The Comparison

Why this matters

Decisions are hard when you have multiple options with different trade-offs across multiple criteria. AI is excellent at forcing that structure: making trade-offs explicit, weighting criteria, and cutting through the fog of vague preferences. This drill gives you a reusable pattern for any decision where you have at least two options and at least three criteria.

How to do it

1. 1

   Pick a real decision you are facing or have recently made

   Best decisions to use: tool selection (which CMS to use, which vendor to hire), career choices, major purchases, strategic directions. Must have at least 2 options and 3 criteria.

2. 2

   Use the comparison framework prompt

   Tell Claude the decision, list your options, and let it propose the criteria — then refine them based on what actually matters to you.

3. 3

   Assign weights to the criteria

   After seeing the criteria, assign weights (1–5) based on importance to your specific situation. This is where your judgment matters — Claude doesn't know your priorities.

4. 4

   Review the weighted recommendation and ask "what am I missing?"

   The final step is adversarial: ask Claude to argue for the option it ranked lowest. This surfaces blind spots in your criteria.

The prompt

I need to decide between these options: [LIST YOUR OPTIONS]

The decision is about: [WHAT YOU ARE CHOOSING]

My context: [2-3 sentences about your situation, timeline, and what matters most]

Please:
1. Propose 6-8 criteria I should evaluate these options against (based on my context)
2. Create a comparison table with these criteria as rows and options as columns
3. Score each option on each criterion (1-5 scale with brief justification)

I will then assign weights to the criteria and ask for the weighted recommendation.

Based on the comparison above, here are my criteria weights (1=low importance, 5=critical):

[LIST EACH CRITERION AND ITS WEIGHT]

Now:
1. Calculate the weighted score for each option
2. Give me the recommendation with the highest weighted score
3. Then argue for the option that ranked lowest — what would have to be true for it to be the better choice?

Success criteria

• ✓You built a comparison table with at least 2 options and 4+ criteria
• ✓You assigned weights based on your actual priorities
• ✓You reviewed the devil's advocate argument for the losing option
• ✓The recommendation matches or clarifies what you already believed — or genuinely surprised you

Common mistakes