Asked Any Good Questions Lately?
Here’s how to train the most underrated skill in modern thinking.
On a crisp October morning in 1930, a young engineer at Toyota stopped an assembly line because a single bolt on a door hinge didn’t feel right. It wasn’t loose. It wasn’t broken. It just felt… off. Instead of rushing to fix it, he asked a question: Why does it feel different today?
Five “whys” later, the team discovered the issue wasn’t the bolt at all, it was the humidity. Overnight, a subtle rise in moisture had warped the calibration tool used on hundreds of cars. A question about a feeling saved millions of dollars in potential recalls. That story has become legend inside Toyota’s factories, but what’s striking isn’t the cleverness of the engineer, it’s the discipline of the question. He didn’t jump to a conclusion or reach for a manual. He didn’t assume he already knew the answer. He paused, wondered, and asked questions.
We love stories of genius, the inventor who sees what no one else sees, the leader who “just knows.” But more often, insight comes from something quieter: an ordinary person who refuses to let a simple question die too soon. In almost every field, the pattern repeats. A scientist notices an anomaly in a data set and asks why. A teacher realizes a student’s wrong answer reveals a deeper misconception and asks what if I approached this differently. A therapist, a writer, a leader-all begin not with certainty, but curiosity.
We tend to think good thinkers are defined by what they know. But real intelligence often shows up in what we’re willing to ask. That’s the paradox of modern thinking: we’ve built our lives around finding answers-yet we rarely stop to examine the quality of our questions. We may spend years working to improve how we remember, how we take notes, and how we organize information. But we rarely train the one skill that activates all the others: asking better questions.
Questioning I am speaking of isn’t just about gathering facts-it’s the act that turns facts into understanding, and understanding into wisdom. It’s how the car engineer prevents a recall, how a journalist uncovers a hidden truth, and how each of us learns to make sense of our own thoughts. So before diving into the next strategy, theory, or productivity method, try this instead: Ask yourself, How good am I at asking questions-and how would I even know?
Surface-Level Thinking: The Hidden Default
Think about something as trivial as your favorite color. Could you explain why it’s your favorite? Most of us can’t we’ve just accepted it on autopilot. That same mental autopilot drives countless choices we make every day.
Everywhere we turn, we are pressured to do things faster, so much so that deeper inquiry feels like a luxury. We skim, scroll, and “collect” information, but rarely slow down to ask the questions that give those answers meaning. The truth is that information is only valuable when paired with a meaningful question. An answer without context is just a disconnected fact or opinion. Before accepting anything as “useful,” try asking:
Why do I need to know this?
What problem does this solve?
How would things be different if I applied this information?
How will I know if it’s right or wrong?
What others questions should I be asking?
Mini habit: Before acting on new information, spend 90 seconds answering those four questions. You’ll think better almost immediately.
Three Techniques for Deeper Questioning
In my professional life as an educator, I have worked hard to develop the habit of challenging my students’ assumptions through three questioning techniques. Now, I will admit it took me a while to adopt these strategies in my personal life. But when I started doing it consistently, it was a game-changer and opened the door for more profound meaning in my life. Here are the three simple questioning techniques that have shaped my thinking.
1. The Five Whys
Originally developed by Sakichi Toyoda, the founder of Toyota Industries and later popularized in the 1950s by Taiichi Ohno as a core practice in the Toyota Production System, the Five Whys is a deceptively simple yet powerful technique for uncovering root causes. Start with a statement or problem. Then ask “why?”, not once, but five times (or until you hit the root cause or fundamental issue).
Example:
I’m procrastinating on the report.
Why? It feels too big.
Why? I’m unclear on the decision it will inform.
Why? I never asked the stakeholder what they actually need.
Why? I assumed the template was enough.
Root: I need a short call to clarify the decision and criteria.
Let’s say you’re considering a career change, because you feeling unfulfilled at your current job.
Ask why you’re unhappy. Perhaps it’s because you feel unchallenged.
Ask why you feel unchallenged. Maybe it’s because you’ve mastered your current role.
Ask why that’s a problem. Perhaps because you value growth and learning.
Ask why growth matters to you. The answer might reveal core values about personal development that inform not just this decision, but many others.
The key benefit of going through this exercise is that it stops you from treating symptoms and helps your uncover what matters most, the real issues, so your actions are informed and deliberate.
2. Negating the Question
We usually ask questions in the positive: Why should I do this? or What are the benefits? Try flipping it: Why shouldn’t I do this?What could go wrong? Who might see this differently?
Changing the frame forces a new perspective without triggering defensiveness. If your “why nots” are weak, your plan gains confidence; if they’re strong, you’ve just prevented a mistake.
Try this: List three reasons not to proceed. If you can’t find any, move forward, but pay attention to what you learn.
This technique draws on cognitive restructuring principles used in therapy, where questioning assumptions is a fundamental tool for changing thought patterns. By asking yourself questions like What evidence contradicts my belief? What would happen if the opposite were true?, you develop more balanced, realistic thinking. Perhaps the most significant benefit to negating your questions is it often reveals blind spots-the considerations you’ve overlooked because you were focused only on positive framing.
3. Compare and Contrast
The human brain is remarkably good at understanding things through comparison. When you ask What is this like? How is it different?-you activate cognitive processes that create deeper meaning through connection-making. To put this method into action, make two lists-similarities and differences-and aim for five of each. Then ask, So what? And notice what choices or insights emerges. This simple (synonym) technique forces the brain to map patterns instead of just collecting isolated facts. It’s simple, powerful, and endlessly reusable.
Building the Questioning Habit
All of the techniques I shared will only matter as much as they become habits of thinking. The good news: questioning fits anywhere. It doesn’t have to be formal, but it must be deliberate. The key is to practice them across multiple contexts: conversations with others, private reflection, consuming media, and reading. For example:
In conversation: Ask one follow-up before offering your view.
In reflection: Revisit a decision you made today-what question could have improved it?
With media: Pause to ask who benefits, what’s missing, and how to verify.
While reading: Set pre-questions (what do I want to learn?) and post-questions (what changed for me?).
Where you practice doesn’t matter-consistency does. So, a great way to start building your consistent questioning habit is to choose to preferred format for reflection. If you prefer writing consider keeping a question journal where you record questions that arise and your evolving thoughts about them. For those who prefer to process verbally, recording yourself asking and answering questions and you can reveal patterns in your thinking organically. If you feel writing or verbal recording is too great of barrier for your to get started, simply practicing questioning in your mind-during commutes, before sleep, or while walking, can also build the questioning habit without requiring additional time. The goal is to make questioning instinctive rather than effortful.
The Compounding Benefits
Better questions lead to better answers. Better answers sharpen your thinking. Sharper thinking brings clearer decisions and a more intentional life. Like compound interest, the gains accumulate quietly, day by day, question by question. Start small. Choose one technique and use it today, then again tomorrow. The skill will follow the habit, and your life will follow your questions.
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