7 ChatGPT Prompts to Make Decisions Like a CEO

I need to make an important decision about [describe your decision/problem briefly]. As an experienced CEO, help me analyze this through a comprehensive strategic framework. Please provide:

1. OBJECTIVES ANALYSIS: What are the core objectives I should prioritize in this decision? What does success look like in 1 year? In 5 years?

2. STAKEHOLDER IMPACT: Identify all key stakeholders affected by this decision and analyze how each might be impacted (positively and negatively).

3. OPTION EVALUATION: Present 3-4 distinct approaches to this decision, including maintaining the status quo. For each option, provide:
- Key advantages and potential upside
- Primary risks and potential downside
- Resource requirements (time, capital, personnel)
- Timeline considerations

4. DECISION CRITERIA: What specific metrics or criteria should I use to evaluate success?

5. RISK ASSESSMENT: What are the biggest risks with each option? How might they be mitigated? What contingency plans should be considered?

6. TIMING CONSIDERATIONS: Is this a reversible or irreversible decision? Is there value in delaying the decision? Is there a cost to waiting?

7. RECOMMENDATION: Based on the analysis, what approach would you recommend and why?

Please structure your response for clarity and focus on actionable insights rather than general advice.

I'm considering [describe the decision you're facing]. To ensure I'm seeing all perspectives before deciding, simulate a virtual executive board debate with 4 different experts who hold contrasting viewpoints on this matter.

Create the following personas, each with different expertise and perspective:

1. The Growth Advocate: Focuses on opportunities, expansion, and optimistic outcomes
2. The Risk Manager: Concentrates on identifying potential pitfalls and protecting downside
3. The Operational Expert: Considers practical implementation challenges and resource implications
4. The Strategic Visionary: Evaluates long-term alignment with broader goals and values

For each expert:
- Provide their name, brief background, and core perspective
- Present their main arguments for or against the decision (minimum 3 points per expert)
- Include what specific evidence or experience informs their view
- Note what they believe others are overlooking

After presenting all four perspectives, please:
1. Identify the key tensions and trade-offs between these viewpoints
2. Suggest 2-3 potential compromise positions that address multiple concerns
3. Provide a balanced final recommendation that incorporates the strongest insights from each perspective

Format this as a dialogue followed by your analysis, highlighting blind spots I might have in my current thinking.

I need to make a decision about [describe your decision/situation]. Help me apply first principles thinking like Elon Musk to break this down to its fundamental elements and rebuild a solution from the ground up.

Please follow this structured approach:

1. PROBLEM DECONSTRUCTION:
- What is the core problem I'm trying to solve?
- What are the fundamental truths or principles that apply to this situation?
- What conventional wisdom or assumptions might be clouding my thinking?

2. QUESTION ASSUMPTIONS:
- List the 5-7 key assumptions most people make when facing this type of decision
- For each assumption, explain:
a) Why this assumption is commonly held
b) Whether this assumption is actually valid in my specific case
c) What happens if we discard or invert this assumption

3. FUNDAMENTALS ANALYSIS:
- What are the non-negotiable factors or constraints in this situation?
- What are the fundamental metrics of success?
- What basic resources, capabilities, or principles can be leveraged?

4. SOLUTION RECONSTRUCTION:
- Based only on verified fundamental truths, what approaches emerge?
- How do these approaches differ from conventional wisdom?
- What novel solutions appear when combining these fundamental elements?

5. IMPLEMENTATION PATHWAY:
- What would be the first principles approach to implementing the best solution?
- What experiments could validate this approach with minimal resources?
- How can the solution be iteratively improved?

Please avoid generic advice and focus on applying rigorous first principles thinking to my specific situation.

I'm trying to decide whether to [describe your decision, e.g., "change careers", "relocate to a new city", "start a business", etc.]. Help me apply Jeff Bezos' Regret Minimization Framework to make this decision with a long-term perspective.

First, explain how the Regret Minimization Framework works and why it's effective for important life and career decisions.

Then, guide me through a structured analysis with the following elements:

1. FUTURE SELF PROJECTION:
- Create three scenarios of my 80-year-old self looking back on this decision:
a) If I choose to pursue this option
b) If I choose not to pursue this option
c) If I delay this decision by 1-3 years
- For each scenario, detail what specific regrets my future self might have

2. REGRET INTENSITY ANALYSIS:
- Which potential regrets would likely be most painful or persistent?
- Which regrets are tied to core values versus temporary circumstances?
- Are there any regrets that might diminish over time versus intensify?

3. OPPORTUNITY COST EXAMINATION:
- What unique experiences or growth might I miss by NOT taking this path?
- What would I be giving up if I DO take this path?
- Which of these sacrifices might I regret more deeply?

4. FEAR VS. REGRET DISTINCTION:
- Help me distinguish between fears driving my hesitation and potential true regrets
- Are my concerns about short-term discomfort or truly about long-term regret?

5. LIFE NARRATIVE IMPACT:
- How would each choice affect the overall story of my life?
- Which choice aligns better with who I aspire to be?
- Which choice is more likely to make for a meaningful life story?

6. CONCLUSION:
- Based on minimizing long-term regret, what course of action would you recommend?
- What specific steps could mitigate potential regrets regardless of my choice?

Please be thoughtful and nuanced in your analysis, addressing the emotional aspects of decision-making while maintaining analytical clarity.

I'm planning to [describe your decision or project]. Before I fully commit, help me conduct a thorough pre-mortem analysis to identify potential points of failure and strengthen my approach.

