Tune into any results call and you’ll hear plenty of smart-sounding questions (and a lot of alpha-male signaling). What you almost never hear are the questions that risk making someone look silly — even when they’re the ones that are really worth asking.
Technical, sophisticated questions are great for showing off, but it’s the simple, ‘dumb’ ones that really crack things open.
Behind every successful investment is a variant perception, something true that others have not realised or fully appreciated. Finding that requires stripping things back to their essentials, and that starts with simple questions.
How does this business actually make money? Who pays, and why do they keep paying? What are its biggest dependencies? What can go wrong? What is already priced in? These are not advanced questions, but they are often the ones skipped over in the rush to have a view.
Most people are reluctant to ask such questions, especially in professional settings. There is status in sounding sophisticated. There is discomfort in slowing down a conversation to clarify the basics. But skipping the basics is often where mistakes begin.
Asking simple questions does more than clarify the facts. It reveals who really understands the subject. Anyone can throw around jargon or regurgitate consensus views. But the ability to explain something cleanly, from first principles, is rare and telling.
It also helps sort the knowable from the unknowable. In investing, uncertainty is unavoidable. No amount of diligence will tell you what next year’s profits will be (exactly), or what sentiment will do to a stock next quarter. But you can understand what drives its revenue, why people buy its products, or what challenges it might face as it grows.
Simple questions help locate the ground you can stand on.
This process is not glamorous. Often, it leads nowhere. You dig into a business, ask your dumb questions, and find yourself back at the consensus. That is fine. What matters is the habit. Because occasionally, you will find something the market has missed, a lazy assumption, a flawed belief, a risk hiding in plain sight. That is where edge comes from.
Crucially, none of this is about being different for its own sake. The goal is not to oppose the crowd, but to think independently. There is a difference. A variant perception, at least a valuable one, means holding a view that is both non-consensus and correct. Getting there requires humility, not arrogance.
It is worth reflecting on how rarely people in finance say “I don’t know.” The culture rewards certainty, even when that certainty is unfounded. But the best investors are comfortable with doubt. They know which questions they have answered well, which remain open, and where they are simply guessing.
Building this discipline takes practice. It can be formal, through checklists, post-mortems, written investment cases, or informal, through constant inquiry and discussion. Either way, the point is to keep returning to the foundations. What do I think I know? How do I know it? Where might I be wrong?
Over time, this habit compounds. Investors who cultivate it develop a sharper sense of what matters and what does not. They waste less energy chasing noise. They stay anchored in reality, even when the mood of the market swings.
In short, they become better not by knowing more facts, but by asking better questions.
For anyone investing on the ASX or beyond, this is not just a matter of style. It is a source of genuine advantage. Most investors are busy performing knowledge, not pursuing it. The rare few who stay curious, who are willing to look a little foolish in the service of understanding, are the ones most likely to spot opportunity and to avoid the traps that others confidently walk into.
Simple questions, asked with rigor and humility, are what turn information into insight. They are what separate the thoughtful investor from the crowd.
If, that is, you have the modesty and courage to ask them.
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