20 Advanced AI Prompts for Deep Critical Thinking
Artificial intelligence systems can be powerful allies for rigorous thinking and complex problem-solving—if you know how to prompt them effectively. These advanced prompts are designed to elicit sophisticated analysis, challenge assumptions, and generate unique insights across various domains.
Unlike basic prompts that yield simple answers, these prompts leverage proven frameworks from decision science, systems thinking, and epistemology to help you explore problems more deeply and arrive at more nuanced conclusions.
Whether you're using ChatGPT, Claude, Gemini, or other AI assistants, these 20 carefully crafted prompts will help you unlock their full analytical potential. Each prompt includes clear instructions and can be customized for your specific needs—perfect for researchers, analysts, strategists, and anyone seeking deeper insights.
20 Powerful AI Prompts for Deeper Analysis
Select any prompt below, replace the bracketed sections with your specific topic or question, and use it with your preferred AI assistant. These prompts work best with more advanced AI models that can handle complex, multi-part instructions.
Task Decomposition
I need to accomplish [complex task]. Break this down into a detailed, step-by-step process with the following: 1) A logical sequence of smaller subtasks, 2) The specific skills or knowledge needed for each step, 3) Potential obstacles I might encounter at each stage and how to overcome them, 4) How to verify that each step has been completed successfully before moving to the next, 5) Estimated time requirements for each component, and 6) Resources or tools that would make each step easier.
Best for: Breaking down complex projects or goals into manageable steps
Comparative Analysis
Compare and contrast [topic/concept A] and [topic/concept B] by analyzing: 1) Core principles and key characteristics of each, 2) Historical development and major contributors, 3) Strengths and limitations of each approach, 4) Specific contexts where one might be preferable to the other, 5) How they might complement each other or be combined, 6) Common misconceptions about each, and 7) Current trends and future directions in both areas.
Best for: Understanding similarities and differences between related concepts
First Principles Reasoning
Explain [complex topic/concept] using first principles thinking. Start with the most fundamental truths or elements that cannot be deduced from other assumptions. Then: 1) Build up a logical framework step by step, 2) Explain counterintuitive aspects that emerge from these fundamentals, 3) Identify where conventional thinking about this topic goes wrong, 4) Demonstrate how understanding the first principles leads to novel insights, and 5) Suggest how this understanding can be applied to solve related problems.
Best for: Developing a deeper understanding of complex topics from fundamental principles
Mental Models Application
Apply the following mental models to analyze [situation/problem/decision]: 1) Second-order thinking (considering the consequences of the consequences), 2) Inversion (thinking backward from the goal), 3) Probabilistic thinking (considering the range of possible outcomes), 4) Opportunity costs, 5) Systems thinking (considering feedback loops and emergent properties). For each model, explain the insights it generates and how it changes your understanding of the situation.
Best for: Applying structured thinking tools to analyze situations from multiple angles
Decision Matrix Creator
Help me create a comprehensive decision matrix for choosing between [options] for [specific goal/purpose]. Include: 1) At least 8 relevant evaluation criteria with different weights based on importance, 2) A scoring system with clear definitions for each level, 3) A thorough evaluation of each option against all criteria with explanations, 4) Calculation of final weighted scores, 5) Sensitivity analysis for how changes in criteria weights might affect the outcome, and 6) Discussion of non-quantifiable factors that should also be considered.
Best for: Making complex decisions with multiple factors and options
Socratic Dialogue
Engage me in a Socratic dialogue to deepen my understanding of [concept/topic]. Ask me a series of progressively deeper questions that: 1) Expose gaps or contradictions in my current thinking, 2) Guide me to discover key insights through my own reasoning, 3) Help me refine and articulate my own perspective, 4) Challenge my assumptions without telling me what to think, and 5) Lead me toward a more nuanced understanding. I'll respond to each question before you ask the next one.
Best for: Developing your own understanding through guided questioning
Evidence Evaluation
Evaluate the strength of evidence for the claim that "[controversial claim]." Please: 1) Identify the strongest evidence supporting this claim and assess its validity, 2) Identify the strongest evidence against this claim, 3) Examine methodological strengths and weaknesses of key studies, 4) Discuss potential biases in the research and reporting, 5) Compare the quality of evidence on both sides, and 6) Provide a balanced assessment of what conclusions are justified given the current state of evidence.