Assume it's one year in the future and this decision/project has failed completely. Create a detailed pre-mortem analysis with the following components:

1. FAILURE SCENARIO:
- Write a detailed narrative of what the failure looks like
- Describe the key negative outcomes and consequences
- Outline the critical indicators that show this has truly failed

2. ROOT CAUSE ANALYSIS:
- Identify at least 7 distinct possible causes of failure, including:
a) Internal execution failures
b) External/market factors
c) Resource constraints
d) Timing issues
e) People/team challenges
f) Unexpected competitive responses
g) Fundamentally flawed assumptions

3. PROBABILITY ASSESSMENT:
- For each failure cause, estimate the relative probability (high/medium/low)
- Which failure modes are most concerning and why?
- Are there any compounding or cascading failure risks?

4. EARLY WARNING SIGNALS:
- What specific, measurable indicators would provide early warning for each failure mode?
- What thresholds or trigger points should prompt intervention?
- How and when should these warning signals be monitored?

5. PREVENTATIVE MEASURES:
- For each major failure risk, what specific preventative actions could be taken now?
- Which adjustments to the original plan would create the most resilience?
- What contingency plans should be developed in advance?

6. RISK MITIGATION PRIORITIZATION:
- Which 3-5 preventative measures would provide the greatest reduction in overall risk?
- What is the appropriate resource allocation for risk mitigation?
- Are there any risks that simply cannot be adequately mitigated?

7. REVISED APPROACH:
- Based on this pre-mortem, should I proceed with the decision/project?
- If yes, what specific changes to the approach do you recommend?
- If no, what alternatives might achieve similar objectives with less risk?

Be brutally honest in your assessment while maintaining a constructive approach. The goal is to strengthen my decision/plan or reconsider it if the risks are too great.

I need to make a decision about [describe your situation]. Help me create a comprehensive decision journal entry that documents my thinking process and creates accountability. Simulate how a CEO might document this decision to review later.

Please create a structured decision journal with the following sections:

1. DECISION OVERVIEW:
- What specific decision needs to be made?
- What is the deadline for this decision?
- Is this a one-time, reversible, or recurring decision?
- What is the significance/impact level of this decision?

2. CONTEXT & CONSTRAINTS:
- What is the current situation that necessitates this decision?
- What specific constraints am I operating under?
- What resources are available to implement this decision?
- What are the key external factors influencing this situation?

3. OPTIONS CONSIDERED:
- List all viable options being considered (minimum 3-4)
- For each option, document:
a) Core advantages and desired outcomes
b) Key disadvantages and concerns
c) Resource requirements
d) Timeline implications

4. DECISION CRITERIA:
- What specific criteria am I using to evaluate options?
- How am I weighting each criterion in importance?
- What metrics or indicators will determine success?

5. MENTAL & EMOTIONAL STATE:
- What is my current mental and emotional state making this decision?
- Am I under unusual stress, time pressure, or influence?
- What cognitive biases might be affecting my judgment?
- How confident am I in the information available?

6. EXPECTED OUTCOMES:
- What specific outcomes do I expect if this decision succeeds?
- What potential negative consequences should I prepare for?
- What specific indicators will show if this decision is working?

7. REVIEW TRIGGERS:
- When specifically should this decision be reviewed?
- What changes in circumstances would trigger an immediate review?
- What specific metrics will be tracked to evaluate effectiveness?

8. FINAL DECISION & RATIONALE:
- What is my chosen course of action?
- What were the decisive factors in making this choice?
- What key trade-offs am I accepting with this decision?
- What is my level of confidence in this decision (1-10)?

Format this as a formal decision document that I could review in the future to evaluate my decision-making process and outcomes.

I'm considering [describe your decision]. Help me apply second-order thinking to look beyond immediate outcomes and understand the cascading effects of this decision.

Please guide me through a structured second-order thinking analysis with the following components:

1. DECISION SNAPSHOT:
- Summarize the decision and its immediate first-order consequences (both positive and negative)
- Identify key stakeholders directly affected by the initial decision

2. TIME HORIZON EXPANSION:
- Analyze potential consequences across multiple time horizons:
a) Short-term (0-6 months)
b) Medium-term (6-18 months)
c) Long-term (18+ months)
- For each time horizon, identify how effects might evolve or compound

3. SECOND-ORDER EFFECTS MAPPING:
- For each major first-order outcome, identify 2-3 potential second-order effects
- For the most significant second-order effects, extend to possible third-order effects
- Identify any potential non-linear outcomes or tipping points

4. FEEDBACK LOOP IDENTIFICATION:
- What positive feedback loops might amplify certain outcomes?
- What negative feedback loops might create self-limiting effects?
- Are there potential delayed feedback mechanisms to monitor?

5. STAKEHOLDER RESPONSE PREDICTION:
- How will different stakeholders likely react to first-order effects?
- What actions might they take in response?
- How could these reactions create additional consequences?

6. SYSTEM INTERACTION ANALYSIS:
- How might this decision interact with other systems or decisions?
- Are there potential cascading failures or unexpected synergies?
- What second-order effects might emerge from these interactions?

7. UNINTENDED CONSEQUENCES EXPLORATION:
- What are potential unintended consequences not immediately obvious?
- Which stakeholders might be affected indirectly?
- What assumptions, if wrong, could lead to surprising outcomes?

8. OPPORTUNITY IDENTIFICATION:
- What second-order opportunities might emerge that aren't immediately obvious?
- How might I position to capitalize on these secondary effects?

9. REVISED DECISION APPROACH:
- Based on this analysis, should I modify my decision or implementation approach?
- What monitoring systems should I put in place to track evolving effects?
- What contingency plans address the most concerning second/third-order effects?

Think deeply about complex systems and emergent behaviors rather than just linear cause-and-effect. Challenge my first-level thinking and help me see around corners.