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At the Round Table with Technology Expert, Robert Sherwood

April 11, 2023

In this episode…
Our guest, Robert “Bob” Sherwood, has been a senior board member to 30 companies, was profiled in Fortune and Business Week, was the winner of the 1995 Entrepreneur of the Year, sponsored by Ernst & Young, NASDAQ, and Inc. Magazine, presented seminars on Leadership and Technology to more than 3000 executives, and as an Expert Witness, he has testified in court on behalf of such prominent companies as Google, Yahoo!, and Facebook. Bob holds a Series 65 license which covers laws, regulations, ethics, retirement planning and portfolio management.

On this episode, Bob shares stories about the importance of preparation. Whether it is understanding the basic case details before the initial interview or how law firms prepare their experts for the cross-examination, preparation plays a large role on your success as an expert. Bob emphasizes, “You have to prepare much more than you think you should . . .”

Being a successful expert witness is not just about preparation. It’s also about growing with your role and learning to adapt. Early on, Bob did all the expert witness work himself, but realized later that having an effective team in place will benefit him and those attorneys that hire him. For him, having a great editor saved money and time.

Additional insights are shared in this episode, including how to organize case files, the expert’s role on the stand, and not taking cross-examination personally. He expands on this last point, “Experts should realize that no matter how challenging the question is, no matter how personal the questioning gets . . . the lawyer is doing their job.” The benefit of understanding this is that the same lawyer that cross-examined you “may come back and hire you two or three years later because they know you understand that.”

Episode Transcript:

Note: Transcript has been lightly edited for clarity.

Host: Michelle Loux, Assistant Project Manager, Round Table Group

Guest: Robert Sherwood, President, SmartText Corporation and President, Identimap, Inc

Michelle Loux: Thank you for joining us today at Discussions at the Round Table. I am your host, Michelle Loux. Today my guest is Bob Sherwood. He is the president of SmartText Corporation. Thanks, Bob, for joining me. Please tell us about your background. What are you doing, and how did you start as an expert witness?

Robert Sherwood: I have been in technology for about 40 years. We worked in Silicon Valley for a while and developed products. I created the company and all the software we are looking at on this computer screen. It is 16.7 million colors. We wrote the software for Apple and IBM. I got into this business after one of the companies I started went public; my wife and I, who are both from the Midwest, decided to come back to the Midwest for a couple of years. When I was back in the Midwest, I got a call from my local law firm, and they said, “We need an expert witness that has technical and financial knowledge and experience. I taught finance at Stanford, KSU, and MU, so I had both. I had no idea what an expert witness was when I started, except for watching TV. I did not have a clue. When they asked me, I asked, “What do I do? What am I supposed to do?” As it turned out. I was lucky because we eventually worked with a law firm in Washington, D.C. They were a big law firm, and they put their experts through extensive training. For example, they brought in a psychologist and told us how to dress. They brought in proxies. I had no idea what was going on. They had all these people telling us how to dress. How to look, to sit in the courtroom, and to respond to questions. I went through this extensive training, not knowing where it would lead me, but it was training for trial. We won the trial, and it turned out. It was a prominent law firm. I did not understand that then. People started hiring me because this distinguished law firm blessed me and put me through training. That is how I knew what expert witnesses do.

Michelle Loux: Have you found during your career as an expert witness that different law firms offer different levels of training?

Robert Sherwood: You have nailed one of the significant distinctions in law firms. I can tell you that the law firms that I work with, and I will call them major law firms, will spend an extensive amount of time prepping their experts for depositions. I found out that without being critical of the smaller law firms, they are, but they do not spend as much time prepping you. The big law firms have unlimited budgets and will put you through everything. For example, I went through a trial four or five months ago, and the law firm hired another lawyer who would bring us to tears every day while we were prepping for the trial. He would humiliate and intimidate us, and he was harsh. When we finally went to trial, we were all prepared. You nailed it. That is, the distinction on the preparation side is significant. For example, one of the questions I always ask law firms during the interview process is, “Do you prep your experts?” and “How much time do you spend doing it?” That is a crucial thing for me. I do not think you can be good as an expert unless you get good preparation from a law firm.

Michelle Loux: What do you think is the best thing you have taken away from that preparation? What is something that maybe you have applied outside the courtroom that is useful to you?

Robert Sherwood: I would say to practice listening even though my wife says I am not a good listener. You do work on listening to the specifics of the classic question, “Do you know what time it is?” A good expert says, “Yes.” The amateur says, “4:30.” They did not answer the question. So that is the classic example of listening; I have learned to listen carefully and only answer the question. Do not provide information beyond question. If the lawyer wants you to elaborate, he will ask you another question.

Michelle Loux: You touched on the initial interview questions you asked. What else do you ask the attorney when trying to learn about the case in front of you?

