The Power of Socratic Questioning: Thinking Like a Philosopher in Everyday Life

You’re at a family holiday dinner, and your cousin is confidently explaining why their latest investment in a promising new cryptocurrency is the next big thing. Instead of launching into a counterargument about market volatility, you take a sip of your drink, tilt your head, and ask, "But how do you know that’s true?" Suddenly, the energy shifts. They pause. They frown slightly. They start to second-guess themselves. That, my friend, is the magic of Socratic questioning.

The Art of Asking the Right Questions

Socrates, the granddaddy of philosophy, was never about just telling people what to think. Instead, he had a much more entertaining approach. By asking questions so piercing that they could unravel even the most confident person’s beliefs. He didn’t do this to be annoying (though some found it quite irritating), but because he knew that the right questions lead to deeper understanding.

Rick isn’t one for accepting things as they are, his nihilism bringing the value of everything Morty and he experience into question. These questions aren’t used to stir the pot though, they are Ricks way of cutting through the noise to reveal something more. Whether he’s challenging the very fabric of reality or poking holes in the self-assured assumptions of others, his questioning style of “What’s the point of all this?” “What if everything you’ve been told is just a lie?” isn’t about forcing his answers upon the questioned, but to induce character development.

Morty likewise was always having to ask questions in a way that may appear like playing catch up. But when looking deeper to each out burst it was always challenging the morality of his grandpa Ricks irrational behaviour.

Rick and Morty don’t care about being polite or easy to listen to, they care about getting to a truth. And just like Socrates, Rick knows that when you ask the right questions, the answers you uncover are often as surprising as they are eye-opening, even if Morty’s questions are usually leaving him disillusioned and dismayed. Sometimes they’ll hit you with a dose of reality, and sometimes, they’ll make you laugh at how absurd it all is.

Socrates had the same approach of asking questions that made people uncomfortable enough to rethink everything, and in the process, uncover truths that were often more complex or hilarious than anyone ever imagined. Just like Rick and Morty, Socrates wasn’t afraid to dig deep and challenge the status quo, even if it meant causing a little chaos along the way.

The Ethical Value of Socratic Questioning

At its core, Socratic questioning isn’t just about winning arguments, it’s about intellectual humility, curiosity, and the pursuit of truth. It’s a form of ethical reasoning, one that forces us to recognize the limits of our own knowledge and seek out better answers. This encourages us to consider why we believe something, how we arrived at that belief and what might happen when it’s questioned. It’s not about being right, its about getting to the best, most informed truth possible.

Hopefully you’ll recognize this approach from my favorite Captain, Jean-Luc Picard. Instead of barking orders or forcing his opinion, he would often lead his crew by asking the right questions. He challenged assumptions and made people think deeply before acting. That’s leadership through philosophy, and it’s a masterclass in ethics. Picard wasn’t about giving answers, he empowered others to find their own.

Socrates himself believed that unexamined beliefs lead to injustice. If we accept everything at face value, (whether it’s political rhetoric, corporate claims, or even our own biases) we risk making decisions that are harmful or misguided. By questioning what we know, we don’t just sharpen our intellect, we create a more just and thoughtful world. As seen by Aristotle in the ethics of virtue.

Virtue Ethics, like Socratic questioning, isn't about blindly following rules or aiming for the greatest good in a utilitarian sense. It’s about becoming the kind of person who consistently makes good, moral decisions. Aristotle argued that we should focus on developing virtuous traits like wisdom, courage, and temperance, through reflection and conscious action. This is where Socratic questioning aligns perfectly. It encourages us to examine our own reasoning, test our assumptions, and cultivate the virtues that will help us make ethically sound choices.

By applying Socratic questioning, we don’t just seek knowledge for its own sake, its about challenging ourselves to grow in virtue, refining our ethical compass. When we adopt this mindset, we begin to question more than just the facts. We question the motivations, the biases, and the systems that shape our world. Just like Picard guiding the crew of the Enterprise against the Borg, or a challenge by Q, Socratic questioning challenges us to become better versions of ourselves, capable of navigating a complex, morally nuanced universe with wisdom and justice at the forefront.

In the end, the value of Socratic questioning lies not just in the answers it uncovers, but in the transformative process it sparks. It’s a tool that empowers us to make thoughtful, ethical decisions. No matter whether we’re leading a crew, running a business, or making choices in our personal lives the potential growth becomes evident.

Socratic Questioning in Cognitive Behavioral Therapy (CBT)

Beyond philosophy and ethics, Socratic questioning is one of the most powerful tools in modern psychological therapy. Cognitive Behavioral Therapy (CBT), one of the most widely used and evidence-backed therapeutic approaches, relies heavily on Socratic questioning to help people untangle unhealthy thought patterns.

