Ever notice how lawyers always think their side should win? This applies to me as much as anyone. I’ve always found it an interesting dynamic in litigation. Turns out, people are just wired this way.

From the book Mindwise: How We Understand What Others Think, Believe, Feel, and Want, by Nicholas Epley:

In one experiment, equally human volunteers were randomly assigned to argue a hypothetical court case, either for the prosecution or for the defense. Despite being randomly assigned to these roles only moments before, volunteers quickly came to believe that their own side’s case was stronger than the other side’s case. More important, this wasn’t just posturing; they seemed to really believe it, and they also thought the judge would rule in their own side’s favor.

This phenomenon can cause huge blind spots in an attorney’s game.

At its worst, an attorney believes their side should win, thinks everyone else knows it (including the opposing side) and does not give serious consideration to the possibility that they might lose. This is a classic rookie lawyer mistake. But there is a cure: losing.

At the other extreme is a complete cynic. The complete cynic still believes that their side should win, but assumes they will lose because there is no justice in the world. I don’t see this much. My theory is that if anyone thinks like this they leave the profession.

Between the two extremes is a huge gulf where the vast majority of litigators operate. We all have a blind spot. But the best litigators learn how to manage their blind spot.

The ability to objectively analyze a case and weigh its strengths and weaknesses is a huge skill. Some lawyers really don’t ever get there. They learn that their side isn’t always going to win, but they just can’t get to the point where they can think through the losing scenario before it happens.

You see it occasionally watching trials that you aren’t involved in. One side is clearly winning–everyone in the courtroom knows it. Everyone, that is, except the lawyers on the side that is losing. They aren’t getting it. They are totally blinded by their personal belief in their case.

Go watch a trial with good experienced trial lawyers and you will not see that look on either side of the courtroom. A thinking lawyer with a lot of trial experience knows they their side might lose no matter how great it feels like the trial is going.

Lawyers get huge respect in the profession when they can not only analyze the strengths and weaknesses of both sides’ case, but will also openly discuss it with opposing counsel. These lawyers have reputations as straight shooters and are among the most respected in the profession.

It’s a lot easier to process the opposing lawyer telling you where your case has problems when he also admitting that his case isn’t bullet proof. These sorts of discussions often lead to settlements that both sides feel pretty good about.

One thing that can help young lawyers process “I believe we should win” blind spot is to think in terms of odds. What are the percentage odds that our side would win a trial of this case? If you know the case will make it to the jury, then your analysis should almost always rate your opponent’s odds of winning as at least 25%.

A 75% chance of winning still makes you a 3 to 1 favorite to win. But people who don’t think about the math don’t understand how often that 1 out of 4 chance is going to look them up. Again, there is a cure for this: losing.

Show me a lawyer who has never lost a trial and I will show you a lawyer with a huge blind spot about whether their side might lose. It’s a big reason that trial experience is irreplaceable. It’s not just the knowing how to present the case in trial. Trying cases also teaches lawyers how to analyze cases from the outset.

I don’t think a lawyer has to have tried 50 of 100 cases to get it. But they need to have won a few and lost a few. But many lawyers calling the shots in litigation haven’t. Know who I am talking about?