Robert Sherwood: I try to prepare well. I believe in doing my homework, so if I have an interview, I will spend anywhere from one to five hours preparing for the interview. I will read the complaint and any other documents they have given me in detail. I will not only read them but also examine them as if I were going to be questioned about them. I want to go into the interview knowing the background material on the case for several reasons. I prepare extensively for an interview, even if it is a minor interview where you only have 30 minutes. I am preparing for it, and that is important. I do not believe many experts do it. Generally, they do not want to know where you were born, but they want to know what is relevant. They also want to know that the typical question is, please match your background with the issues of the case. So, that question is coming. If you do not have a prepared answer, you are not doing an excellent job in the interview. I have coached other experts that have entered the business and said, “You have to prepare much more than you think you should because of what they will ask you. You will not do a good job if you do not have a well-prepared answer.”

Michelle Loux: Reading more about your background, you wrote contract software for attorneys. What about your contracts? Have you added any special terms now that you have been in the expert witness business for a while? Are there important things you have added along the way in that contract?

Robert Sherwood: There are things I delete when I see them. One is liquidated damages. Another is insurance requirements in terms of adding positive things. I always add that if I do not receive payment or if they do not recover the money to pay me by a specific time, I reserve the right to stop work. Many experts do not do that, but attorneys stop work if they do not get paid. I am no different. I can sell my time and brain but expect to receive payment.

Michelle Loux: Why would you hesitate on the insurance piece for a contract?

Robert Sherwood: Mainly because their insurance might have an unreasonable requirement. For example, maybe they want two or three million in insurance, which is more than I want to carry. I want to be very careful about any expense I am required to incur in addition to what I take. Now most of them do not have insurance provisions, but some do. Many brokers that help experts get business have liquidated damage clauses. I recommend that experts do not sign any new damage clause, which is unique; brokers are adding those things now.

Michelle Loux: What do you know now that you wish you knew when you first became an expert witness?

Robert Sherwood: I wish I had known that I needed to get a team early. When I started, I thought I had to do everything: check my sites and documents and check if every URL was correct. That is not a good way for an expert to spend their time. Some people can do that faster. They are better at it than experts, so I got my team together about halfway through my expert witness career. Now, the team for me consists of at least two good researchers. An expert should not spend their time researching Google on some issue. An expert can hire a good researcher for a quarter of what you hire the expert for, and they do a good job. So, I have two researchers and have used them for 10 or 15 years. Usually, I have my team do one good deep dive. A computer programmer should also be part of the team. I can write software, but it gets more complicated daily and takes more specific experience. I have a deep-dive computer programmer that I use. The last part of my team is an editor. I am a good writer and have written a few books, but some editors are unbelievable. If you get a good editor on your team, your reports will look five times better, and you will not spend much time on commas, periods, and semicolons. Even if you can do that, an editor can do it faster and better.

I made changes to my document and then gave it to an editor, and it came back looking like somebody bled on it. There are so many corrections to make. I thought I had every comma I needed, but I missed 36, but that is their business. Your team focuses on your business. As an expert, you focus on technology and understanding how to go into a deposition. Let me close with this: I thought I must do all these things myself when I first started. Then I realized that there are some things I do not do well and others I do better. I realized lawyers were okay with that. They say, “I will get a bill for your team’s work. We understand they are cheaper than you are. We would rather have them editing than you.” Now, I do not have any problem. For every job I start, I use my team.

Michelle Loux: How do you organize yourself, and are there other productivity tools you apply to keep track of multiple cases coming your way?

Robert Sherwood: To me, there are two parts to that. First is organizing it on your calendar. For example, the calendar might have the report date, the draft report date, and any important dates you must produce something. I use a method that Intel used in Silicon Valley: the red, yellow, and green methods. So, if the report is due February 4th, I will put it on my calendar in red, which means it is due on the 4th. A date in yellow needs research. If discovery is needed, I will put it in green. Now, I have three colors when I look at my calendar. Red means I must meet those dates and cannot delay. Green dates are those that I want to meet, but I could probably miss them and not be in trouble. Those in yellow are discovery dates.

First is organizing the material on my calendar based on the attorney’s timeline. The second, in my case, is sending documents to my editor, my document manager. When papers come in, they will go to my editor and create folders for each project. We have a template for the administration area of the folder. I receive the documents from the invoicing site, which go by dates. If I receive 20 documents on February 14th, my editor will put them into a folder for February 14th. If I receive more documents on February 21st, we will organize them by the date we receive them. Now there is another way to do it. We used to do it by document type, complaint, reply, and report. We now prefer to do it by a timeline because when we try to find out what we did, we think about when. The acid test for us on a document is when we receive it. It would be in the February folder if we got it in February. We organize by timeline.

Michelle Loux: Can I ask you, have you had any litigation matters in artificial intelligence? It is a hot topic, have you seen it come across your desk?

Robert Sherwood: I have not interviewed for a specific AI project. Many projects fall under that buzzword but are not pure AI projects. In some projects, you feed information to a database that makes modifications. The person interrogating that database has the latest information before it spits out another answer. You did not ask this, but I will tell you that patent litigation is part of the increasing litigation business. There are so many patents out there now. Last year, 300,000 patents were issued. Many law firms see that as an opportunity. I probably get interviewed for a patent case once a week or once every two weeks.

