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Learning to Love the Socratic Method (vs. just being an asshole)

Midjourney image for the prompt, “Socrates arguing with a single robot in ancient greece”

One of my least favorite subjects in college was Philosophy. I was a hard science major, after-all, and philosophy was a boring waste of time.

I also went to a Catholic, liberal arts college where I had to take at least 3 philosophy courses?—?a requirement for every student.

Luckily, there were a few teachers who made Philosophy very easy by basically making them history lessons, where I just had to regurgitate the basics.

But like most ill-conceived, hard opinions one forms in their youth, 20 years later I’m kicking myself for two things:

  1. Not taking more challenging/interesting philosophy teachers
  2. Not taking philosophy more seriously

In the past few years, thanks in part to Ryan Holliday, I’ve gotten more interested in philosophy?—?primarily the Stoics.

But I’m also learning, surely not for the first time, how impactful ancient philosophy has been on government, society, and leadership.

As I read some of Holliday’s work and listen to political podcasts, lots of names come up that are vague memories from an era where I thought I already knew everything I needed to know.

It’s a shame, really, because the one philosopher I remember the most about is Socrates, who had a core belief that true wisdom comes from recognizing our own ignorance.

And today, I’m drawing from his teachings to better deal with conflicts in real life, and online.

The Socratic Method in Online Debate

Lately I’ve been thinking a lot about Socrates with respect to how I respond to spammy, unscrupulous, or just plain disagreeable people online.

My approach has generally been curt, direct, somewhat mean responses. But after getting a taste of my own medicine recently?—?I’ve been doing more cold outreach to build relationships that hopefully turn into professional engagements?—?I started to wonder if there’s a better approach to dealing with those kind of messages.

For what it’s worth, I don’t think I’m being spammy, unscrupulous, or pushy. But that’s really in the eye of the beholder.

I feel like a better approach might be the Socratic Method. Here’s how Chat-GPT distills it:

  1. Positing a question or problem.
  2. Challenging assumptions and perspectives.
  3. Analyzing the implications of arguments.

Socrates would use this approach in debates to get people to contradict themselves, while at the same time getting them to examine their own understanding of the subject at hand.

So how could I use this online for spammy, unscrupulous, or just plain disagreeable people?

My instinct has always been to fire back at people who act a certain way online?—?to “burn” them and move on.

As I write this, it already kind of feels like I waste my time…because the truth is very few people have been convinced by a tweet to change their mind.

But the Socratic Method allows for the interlocutor (someone who engages in debate?—?I just learned that word!) to give their own answers, potentially contradict themselves, and hopefully change their mind/approach.

I mean…it’s kind of like Inception.

How This Might Play Out

For example, someone recently reached out to include me in a “Top 15 Inspiring Podcasters” article for a well-known publication?—?which is an honor, until they told me they want $800 for inclusion.

I responded by saying, “So it’s more like 15 Podcasters who paid us to be listed.”

That’s kind of an asshole response, even if it is true. In other words, it’s not changing hearts and minds.

If I had taken the Socratic approach, the conversation may have gone something like this:

Joe: “Does this imply I’m included in the article already, and I’d pay for a higher slot, or that I’d pay to be in the article? If it’s the latter, what happens if you don’t find 15 people to pay you?”

Writer: “You will have to pay in order to get featured in this article. This is paid PR. We do research and have strict criteria for inclusion. We’ve never had unpaid slots.”

J: “Oh that’s interesting. How do you let readers know that the people included in this list have paid to be on the list?”

W: “We don’t disclose. This is still a researched, well written article. We use the payment as a filter out the vast number of podcasters we could include on the list.”

J: “ Oh…hmm. What does the publication think about this?”

W: “We work with them regularly and they have not addressed this as a problem.”

J: What other publications have you worked with? Anyone like the NYTimes, WSJ, LA Times, etc.?”

W: “No. They don’t want these types of articles from us.”

J: “Why not?”

W: “They require disclosures.”

J: “Why do you think that is?”

W: “…”

Now, I fully recognize that a grifter (such as the folks in this example above) is always going to grift, and this might not be effective.

But presenting the challenge and being able draw out the conclusion instead of explicitly stating it tends to be a more effective way to argue in general.

It’s an approach that takes you from being an aggressor to being more of a teacher.

And while Socrates still annoyed people with this approach (they did call him the “Gadfly of Athens), if Plato’s works are to be believed, it was an incredibly effective approach to debate.


Learning to Love the Socratic Method (vs. just being an asshole) was originally published in Thoughts from Joe Casabona on Medium, where people are continuing the conversation by highlighting and responding to this story.

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