In this podcast episode,  Learn how to ask intelligent questions and hold more meaningful conversations with lessons from Socrates. Get the tools and mindset shifts you need to connect with others and be a memorable conversationalist.

Transcript

In today’s episode, we’re turning to one of the most influential minds in philosophy and a master of dialogue for tactics on how to ask intelligent questions and hold meaningful conversations.

The structure for this episode will be 5 lessons broken into 3 parts. First I’ll share the lesson from the philosopher and why it matters. Next, I’ll share the biggest takeaways from the lesson as it relates to improving conversational skills. Last, I’ll share some examples of how you can apply the lesson in your own conversations to have more meaningful dialogue. 

If you think about it, life is kind of like a dinner party I spoke about at the start. How so?  We’re often in close proximity to people who could change our lives in small ways or large ones. But it’s all too easy to glide along the surface, never truly connecting with those we cross paths with. Our colleagues, friends of friends, strangers at events. With these lessons, you’ll be empowered to go a step further in your discussions. 

Alright my dialogue devotees, let’s jump in.

Problem 

I want you to think of the typical questions people ask when speaking with others. What comes to mind? 

• How are you? What do you do for a living? Where are you from? 

These commonplace questions may serve as an entry point but they are by no means going to unlock deeper connections or leave a lasting impression. If you want to reap the intellectual and social benefits of meaningful conversation, you need to approach them differently than the average joe. 

To aid us, we’re turning to someone who could speak for hours on end with friends and strangers alike, posing meaningful questions that philosophers wrestle with to this day. Say hello to Socrates aka the father of western philosophy. Perhaps you’ve heard of him?

Socrates was born in 469 B.C. and lived in Athens where his pursuit of wisdom took him all around the city asking his fellow citizens and students moral and weighty questions like “what is virtue?” To research before this episode, I consulted a few different books. In The Story of Philosophy, Will Durant describes Socrates as someone who “went about prying into the human soul, uncovering assumptions and questioning certainties…”

In short, Socrates was a master of questions and while this ultimately did not earn him popularity with the citizens of Athens (he was put on trial for corrupting the youth and sentenced to death), there are some valuable lessons we can take from this influential philosopher to improve the caliber of our conversations. Only in this instance, we’ll try not to infuriate anyone and get put on trial. Sound good? 

Note on Socrates before we jump in: He never actually wrote down his ideas so what we know of him comes from secondhand accounts from his students like Plato (stay tuned for an upcoming episode on him, btw. We’ll dive into how to be a more persuasive speaker.) So throughout this episode, quotes and lessons from Socrates are not firsthand. 

Still, there’s much we can take away from his life, teachings, and impact on his students that are relevant today, thousands of years later. Reading and learning about this has made me a better conversationalist and I hope it will for you too. 

Let’s dive into the lessons. 

1. Approach each interaction with intellectual humility.

Socrates believed that true wisdom began when you realized how little you actually know. He famously said, “ I am the wisest man alive, for I know one thing and that is that I know nothing.” This story of Socrates visiting the Oracle of Delphi is a famous one. It led Socrates to go around the city, asking some of the supposedly wisest citizens of Athens questions that struck at the core of their society.  He asked:

•  What is justice? What do you mean by virtue?

His practice of ongoing questioning to define terms and reveal underlying beliefs, known as the Socratic method, is widely considered to be his greatest contribution to Western Philosophy. He didn’t proclaim to know the answers but was focused enough in his pursuit of wisdom to ask the questions. 

What does this mean in terms of improving our conversation skills? 

Well, adopting the mindset that you know less than you think is surprisingly beneficial. 

It’s helpful in a number of ways. 

1. One, it lifts the burden (often self-imposed) of feeling like we need to know it all. This posturing is unattractive and it can prevent us from learning. 

Take this example. I was once on a date with a man who was an academic, PhDs very intelligent. I mentioned a columnist by name saying “Have you ever heard of this writer?” He said “Yes, of course, I’ve heard of him. Which was odd because the writer I mentioned is a woman. Immediately I knew he was only pretending to know so that he didn’t come across as ignorant. 

This is a small example but think of all the many ways it extends. If each person in a room is posturing, pretending to know more than they actually do, the milieu is not one of productive discussion but of stagnant dialogue. Relieve yourself from this burden by simply admitting that you don’t know something. You’ll learn much more this way. 

2. Second, this mindset shift provides a great opportunity for you to form a bond with those you’re speaking with. A hallmark of meaningful conversation is that both parties come away having learned something valuable. So rather than blindly nodding your head or changing the subject when someone mentions something you’re unfamiliar with, lean into it. 

