Steven Molo on Forum Sensitivity, Risk, and Building a Courtroom Advantage

Hello and welcome to today's episode of The Litigator's Edge, the podcast where innovative attorneys reveal the strategies that have transformed their legal practice. My name is Aniket Sawant and I'm co-founder and CEO of Threadeo. My guest today is widely recognized as one of the country's leading courtroom advocates, a litigator described by Chambers as dazzling, fearless, and a force to be reckoned with.

He is a founding partner of MoloLamken, a firm he launched in the midst of the 2009 financial crisis with a bold vision to create an elite litigation boutique focused on results rather than process. Whether he's representing foreign sovereigns, global corporations, or inventors in high-stakes IP disputes, he brings a rare combination of Chicago prosecutor grit and Supreme Court intellect to the courtroom. It's my pleasure to welcome Steven Molo to the podcast. Welcome, Steven.

Thank you very much. I'm so delighted to be here today.

It's my pleasure. As you know, I love to ask each of my guests to share either a fun fact about themselves or a cringe joke. Which will it be for you?

I don't go watch for cringe jokes when they're about me. I grew up on the south side of Chicago in a neighborhood that was probably two miles from where the current Pope grew up. So, I guess that's a fun fact.

That's great. Well, that actually is a great segue into my next question. I really do consider every guest who makes the time to be on this podcast as a superhero, and every superhero has an origin story. I would love for our audience to learn yours.

So, I grew up on the south side of Chicago. Neither of my parents had gone to college. I went to college and law school at the University of Illinois, which is about 130 miles south of Chicago. I began my career in Chicago as a prosecutor, and then was with Winston & Strawn for about 16 years. I was a senior litigation partner and a member of the executive committee at a pretty young age, and then I was recruited by Shearman & Sterling to come to New York and join the litigation practice there.

I was there for five years and then formed MoloLamken in October of 2009. Along the way, I was able to get a great deal of experience in the courtroom. I spent a lot of time trying cases and arguing appeals. In the first almost four years that I worked for the government, I had extraordinary opportunities for a young lawyer to be involved not just in routine things like a preliminary hearing, but cases that were tried generally two days to two weeks. I got a chance to understand a little bit about trying cases to a jury as much as you can understand when you're 25 or 26 years old.

Were there any formative or memorable matters that you had the opportunity to be a part of in that early stage of your career? And at a high level, what would you recommend for our audience regarding the difference between arguing your point in front of one judge versus multiple judges?

Instead of three one-thirds of a judge, is the way some of my friends on the court will say. As far as formative things along the way, I've always been someone who really has tried to gain something from every representation that I have, whether it's a large multi-party case involving reams of evidence and data, or something much simpler. I enjoy the advocacy itself. I enjoy being in a courtroom.

But in terms of early experiences, the very first case I tried, I hadn't been admitted to the bar, but I had a provisional license in Illinois at the time to appear for the government. Within the first year, I was the principal author of a brief in a case that went to the Supreme Court of the United States and resulted in a 9-0 reversal in our favor. I didn't argue that case, but I was very much central to the drafting of it. It's those sorts of experiences that inform your thinking going forward.

That's fantastic. You were representing the government, so you must have been in your 20s when this happened?

Exactly. For that particular case, I think I was 26 years old. It's that opportunity to get on your feet to argue before judges, to make mistakes. If you're not making mistakes, you're not learning.

I remember a very early cross-examination that I did where a witness gave an answer completely the opposite of what I was looking for. I looked over to my trial partner with a horrified look on my face. When I sat down, he said, "You know, when you take an arrow through the heart, you don't want to let anybody know that and don't let it show so obviously."

Going back to the second part of something you said—the difference between arguing in front of one judge versus multiple judges. Just a quick high-level take on that?

One of the things that I consistently preach to our team is the importance of forum sensitivity. Writing the perfect brief for the Supreme Court of the United States is one thing. Writing a letter to a magistrate who's dealing with 400 cases on her docket on an issue relating to a discovery dispute is quite another. Being attuned to who you're communicating with is central to successful communication.

"The number one foundational principle of successful communication is to be empathetic. Empathy means putting yourself in the position of the person you are trying to persuade."

Be aware: is this a court that tends to be an active, hot bench, or is it a court more inclined to just take presentations? With courts of appeals where there are three judges, you may not know who your panel is until the morning of the argument. So you're writing more for the court, not any single judge.

As to individual judges, if you're going to appear before a magistrate judge about a discovery dispute, consider what else that judge has going on that day. Are they in the middle of a trial? How much time did they really have to think about this? Did you provide a pathway to the outcome that you're looking for, and have you offered practical solutions, not just some theoretical solution?

That's such wonderful advice, Steven. You highlighted thinking about whether this is the appropriate procedural issue, and what really stood out to me was using "think about the judge and what their day might be looking like" as an input.

Exactly. Where does this case fit within that? Are you swinging for the fences on something where there's absolutely no chance you're going to hit the ball out of the park, or are you being more thoughtful about giving them a pathway to what it is that you're asking for?

Obviously, you've received multiple accolades for your performances in the courtroom. Part of that is natural ability, but I'm sure part of it is also training. What advice would you give to someone who wants to grow and become the trial lawyer that you are?

Get on your feet in any way that you can. It really doesn't matter if it's a case in traffic court or a case in the Supreme Court. It's important to practice that art of persuasion.

The National Institute of Trial Advocacy (NITA), which I've taught at from time to time, is a phenomenal program. All of our associates, when they come to the firm, take both their deposition training course and their trial practice course to get that fundamental foundation.

