A Case for Asking Better Questions

Louis Pasteur’s aphorism—“Chance favors only the prepared mind”—is often trotted out in the context of scientific breakthroughs or serendipitous discoveries. Yet its deeper implication isn’t just about being ready when opportunity strikes. It’s about cultivating a habit of curiosity and, crucially, asking the right questions. If your mind is unprepared, you won’t even recognize the chance when it presents itself, let alone seize it.

The problem is, most setups don’t favor questions. University lectures are prime offenders—those solemn rituals where a lecturer drones on while the audience collectively tries to avoid eye contact, lest they be called upon. Conferences and corporate meetings aren’t much better. The speaker asks, “Are there any questions?” and the audience freezes as if they’ve just been caught sneaking into a restricted area. The result? A parade of non-questions like, “This is more of a comment than a question,” or worse, silence.

It wasn’t always this way for me. Early in my career, during an internship, my boss at the time, Kajsa, gave me some advice that felt radical: “Always ask a question.” She added, with a mischievous grin, “But be careful. People will remember you for it, so make it count.” That combination of encouragement and mild threat has stuck with me ever since. Asking questions isn’t just an exercise in curiosity; it’s a public performance where stakes are high. Do it wrong, and you risk being remembered as the person who asked, “Why is the sky blue?” during a panel on private equity trends.

Questions That Break the Ice

The act of asking a question is deceptively simple, yet it’s fraught with peril. It requires you to admit ignorance—never a comfortable position, especially in a room full of experts. But it also demands that you challenge the status quo, which can be just as daunting. A good question doesn’t just clarify; it opens up new lines of inquiry. A bad question, on the other hand, closes doors or derails the discussion entirely.

Kajsa’s advice taught me that asking questions is both a skill and a responsibility. At the time, I interpreted her words narrowly: always ask something during a meeting or talk to prove you’re paying attention. Over time, I’ve come to see the broader lesson: asking questions is how you prepare your mind to recognize opportunity.

Pasteur was right: chance does favor the prepared mind. But preparation isn’t just about reading the material or knowing the context. It’s about asking questions that push the boundaries of your understanding. The best questions make others pause and think, “I wish I’d asked that.” The worst make them wish they could excuse themselves to the bathroom.

Why We Avoid Asking Questions

Most environments actively discourage questioning, even when they claim to value it. Universities and workplaces are notorious for rewarding compliance over curiosity. Lectures often prioritize “covering material” over fostering dialogue, and corporate meetings frequently mistake silence for agreement. The few brave souls who dare to ask a question are usually met with either exasperation (from the speaker) or admiration (from everyone else who secretly wanted to know the same thing).

This aversion to questioning isn’t just cultural—it’s psychological. Nobody wants to risk looking stupid, especially in a professional setting. But as Nassim Taleb argues in The Black Swan, the most impactful events and ideas often arise from outliers—questions and observations that defy conventional thinking. If you’re too afraid to ask the question everyone else is avoiding, you may miss the chance to uncover something extraordinary.

The Art of the Prepared Mind

Preparing your mind doesn’t mean memorizing facts or rehearsing answers; it means developing a mindset that’s open to the unexpected. Andrew Grove’s Only the Paranoid Survive offers a corporate version of this principle. Grove argued that “strategic inflection points”—moments when a company must radically adapt or die—can only be recognized by leaders who are perpetually questioning their assumptions.

This kind of preparation requires more than intellectual curiosity. It demands humility—the willingness to admit what you don’t know—and courage to confront the unknown. As Kajsa warned me, people remember your questions, so they had better be thoughtful. But the rewards are worth the risk. A prepared mind doesn’t just seize opportunities; it creates them.

Lessons from Star Trek (and Elsewhere)

Captain Benjamin Sisko of Star Trek: Deep Space Nine exemplifies this mindset. Unlike the swashbuckling Captain Kirk or the cerebral Captain Picard, Sisko navigates moral gray areas with pragmatism and an eye for the long game. In the episode “In the Pale Moonlight,” he confronts an ethical dilemma that forces him to ask: “What am I willing to sacrifice for the greater good?” Sisko’s willingness to question his own principles—not just the situation at hand—sets him apart as a leader.

Closer to home, podcasts like EconTalk and The Remnant thrive on asking the kinds of questions that others shy away from. Russ Roberts of EconTalk doesn’t just probe his guests’ expertise; he challenges their premises, often pushing them to refine their arguments in real time. Jonah Goldberg of The Remnant similarly revels in intellectual combat, using humor and humility to disarm even the most contentious debates. Listening to these shows is like auditing a masterclass in curiosity and critical thinking.

Tools for an Open Mind

So how do you cultivate a questioning mindset? Here are some practical tools:

1. Socratic Questioning: Channel your inner philosopher by asking, “What assumptions underlie this?” or “What evidence supports this claim?” Socratic questioning is a powerful way to peel back layers of complexity.
2. Reflective Listening: Instead of planning your next argument, focus on understanding the speaker. Summarize what they’ve said to confirm your interpretation before responding.
3. Mental Models: Adopt frameworks like Taleb’s antifragility or the power law to challenge linear thinking. These models help you see the world in terms of probabilities and systems, not certainties.
4. Note-Taking: During meetings or lectures, jot down (or type it into your phone) not just what’s said but what you’d like to ask. This habit primes your mind to identify gaps or inconsistencies in the material.

Final Thoughts: The Courage to Question

Being remembered for a great question is a badge of honor. Being remembered for a bad one is, at worst, a mildly embarrassing anecdote. Either way, you’re better off than the anonymous masses who sat silently, too afraid to speak up. As Kajsa taught me, the act of asking a question—however imperfect—signals that you’re engaged, curious, and unafraid to challenge the status quo.

Open-mindedness isn’t just about entertaining new ideas; it’s about interrogating old ones. It’s the willingness to confront your own biases, ask uncomfortable questions, and embrace uncertainty. Whether you’re sitting in a university lecture, a corporate boardroom, or the captain’s chair of the USS Enterprise, the lesson is the same: chance favors the prepared mind, but only if it dares to ask.