GENCO MEMO-11-25-24: What Book I Recommend to Start With When Wanting To Become More Persuasive

An Image of a print as one walks out of our Firms’s main Conference Room

Recently, one of our associate attorneys came to me and asked, 'What books should I study to get better as a trial lawyer?'

It’s a question I love to hear, because it tells me they understand that becoming an effective advocate is a journey—one that requires continuous learning and reflection.

Without hesitation, I told them to start with Cicero.

As a trial lawyer, my craft is persuasion.

I’m paid to convince judges, juries, and opposing counsel through words, logic, and presence.

But persuasion is not a modern art. Its foundations were laid centuries ago, most notably by Marcus Tullius Cicero, a Roman statesman, orator, and philosopher whose techniques are as relevant in the courtroom today as they were in the Roman Forum.

When anyone comes to me serious about sharpening their persuasion skills, I recommend starting with How to Win an Argument: An Ancient Guide to the Art of Persuasion by Cicero, edited by James May.

This book is a distilled collection of Cicero’s greatest lessons on rhetoric, adapted for modern readers. It bridges ancient wisdom with the realities we face in courtrooms every day.

Here’s my summary of some basic takeaways from the book.

---

First, Who Was Cicero, and Why Does He Matter?

Cicero (106–43 BCE) was Rome’s most celebrated lawyer, orator and a prolific writer on rhetoric and philosophy.

As a lawyer and statesman, he argued high-stakes cases and navigated Rome’s treacherous political arena. Cicero’s ability to craft arguments that swayed powerful audiences made him a legend.

What sets Cicero apart is his holistic approach to persuasion. He believed that winning an argument required more than logic; it demanded emotional resonance and the speaker’s credibility. These principles—logos, pathos, ethos—are the foundation of rhetorical theory and remain the bedrock of effective advocacy.

Cicero’s works have influenced some of history’s greatest minds, from St. Augustine to the Founding Fathers.

For trial lawyers, his writings are a masterclass in persuasion, blending intellectual rigor with practical techniques.

This is where I started many years ago.

---

What Makes May’s Book Essential for Trial Lawyers?

James May’s How to Win an Argument is a curated guide to Cicero’s rhetorical wisdom. In other words, May selects passages from Cicero’s most important works, including De Oratore and Brutus, and provides commentary to make them accessible for contemporary readers.

The book also emphasizes practical strategies rather than abstract theory, making it perfect for lawyers who want actionable insights.

May organizes the material around key aspects of rhetoric, such as:

• Crafting compelling arguments.

• Engaging your audience emotionally and intellectually.

• Responding to opposition effectively.

• Delivering your message with style and presence.

The result is a concise, readable manual that captures the essence of Cicero’s teachings and shows how they apply in the modern world.

---

Some Practical Takeaways for Trial Lawyers (And Anyone Wanting the Power to Persuade Others)

Here are some of the key ideas from the boor:

• Know Your Audience
  Tailor your argument to the jury, judge, or opposing counsel. Cicero taught that persuasion hinges on understanding your audience’s values, emotions, and biases.

  • For example, when addressing a jury, consider their likely background and experiences—use relatable stories that evoke empathy. If speaking to a judge, focus on logical clarity and adherence to legal principles, as judges often value structure and precedent. When negotiating with opposing counsel, appeal to their practical interests, such as saving time or reaching a compromise that benefits both sides. By aligning your approach with what matters most to your audience, you increase your chances of persuading them effectively.

• Structure Your Arguments Strategically
  Use a clear framework: start strong to grab attention, present your case logically, refute counterarguments, and end with a memorable conclusion.

  • For example, you can use the Monroe’s Motivated Sequence, which involves: (1) grabbing attention, (2) establishing the need or problem, (3) presenting a solution, (4) visualizing the benefits, and (5) calling for action. Another effective framework is the IRAC method—Issue, Rule, Application, Conclusion—which is particularly useful for structuring legal arguments clearly. Additionally, you can use the Problem-Solution-Benefit approach, where you define the problem, explain your solution, and highlight the benefits to the audience. These structured methods help ensure that your argument flows logically and persuasively.

• Establish Credibility (Ethos)
  Before you argue, show you’re trustworthy. Your integrity and authority are as persuasive as your evidence.

  • For example, establish your credibility by sharing relevant experience or qualifications early in the argument. If you’ve handled similar cases successfully, mention it briefly to demonstrate your expertise. You can also build trust by acknowledging valid points from the opposing side, which shows that you are fair-minded and focused on the truth rather than simply winning at all costs. Also, use clear, honest language—avoid exaggeration or making promises you can’t keep, as I have found that these can quickly undermine credibility.

• Appeal to Emotion (Pathos)
  Facts alone rarely win cases. Connect with your audience on an emotional level—whether it’s anger, empathy, or a sense of justice.

  • When arguing a wrongful death case, evoke the sense of loss and injustice by sharing personal stories about the victim's life and the impact on their family. In a case involving negligence, emphasize the anger and frustration of those affected by the defendant's carelessness. Alternatively, when defending a client who has made a genuine mistake, appeal to the empathy of the jury by highlighting the remorse your client feels and their efforts to make amends. Emotional connection can humanize your argument and make it more compelling to those listening.

• Use Silence and Timing
  Cicero believed delivery was as important as content. Pause strategically to let key points sink in and convey confidence.

  • For example, when making a critical argument, pause after presenting a strong piece of evidence to let it resonate with the audience. This moment of silence allows the gravity of your point to be fully appreciated. Similarly, when refuting an opponent's claim, a deliberate pause afterward can emphasize your certainty and leave room for the opposing side's argument to lose momentum. Pausing can also help manage the pacing of your speech, giving the impression of careful consideration and authority.

• Prepare for the Opposition
  Anticipate the other side’s arguments and dismantle them before they gain traction. Cicero excelled at preempting counterarguments.

  • When preparing a case, I make a list of potential objections that the opposing side might raise. I address these proactively within my presentation by offering counter-evidence or alternative interpretations before the opposition even brings them up. This technique not only weakens the impact of their arguments but also positions me as thorough and prepared. Cicero often used this method by framing potential objections as misunderstandings or oversights, allowing him to confidently dismiss them while reinforcing his own narrative.

• Practice Style and Wit
  Language is your tool. Cicero used humor, metaphors, and striking imagery to make his speeches unforgettable.

  • Cicero often used humor to disarm opponents and create a connection with his audience, making his arguments more relatable. He also employed vivid metaphors, like describing political corruption as a disease eating away at the republic, which helped his audience visualize abstract issues in concrete terms. Striking imagery, such as likening the plight of the Roman people to a ship lost in a storm, evoked strong emotions and made his message resonate. Incorporating these elements can make your arguments more memorable and impactful.

---

That is all.

Enjoy this Thanksgiving week.

---