Best for: Evaluating the strength and quality of evidence on controversial topics
Intellectual Steelmanning
Steelman the following argument (present the strongest possible version of it, even if you disagree): "[argument or position statement]." In your steelmanned version: 1) Clarify and strengthen the core logic, 2) Add the strongest supporting evidence not mentioned in the original, 3) Address potential objections preemptively, 4) Incorporate nuance and acknowledge valid limitations, 5) Use precise, accurate language, and 6) Ensure the argument would be recognized and accepted as fair by someone who holds this position.
Best for: Understanding the strongest version of positions you disagree with
Paradigm Shifter
Help me see [topic/situation/problem] through multiple paradigms or frameworks. For each of the following perspectives: [list at least 3 different disciplines, theories, or worldviews], explain: 1) The core assumptions and values of this paradigm, 2) How it would interpret or approach the situation, 3) What unique insights or solutions it might generate, 4) Its potential blind spots or limitations, and 5) How combining insights from this perspective with others might lead to a more comprehensive understanding.
Best for: Viewing issues through different intellectual frameworks or disciplines
Expert Panel Simulation
Simulate a panel discussion between 4-5 leading experts with different viewpoints on [topic/question]. Include: 1) Expert A who believes [perspective 1], 2) Expert B who argues [perspective 2], 3) Expert C who advocates for [perspective 3], etc. For each expert, represent their strongest arguments, supporting evidence, responses to other panelists, and their unique insights based on their background. Include specific references to their relevant work where appropriate. Conclude with points of consensus and remaining areas of disagreement.
Best for: Understanding how different expert perspectives approach a problem
Cognitive Bias Detector
Analyze the following situation/decision/reasoning for potential cognitive biases: "[describe situation or thinking process]". For each relevant bias you identify: 1) Explain what the bias is and how it typically operates, 2) Point out specific elements in the situation that suggest this bias might be present, 3) Describe how this bias might be distorting perception or reasoning in this case, 4) Suggest practical strategies to counteract or minimize the bias, and 5) Explain what a more objective assessment might look like.
Best for: Identifying how cognitive biases might be affecting your thinking
System Dynamics Modeling
Create a system dynamics analysis of [complex system or problem]. Include: 1) Key variables and how they interact (causal loops), 2) Identification of reinforcing and balancing feedback loops, 3) Potential delays in the system that might cause oscillations, 4) Leverage points where interventions would have the greatest impact, 5) Possible unintended consequences of common interventions, 6) How the system might behave under different scenarios, and 7) A visual representation of the system that clarifies these relationships.
Best for: Understanding complex systems with feedback loops and interactions
Assumption Hunter
Identify and examine the key assumptions underlying [statement, argument, plan, or prediction]. For each assumption: 1) Articulate it clearly, even if it's implicit in the original, 2) Assess its plausibility based on available evidence, 3) Explain the impact on the conclusion if this assumption proves false, 4) Suggest ways to test or validate this assumption, and 5) Offer alternative assumptions that might lead to different conclusions. Focus particularly on assumptions that are hidden, questionable, or taken for granted.
Best for: Uncovering hidden assumptions in arguments or plans
Falsification Tester
Apply Karl Popper's principle of falsifiability to [theory/claim/belief]. First, explain the theory clearly. Then: 1) Identify what specific, observable evidence would prove this theory false, 2) Evaluate whether the claim is structured in a way that makes it unfalsifiable, 3) Describe experiments or observations that could potentially disprove it, 4) Assess whether proponents of this view have modified it to accommodate contradictory evidence, and 5) Compare its falsifiability to alternative theories in the same domain.
Best for: Testing whether theories or claims can be disproven
Scenario Planning
Develop a scenario planning analysis for [organization/industry/situation] looking [timeframe] years ahead. Create 4 distinct scenarios based on key uncertainties: 1) For each scenario, provide a compelling narrative of how events unfold, 2) Identify early indicators that would suggest we're moving toward each scenario, 3) Analyze implications and strategic considerations for each possible future, 4) Highlight robust strategies that would be valuable across multiple scenarios, 5) Identify contingent strategies specific to each scenario, and 6) Suggest a monitoring system to track which scenario is becoming most likely.
