Eight Books to Argue Well

Eight Books to Win an Argument

Why do people share quotes?

There's a nugget of truth that seems to hold, regardless of their context. Their echo stretches over time. Take the idea of service, for example. Being on the receiving end of the extra mile appeals. It paints a vivid picture.

It takes work to figure out the place where a word is most effective. The odds increase in your favor if you're using a proven structure to build the image.

“Anyone who conducts an argument by appealing to authority is not using his intelligence; he is just using his memory,” is itself a good argument, in a small space. Leonardo Da Vinci was a master at observing and documenting human behavior.

Memory is one of the five canons of rhetoric or phases of developing a persuasive speech as first codified in classical Rome. The others are invention, arrangement, style and delivery. Now you're probably seeing why effective comedy is hard.

The truth is we'd all like to be more persuasive, to say the right thing at the right time and turn a situation in our favor. I'm not talking about social media, though learning to argue well can help there, too.

No, I'm talking about wins closer to home. Kids not following the rules? Boss not listening to you? Need to solve disagreements with your partner? Just like many writers and leaders have done in the past, you can learn to structure what you say and write to get more of what you want.

Words are powerful when you can enlist them to create a desirable picture in the other person's mind.  The effort you take to figure out what makes an argument persuasive helps your words stand up for you.

The art of persuasion is as old as human kind. Here are eight books worth considering if you're working on your skills.

The classics


Rhetoric by Aristotle is the foundational book on the art of persuasion. The philosopher outlines practical and aesthetic elements and their proper combination in an effective presentation, oral or written.

Aristotle analyzes rhetoric and finds that it has 3 main applications:

  • judicial, or talking about past events
  • deliberative, or talking about future courses of action
  • epideictic, or talking about the present, which is mostly connected with formally praising and blaming people

Most useful ideas: the role of language in achieving precision and clarity of thought. In terms of persuasion, how you say things is as if not more important than what you say.

Aristotle was a Greek philosopher and polymath during the Classical period in Ancient Greece. Taught by Plato, he was the founder of the Lyceum, the Peripatetic school of philosophy, and the Aristotelian tradition.

“If there are two definitive features of ancient Greek civilization, they are loquacity and competition.”


How to Win an Argument: An Ancient Guide to the Art of Persuasion by Marcus Tullius Cicero, a master of the craft. The book combines rhetorical wisdom with passages from Cicero's legal and political speeches to show his powerful techniques in action.

Most useful ideas: the invention and arrangement of proofs,” and the use of appropriate language. Appropriateness involves choosing: the scale of the speech, its tone, and its overall approach in a way suitable to the context and audience.  

Marcus Tullius Cicero (106 BC – 43 BC) was ancient Rome’s greatest orator, Roman philosopher, statesman, lawyer and political theorist. During his time, verbal persuasion was an important part of daily life. He wrote several important books that helped teach his fellow citizens to, “Plan and execute a successful speech in public, in other words, to win an argument.”

“Once you have surrounded the entire place with the nets of your thought, at least if practical experience has sharpened your skill, nothing will escape you, and everything that is in the subject matter will run up to you and fall into your hands.”

The pragmatic


The Elements of Rhetoric. How to Write and Speak Clearly and Persuasively by Ryan N.S. Topping covers the fundamentals of logic, grammar, how to recognize and avoid logical fallacies, the wisdom of studying the classics, and so much more.

Most useful ideas: it's an excellent self-examination tool. As you practice, observe what you do with your body as well as the words.

Ryan N. S. Topping is a Fellow of Thomas More College of Liberal Arts. A native of Saskatoon, Canada, he earned his M.Phil. and D.Phil. in theology from Oxford University.

“Moderns maintain a peculiar relationship with rhetoric. We no longer teach it to our young, nor demand it of our wise. What since ancient Athens was considered an essential skill for a free citizen has now largely been consigned to hucksters and to the tarmacs of used car dealerships. The tragedy is that we abandoned the art on purpose. About the same time the Russians flung Sputnik into space, in the name of progress American, Canadian, and British educators tossed the old grammar and style books onto the intergalactic rubbish heap of history. The past was trashed. In a scientific age, so the reasoning went, questions of philosophy, of beauty, of sex, of God, could be set aside in favor of technological solutions. The science was settled. Just the same, the timing couldn’t have been worse.”


