Give Claude a Problem, Not Just a Question

Difficulty: Intermediate · Estimated time: 15 min

What You'll Learn

How to get Claude to properly analyse a document or dataset instead of skimming it.

How to have it compare options against criteria you actually care about.

How to walk it through a genuinely hard problem step by step rather than asking a one-line question.

Why This Matters

A one-line question gets a one-line-quality answer. The real value of Claude shows up on harder tasks — working through a messy document, weighing up options with real trade-offs, reasoning through a decision — and those need you to hand over the actual problem, not a compressed version of it.

The Concept

Claude answers the question you actually ask, at the depth you ask it. "What do you think of this contract?" gets a shallow, generic answer. "Read this contract and flag anything that favours the other party more than is standard" gets real analysis, because you've told Claude what to look for and why.

The same logic applies to comparisons and hard decisions: Claude is much better comparing option A vs B against three criteria you name than guessing which three criteria matter to you. And for a genuinely hard problem, asking it to think step by step — laying out reasoning before landing on a conclusion — produces noticeably better results than asking it to jump straight to an answer.

Step-by-Step

State the actual problem, not a summary of it — paste the full document or dataset where possible.

Say what you're trying to decide or find out, not just "analyse this."

For comparisons, name the specific criteria to weigh options against (cost, speed, risk, fit — whatever matters here).

For hard problems, explicitly ask Claude to think through it step by step before giving a final answer.

Ask it to show its reasoning, not just the conclusion — this makes it easier to catch a flawed assumption.

If the first pass misses something, point at the gap directly rather than re-asking from scratch.

Example

Prompt:

"Here are two vendor proposals [paste both]. Compare them against three criteria: total cost over 12 months, onboarding time, and contract flexibility. Lay out the trade-offs for each, then give me a recommendation with your reasoning."

Good response looks like: a clear breakdown per criterion (not just prose), explicit trade-offs named, and a recommendation that references the actual numbers from the proposals rather than generic pros/cons.

Try This

Take a document or decision you're sitting on right now and ask Claude to analyse it against 2-3 named criteria, with reasoning shown.

Copy This

Here is [DOCUMENT / DATA / SITUATION]:

[PASTE]

I need to decide: [THE ACTUAL DECISION]

Compare/analyse this against these criteria:
1. [CRITERION 1]
2. [CRITERION 2]
3. [CRITERION 3]

Think it through step by step, show your reasoning, then give a clear recommendation.

Common Mistakes

Summarising the document yourself before pasting it in, losing the detail Claude needed.

Asking "what do you think?" with no criteria, then being unimpressed by a generic answer.

Accepting the first conclusion without asking Claude to show how it got there.

Level-Up Tip

For a genuinely high-stakes decision, ask Claude to argue the opposite case afterwards ("now make the strongest case for the other option") — it's a fast way to stress-test a conclusion before you commit to it.

Action Checklist

○Pasted a full document or dataset instead of a summary of it.

○Named specific criteria for a comparison instead of asking generically.

○Asked Claude to reason step by step on a real problem.

○Reviewed the reasoning shown, not just the final answer.

Next Guide

Next: 09 — Brainstorming That Doesn't Just Give You Obvious Ideas, on getting past Claude's first, safest round of suggestions.

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What you will learn