written by
Erick Cloward

297 - From Socrates to Seneca: The Timeless Power of a Good Question

Ask 10 min read , May 8, 2024

Do you ask questions? And what I mean by that is, do you go into conversation or arguments thinking you already know everything? Today I want to talk about the importance of staying curious and how to ask useful questions.

“He who knows only his own side of the case, knows little of that.”
—John Stuart Mill

Far too often we think that we know everything about a situation and forget to approach things in a way that could be useful. We decide that we know the answer and we spend our time trying to convince the other person that we have the right answer and they should agree with us.

Now it is possible that we have right answer. Maybe we’re an expert in a certain domain, and we really do know what we’re talking about. But time and again it’s been shown that good communication is not just about stating the facts confidently and expecting them to be accepted.

The Importance of Asking Questions

When we take the time to ask questions, then we start to understand how others think. In doing so we might actually be able to clarify what they might not understand. We’re also able to gain insight into their biases and preexisting beliefs, which color their perspectives. It can also help us to see our own biases and beliefs and how they might be coloring our own perspectives.

Asking questions shows that we’re interested in trying to understand the other person and want to have a real conversation with them, rather than just trying to talk to or at them. Also, by showing interest in others we show that what they have to say matters, even if we disagree with them.

Marcus Aurelius reminds us to, “Accustom yourself not to be disregarding of what someone else has to say: as far as possible enter into the mind of the speaker.” By trying to put ourselves in the other person’s shoes, and see things from their perspective, we gain a better insight into how they view the world.

The Stoic Approach to Questions

The Stoics teach that in order to live a good life, we need to live a life according to virtue. One of the cardinal virtues of Stoicism is wisdom. Now wisdom is not just knowledge, but how to apply knowledge into practical experience, and they way that we gain wisdom is to be curious and always be willing to change our opinions.

The Stoics even teach us to question ourselves constantly and to never take something at face value. We can see this from the Stoics concept of impressions and assent. When we perceive something, we are exposed to an impression. Once we have agreed that what we perceived is accurate, then we assent or agree to it. But taking the time to question ourselves, we can get better at recognizing our own logical missteps, and be more forgiving of others when they fall into the same traps. As Marcus Aurelius reminded himself, "Question your assumptions."

Indifferents

Nothing is more frustrating than having a conversation with someone that is trying to change your opinion on something. One tool that be can useful when having conversations with others is to remember the Stoic idea of indifferents. This means that anything outside of your will, meaning your thoughts, choices, and actions is outside of your control. The most important thing outside of your control is what others think, say, or do, so the less you try to control other people, the more likely you are to have a good conversation with them.

By remembering that you don’t have control over another persons opinion, you stop trying to control the conversation and the other person. And when you think about it, why does it matter what someone else thinks? Why is it important that they agree with you?

One of the things that I’ve worked on in my life is not worrying about if others agree with me. When I was younger, I would often get into arguments with people I cared about because I needed that validation. I needed them to agree with me because if they didn’t, I felt like there was something wrong with me. If I believed I had the right answer or opinion on something and they didn’t adopt the same opinion, I took it as a personal rejection. It took me a long time to understand that people can think differently than me, and they can still love me.

Benefits of Asking Better Questions

Better Connections

Asking questions can strengthen relationships by showing interest and respect for others' perspectives. It shows them that you are truly interested in them, and not just trying to convince them the rightness of your opinion. Even if at the end of it you agree to disagree, at the very least you’ll have deeper understanding of the other persons point of view, and shown respect in trying to understand why they have their perspective.

Better Decision Making

When you ask more questions, you improve your ability to make decisions. Thorough questioning leads to better-informed decisions, reducing errors from assumptions. You may be the smartest person in the room, but you still can’t know everything. Taking the time to truly understand something increases your own wisdom. In short, you might be misinformed or lack some crucial piece of knowledge. Being humble and asking questions is way to not only gain knowledge but sharpen your wisdom.

John Stuart Mill, a British philosopher and economist summed it up nicely, writing, “He who knows only his own side of the case, knows little of that. His reasons may be good, and no one may have been able to refute them. But if he is equally unable to refute the reasons on the opposite side; if he does not so much as know what they are, he has no ground for preferring either opinion.”

