The Case You Don’t Want to Lose
You’ve done your research. You know the statutes, the precedent, the facts of your case. You walk into the courtroom confident that your argument is solid. Then opposing counsel stands up and dismantles your position with a counterargument you didn’t see coming.
It’s a scenario that every litigator dreads, and it’s entirely preventable. The difference between a good argument and a winning one isn’t just knowing your own case. It’s anticipating what the other side will say and building your position to preempt it.
Why Most Attorneys Prepare Backward
Traditional legal preparation focuses on building the strongest possible case for your client. You gather evidence, develop your theory, and present your best arguments. It’s logical, thorough, and often insufficient.
The problem with this approach is that it operates in a vacuum. You’re preparing as if you’ll be the only voice in the room, but litigation is inherently adversarial. The other side gets to respond, and if your argument doesn’t account for their best counterpoints, you’re vulnerable.
Early in practice, I argued a significant motion for a client and obtained an unfavorable result. The law was against me, but I had built my arguments around the strongest position for my client rather than anticipating the opposition’s strongest argument. That loss changed how I prepare for every significant argument, whether in trial or appellate court.
Script the Opposition’s Best Case
Now, before I finalize any major argument, I script the best counterargument the other side could make. Not the argument I hope they’ll make, or the weakest version of their position. I write out the most compelling, well-reasoned response they could possibly offer.
This exercise forces you to see the weaknesses in your own case before opposing counsel does. It reveals the gaps in your logic, the facts you’ve glossed over, and the precedent that cuts against you. Once you know where you’re vulnerable, you can shore up those weaknesses before you ever set foot in court.
The goal is to make sure your position preempts their argument, rather than just presenting your own case. If you can address their strongest points in your opening brief or initial argument, you control the narrative. You’re not reacting. You’re leading.
How to Build Anticipatory Arguments
Start by putting yourself in the opposing attorney’s shoes. What would you argue if you had their facts and their client’s interests? What statutes, cases, or equitable principles would you lean on? Where would you attack your opponent’s case?
Write it out. Don’t just think about it. The act of scripting forces clarity. You’ll notice patterns, identify themes, and spot vulnerabilities that remain invisible when you’re just mentally rehearsing.
Once you’ve drafted their best argument, review your own position. Does your opening brief address their likely counterpoints? Have you cited the case law that distinguishes their precedent? Have you framed the facts in a way that makes their argument less persuasive?
This anticipatory form of practice has proven to create favorable results for clients. It doesn’t guarantee a win, especially when the law or the facts are against you, but it ensures you’ve done everything possible to position your case for success.
Preparation as a Professional Standard
Diligence and hard work matter in any profession, but in litigation they’re non-negotiable. You owe it to your clients to approach each matter with the same carefulness and concern you would for your first client. That means never presuming you’re beyond learning something new and maintaining an appetite for a better understanding of the law and a better way to serve.
The attorneys who consistently deliver results aren’t necessarily the ones with the most experience or the longest list of wins. They’re the ones who prepare as if every argument matters, because it does. They’re the ones who take the time to think one step ahead.
Start With the Next Motion
The next time you’re preparing for a hearing, a deposition, or a trial argument, add one step to your process. After you’ve built your case, take an hour and write the other side’s best response. Script it as if you were their attorney and your job depended on it.
Then read what you wrote and ask yourself: does my argument hold up? If not, revise. If so, you’re ready.
Preparation is more than knowing the law. It’s knowing what the other side will do with it.