Best for: Planning for multiple possible futures in uncertain environments
Lateral Thinking Challenge
Help me approach [problem/challenge] using Edward de Bono's lateral thinking techniques. Apply these specific methods: 1) Random entry (introduce an unrelated concept to trigger new associations), 2) Provocation (suggest outrageous ideas that challenge assumptions), 3) Concept extraction (identify underlying principles that could be applied differently), 4) Challenge assumptions (question the unnecessary limitations I've placed on solutions), and 5) Alternative perspectives (how would different people or disciplines approach this). For each technique, generate multiple novel approaches.
Best for: Generating creative solutions by breaking out of conventional thinking
Decision Journal Template
Create a comprehensive decision journal template for [specific type of decision]. The template should include sections for: 1) Clear framing of the decision and desired outcomes, 2) Documentation of my current mental and emotional state, 3) Key factors influencing the decision with weighted importance, 4) Explicit statement of my assumptions and confidence levels, 5) Alternative options considered and why they were rejected, 6) Expected outcomes and probability estimates, 7) How I'll evaluate the quality of this decision regardless of outcome, and 8) Review triggers to revisit and learn from this decision later.
Best for: Making better decisions by documenting your thinking process
Root Cause Analysis
Conduct a thorough root cause analysis of [problem/failure/situation] using multiple methodologies. Include: 1) The 5 Whys technique to trace the issue to its origins, 2) A fishbone/Ishikawa diagram identifying causal factors across categories (people, processes, technology, etc.), 3) A systems thinking approach that identifies feedback loops and interactions, 4) Analysis of both proximate and ultimate causes, 5) Distinction between contributing factors and the root cause(s), and 6) Specific, actionable recommendations to address each root cause identified.
Best for: Identifying the true causes of problems rather than symptoms
Contrarian Reasoning
Present a well-reasoned contrarian perspective on the commonly accepted view that "[widely held belief or consensus position]". Your analysis should: 1) Steelman the conventional wisdom first to demonstrate understanding, 2) Identify potential flaws in the standard reasoning, 3) Present the strongest alternative viewpoint with supporting evidence, 4) Explain what most people might be overlooking or misunderstanding, 5) Discuss historical examples where the consensus view was similarly wrong, and 6) Explore the implications if the contrarian view proves correct.
Best for: Challenging consensus views with reasoned alternative perspectives
Scaffolded Learning Path
Create a scaffolded learning path to help me progress from beginner to advanced level in [skill/subject]. Structure this as a progressive curriculum that: 1) Breaks the subject into clear prerequisite chains and concept dependencies, 2) Starts with foundational concepts before moving to more complex applications, 3) Includes specific resources (books, courses, projects) for each stage of learning, 4) Provides clear milestones to assess mastery before moving forward, 5) Includes deliberate practice exercises to reinforce each concept, and 6) Addresses common misconceptions or sticking points at each stage.
Best for: Creating structured learning plans for mastering new skills or subjects
Principles for Effective AI Prompting
To get the most value from these and other AI prompts, keep these principles in mind:
- Be specific about your goals and what constitutes a helpful response
- Break complex requests into clear, logical components
- Specify the format, depth, and style of response you want
- Include relevant context and constraints the AI should consider
- Request multiple perspectives or approaches rather than a single answer
- Ask the AI to explain its reasoning process, not just conclusions
- Iterate on responses by asking for clarification or deeper analysis
Understanding AI Limitations in Critical Thinking
While powerful, AI systems have important limitations to keep in mind when using them for critical thinking:
- Knowledge limitations: AI can't access information beyond its training data cutoff
- Reasoning boundaries: AI may struggle with complex causal reasoning or genuine creativity
- Confidence without certainty: AI can sound confident even when uncertain or incorrect
- Lack of lived experience: AI doesn't truly understand human experiences it discusses
- Absence of values: AI doesn't have intrinsic values to guide judgment in ethical matters
- Potential for hallucination: AI may invent plausible-sounding but false details
- Sensitivity to framing: How you phrase a question can significantly influence responses
For best results, use AI as a thought partner rather than an authority. Verify important information, critically evaluate suggestions, and use your own judgment when making consequential decisions.