If you want to learn more about Cicero's advice on debating, I suggest How To Win An Argument - a collection of Cicero’s writing on argumentation and oratory. The book details his advice on persuasive speaking, building arguments, convincing audiences, and winning debates. The book, while recommended, is only a selection of Cicero’s writing, so I also suggest the original texts.
This post succinctly highlights 5 of Cicero's most important pieces of advice on debate and rhetoric:
1. Rhetoric is Admirable and Open Debate is Indispensable to Free Societies
Here, Cicero reflects on the beautiful ability of speech to change people's minds and how necessary this is to civil society. Of course open debate is paramount in a free society because without it, how else are we to peacefully settle disputes? Without open debate, violence is more likely. Though not explicitly mentioned here, Cicero's position on the importance of debate in free societies is likely informed by his pointed dislike of war, which he considered quite undesirable.
2. Good Character Matters
Cicero is saying here that eloquent sophistry from a person who lacks patriotism and morality is especially dangerous. The rhetorically skilled sophist who lacks wisdom and patriotism, is a much worse citizen and far more unhelpful for society than the principled wise man who simply lacks persuasive speaking ability.
3. Use This Technique to Make Counter Arguments
Here, Cicero notes that arguments can be refuted in several ways: by questioning the premises, by pointing out the the conclusion doesn't follow from the premises, or by pointing out that the structure of the argument itself is a fallacy. Attacking someone's character for example, rather than debating the facts at hand, is a fallacy called ad hominem. That is no way to win an argument and it makes you look stupid.
On the other hand, if someone makes a good argument, in order to win a debate you must counter it with an equally good or even better argument.
4. How You Deliver Your Argument is the Most Important part of Winning a Debate
Putting even a good argument across poorly will make you loose a debate. There are always more tactful, charitable and erudite ways to deliver points which will help convince people that you are correct (and also not an emotionally-driven, illogical maniac).
5. Become a Better Writer to Become a More Skilled Speaker
Cicero is saying that the worst debaters neither read much or write on a given topic. Those who read, reflect on a subject and prepare for debates are better off, but those who read and then also become skilled writers on a topic are surely the best debaters. This is likely because you learn something well by teaching it to others.
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