Lesson Content

Comparison is a strength Claude is underused for.

Claude can hold multiple options in context simultaneously and analyze them against any criteria you specify. This makes it an exceptionally useful tool for evaluating competing approaches, tools, vendors, strategies, or decisions – if you ask for it specifically.

The key is providing both the options AND the criteria. Do not ask Claude to pick the best option without telling it what "best" means for your situation.

Structured comparison prompting.

The most useful comparison format provides:

1. The options to compare (2-4 works well)
2. The criteria that matter for your decision
3. Any constraints that eliminate options outright
4. What you want Claude to produce: a table, a recommendation, a ranked list, a pros/cons analysis

Example:

Compare these three approaches to onboarding new remote employees: (A) self-paced video library, (B) live cohort training sessions, (C) 1:1 shadowing with a buddy. Evaluate each against these criteria: cost, time-to-productivity, scalability to 50 new hires/year, and manager time required. Format as a comparison table. Do not make a final recommendation – I will decide after seeing the comparison.

Pre-mortem prompting.

A pre-mortem is a technique from project management: before a project begins, imagine it has failed and ask "why did it fail?" This surfaces risks that forward-looking planning misses.

Claude can run a pre-mortem on any plan or decision. Prompt: "Imagine it is [6 months from now] and this [plan/decision/project] has failed. What are the three most likely reasons it failed? For each, what early warning sign would have appeared?"

This prompting pattern produces more actionable risk identification than generic risk analysis because it forces specificity: not "communication might be a problem" but "the team lead left after month two and there was no knowledge transfer plan."

Steelmanning opposing views.

If you are building an argument, planning to make a recommendation, or preparing for a debate or negotiation, ask Claude to steelman the opposing position. "Give me the strongest possible argument against the position I just outlined" or "Argue for Option B as compellingly as you can, even though I'm currently leaning toward Option A."

Steelmanning helps you understand counterarguments at their strongest – so you can address them rather than be surprised by them. It also sometimes reveals that the opposing view has merit you had not considered.

The red team technique.

For plans or proposals that will face scrutiny, ask Claude to play the role of a specific skeptical reviewer: "Act as a risk-averse CFO reviewing this proposal. What objections would you raise and what data would you demand?" The more specific the reviewer role, the more targeted and useful the critique.