Michelle Loux: Thinking back on the cases you have worked on, what insights have you taken away from them, or maybe it was an aha moment for you as an expert witness?

Robert Sherwood: I have a recent trial incident I think is beneficial for experts to hear. I am testifying at a trial, and there was another expert. This other expert, let’s call him Jack, is on the witness stand. His attorney is asking Jack questions. The questions the attorney is asking him are binary-type questions. He wants the witness to say yes or no. This witness is a knowledgeable person who has written a couple of books. He is a professorial Santa Claus, looking, guy. Every time he got a question, he could not stop talking. The judge started admonishing him, and he would say, “Jack, just answer the lawyer’s question.” Do not go on like you are having an epiphany or something. He just kept doing it and got admonished maybe four or five times, which caused him to lose all credibility with the jury. I almost learned that the hard way. When you are in a trial, and your lawyer asks you questions, you do not have to guess what he wants. Just answer the questions. He knows what he wants and will get you there.

Sometimes an expert gets asked a question on the witness stand under oath. The witness knows what he will reply. He must be truthful, but he is damaging to his client. What should he do? He can trust that his lawyer during cross-examination will clear that up. Experts I have talked to say, “What do I do? I am going to have to say something negative.” I said, “Do not worry about it. What you need to do is answer truthfully. A lawyer will come back to you and ask you to explain it but do not explain it yourself. Then act like, “Oh gosh, I just said something negative about my client. I better clear it up by now by saying something positive.” That is not what an expert should do. One of the first rules, and I am sure Michelle, you know this, is you always tell the truth. I find that experts think about that but still get nervous. I have learned that focusing on that makes you less nervous. When I go on a witness stand, I do not have to worry about anything.  If I know the answer, I answer it.  If I do not know, I say, “I do not know.” Because I can trust my lawyer to ask me questions. The lawyer’s job is the proponent of the client; the expert is not. If you will, I am their proponent of truthfulness, so be truthful and let your lawyer advocate for your client.

Michelle Loux: Do you find in the cross-examination conversation with your attorney they say, “You are going to go with this, and I am going to lead you with this. The other attorney will do a cross, but I will take you back here.” Is that talked about before you get on the stand?

Robert Sherwood: This is an excellent observation on your part because lawyers with good preparation discuss it with practice. Recently, for example, I was being prepped, and the lawyer asked me a question, and I answered it. The lawyer said, “Well, that is a negative for the client.” I said, “Well, you asked the question, and I answered it. If you want clarification, then ask me another question.” Do not ask me to change my reply when I hear that question because I will not think, “Oh sure, when I answered this in prep, I answered it this way, and that was negative.” I am not going to remember all that. If you ask me a question, I will tell the truth. It is going to be damaging to your client. It is your job as a lawyer to clear that up. Not me. I do not have to do that. It is a great irony, right? The same client pays me, and I am theoretically not an advocate of the client. With truthfulness and expert technology, I want to put the client in the best light possible. But I am not an advocate for the client.

Michelle Loux: Any last stories you would like to share with us about being an expert witness?

Robert Sherwood: I recall that I was testifying for Yahoo!, and the other attorney was hard on me. He got personal, but I did not take it personally because I knew that was his job. If there is a story in there, it is that. Experts should realize that no matter how challenging the question is, how personal the questioning gets, such as “Doesn’t the client pay you?” or “Aren’t you paid for your opinion?” Never take those things personally. What happens is many of the lawyers recognize what they are doing. In this case, when the trial was over, the lawyer came out and apologized, he said,  “I am sorry.” I said, “Yeah, I understand. That is your job.” Well, guess what? That same law firm hired me for other cases about three years later. So, if you do not take it personally and realize they are doing their job. They know their job. They are happy to learn that the expert understands their position. They will come back to you in the future so if there is an insight there for future experts. If you do not take these things personally. If you realize people are doing their jobs, they may come back and hire you two or three years later because they know you understand that.

Michelle Loux: Right, being professional as an expert witness. Thank you so much, Robert, for your time. I appreciate you coming to our show.

Robert Sherwood: Michelle, I enjoyed it. Thank you for your questions. I hope this was valuable to your listeners, viewers, and those listening to your podcast. Thank you much. I appreciate it.

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After a quarter century helping litigators find the right expert witnesses, Round Table Group’s network contains some of the world’s greatest experts. On the Discussions at the Round Table podcast, we talk to some of them about what’s new in their field of study and their experience as expert witnesses.

At the Round Table with Technology Expert, Robert Sherwood

Robert Sherwood, President, SmartText Corporation and President, Identimap, Inc

Mr. Sherwood has authored 14 books, hosted his own radio program, taught at KU, MU and Stanford graduate schools of business, earned MBA and MS degrees, received an honorary Doctorate, founded 2 Silicon Valley technology companies and directed businesses in South Africa, Europe, and the Middle East. He was president and founder of a venture capital firm capitalized by Ewing Kauffman, past owner of the Kansas City Royals.