Imagine your brain as a snarky narrator feeding you negative thoughts of self speak like "I always mess things up." Instead of accepting that, a CBT-trained therapist (or your own inner Socrates) would ask, "Always? Can you think of a time when that wasn’t true?" Suddenly, the certainty of that thought cracks. "What evidence supports this belief? What evidence contradicts it?" With each question, the grip of negative thinking loosens, allowing a healthier, more realistic perspective to emerge.

The god of mischief Loki, thrives on twisting perspectives, exposing contradictions, and forcing people to confront uncomfortable truths. Where he may challenge Thor’s naive worldview or exposing the Time Variance Authority’s hypocrisy, Loki’s sharpest insights often come when he turns that scrutiny on himself. When Loki was forced to question his own identity “Am I truly destined to be the villain?” That’s Socratic questioning in action, he had to challenge the stories being told to himself and make space for something new.

Why Socratic Questioning Matters in Business

If you think Socratic questioning is just for philosophers and therapists, think again. In the business world, it’s a game-changer. Whether you’re leading a team, handling customer relations, or making strategic decisions, the ability to ask the right questions can mean the difference between success and failure.

Great leaders don’t just issue commands, they probe, they challenge assumptions, and they force their teams to think critically. Steve Jobs was famous for asking, "Why does it have to be this way?" That one question led to some of the most innovative products in history. Similarly, in sales and customer success, asking questions like "What problem are we actually solving for you?" can uncover needs the customer didn’t even realize they had.

As a brilliant woman I know, Jackie Rafter of Higher Landing, would point out what are the Important Pain-points? And Why? Asking again and again, and again having any of her clients questioning their own perspectives to their value proposition in the most amazingly ethical way possible. I can speak from experience, it has you diving deeper to resolve what you know about yourself, not having someone else tell you who you are.

In meetings, instead of shutting down ideas, a well-placed "What evidence supports this approach?" or "What’s the worst that could happen if we did the opposite?" fosters an environment where creativity and critical thinking thrive. In short, Socratic questioning in business isn’t just about avoiding mistakes, it’s about ethically unlocking new possibilities, and profits.

Why Socratic Questioning Is More Relevant Than Ever

In a world overflowing with hot takes, clickbait headlines, and social media debates that escalate faster than a reality TV argument, Socratic questioning is the secret weapon you didn’t know you needed. It slows things down. It forces people (yourself included) to think beyond knee-jerk reactions and actually engage with ideas.

Scooby-Doo and gang never just accepts the initial explanation of a "monster." They investigate, ask questions, and dig deeper. They don't just assume the spooky figure is a ghost; they look for clues, examine the evidence, and challenge assumptions. "Could it be someone in a costume?" "What's their motive?" "Where are the footprints leading?" These are all Socratic-style questions, driving the investigation forward. Just like Scooby and the gang unmasking the real culprit, Socratic questioning helps us unmask the underlying assumptions and biases that often cloud our judgment. It helps us get past the surface-level "monster" of an idea and uncover the real story.

At a family dinner, and your uncle declares, "AI is going to take over the world!" Instead of rolling your eyes, you lean in with a smile. "Interesting! What makes you say that?" You’ve now opened the door to a much richer discussion, one that might actually lead to new insights rather than a shouting match.

How to Channel Your Inner Socrates (Without Becoming That Guy at Parties)

Want to ask great questions without turning every conversation into a philosophy seminar? The key is to keep it playful, engaging, and about discovery—not debate.

• Be Curious Like an Explorer, Not a Prosecutor. The best thinkers ask questions like they’re uncovering lost treasure, not cross-examining a witness. "Huh, I’ve never thought about it that way, please tell me more!" works way better than "Actually, you’re wrong, and here’s why."
• Use Humour as Your Secret Weapon. A well-timed joke can open more doors than a battering ram. "Wait, so you’re telling me pigeons are part of an elaborate surveillance network? Alright, break it down for me—who’s running the operation?" A little charm keeps the shields down.
• Challenge Yourself Before Challenging Others. Before you go all-in defending your beliefs, take a second: "What if I’m wrong?" The best way to sharpen your thinking is to question your own assumptions first. Think of it as stress-testing your own ideas before launching them into the world.
• Guide, Don’t Lecture. The smartest people don’t just drop truth bombs, they help others connect the dots. Instead of saying, "You’re thinking about this all wrong," try, "That’s an interesting perspective, have you ever looked at it this way?" You’ll get better conversations and fewer eye-rolls.

Not In A Galaxy Far-Far Away

Socratic questioning isn’t about being a know-it-all. It’s about being an ask-it-all. It’s about transforming everyday conversations into meaningful explorations. It’s about thinking deeper, engaging better, and sometimes, just watching someone hilariously trip over their own assumptions.

So the next time you hear an outrageous claim, don’t argue. It’s time to negotiate like a Master Jedi. Just smile and ask, "But how do you know that’s true?" Socrates would approve, and so would Master Yoda.