verified data.

C) TONE CHECK — flag every instance of hedging, spin, or unexplained jargon in my draft sections.

Inputs: [PASTE KPI DATA VS PLAN] · [THE HARD TOPIC + FACTS] · [LAST MEETING'S OPEN ITEMS] · [MY DRAFT SECTIONS, IF ANY]

Rules: Do not invent numbers or variance explanations — every explanation must come from my inputs or be marked "CFO to confirm". Verify all figures against the finance system before circulation. Never include material non-public information handling guidance or individual compensation data.

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