Craft cross-examination questions to chip away at direct testimony

August 24, 2021

Chicago Daily Law Bulletin – August, 2021
by Jeffrey J. Kroll
Jeffrey J. Kroll is a founding partner of Kaveny + Kroll LLC. He has achieved settlements and verdicts in a wide range of cases, from trucking accidents to medical malpractice to sports safety cases. He can be reached a

The more I think about it, the more I realize I say things far more often than I actually do them. I tell my son, Jack, he needs to work out to stay healthy. Yet, one would think that I am in some type of fitness protection program as I can no longer be found in any health club in the Chicago area. I tell my 13-year-old daughter to get off her phone and stop doing a TikTok video or abusing some other useless apps; however, as I say this to her, I realize I am still looking at my phone and not even looking at her when instructing her to get off the phone.

In my 30-something year career, I have been fortunate to have been asked to speak around the country on various trial topics. Professor Irving Younger first introduced trial lawyers to his Ten Commandments of cross-examination back in 1978. One of the comments I typically will mimic from Professor Younger to young lawyers regarding the topic of cross-examination is “do not ask a question you do not know the answer to.” Yet, I am constantly asking adverse witnesses questions when I am not sure of the answer. Granted, I am confident I can handle any potential answers, whatever they may be. Academics generally tend to follow and accept this commandment, while trial lawyers view it with some skepticism. Yes, a skeptic I am. Sadly, I wish this was limited to these three topics.

Which got me thinking about the topic of cross-examination. Too many people do not have clear goals or objectives when they stand up to cross-examine an opposing witness. I like to put my goals at the top of the first page. On the last page, I write, “have I accomplished my goals?” It sounds simple to accomplish your goals but it is not. If you do not have a plan and execute your plan for that particular witness, failure is inevitable.

When we cross-examine, you must use that witness to prove facts, theories or, hopefully, advocate the favorable theme for your case. During each and every cross-examination, the objective is to communicate your side of the case to the jury through their witnesses. In other words, have the witness commit to factors essential to your case. Planning a series of questions to communicate a conclusion without expressly stating it, involves carefully arranging and leading the jury to your unspoken conclusion. The amount of time for a meticulously conducted cross-examination is inordinately more time than you will typically imagine. Remember, all roads lead to closing arguments.

Another major objective during cross-examination is to discredit the opposing witness. It can be devastating to your opponent’s case to demonstrate that the testimony of their witness is now inconsistent with the position he or she has previously taken in prior testimony, writings or relied upon literature. An effective cross-examination will systematically whittle away the credibility of the direct testimony. Knowing each and every piece of paper in that file, as well as every word in each deposition, will assist you in discrediting the opposing witness.

Preparation is the ultimate arrow in your cross-examination quiver. As experience lends itself to judgment decisions when it comes to driving and life, perhaps preparation mixed with that same experience allows the trial lawyer to work from what they know. Doesn’t work with junior attorneys, or children, but at the end of the day, the time spent learning and the experience spent doing (or not doing and learning from those mistakes) ultimately make the difference.

I am the master of cliches. I do believe that progress involves risk. You cannot steal second base with your foot on first. And yes, you can ask cross-examination questions without knowing the answer to them. Maybe I am not a hypocrite. However, do me a favor. If you see my kids, just tell them to do as your dad says and not as he does.