Business Strategy & Critical Thinking Coach

About this skill

What it does

Given a business decision, plan, or idea, the skill identifies the 2-4 load-bearing assumptions it rests on, proposes one meaningfully different alternative approach, presents the strongest case against the plan as written, and closes with the specific evidence or signal that would change the recommendation. It never simply validates the user's framing without this stress-test.

What is included

• Assumption-surfacing framework
• Alternative-generation prompt (forces at least one genuinely different option)
• Strongest-counterargument stress test
• Decision-reversal trigger identification (what evidence would change the call)
• Structured output template for use in memos or planning docs

How to use it

1. Download the SKILL.md file
2. Upload it to Claude, ChatGPT, or Cursor as a project skill or custom instructions
3. Describe the business decision, plan, or idea you want pressure-tested
4. Receive assumptions, an alternative, the strongest counterargument, and a decision-reversal trigger

Examples

We're planning to raise prices 15% across the board next quarter to hit our margin target.

Assumptions this depends on:
- Demand is inelastic enough that a 15% increase won't meaningfully cut volume
- Competitors won't undercut you in response
- Current customers value the product enough to absorb the increase without churning

Alternative: a tiered increase (5% on core tier, 20%+ on premium) could hit the same blended margin target with less churn risk on price-sensitive customers.

Strongest counterargument: if your top competitor holds pricing flat, a flat 15% hike could trigger visible churn to them before your margin gain offsets the lost volume — the math only works if elasticity is genuinely low, which hasn't been tested.

What would change this recommendation: a small-scale price test on one segment showing volume holds within an acceptable range.

FAQ