Prompts / Management & Leadership

CEO decision making ChatGPT prompts

This prompt creates a decision brief for a CEO-level choice, including options, trade-offs, risks, and a communication plan. Use it when the decision affects priorities, people, capital, or the company’s direction.

PromptOpen ChatGPTOpen Claude
Help me prepare a CEO decision brief for [DECISION]. The company context is [COMPANY CONTEXT]. The desired outcome and decision horizon are [OUTCOME AND TIMING]. The viable options are [OPTIONS], and the non-negotiable constraints are [CONSTRAINTS]. Relevant evidence, stakeholder views, and unknowns are [EVIDENCE AND VIEWS].

Treat this as a decision-support exercise, not an attempt to validate my preferred option. Produce a concise brief with these sections:
1. Decision statement: what is being decided now, what is explicitly out of scope, and the cost of delay.
2. Options table: include status quo plus each viable option. Compare strategic fit, customer impact, financial exposure, reversibility, execution capacity, second-order effects, and key dependencies.
3. Assumption register: label each critical premise as supported, uncertain, or speculative; identify what evidence would change the decision.
4. Risk and mitigation plan: distinguish reversible risks from irreversible ones and name leading indicators.
5. Recommendation: choose a path only if the evidence supports it; otherwise recommend the smallest decision or experiment that reduces uncertainty.
6. Team communication: draft a 150-word internal message explaining the decision, rationale, trade-offs, owner roles, and the next review point.

Do not invent revenue figures, employee sentiment, customer demand, legal conclusions, or competitor information. Do not disguise a people decision as an efficiency exercise; state affected roles, decision rights, and transition needs where relevant. For legal, employment, tax, or fiduciary matters, identify questions for qualified counsel or advisors.

Before answering, check that each option is evaluated with the same criteria and that the recommendation does not rest on an unmarked assumption. Ask up to 3 clarifying questions only if a required input is missing.

Fill in

PlaceholderWhat to enterExample
[DECISION]Enter the specific decision that needs to be made now.whether to pause new enterprise sales for one quarter to rebuild onboarding
[COMPANY CONTEXT]Enter the company stage, business model, team size, and relevant operating conditions.a 34-person B2B SaaS company selling workflow software to mid-market operations teams
[OUTCOME AND TIMING]Enter the intended result and the deadline or time horizon for the decision.reduce 90-day churn before the January renewal cycle; decide by October 15
[OPTIONS]Enter the realistic alternatives, including the option to do nothing if it is viable.continue sales and make minor onboarding fixes; pause enterprise sales and rebuild onboarding; limit sales to existing pipeline while rebuilding
[CONSTRAINTS]Enter the budget, capacity, contractual, strategic, or timing limits that cannot be ignored.four product engineers, 14 months of runway, and signed enterprise commitments must be honored
[EVIDENCE AND VIEWS]Enter known facts, metrics, stakeholder perspectives, and material unknowns.90-day churn is 18%; support tickets cluster around setup; sales sees strong demand; product estimates a six-week rebuild

How to use

  1. State the decision narrowly enough that the model can identify what is in and out of scope.
  2. Include the status quo among the options and enter evidence that contradicts your current view as well as evidence that supports it.
  3. Use the assumption register in the leadership discussion before treating the recommendation as a decision.
  4. Follow up with: “Draft the one-page board update for the selected option, marking every forecast as an assumption.”

Variations

Board memo

Use this when directors need a decision-ready view before a meeting.

Variation
Draft a board memo on [DECISION] for [COMPANY CONTEXT]. The options are [OPTIONS], the relevant metrics and evidence are [EVIDENCE], and the requested board action is [REQUEST]. Keep it to 500–700 words with a recommendation, alternatives considered, financial or operational exposure, decision deadline, and specific questions for directors. Separate reported facts from forecasts and assumptions. Do not invent metrics, market comparisons, or legal advice. Flag information that counsel, finance, or management must verify. Ask up to 3 questions only if a required input is missing.

Decision meeting

Use this when the leadership team needs a focused meeting rather than another open-ended discussion.

Variation
Design a 45-minute leadership decision meeting for [DECISION]. Attendees and their roles are [ATTENDEES]; options are [OPTIONS]; pre-read evidence is [EVIDENCE]. Provide a timed agenda, the decision rule, questions that surface dissent, a method to record assumptions, and a close that assigns owners and dates. Prevent the meeting from reopening settled scope or turning into status updates. Do not assign authority that I have not specified. Check that the agenda leaves time to decide, not just discuss. Ask up to 3 questions only if needed.

Post-decision review

Use this after implementation to learn without blaming individuals.

Variation
Create a post-decision review for [DECISION] made on [DATE]. The expected outcome was [EXPECTED OUTCOME], the observed results are [RESULTS], and relevant events are [TIMELINE]. Produce a blameless review separating decision quality, execution quality, and outcomes influenced by uncertainty. Identify what was known then, what was assumed, which signals were missed, and three process changes for future decisions. Do not use hindsight to claim the result was obvious or invent causal explanations. Ask up to 3 questions only if inputs are missing.

Tips

  • Write the actual decision as a verb and object, such as “limit new sales to existing pipeline,” rather than “improve onboarding.”
  • Compare status quo using the same criteria as change options; otherwise its risks disappear from the discussion.
  • Make reversibility explicit because a reversible pilot needs a different evidence threshold from an irreversible commitment.
  • For decisions affecting roles or compensation, involve employment counsel and the appropriate leaders before communicating conclusions.

FAQ

Should the CEO ask AI to make the decision?

No. AI can organize evidence, expose assumptions, and draft materials, but accountable leaders must make the decision and validate the inputs.

How many options should be included?

Three to five viable options usually allow comparison without creating false choice. Include status quo when it is truly available.

Can this help with layoffs or compensation changes?

It can structure questions and communication drafts, but employment, legal, and human consequences require qualified counsel and direct leadership judgment.

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