Increased Self-Awareness

Questions lead to introspection, aiding in personal growth and alignment with your values. When you have a good conversation with someone, you’re not only examining the other persons thinking process, you’re working through your own, which can help you to see faults and biases in your own way of thinking. As Epictetus taught, “It is impossible for a man to learn what he thinks he already knows”.

How to Ask Better Questions

First off, be honest with your questions. If you’re going into a conversation or argument simply to prove the other person wrong, you’re not going to make any headway. Being combative, such as just being contrarian and just taking the opposite perspective just to score points isn’t going to do either of you any good.

Next, as open-ended questions that provoke thought rather than those that elicit yes/no answers. You’re trying to understand their perspective, and yes/no questions don’t give you any context or insight to why they think the way they do.

When the person responds, practice active listening, which means listening to understand, not to respond. If you’re focusing on what you’re going to say next you’re going to miss some key information, and you’re simply showing that you’re not real interested in what the other person has to say.

Another important thing is to do so at the appropriate time and context. If you’re having a difficult conversation with someone, make sure it works for both of you. If either of your are tired or not in a good headspace, it may not be the best time for a deep dive into a difficult topic. Also, the other person has to be open to it. Sometimes people don’t want to have their opinions and perspectives questioned. So, be smart, and be kind, and let it go if it’s not the right time and place.

Lastly, use follow-up questions. Follow-up questions show active engagement and help dig deeper into issues. If someone answers your questions, go deeper to be sure that you clearly understand their answer. I’ve often found some pretty big flaws in my own thinking because someone asked me a question to dig a little deeper.

Practical Examples and Techniques

One of the greatest examples from philosophy about how to ask questions is Socrates. Socrates’ way of teaching was mostly to ask questions, and let his students and others he was speaking with come up with their own conclusions. He also entered the conversations humbly, and almost as more of a facilitator rather than an expert.

One of my favorite examples of this is in Plato’s Latches, where Socrates and other discuss why bravery is. First he enters the conversation with humility and honesty, stating: “Well, Lysimachus, I shall try to advise you about this matter as best I can, and what is more, I shall also do everything else you are asking me to do. However, since I am younger than anyone else here, and less experienced than they are, I think that what is most fitting is that I first listen to what they say and learn from them. Then, if I have anything to add to what they say, I should provide instruction at that stage, and try to convince yourself and these men too.”

As the dialogue progresses, a definition of bravery is put forth as someone who is willing to stay and fight at his post when the enemy is advancing. Socrates then clarifies that he is looking for a definition for bravery that could be applied to all military situations. A second definition is put forward that courage is "a certain perseverance of the soul”. Socrates then asks if a solider was fighting while retreating would not also be brave, if retreating was the more prudent thing to do? Laches, one the participants in the discussion, concedes that a retreating solider could also be considered to be brave in some circumstances.

Now, I’m not going to go on with the rest of the dialog because it is rather lengthy, but the point is that Socrates, rather simply stating an opinion on what it means to be brave, was willing to ask questions, and ask for clarifications. He also was humble and came into the conversation with an honest perspective of trying to understand the topic. As Epictetus teaches us, “If you want to improve, be content to be thought foolish and stupid.”

In my own life, I often used to dominate conversations with my opinions and knowledge, to the point where I would often annoy people because the conversation was all about me. I wasn’t necessarily rude, but other people didn’t feel like they were part of the conversation because I was too busy talking. Much of this was due to my own insecurities and wanting others to like me because of the stuff that new. The way that I helped break myself of this habit was to write the number 3 on my wrist to remind myself to ask 3 questions to anyone I was talking to. This helped me to be more aware of how much I was talking and to include others in the conversation.

Conclusion

Asking better questions, and actually listening to the answers is an important aspect of creating clear and helpful communication with others. It shows that we care about them, and are willing to try and understand them, even if we disagree with them. We can also keep in mind that the Stoic teach us to remember that other peoples opinions are not something that we can have control over, which helps us to not worry about trying to change their opinions, fostering a more inviting environment for others to share their honest opinions without judgment, building stronger connections and more understanding with those we care about.


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stoicism self-awareness Epictetus Marcus Aurelius Seneca Socrates John Stuart Mill