Ask questions that lead to deeper revelations. Why do you find that person admirable? What was the significance of that historical event? Will you explain that term you mentioned related to your hobby? I’ve never heard of it. This is a win-win because people love to teach others, especially when the topic revolves around something they enjoy. 

3. Lastly, when you embrace the idea that you know very little, you become thirsty for knowledge, just like Socrates was. In fact, it’s believed he once said that “ There is only one good, knowledge, and one evil, ignorance.” He believed that knowledge was necessary for virtue. The pursuit of knowledge will look different from person to person as different topics/ideas hold our interest. This is alright. The point here is that you should be someone who is genuinely seeking to learn more about the world and about yourself. This makes you leagues more interesting than someone who is complacent does not seek to learn new things. 

What does this look like in conversation? 

Letting go of the need to know it all. You’re speaking with someone and they work in finance. They mention that they specialize in a process that you’re not familiar with, trading on leverage. Instead of letting that term pass by and acting as if you know it, ask “Could you break that down for me? What does that involve?” They get to come across as knowledgeable, you learn something you otherwise wouldn’t have known. 

Inquiring about those who impress you. If you’re in a conversation with others who really impress you, don’t shrink away from the discussion. Instead, strive to learn about their lives and the decisions they made, the influences that shaped them, etc. that allowed them to get to where they are. If they are talking about a business they founded, you can ask why they decided to go into that sector. Was it knowledge? Connections? Circumstance? People generally enjoy sharing origin stories so you can apply this principle in many ways. 

One great question to ask is “who do you admire/look up to?” A similar one is to ask who their favorite authors are. These signal that you are someone who wants to learn more. 

The topic of pursuing knowledge leads us to our next tip for formulating better questions. This one is SO IMPORTANT (you can’t see my notes but it is bolded babes).  Tip #2

2. Enrich your mind to be a better conversationalist

Think about going to the gym. To have a great workout, you need to fuel your body properly. The same principle applies to your mind. If you want to formulate cohesive, meaningful, thought-provoking ideas in conversation, you have to immerse yourself in reading. Wisdom in, wisdom out. 

Socrates urged his students to employ time- a limited resource- immersing themselves in the ideas and writings of wise men. That way, they were familiar with the prevailing ideas of the day and of past thinkers. Imagine how much more depth this allowed them to have when forming ideas and debating with others.

What’s that? You want another quote from Socrates? Well I have one, At least one that may have been said by him. Here goes: 

“Employ your time in improving yourself by other men’s writings so that you shall gain easily what others have labored for.” 

This quote really resonates with me in the information age because we have SO many options of where to turn our attention. But just like Socrates and his students, we have limited time. So it’s important to prioritize nourishing our minds, and seeking out wisdom regularly. 

What does this mean in terms of improving our conversation skills?

I see the goal of improving conversation skills as inextricably linked to improving oneself. In other words, to be a smarter, more interesting conversationalist, you must first be a smarter, more interesting person. And how can we do this? By reading of course. 

The power of reading is difficult to overstate. If you’re big into self-improvement content, you may have heard of Jim Kwik, bestselling author memory coach. On Kwik brain, his podcast, Jim refers to reading as a superpower because it allows you to download decades of wisdom in hours or days. This is so true and something you need to take advantage of. 

So, to sharpen your mind and in turn, your ability to speak with others, make reading a part of your routine. For me, this has meant diving more into philosophy (hence the birth of this podcast) and also reading the classics that have stood the test of time because these address recurring ideas and perspectives that show up time and time again in media, stories, art and of course all these things flow into conversations. 

What does this look like in conversation? 

Knowing enough to ask the right questions. I was a birthday party speaking with a man who told me he was from Myanmar and quickly said, you’ve probably never heard of it. Clearly, he was used to people giving him a blank stare when he shared where he was from. Fortunately, I had read about Myanmar in an article years ago and remembered that the country used to be called Burma. So I said oh yes Myanmar it used to be Burma right? His face lit up and we  continued to chat. I asked him to tell me more about his country. We ended up chatting about other topics that had nothing to do with his country. 

Because I read, I knew a bit more about the topic than he expected and it fostered goodwill with him. We ended up not talking all that long about his country and that’s not the point. The point is that I knew enough to ask a question and continue the convo from there. 

Recognizing underlying ideas. Reading can help you identify ideas and patterns in conversations. Take this story for example. I was at an event in DC with lots of policymaker types. A group of us were in a semicircle and a woman mentioned the importance of examining the purpose of the filibuster. She was saying that it’s important to consider why it was put in place by those before us and deeply think about if we are in the right to do away with it. A man next to me simply responded, so Chesterton’s fence? He had read the idea voiced by Chesterton and immediately knew the woman was suggesting this idea.

