Question: Are you asking the “right” questions?
- In journalism — as in business and investing — the best answers often come from knowing which questions to ask.
- If you simply take things at face value — following the herd, chasing trends — you’re likely to miss the deeper forces at play.
- One of the simplest yet most powerful questions that can point the way to success is “Why?”
In 1905, Albert Einstein was working as a patent clerk in Switzerland when he asked one of the most profound questions in the history of physics: “What would happen if I rode alongside a beam of light?” The question was simple but counterintuitive. It was also, in retrospect, a monumental moment in science.
While physicists at the time were busy refining Newtonian mechanics and grappling with the nature of the ether, Einstein’s question challenged the foundational assumptions of the day. Focusing on this question led Einstein to the development of the special theory of relativity, which fundamentally altered humanity’s understanding of time, space, and energy.
The point: it wasn’t the complexity of his equations that made Einstein a revolutionary thinker — it was his ability to ask the right question. The power of asking good questions is not limited to the realm of physics; it permeates business, investing, and even our daily lives. If you’re focused on finding quick answers, you’ll likely miss the bigger picture. But if you master the art of asking the right questions, you’ll open up new possibilities that others haven’t even considered.
As someone who has spent years in investigative journalism, I’ve found that the best stories don’t come from the answers — they come from knowing which questions to ask. The same is true in business and investing. Whether you’re looking for a new investment opportunity or trying to build a long-term business strategy, asking the right question is the key to unlocking success. But how?
The journalist’s approach to questions
In journalism, it’s easy to think the job is about finding facts and tying them together into a story. But my most memorable stories were born not from facts, but from an itch — something that didn’t quite sit right. I’d be interviewing a source, and there’d be a gap in the narrative. I could sense it, but I didn’t yet know what it was. The magic happened when I asked the right question — the question that opened up a new line of inquiry that unraveled the story I hadn’t even realized I was chasing.
After a few conversations and a carefully placed question about the company’s origins, the real story began to unfold.
I remember working on a piece about a small-town entrepreneur who had suddenly gained national recognition. Everything on the surface seemed straightforward — he had a good product, the timing was right, and the market responded. But something felt off. I couldn’t put my finger on it, but instead of charging ahead with assumptions, I slowed down and asked more questions. What was it that made him different? How had his business really taken off? After a few conversations and a carefully placed question about the company’s origins, the real story began to unfold: he hadn’t started from scratch — he had taken over a family business that was deeply entrenched in the community, and this was the hidden foundation of his success.
The right questions unlocked everything. Likewise with business and investing. If you simply take things at face value — following the herd, chasing trends — you’re likely to miss the deeper forces at play. Asking the right questions helps you uncover what’s beneath the surface, and that’s where the long-term opportunities lie.
Asking questions in business
Let’s look at a real-world example: Jeff Bezos. In the early days of Amazon, while most tech entrepreneurs were focused on building flashy websites or monetizing digital ads, Bezos was asking a different set of questions. Instead of asking, “How do I build the next big tech startup?” he asked, “How can I use the internet to sell things people already want in a more efficient way?”
That question led him to books: products that had a well-established market but could benefit immensely from online distribution. The question shifted his focus from being just another tech startup to becoming a logistics and customer experience powerhouse. Amazon succeeded not because it found a new way to answer old questions — but because Bezos asked new questions entirely.
A more compelling example of asking the right question in investing can be found with Howard Marks, co-founder of Oaktree Capital. During the 2008 financial crisis, many investors were panicking, selling off assets in response to plummeting markets. However, Marks approached the situation entirely differently. Four days after the Lehman Brothers collapse in September 2008, Marks issued a now-famous memo titled: “Nobody Knows.”
Instead of asking, “How do I build the next big tech startup?” [Jeff Bezos] asked, “How can I use the internet to sell things people already want in a more efficient way?”
In the piece, he asks: “Will the financial system melt down, or is this merely the greatest down cycle we’ve ever seen? My answer is simple: we have no choice but to assume that this isn’t the end, but just another cycle to take advantage of.”
In the end, asking the right question offered an advantage. Rather than getting swept up in the short-term chaos, Marks focused on understanding the broader market psychology and identifying where opportunities lay amidst the distress. By asking this question, he was able to spot high-quality distressed assets at discounted prices, knowing that fear had pushed their value far below intrinsic worth. This insight allowed him to make some of his best investments during a time when others were fleeing the market.
Marks’ ability to ask a deeper question about investor psychology rather than focusing solely on financial metrics is what set him apart. He understood that to be a successful long-term investor, you need to question not just the fundamentals of companies but also the emotional drivers of the market. The lesson? Sometimes the best investing decisions come from asking, “What is the real driver behind this market movement?” rather than simply, “Is this stock a good buy?” This allows investors to gain insights into hidden opportunities and avoid herd mentality, especially in times of extreme market volatility.
The power of asking “Why?”
One of the simplest yet most powerful questions in both business and investing is “Why?” Take Elon Musk, for example. Before Tesla became a household name, the electric vehicle market was small, niche, and unproven. Most car companies asked, “How can we make electric cars affordable?” That was the wrong question. Musk asked a different question: “Why aren’t electric cars already better than traditional cars?”
That “why” unlocked a different approach. Instead of trying to compete directly on price with gasoline cars, Musk focused on making a car that was better — faster, more desirable, and more fun to drive. He didn’t ask how to compete in a crowded market — he asked why the market hadn’t already shifted. That question changed everything.
Three ideas for asking good questions
So how do you ask better questions? Whether in life, business, or investing, here are three actionable steps:
- Ask open-ended questions Open-ended questions are a powerful tool because they don’t limit the answer to a simple yes or no. They invite deeper reflection and can open up entirely new avenues of thought. Instead of asking, “Is this investment risky?” ask, “What risks am I not seeing here?” or “How could this business model evolve in the next five years?” This approach encourages you to think beyond surface-level answers.
- Embrace the beginner’s mindset Often, we think we know the answers, or we rely on assumptions to guide us. But one of the most effective ways to ask good questions is to approach situations with a beginner’s mindset. Act as if you’re learning about the subject for the first time. It helps eliminate bias and opens the door to asking the “dumb” questions — because those questions often lead to the most insightful answers. In business meetings or when researching investments, don’t be afraid to ask, “Why does this work this way?” or “What if we approached this problem from a completely different angle?”
- Focus on long-term implications In business and investing, the most valuable questions often focus on the long-term. Instead of asking, “How can we maximize profits this quarter?” ask, “How does this decision affect us five or ten years from now?” In investing, instead of asking, “Is this stock going up next year?” ask, “What is this company’s competitive advantage, and how sustainable is it over time?” These kinds of questions force you to think more strategically and can lead to better long-term decisions.
The right questions lead to the right answers
The art of asking good questions is a skill that takes time to develop, but it’s incredibly valuable. The best journalists, business leaders, and investors know that it’s not about having all the answers. It’s about knowing how to ask the right questions. When you ask the right questions, the answers will follow — and more often than not, those answers will lead you to opportunities others missed entirely.
So next time you find yourself searching for an answer, pause. Ask yourself: am I asking the right question?
