
Steelman Major Decisions
Uncover the real question and decide
Description
Before making a major decision, don’t rush to a snap judgment. This skill helps you think the problem through before reaching a conclusion: clarify the real problem you need to solve, surface hidden assumptions you may not realize you’re making, steelman the strongest arguments on both sides, identify the critical point of disagreement—the condition that would flip the conclusion—and finally ask you the one question most likely to change the outcome. After you answer, it gives you a clear judgment and concrete action steps—not the empty claim that “both sides have a point.” Use it for career choices, technology selection, product direction, business decisions, investment judgments, team disagreements, and any moment when you find yourself saying, “Help me think this through.” How to use it: Enter the decision you’re wrestling with. For example: “Should I leave my big-tech job to start a company?” “Should we use option A or B for this solution?” or “Should we cut this product line?”

Steelman Major Decisions
Uncover the real question and decide
Description
Before making a major decision, don’t rush to a snap judgment. This skill helps you think the problem through before reaching a conclusion: clarify the real problem you need to solve, surface hidden assumptions you may not realize you’re making, steelman the strongest arguments on both sides, identify the critical point of disagreement—the condition that would flip the conclusion—and finally ask you the one question most likely to change the outcome. After you answer, it gives you a clear judgment and concrete action steps—not the empty claim that “both sides have a point.” Use it for career choices, technology selection, product direction, business decisions, investment judgments, team disagreements, and any moment when you find yourself saying, “Help me think this through.” How to use it: Enter the decision you’re wrestling with. For example: “Should I leave my big-tech job to start a company?” “Should we use option A or B for this solution?” or “Should we cut this product line?”
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