I find valuable insights in the Artistothle or Schopenhauer books, which is both fascinating and frustrating, as I'm expecting more modern books to be on the subject.
Another discovery is the books for argumentation for lawyers – seem to be a decent mix of philosophical depth and practicality.
I had hoped to find good books from the debating community, but most recommendations are paper-only from the 80s/90s, or overly focused on competitive debates.
This search for good resources on the fundamentals of argumentation seems to be quite a challenge. Perhaps I can find some good recommendations from the HN community.
"Arguing" invokes thoughts fighting; attacking the other side's beliefs. The natural response to attack is defense, no matter how wrong/incorrect the beliefs may be.
On the other hand, "persuasion" is working together; starting with where beliefs are common; not where they differ. Persuasion doesn't try to force people to change their mind, instead it offers them the opportunity to change their mind. This allows the other side to change their mind on their own.
Most people make decisions (beliefs) based on emotion, then later back them up with logic. So it is usually more effective to work at the emotional level than the logical level.
Finally, probably the most important lesson is not all people can be persuaded. If a person doesn't have even the tiniest desire to change their mind, no amount of persuasion/arguing can change them.
I learned most of this from direct response marketers, the guys who (are madly successful) at getting you to buy things.
This book is based on similar techniques: "Stop your divorce!: How to stop your divorce or lover's rejection ... even if you're the only one who wants to stop it"[1]
I've found the Socratic method to be an effective way to persuade people. Ask questions, figure out why a person believes what they believe. Do your best to "steelman" their point of view, and then share yours. A lot of the time, people just want to be heard.
Argumentation is one path and tactic for achieving an alignment with a group of people. However, framing anything as combative can have some negative tradeoffs.
My experience is that more cooperative tactics like intent listening, questions, and yes-and can help broker a positive alignment with fewer negative tradeoffs.
If you switch mindsets you'll find lots of business books about effective communication, persuasion, and change management.
Good luck!
Critical Thinking: An Introduction to the Basic Skills, written by William Hughes, Jonathan Lavery, and Katheryn Doran.
I'm guessing being able to express what you've learned permissively is the most important part of arguing effectively?
In which case, for the US I'd probably look into ToastMasters (or maybe a debate club if your in a college area)
understanding your counterparts matters more than winning arguments.