Analysis & Decision-Making Prompts

Templates for comparing options, evaluating risks, structuring decisions, and making sense of complex situations.

Compare Two Options

When to use it: You’re deciding between two paths and want a structured, honest comparison.

Compare [OPTION A] vs [OPTION B] for my situation.

My situation: [BRIEF CONTEXT — what you're trying to accomplish, constraints, priorities]

Give me:
1. A pros/cons table for each option
2. Which option you'd recommend given my situation and why
3. The one thing that would make you change that recommendation

Be direct. Don't hedge excessively.

!!! example “Filled-in example” Compare building a custom internal tool vs buying an off-the-shelf SaaS solution for my situation.

My situation: Small team of 8 people, limited engineering bandwidth, the workflow we need to automate is fairly standard but we have one unusual requirement.

Give me:
1. A pros/cons table for each option
2. Which option you'd recommend given my situation and why
3. The one thing that would make you change that recommendation

!!! tip Ask it to steelman the option it didn’t recommend — it often surfaces the strongest case you haven’t fully considered.

Analyze Data and Find Patterns

When to use it: You have a dataset, report, or set of numbers and want to know what’s actually going on.

Analyze the following data and tell me:
1. The most important patterns or trends
2. Anything surprising or anomalous
3. What questions this data raises that it doesn't answer
4. If you had to summarize the story this data tells in one sentence, what would it be?

Data:
[PASTE YOUR DATA, TABLE, OR SUMMARY HERE]

Context: [WHAT THIS DATA IS, WHAT IT MEASURES, ANY RELEVANT BACKGROUND]

!!! tip If your dataset is large, paste a representative sample and describe the full dataset. Claude can extrapolate patterns and flag what additional data would be useful.

Create a Decision Framework

When to use it: You’re facing a recurring type of decision and want a consistent, principled way to make it.

Create a decision framework for: [TYPE OF DECISION]

Context: [WHAT MAKES THIS DECISION HARD, WHAT FACTORS MATTER]

The framework should:
- List the key criteria to evaluate
- Suggest how to weight them relative to each other
- Identify the most common traps or biases in this type of decision
- Give me 3-5 questions I should answer before deciding

Keep it practical — something I can actually use quickly, not a theoretical model.

!!! tip After getting the framework, test it against a real past decision to see if it would have led you to the right call.

Research a Topic and Summarize Key Findings

When to use it: You need to get up to speed on something quickly and want the most important information without reading everything.

Give me a research summary on: [TOPIC]

I need to understand:
- The basics (assume I know [LEVEL: nothing / the fundamentals / the field but not this specific area])
- The most important things to know
- Where experts currently disagree or where the evidence is uncertain
- Practical implications for [MY CONTEXT OR USE CASE]

Format as: [structured bullets / short paragraphs / key questions and answers]
Length: [concise overview / standard summary / detailed briefing]

!!! tip Add “Cite what you’re uncertain about” — it makes the output significantly more trustworthy by flagging where you should verify independently.

Evaluate Risks and Tradeoffs

When to use it: You’re about to make a decision or take an action and want to think through what could go wrong.

Help me evaluate the risks and tradeoffs of: [DECISION OR ACTION]

For each risk:
- Describe it clearly
- Rate the likelihood (low/medium/high)
- Rate the impact if it occurs (low/medium/high)
- Suggest a mitigation

Also identify:
- The most likely way this goes wrong
- The worst-case scenario
- What I might be overlooking because I'm too close to this

Context: [RELEVANT BACKGROUND ON YOUR SITUATION]

!!! tip Explicitly ask “what am I not thinking about?” Claude will often surface blind spots that a focused risk analysis misses.

Break Down a Complex Problem

When to use it: A problem feels overwhelming or tangled and you need to see the pieces clearly before you can solve it.

Help me break down the following problem into manageable parts.

Problem: [DESCRIBE THE PROBLEM IN AS MUCH DETAIL AS YOU CAN]

I want:
1. The core components or sub-problems within this
2. Which parts are dependent on each other vs which can be tackled independently
3. A suggested order of attack — where should I start?
4. The one part of this that's most likely to unlock everything else

Don't solve it yet — just help me see the structure clearly.

!!! tip This works especially well for problems that feel like one big thing but are actually several tangled problems. The decomposition step alone often reveals the path forward.

Devil’s Advocate

When to use it: You have a plan you like and want someone to stress-test it honestly before you commit.

I have the following plan. Play devil's advocate — give me the strongest possible argument against it.

My plan: [DESCRIBE YOUR PLAN]

Don't be diplomatic. Find the weakest points, the assumptions that could be wrong, and the ways this could fail. Then tell me what would need to be true for those concerns to be fatal vs manageable.

!!! example “Filled-in example” I have the following plan. Play devil’s advocate — give me the strongest possible argument against it.

My plan: Launch a subscription newsletter in my industry niche, charge $15/month, build an audience of 500 paying subscribers in the first year.

Don't be diplomatic. Find the weakest points, the assumptions that could be wrong, and the ways this could fail. Then tell me what would need to be true for those concerns to be fatal vs manageable.

!!! tip After the devil’s advocate response, follow up with: “Now steelman the plan — what would have to be true for this to work better than expected?”

SWOT Analysis

When to use it: You need a structured strategic analysis of a business, product, decision, or situation.

Create a SWOT analysis for: [SUBJECT — a business, product, idea, plan, or situation]

Context: [RELEVANT DETAILS — industry, stage, constraints, competitive landscape]

Format it as a clean 2x2 table. After the table, give me 2-3 sentences on the most important strategic insight the SWOT reveals.

!!! tip A SWOT is most useful when the Threats and Weaknesses are specific, not generic. Ask Claude to “be specific — avoid generic business risks like ‘competition’ without specifying which competitors and why they’re a real threat.”

Identify Assumptions in My Thinking

When to use it: You want to pressure-test a plan, argument, or belief before acting on it.

I'm going to describe a plan (or belief, or argument). Identify the key assumptions embedded in it — things I'm taking for granted that may not be true.

For each assumption:
- State it clearly
- Rate how confident I should be that it's true (high/medium/low)
- Explain what happens to the plan if that assumption is wrong

My plan/belief/argument:
[DESCRIBE IT IN DETAIL]

!!! tip This is one of the most underused prompts in this library. Most bad decisions aren’t wrong reasoning — they’re reasoning built on unexamined assumptions.