Doing the best you can to master the rules of evidence is critical. Because so few cases get tried, so few lawyers really have experience trying a lot of cases. People ignore the rules of evidence. Being a master of the rules of evidence is a tremendously important tool to being successful as an advocate—and not being afraid to take calculated risks.

The book you co-wrote, Your Witness on Cross-Examination, is considered a benchmark. In an era where attention spans are continually shortening and people have "TikTok brain," how has the fundamental art of persuasion changed? How do you keep a jury dazzled?

It goes back to the idea of forum sensitivity and empathy. Understanding that people do have very short attention spans and not overburdening them with too much information. Having the courage to edit—which very few lawyers do. When it comes to trial, they want to do more, more, more. Sometimes less is better. You must create vehicles for delivering information that are digestible, understandable, and memorable for the jurors.

Switching gears a little bit. In 2009, at the height of the financial crisis, you decided to co-found your own law firm. What was the decision behind that? How did you know it was the right time?

I was probably always a bit more entrepreneurial than most of my partners at the firms I had practiced at. I felt that had I not done this, it would have been something I wondered about the rest of my career.

2009 was a terrific time. I had met Jeff Lamken a few years earlier. Jeff is a phenomenal lawyer, and his specialty really is in appellate advocacy. We had a shared set of values and ideas about how clients are best represented. At that time, there was a huge amount of disruption, and disruption is a litigator's friend.

Clients were rethinking their legal spend, looking for ways to spend less money, yet the problems they had were growing. We started out relatively early in the litigation boutique space compared to now. We started with a very clear vision and a detailed strategic plan. They say execution eats strategy, but we've been fortunate enough to be persistent for 16 years, and the results have spoken for themselves.

Your firm handles civil, criminal, and regulatory matters representing both sides of the "V"—plaintiffs and defendants. How does that dual perspective sharpen your instincts as an advocate?

When you start out prosecuting cases, obviously you're akin to a plaintiff. But in a large law firm, you're doing mostly defense-side work. One of the fundamental beliefs that Jeff Lamken and I share is that the best lawyers are creative.

"Creativity is promoted by seeing a lot of things... The things I've learned from plaintiff's work, I apply to the defense side. And the things I learned on the defense side, I apply to the plaintiff's side. It just makes you better."

We do a lot of plaintiff work because we like it. It's interesting, and it can be lucrative, despite the fee arrangement risks. But defense work finds its way to us as well, and we do no less a thorough and zealous job there. It gives you a better perspective on everything.

Obviously, your firm is a boutique, which means you might be smaller in raw numbers relative to big law firms. How do you leverage technology to sort of be on par and deliver results against a firm that might have five times the number of associates?

In many of the ways you would expect: using the best tools in electronic discovery, and trying to maintain flexibility. We try to be nimble and not overcommit to anything, so we don't miss the next thing that may come along. People in the firm are pretty tech-savvy, and we are experimenting with some of the AI tools out there now. I think that will have a significant effect as time goes on.

Where do you draw the line in terms of what you allow technology to do versus where the human, empathetic advocate has to step in?

We're still in a relatively nascent stage with AI in the legal world. Over time, the quality of those tools and their ability to approach problems with an empathetic perspective is going to increase at exponential speed.

But I'd like to think there are still things a trial lawyer will be able to do. For instance, understanding that you're in rural Oklahoma, and knowing that while the statistics show one approach, given this particular judge, a slightly different approach is called for. That's something developed through judgment.

Even once we reach AGI, the computers won't necessarily possess that same level of empathy and judgment required to achieve a successful outcome. The margin between success and failure can often be razor-thin. Any legitimate advantage I can get, I'm looking for. But that judgment is where lawyers will still add the greatest value.

For an earlier career attorney who's looking to essentially be not just a great legal scholar but a great trial lawyer, what's some advice you would give them?

Get on your feet. Work at an organization that lets you do that. I spent time this morning on the phone regarding a matter that was sensitive for a client, but it wasn't going to generate a huge fee or require me to necessarily be in court. In a different firm we would have turned this down. But I saw it as an opportunity for one of our associates to actually get into court, conduct the examinations, and make the argument.

My view is that ultimately that will help our bottom line because it will get those lawyers better, sooner. Work in a place that appreciates that and puts a premium on it.

For the GC or in-house counsel facing a significant "bet-the-company" type crisis, what is the first thing that they should think about when they need to choose outside counsel?

Does the lawyer understand what your business goals are? The first question we ask every client in every matter is: What does success look like? Just because you've been sued doesn't mean you've really thought through the outcome you want.

Second, find a team with a broad vision. We refer to ourselves as advocates first, subject-matter specialists second. Our skill is the skill of persuasion. You need someone who can look at the playing field and not just see it in a narrow way.

Lastly, having lawyers that are willing to take calculated risks. Lawyers by nature are very conservative and risk-averse. Very little is achieved throughout humankind without taking some risk. Make sure whoever you have isn't just somebody who's going to parrot back the most conservative approach. You want someone willing to push back if a reactive approach has a bigger long-term negative consequence.

That's incredible. Final question for you: is there a question I should have asked you, but I didn't?

Not really. A lot of people ask—I have a case that's going to trial for Elon Musk in May, and that's an interesting matter, but a lot of it has been public and we're obviously getting ready for that with a summary judgment hearing coming up soon.

But the variety of things that I do continues. I had a big contract dispute between two pharmaceutical companies in an ICC arbitration, and a trial in Delaware over the valuation and sale of a very large oil company owned by a government. Hopefully, this will continue to let me keep learning and having fun doing what I've done my whole professional life.

That's amazing. Steven, I certainly learned a lot and had a lot of fun speaking with you today. Thank you for your time and your insights.