You draft your position. The theory holds, the facts line up, you file feeling confident. Then their response lands, and they have reframed everything. The facts you read as clearly yours now look ambiguous. The argument you waved away turns out to be sharp. They found the gap you did not.
What happened is quiet and common: you tested your position against the weak version of their case — the one you imagined — instead of their strongest one. In five years of litigation I did this more often than I would like to admit. You are invested in your client’s story, so your mind builds a strawman of the other side and knocks it down. It feels like preparation. It is not.
Steelman, not strawman
A strawman is a distorted, easy-to-beat version of the other side’s argument. A steelman is the opposite: the strongest possible version of their position, articulated more clearly than they might manage themselves. You build the steel figure, then test your case against that. If it survives, you actually have something.
You do not need their brief to know what that steel version looks like. You can generate it now, while there is still time to adjust your strategy. A model has no client to please, so when you ask it to make the other side’s case as strong as possible, it will — not the version that makes you feel good, the one that would work.
The prompt
Construct the strongest possible counterargument to my legal position.
Make the opposing side's case as compelling and logically sound as you
can — do not weaken it to reassure me.
My position:
[your legal theory, the key facts you rely on, what you expect them
to argue]
Now build the STRONGEST version of their case:
1. REFRAME THE FACTS — how do they tell the story so their position
looks reasonable? What do they emphasise, what do they minimise?
2. ATTACK MY REASONING — where are the assumptions and logical gaps?
Be specific.
3. ALTERNATIVE FRAMEWORK — what different way of analysing this favours
them?
4. WHAT I'M OVERLOOKING — what obvious counterargument am I blind to
because I'm too close to my own case?
5. THEIR BEST OUTCOME — if they won, what would the reasoning be?
If my position cannot survive their best argument, I need to know now,
not after I file.What it surfaces
Take a supply dispute: your client ordered €600k of custom machinery, it arrived three months late, your client withheld the final €180k, and the seller is suing for payment. Your theory: the delay was a material breach that justifies withholding.
You expect the seller to argue “we were only a bit late, it works fine, pay us.” Run the steelman, and a stronger case comes back. The contract names a delivery date but never makes time of the essence. Your client accepted delivery, installed the machinery, and ran it in production — and accepting performance, even late performance, undercuts a later claim that the delay was material. The “quantifiable damages” are, so far, unproven. Their real argument is not “we were a bit late.” It is “you accepted it and used it, so pay for it.”
You still have a case. But it is a different one: acknowledge the payment obligation, pivot to damages you can actually prove, negotiate an offset. You make that shift before filing instead of in a panic six weeks after — when their brief makes exactly these points and you are already positioned to answer.
When to reach for it
Before you file anything in a dispute. Before you respond to their brief. Before settlement talks, to find your real leverage rather than the imagined kind. And especially when you feel very confident — confidence is often the sign that you have only argued against the weak version.
The instinct is one every good litigator already has: assume opposing counsel is smart, find the holes before they do. This just makes it systematic instead of occasional, and it does it while you still have room to move.