How to Anticipate the Strongest Argument Against Your Position
Steelmanning your own opposition is a skill, not an instinct. Here's the five-step method for predicting the strongest case a smart opponent would make — before they make it.
You hold a position you've thought about. Maybe deeply. You've considered some objections; you've worked through some counterarguments; you feel reasonably solid. Then you encounter someone who disagrees with you — at a conference, in a meeting, in an article — and they make a point you genuinely hadn't considered. Not a weak point you can dismiss. A real one. The position you walked in with is now on its back foot, and you're realizing you'd been arguing with strawmen of the opposition, not the opposition itself.
Predicting the strongest counter to your own view is a skill — and not the one most people develop naturally. The default is to imagine weak versions of the opposition, because weak versions are easier to defeat. The discipline of imagining the strongest version is what separates careful thinkers from confident ones. Five steps to actually do it.
Find someone smart who disagrees and read them
Don't predict the opposing case from scratch — find someone who's already made it and read them carefully. Pick the most intellectually serious person on the other side, not the loudest. Read them in their own words, not paraphrased by people who agree with you. Most failures of steelmanning come from getting the opposing case secondhand, filtered through allies who flattened the strongest parts. Go to the source.
Translate the position into your own values
A strong version of an opposing argument shows what's appealing about the position to a reasonable person — not what's wrong with it. Try to articulate why a thoughtful person would hold this view, in terms that connect to values you also hold. If you can't find the appeal, you haven't yet understood the position. Most positions held by smart people have a real underlying logic; finding it is the work.
Identify the assumption your view depends on
Your position rests on some assumption — about how people behave, what's likely to happen, what matters most. Find it. Then ask: what argument would attack this assumption directly? That's usually the strongest counter. If your position assumes markets correct themselves, the strongest opposition will challenge that; if it assumes a particular value should win, the strongest opposition will surface a competing value. The assumption is the load-bearing wall. Test it.
Imagine the empirical case being wrong
Most positions rely on some claim about facts: about trends, outcomes, evidence. The strongest opposition will often challenge the empirical case directly — by citing evidence that points the other way, or by reinterpreting the same evidence. Anticipate this. What facts, if true, would weaken your position? Are any of them actually true? An honest audit of the empirical case is often where weak positions get caught and strong ones get reinforced.
Test the steelman by trying to defeat it
Once you've built the strongest version of the opposing case, try to defeat it. Not by repeating your original arguments — by engaging with the steelman directly. If you can defeat it, your position is in better shape than it was. If you can't, you've discovered something important about the limits of your view. Either outcome is valuable. The version of you that's done this work is the one whose conclusions actually hold up.
Face the strongest version of the opposing case
Debate Me generates the steelman against any position you state — multi-turn, in five debate formats, with fallacy flags and Rematch mode that targets the blind spots from your previous debates.