A set of 30 challenging questions designed to surface blind spots, weak assumptions, and hidden risks before they become problems. Each prompt pushes you to interrogate your own thinking with the skepticism of someone invested in finding flaws.
This isn't about being negative—it's about being thorough. The best time to hear the strongest objection is before the decision is final.
Teams making decisions where the downside matters. Product teams evaluating features. Founders considering pivots. Leadership weighing strategic bets. Anyone who wants to hear the hard questions before someone else asks them.
Use this alone to challenge your own assumptions, or with a small group to systematically surface doubts and test conviction.
Work through the prompts one at a time. Some questions will feel irrelevant. Others will land hard. Pay attention to the ones that make you uncomfortable—those are usually the ones worth discussing.
Take notes as you go. You don't need to answer every question. The goal isn't to kill the idea—it's to strengthen it by acknowledging what could go wrong.
This is not a brainstorming tool. It's not designed to generate ideas or build consensus. It won't tell you what to decide. It will, however, help you see where your reasoning is shaky before you act on it.