Socratic Questioning: How to Think Deeper

“I know you won’t believe me, but the highest form of human excellence is to question oneself and others.”
– Socrates

Most people's thinking is shallow. They read an article online about a hot new stock, deciding right then and there to buy it. They take fitness advice from their average-joe coworker who isn't in great shape. There's a plethora of awful information out there in the form of articles, videos, books, word-of-mouth, and more, and people take it because it's convenient.

Such shallow thinking might be fast, but it's a poor way to develop an understanding of any subject matter. How can you be sure that the information you've gotten is solid? What's worse is that shallow thinking can often lead to trouble. In our examples above, it could have been big financial losses in the stock market or personal injury with the wrong fitness routine.

To avoid such mistakes, you must learn to think deeper, to fully understand the ideas that you're thinking about and use them in the most effective way. There are many new fads out there about deep thinking, like special meditation techniques or unnatural drugs, but we don't want any of that. What we want is a consistent, natural strategy for thinking deeper, ideally one that has been proven to work well. In this regard, there is no better method than Socratic Questioning.

Socratic Questioning

"I cannot teach anybody anything, I can only make them think."
– Socrates

The deep thinking technique of Socratic Questioning is named after the Greek philosopher Socrates. Socrates is known today as the father of Western Philosophy, having laid the foundation and indeed influenced many prominent philosophers with his ideas: Plato, Aristotle, Carl Jung, David Hume, Friedrich Nietzsche, and others.

Socratic Questioning was one of Socrates's favourite techniques for teaching his students how to think deeply. It works as follows.

During class discussions, Socrates himself would play the role of an ignorant person. Then, he would ask his students very simple, naive questions, almost like a curious child would. With each additional question, Socrates would probe deeper and deeper into the subject being studied to get down to the important details. This forced the students to think very deeply about their subject matter, thus developing a more thorough understanding of it.  

Let's look at an example. Imagine that you are a student who is (or thinks they are) interested in becoming a lawyer. An exchange between yourself and Socrates might go something like this:

Socrates"Why do you want to become a lawyer?"

You — "Because lawyers make a lot of money"

Socrates – "Do all lawyers make a lot of money?"

You – "Some do some don’t, it depends if they are good at it"

Socrates – "Well then, what would make someone good at law?"

You — "They would be very interested in the field of law and like to work a lot"

Socrates – "Are you very interested in the field of law, willing to work many hours each day in it?"

You — "Well I don’t really like working many hours each day..."

This was a simple example but it illustrates the power of Socratic Questioning quite well. In the end, we discovered a very clear and concrete reason why being a lawyer wouldn’t be the right fit. And it was relatively easy, our friend Socrates just had to keep asking us questions!

The best part is that you don't need a wise old teacher to do this; you can do it all on your own. You can pretend to be both the student and the teacher by asking yourself continuously deeper and deeper questions. Thus, you explore and deeply understand any subject that you want. Just keep asking yourself questions until you get to the bottom of it.

Techniques for Applying

The key with Socratic Questioning is to keep going deeper until you get down to the very root of the subject. There are a few techniques that you can use to help you ask better, more critical questions:

#1 Clarify and Explore

Clarify and explore your thinking by askings yourself why.

  • "Why do I think this way?"
  • "Why do people say this?"
  • "Why is this considered a good or bad idea?"

It forces you to push further down the rabbit hole and get to the concrete reason(s) behind things.

#2 Challenge Assumptions

We make assumptions to help simplify our problems. But we must be careful to not let them make us overlook key information.

  • "Will this always be the case? 100% of the time?"
  • "When would this assumption fail?"
  • "What would happen if we changed this variable that we think is constant?"

Breaking assumptions will help you to think outside the box and not miss any key information.

#3 Provide Evidence

Humans are emotional creators so it's not uncommon to hear arguments without any rational or concrete evidence. We must force ourselves to bring evidence to the table to validate our ideas.

  • "Why do people consider this to be true?"
  • "What data or other tangible evidence backs up this claim?"
  • "Is there any counter-evidence that can break this claim?"

Claims must always be backed up by real-world evidence if we are to deemas true. Emotions should never drive conclusions.

#4 Look for Alternatives

It's easy to get stuck with tunnel vision from your own perspective. A helpful exercise for thinking outside the box is to look for alternatives.

  • "What other options are there in this case?"
  • "Are there any counter-arguments?"
  • "Are there any other possible outcomes or situations?"

Looking at ideas from different angles helps you to understand them more holistically and discover even more new ideas.

#5 Checking the Chain Reaction

A single event or idea can have downstream effects on other events or ideas. It's important to think about such chain reactions to develop a comprehensive understanding of the space.

  • "If this idea is true, then what other ideas must also be true?"
  • "How does this property of the system affect the others?"
  • "Let's say that event A happens; what other events are likely to follow?"

Chain reactions help you naturally explore the entirety of the subject at hand to see the multi-order implications of things.


Examples are always helpful for seeing real applications of techniques. Here are a couple of fun examples to give you an idea of what Socratic Questioning looks like in action. Note that these are just examples for illustration, not facts. You can do your own Socratic Questioning to learn about any subject you want!

#1 Learning About Investing

  • Investing in real estate is the best way to make money – Why will it make money?
  • Because real estate gives great returnsIs that always the case though? Or just in specific circumstances?
  • In the long-term, real estate has solid returns in most markets – OK, so that means we'll have to keep an eye on which market we go for. But we originally said real estate is the best way; do we have evidence to back up that claim?
  • There's lots of data showing that real estate gives great returns, although there are other assets such as stocks or fine art that also provide great returns – So it seems that real estate can be a great option, but it's not the only one, and may or may not be the best one depending on the situation

#2 Working from Home

  • Work from home is better than the office! – Why do you say that?
  • I save a lot of time not having to commute – How much time?
  • About 2 hours a day – That's good. But are there any downstream effects? Are you advancing in your career working from home?
  • Well, it's still early days, hard to tell – Why is it hard to tell?
  • Because I won't know until I get a raise or promotion – Is there anything you can do to mitigate this? Or to ensure that in any case, you can continue to advance in your career?
  • Maybe speaking with my manager or going to the office every once in a while for a check-in – Now we have a balance

Further Reading

Practical Ways to Apply Philosophy in Life

The 3 Best Methods to Learn New Things According to Psychology

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