Language in Thought and Action by S.I. Hayakawa. Now in its fifth edition, this book discusses the role of language in human life, the many functions of language, and how language—sometimes without your knowing—shapes your thinking

Most useful ideas: verbal info is like a map that gives you an understanding of the real world. When you're equipped with accurate maps, you're prepared for living a more successful life and reaching your goals. When the map you have is inaccurate, that's when you run into trouble.

Samuel Ichiye Hayakawa was a Canadian born American academic and political figure of Japanese ancestry. He was an English professor, served as president of San Francisco State University and then a United States Senator from California from 1977 to 1983.

We all inherit a great deal of useless knowledge, and a great deal of misinformation and error, so that there is always a portion of what we have been told that must be discarded. It should be noticed that there are three ways of getting false maps of the world into our heads: first, by having them given to us; second, by making them up for ourselves by misreading true maps; third, by constructing them ourselves by misreading territories. But the cultural heritage that is transmitted to us—our socially pooled knowledge, both scientific and humane, has been valued principally because we believe that it gives us accurate maps of experience.

The illuminating


How to Argue and Win Every Time by Gerald Spence. Set up a winning argument providing the best evidence and the best logical case. It's about getting what you want as you communicate with others.

Most useful ideas: if you know a lot about a topic and are arguing with someone who may not be informed, yet is entrenched in a belief/opinion, take a step back and find a constructive way to educate them. Think about how Vinny did it in the courtroom in My Cousin Vinny.

Gerald Leonard Spence is a semi-retired American trial lawyer. He is a member of the American Trial Lawyers Hall of Fame. Spence has never lost a criminal case either as a prosecutor or a defense attorney, and has not lost a civil case since 1969.

Spence's laws of arguing well:

  1. Everyone is capable of making the winning argument.
  2. Winning is getting what you want, which also means helping “others” get what they want.
  3. Learn that words are a weapon, and can be used hostilely in combat.
  4. Know that there is always a “biological advantage” of delivering the truth.
  5. Assault is not argument.
  6. Use fear as an ally in pubic speaking or in argument. Learn to convert its energy.
  7. Let emotions show and don't discourage passion.
  8. Don't be blinded by brilliance.
  9. Learn to speak with the body. The body sometimes speaks more powerfully than words.
  10. Know that the enemy is not the person with whom you are engaged in a failing argument, but the vision within yourself.

The interesting


Great Debates: 24 of the Most Important Questions in Modern Society by Luan Hanratty is a book for Teachers of English as a second language and EAP.

Notes: the debate list includes many modern dilemmas like nature or nurture, globalization, healthcare, distribution of wealth, friends and enemies, social order, reciprocity, free market, commerce and culture.


A Grammar of Motives by Kenneth Burke was published in 1945 as the first volume in a proposed trilogy On Human Relations that was never completed. The second volume A Rhetoric of Motives was published in 1950. There are several pretenders for the third volume, but A Symbolic of Motives was never written.

Notes: both books are dense and rich with ideas. But you'll have to work to extract them. Thinking is hard work.

Volume I: develops the dramatist metaphor / method in general, and the basic terms of analysis with the dramatistic pentad: Act, Scene, Agent, Agency, and Purpose. With this construct, he gets down the basic process of human thought.

Volume II: In making his argument, Burke draws on numerous examples from literature (e.g. Milton and Henry James), popular culture (e.g. pneumatic tubes in grocery stores), politics (e.g. Nazi propaganda and burgeoning Cold War tensions), and philosophy (e.g. Plato and Kierkegaard).

Kenneth Duva Burke was a literary theorist, as well as poet, essayist, and novelist, who wrote on 20th-century philosophy, aesthetics, criticism, and rhetorical theory. He is best known for his rhetorically based analyses of the nature of knowledge and for his views of literature as symbolic action, where language and human agency combine.

“The use of language as a symbolic means of inducing cooperation in beings that by nature respond to symbols.”


Practice really does make better.

It doesn't need to be complicated or risky to do it. You can start seeing a difference with simple things. Next time you have a complaint about a service, try taking a step back and seeing your note as an opportunity to help the company do business better.

Last week I helped a friend write a letter for her sister. It was a delicate topic to approach with a person who often just explodes. In cases like that, you want to structure your note in a way that clearly separates the issue from emotional undertones or judgment. Yet, still communicates you care.

We don't often approach dialogue as an opportunity to negotiate a better relationship. Pity. Arguing well is not a zero sum game. When you know how to examine an issue, you can bridge a gap that helps everyone.


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