The real test of critical thinking is whether you can engage with arguments you hate

We’ve spent thirteen essays learning how to spot bad thinking. Your brain runs on faulty autopilot. You take shortcuts. You defend your ego. Then we learned the tools to analyze arguments – identify premises and conclusions, distinguish deduction from induction, find hidden assumptions.

So – if you’ve been paying attention – you’re now extremely good at finding weaknesses in arguments you already disagree with.

There’s just one problem – and I’ll use myself as an example. Someone from the other political tribe makes a claim, and I immediately start reconstructing their argument in the weakest possible form. I’m looking for the gaps, the fallacies, the hidden assumptions that fall apart under scrutiny. I’m building what philosophers call a straw man – a deliberately weak version of the argument that’s easy to knock down.

It feels good. It feels like thinking. But it’s actually the opposite of good critical thinking.

Nigel Warburton calls this out in “Thinking from A to Z.” The Principle of Charity demands that you interpret arguments in their strongest possible form. Not the weakest. The best case the person could reasonably be making.

This goes against every instinct we’ve developed. But if your goal is actually understanding whether an argument is sound rather than just scoring points, you have to engage with the steel man, not the straw man.

Here’s what that looks like in practice. Someone argues we should reduce immigration because it depresses wages for American workers. The straw man: “Oh, so you just hate foreigners.” That’s satisfying. It also completely misses the economic claim.

The steel man: “You’re arguing that increasing labor supply in certain sectors reduces bargaining power for workers already in those sectors, and immigration policy should account for domestic labor market conditions.” Now you’re dealing with the strongest version. You can evaluate the evidence. You can examine trade-offs rather than just calling someone racist and walking away.

Notice what just happened. By being charitable, I didn’t concede that the argument is correct. I just stated it in a form where I can actually engage with whether it’s correct. This is what Daniel Dennett calls the first step of productive criticism – you should be able to restate someone’s position so clearly that they say “thanks, I wish I’d thought of putting it that way.”

This is extremely difficult because it requires setting aside the confirmation bias we talked about in Essay 6. When you encounter an argument from someone you disagree with, your brain is already primed to reject it. System 1 is looking for reasons to dismiss it. The halo effect from Essay 8 means if you dislike the person, you’re predisposed to find their argument stupid.

Forcing yourself to construct the steel man version fights all of that. It makes you slow down. It engages System 2. It requires you to actually understand what’s being claimed before you decide if it’s wrong.

Here’s the uncomfortable part. When you apply this honestly, you’ll discover that some arguments you thought were idiotic actually have more merit than you realized. Not that they’re necessarily right. Just that the strongest version is harder to dismiss than the weak version you’ve been attacking.

I tested this on myself with arguments for raising the minimum wage. My immediate reaction to business owners complaining was to dismiss them as greedy. That was the straw man. The steel man: “If your business model only works by paying employees wages so low they need government assistance to survive, you don’t have a profitable business – you have a scheme where taxpayers subsidize your labor costs. A real business should generate enough value to pay workers a livable wage.”

That’s the actual argument. You can disagree about what constitutes “livable.” You can argue about regional cost differences. But you can’t just dismiss it as not understanding economics.

This is where critical thinking gets genuinely difficult. It’s not just finding flaws in bad arguments. It’s honestly engaging with good arguments from people you disagree with.

Warburton points out that being charitable is an intellectual exercise. Your opponent might not defend the reconstructed argument. But that’s not the point. You can’t claim good reasoning if you’re only capable of defeating arguments nobody actually holds.

The Principle of Charity is a commitment to intellectual honesty. I will engage with the strongest version of your argument before dismissing it. I will assume you have reasons even if I ultimately conclude those reasons are insufficient.

When stakes are high and you believe someone’s position causes real harm, being charitable feels dangerous. But if you only know how to defeat straw men, you’re unprepared when someone articulates the steel man version.

We’re not playing a game where the goal is feeling superior. The goal is figuring out what’s actually true. This is the real test of critical thinking. Can you state your opponent’s position so well they’d thank you for the clarity? Or are you more interested in caricaturing it so you can win?