Steelmanning — Building the Best Version of the Other Side

Why It Matters

The internet has made straw-manning the default mode of disagreement. Political debates, social media arguments, cable news panels — they almost always attack the weakest version of the other side. A conservative critic attacks the most extreme progressive position as if it represents all progressives. A progressive critic attacks the most extreme conservative position as if it represents all conservatives. Both feel like they’re winning. Neither is engaging with reality.

Steelmanning is rare because it is uncomfortable. To build the best version of an argument you disagree with, you have to temporarily inhabit a worldview that is not your own. You have to think seriously about why intelligent, well-meaning people might hold a position you find wrong. This feels like betrayal — as if understanding the other side weakens your own. It does the opposite. Understanding the strongest version of the opposing argument is the only way to build a response that is genuinely persuasive rather than merely satisfying to people who already agree with you.

Steelmanning also changes you. When you take the other side seriously enough to build its best case, you sometimes discover that it is stronger than you expected. You may not change your mind, but you will understand why the disagreement exists, which parts of your position are genuinely strong and which are assumptions you haven’t examined. This is uncomfortable. It is also the foundation of real thinking.

A Story

The Debate That Changed Rafael’s Mind About Minds

Rafael was assigned the affirmative in a school debate on the motion: “Standardized testing should be abolished.” He agreed with his side, which made preparation easy — or so he thought. He built his case around the arguments he already believed: tests are stressful, they don’t measure real learning, they disadvantage students from lower-income families.

His coach, Dr. Okafor, reviewed his case and said: “Your arguments are fine. Now tell me the best argument for keeping standardized tests.” Rafael rattled off some weak versions: “They make grading easier. Colleges want them. Some people just like tests.” Dr. Okafor shook her head. “Those are straw men. I want the steel man. I want the argument that would make a thoughtful person say, ‘Actually, maybe we do need these tests.’”

Rafael struggled with this. But Dr. Okafor pushed him, and eventually he built a genuine steel man: “Standardized tests, whatever their flaws, provide the only objective comparison across different schools with different grading standards. A student with a 4.0 at an easy school and a student with a 3.5 at a rigorous school look identical on transcripts. The test is the only thing that might reveal the difference. For first-generation college students whose schools lack the resources for impressive extracurriculars, a high test score might be the only signal that gets them noticed. Eliminating the test could actually hurt the students it claims to help.”

Rafael was troubled by his own steel man. It was a genuinely good argument. He still believed abolition was right, but now he could see the trade-offs. When the debate came, his opponents made exactly the arguments he had steelmanned. He was ready. His rebuttal was specific and nuanced: he acknowledged the legitimate concern about comparability and proposed alternatives rather than simply dismissing the need. The judges noted that he was the only debater on either side who showed genuine understanding of the opposing position.

Dr. Okafor told him afterward: “The strongest debaters always know the other side’s best argument better than the other side does.”

Vocabulary

Steel man

The strongest, most charitable version of an argument you disagree with. A steel man includes the other side’s best evidence, most reasonable assumptions, and most compelling logic. Building a steel man requires intellectual empathy — the ability to think from a perspective that is not your own.

Straw man

A weak, distorted version of an argument, constructed to be easily defeated. Straw-manning is attacking a simplified or exaggerated version of the other side rather than the position they actually hold. It feels like winning but proves nothing.

Intellectual empathy

The capacity to understand why a reasonable, intelligent person might hold a position you believe is wrong. Intellectual empathy does not require agreement. It requires genuine effort to see the logic, evidence, and values that make the other position coherent from the inside.

The strongest-version test

Before arguing against a position, ask: “Could the person who holds this view recognize my summary of their position as accurate and fair?” If they would say “that’s not what I believe,” you are attacking a straw man. If they would say “that’s a fair representation, maybe even better than I could have put it,” you have built a steel man.

Guided Teaching

Begin with a demonstration. Pick a topic the student has a strong opinion about. Ask them to state their position. Then ask: “Now give me the best argument against your own position.” Most people’s first attempt will be a straw man — a weak, easily dismissed version of the other side. Push them: “That’s the weakest version. I want the one that actually worries you. The one that, if you’re honest, you don’t have a perfect answer for.”

Walk through Rafael’s story. Notice the progression: his first attempt at the opposing argument was weak (straw men about convenience and preference). Dr. Okafor refused to accept it. The real steel man — about comparability and first-generation students — was genuinely challenging. Ask: “Why was Rafael’s steel man better than his straw man? What made it a real argument rather than a caricature?” The steel man included specific evidence, addressed a real concern, and was internally coherent.

Teach the construction method. To build a steel man: (1) Identify the core concern behind the opposing position — not the talking points, but the underlying worry. (2) Find the best evidence that supports that concern. (3) Articulate the logic as clearly and charitably as possible. (4) Apply the strongest-version test: would the other side recognize this as their position? Practice this with a current topic the student cares about.

Address the emotional resistance. Students will feel that steelmanning the other side is somehow disloyal to their own position. Name this explicitly: “It feels wrong to make the other side sound good. But think about what it gets you: if you can defeat the best version of the argument, you’ve actually won something real. If you can only defeat the worst version, your victory is fake.” Ask: “Would you rather win against a weak opponent or a strong one? Which victory is worth more?”

The surprise discovery. Sometimes, when you build the steel man, you realize the other side is right — or at least more right than you thought. This is not a failure. It is thinking working. Ask: “Is it a sign of weakness to discover that the other side has a point? Or is it a sign that you’re thinking honestly?” The answer matters for everything that follows in this module.

Connect to the module theme. This module is about adversarial reasoning — debate, cross-examination, rebuttal. Steelmanning is the foundation of all of it. If you cannot construct the other side’s best argument, your cross-examination will miss the real points, your rebuttal will address the wrong concerns, and your debate will be theater rather than inquiry.

For Discussion

1. 1.Why does it feel uncomfortable to build the best version of an argument you disagree with? What does that discomfort tell you?
2. 2.Rafael discovered that the steel man for standardized testing was genuinely strong. Has building the other side’s best argument ever changed your mind, even partially?
3. 3.Dr. Okafor said the strongest debaters know the other side’s best argument better than the other side does. Why would that be an advantage in a debate?
4. 4.Is there a limit to steelmanning? Are there positions so harmful that building their best case is irresponsible?
5. 5.How would public political discourse change if everyone was required to steelman the other side before attacking it?

Practice

The Steel Man Challenge

1. 1.Choose a topic you have a strong opinion about. State your position clearly in two or three sentences.
2. 2.Now build the strongest possible case against your own position. Include: the core concern behind the opposing view, the best evidence supporting it, and the clearest logical argument for it.
3. 3.Apply the strongest-version test: would someone who holds the opposing view say, “Yes, that’s a fair representation of my position”?
4. 4.If possible, show your steel man to someone who actually holds the opposing view and ask if you got it right. Revise based on their feedback.
5. 5.Finally, write your rebuttal to the steel man — not the straw man, the steel man. This is the real argument.

Memory Questions

1. 1.What is the difference between a straw man and a steel man?
2. 2.What is the strongest-version test, and how do you apply it?
3. 3.Why did Rafael’s straw man version of the pro-testing argument fail as a debate preparation tool?
4. 4.What is intellectual empathy, and why does it strengthen rather than weaken your own argument?
5. 5.What are the four steps for constructing a steel man?