Chesterton’s fence refers to writings from GK Chesterton about two types of people who want to reform something. One sees a fence and may wish to do away with it. Another will ask why it was erected. In short, do not remove a fence until you know why it was put up in the first place. 

That conversation stuck with me not exactly because of the content but because of how easily the man recalled that idea from his reading. He came across as well-read, competent, not one to be easily fooled. 

3. Ask Questions at a Level Deeper Than the Norm  

We can’t talk about Socrates without discussing the Socratic method. This method of conversation, typically between teacher and student involved continual questioning in an effort to bring to the forefront the underlying beliefs and assumptions held by the other peson.  

Socrates believed that the highest form of human excellence was to question oneself and others. He engaged in prolonged dialogue with his students, fellow citizens (when they allowed it)  asking questions to uncover deeply held beliefs.

It’s important to understand. Up to this point, much of philosophy had centered on the material world. Socrates moved beyond this, asking about morality, ethics, and the very essence of what it means to live a good life. 

Will Durant sums up Socrates’ unique draw beautifully. He speaks of the philosophers before Socrates saying that 

“ for the most part they had been physical philosophers; they had sought for the nature of external things, the laws and constituents of the material and measurable world. That is very good, said Socrates but there is an infinitely worthier subject for philosophers than all these trees and stones and even all those stars; there is the mind of man. What is man and what can he become?” 

Socrates’ ability to hone in on these important questions and put them forth in dialogues with others gave him a magnetic effect, especially on the youth of the city who found these questions important and worthy of struggling with. 

What does this mean in terms of improving our conversation skills?

At its root, asking questions that go depeer is about moving beyond the obvious, the everyday conversation topics. It requires steering the conversation towards those underlying cares, concerns, and even desires that others are voicing. 

To do this, you don’t need to ask the next person you meet “What is the meaning of justice?” or “How would you define a good life?” Instead, you can apply this lesson in a more practical way. Simply think, what’s at the root of the words they are saying to me? How can I better understand them? What deeper motivations/beliefs are driving the person I’m speaking with? 

This lesson is also about stepping outside of yourself to focus more on the other person. Socrates was trying to get to the bottom of what people were saying and what they believed. It’s difficult to do so if you’re preoccupied with your thoughts and opinions. Instead, focus on what the other person is saying. 

It sounds simple, but this active listening will be a huge benefit when it comes to formulating the right questions. After all, if you’re intently focused on your partner’s words and thoughts, you’ll catch little things that provide material for new, specific questions. These are the types of questions that signal that you really are paying attention and that you are genuinely interested. 

What does this look like in conversation? 

Let’s talk applications! 

Asking why questions. Socrates had a deep-rooted curiosity and often asked Athenians why they believed what they did and what they actually meant by the terms they brought up in discussion. Take some of this childlike wonder into your conversations by asking why? 

Example: I’m an engineer. Instead of oh cool do you like it? Or with what firm? Ask why did you decide to become an engineer? What about the job do you enjoy? 

Example: Instead of where are you from? Why are you in xyz city? What made you settle in xyz place? 

Using the Summarize, Compliment, Question formula. Another great way to dive deeper is to ask about underlying motivations. An easy way to do this is to summarize what someone has just told you, include a genuine compliment and end with a question. 

Example: So I broke up with my ex, moved across the country and decided to start fresh here. So far I’m loving it. You can say wow so you left everything behind and relocated to a brand new city. That’s very courageous of you, many wouldn’t do that. Was there a specific aha moment that made you decide to do it?” 

This formula works in so many situations. You can use it when people discuss their career paths, places they have lived, travel experiences, the list goes on. Padding the dialogue with summaries and compliments is also a great way to keep the convo from sounding like an interview.

Uncovering core values. Once you’ve spoken with someone for a while, you begin to get a sense of what matters to them. Some of this will come through words but often it’s more subtle. When you’ve identified a value, you can hone in on it and ask questions that get people to open up about deeper topics. 

Example: A man repeatedly discusses his time in the military and the bonds he made with his classmates in the military academy. You can tell that this experience shaped him and he looks back on it fondly. You ask  “what is the most valuable lesson you gleaned from your service?” Maybe one that you still put into practice each day?

This question allows him to dive deeper into what he considers important. So you get to find out about what he finds valuable and you’ll go into deeper conversations. He gets to speak of something that he associates positive feelings with and you provided that opportunity. 

I encourage you to try this tactic out. Start to tune your ear to hear deeper motivations/values and then ask about them. Most people don’t do this.

Alright my lovely conversation companions that was lesson #3, ask questions at one level deeper than the norm. The remaining two lessons on how to level up your question asking game, and also the bonus list of questions that you can take to use in upcoming conversations are included in part two. See you there!