The doctor is in: Senior attorneys launch ‘Case Doctors’ podcast

Two senior attorneys — John G. Simon and Alvin Wolff — are using their combined 80 years of experience to provide advice to other attorneys live on their podcast, The Case Doctors.

Simon is a managing partner with the Simon Law Firm and Wolff is an attorney with Wolff & Wolff Trial Lawyers. Both attorneys are based in St. Louis. The longtime friends and now podcast co-hosts have known each other for 40 years and frequently turn to each other for legal advice.

In addition to being a fun opportunity to discuss cases with each other, Simon and Wolff said they hope to help other attorneys by putting their experience to good use.

“It’s a way we can give back to the younger lawyers who probably are going to have a difficult time trying as many cases as we have, because a lot of lawyers just aren’t trying cases anymore,” Wolff said.

Missouri Lawyers Media sat down with Wolff and Simon to discuss the podcast, their careers, their thoughts on Artificial Intelligence and their advice for young attorneys.

The changing landscape of the law

Simon and Wolff said they aren’t entirely certain why attorneys aren’t trying cases in court with the same frequency as the years in which they began their legal careers. They said they believe it has to do with the complicated nature of the cases and the ever-growing size of modern case files.

“I was practicing before we had all the electronic transfer of documents and when we asked for documents, they were in a box. We’d get them, copy them and bring them to the office,” Simon said. “And the whole idea was once we have all of these; we can put them all online and it’ll be easier and quicker and faster. And now, instead of one box, there’s the equivalent of 20 boxes because they can send it all to us with the push of a button. It just seems to be way more complicated. Everything takes more time.”

As technology continues to develop and the practice faces the onslaught of generative AI, Simon and Wolff said attorneys should be wary of trusting AI, but that it is a useful tool they use for several aspects of their practices.

“You should be wary about believing anything you get from AI, because you have to check every resource it utilizes,” Wolff said. “I’ve told AI, you’ve given me the wrong answer and it says, I apologize, and it gives me another wrong answer. But a lot of times it’s right. I mean, if I need to get into an area that I know nothing about, I’ll ask AI the question, it’ll give me an answer and then I’ll just go to all the citations and see if it’s correct or not.”

Simon said there are several ways his firm is leveraging AI.

“There are tons of things that we use AI for, mostly generating ideas, generating arguments, getting resources in terms of where to look, how to find experts,” Simon said.

Simon said he doesn’t know what the future of AI holds for the profession. He said he has heard that some people project it will replace lawyers and other professions, and he finds the future of the technology both exciting and unsettling.

“I believe that an attorney doing what we do, needs to learn everything they can about how to utilize AI in whatever shape or form that is,” Simon said. “I don’t know if it’s going to replace lawyers or not replace lawyers, who knows, but I do believe that lawyers who don’t know how to use AI in five years aren’t going to be around.”

Advice for young attorneys

While the technology of the practice has evolved, many of the problems faced by attorneys fall into familiar categories and patterns Wolff and Simon have personally experienced, they said.

The podcast, as of June 17, had three episodes published. Still, Simon and Wolff said they hadn’t come across any questions that really surprised them.

“Everything that’s come in between the two of us, we’ve had an experience similar to it. I haven’t heard one yet that one of us has not had something happen pretty close to what they’re calling in about,” Simon said.

Wolff said he has handled 8,000 legal matters in his 46-year career and noted that when attorneys call or write in with questions, many times their initial problem leads to other related issues. He said the most common problems he hears from younger attorneys are about problem clients. Simon added that opposing counsel is also frequently challenging.

Both attorneys said they learned how to navigate the issues they’ve encountered in their careers by watching other attorneys or asking for help. Their podcast is about offering mentorship on a broader scale to pay that back.

One of the biggest pieces of advice Simon and Wolff had for attorneys at all stages of their careers is to return their phone calls and emails every single day. And they encouraged attorneys to spend extra time checking in and speaking with their clients to build rapport.

Simon and Wolff also cautioned attorneys to know their cases well and shared their personal hacks for doing so.

Simon said he will take a case that has millions of documents and dozens of depositions and condense it down to a 40 or so page summary before the trial. After spending hours memorizing the case, he will step away from it for a few days before coming back to shorten the summary to fit on an index card.

“That index card is everything I want to remember about that case and whether it’s the frame, the theme, the five key documents, whatever it is. The cool thing is, by the time I do that and condense it down to a card in my front pocket, I never look at it. I don’t need to look at it because the case isn’t about all that detail,” Simon said. “It’s about telling a really simple story and letting the jury know why we’re here and what they did wrong, and what the jury can do to fix it or help it and make sure it doesn’t happen again. And I think no matter how complicated a case is, our job is to uncomplicate the complicated.”

Wolff employs a similar strategy and said he tries to get his case down to 25 words.

In the spirit of these two trial hacks, MLM asked Wolff and Simon to summarize their best advice for young attorneys in 25 words or less.

“Return your phone calls, do your homework and go try some cases,” Wolff said.

“I would say that the practice of law is not a sponge bath,” Simon said. “You must fully immerse yourself in the topic at hand and it’s all about Qpreparation. It’s preparation, preparation, preparation.”