How to learn what you don’t know you don’t know: The power of asking better questions

“The wise man doesn’t give the right answers, he poses the right questions” – Claude Levi- Strauss

Knowledge.

We gain it in many ways — through reading, experience, observation, testing, tutoring, lectures, conversations, and more. But not all of these are available exactly when we need them — especially when our inquisitive minds wander off into the wilderness of information, searching for something more.

It is easier to navigate a forest when there is a visible path — even if it is just a rough dirt trail. But not all knowledge comes with clear signposts. Sometimes, you must explore with limited guidance, limited understanding, and no map.

In those moments, it is easy to get lost. That is when you need survival skills — not just to stay on track, but to spot what is useful and what is not. In learning, those survival skills are the questions you ask. And the deeper you want to go, the better your questions need to be.

How my journey helped refine my ability to ask questions.

My improved ability to ask more “right” questions — especially when faced with something that felt completely beyond me — has been shaped and sharpened by the range of experiences I have had throughout my education and career. I have grown to love discovering what I don’t know I don’t know. It is a continuous process of learning and refinement — one that only ends if you choose to stop asking questions.

As a law undergraduate competing in international mooting competitions, I learned to interrogate legal issues by drilling into the fine details, identifying assumptions, and anticipating counter-arguments — and counters to those counters. It was not just about knowing the law; it was about learning to question it, navigate ambiguity, and argue from different perspectives.

Later, I pursued a MSc in International Business — a very different world. Where law was about precision and depth, business demanded breadth and synthesis. I had to zoom out, approach problems from a bird’s-eye view, and see how markets, policies, and people interacted across borders. There was more abstraction, more systems-thinking. Both fields had overlapping concepts, of course, but in my experience, law was micro, detailed, and textual, while business was macro, strategic, and data-driven.

After that, I worked in audit at PwC, where I was thrown into the world of professional accountancy exams without any prior exposure to accounting. That was a steep learning curve. One of the main challenges was identifying what I did not understand, and how best to phrase questions to find the answer. But over time, by breaking problems down and asking better questions, the pieces started falling into place.

While accounting itself was not my passion, I remained fascinated by numbers and decision-making. That curiosity led me to study statistics and econometrics, which ultimately shaped my PhD in International Business. My research combined international law (specifically arbitration), foreign direct investment, country risk, and quantitative methods — an interdisciplinary puzzle that constantly forced me to reframe my thinking and ask sharper questions from multiple angles.

Finding your research question in a PhD requires persistent refinement in both scope and scale as your knowledge expands. That is the key to asking the next question. Being able to shift lens on a problem or challenge significantly heightens your ability to find creative and innovative solutions. Take some time to note down your thought process to tackling a problem or challenge, then analyse your thought processes to see if they follow a similar pattern or trend. If there is a trend and they follow a particular pattern then you may wish to try to engage and learn with other methods of approaching a problem, so that you can approach problems with greater diversity. You are building your critical thinking and analytical skills this way, adding to your tool belt.

That next question.

You will likely face a challenge layered with uncertainty — whether it is preparing for an exam, learning a new skill, or working on a creative project. In those moments, you may not be stuck because of a lack of effort, but because you cannot find the bridge between what you know and what you are trying to understand. That is where asking the next question becomes critical.

This is something I have seen often in mooting. A student might be researching an area of law to support a specific legal argument but struggle to locate the right doctrine, case, or principle to guide them. They are looking for an answer but cannot yet see the question that will uncover it.

Take Jessup, the Philip C. Jessup International Law Moot Court Competition, for example. In teams of two to five, students prepare written and oral submissions — in response to a 20 page long international law problem — over six months. The legal issues are complex, uncertain, and may be underdeveloped in practice. Success does not come from finding clear answers, but from navigating ambiguity and constructing coherent, persuasive and robust arguments. That requires asking the right kinds of questions, even when certainty is elusive.

Over the years, I have participated as a competitor, coach, and judge in both Jessup and the Vis Moot (which focuses on international commercial arbitration, closely tied to my PhD). These experiences have shown me something important: knowledge is useful, but critical thinking is essential.

As a coach, especially in my first year, I spent too much time learning the legal issues inside and out so that I could offer targeted, topic-specific feedback. However, over time — and with guidance from more experienced coaches — I learned that effective coaching does not depend on expertise in every niche. It is about probing students’ arguments and minds, challenging assumptions, and helping them see the flaws and strengths in their reasoning. A good coach or judge asks questions that push students to think deeper and articulate more precisely.

If you are ever stuck — creatively, academically, or professionally — consider stepping away for a while. Try learning something entirely unrelated. It might give your mind the freedom to process ideas subconsciously, which often leads to a random Eureka moment. That has happened to me — while playing video games, piano, or engaging in sports. You will be surprised how productive it is to sometimes not work on your work.

Learning something new also exposes you to different ways of thinking. It can reshape your mindset and help you develop alternative problem-solving strategies. You will return to your original challenge with new tools, new perspectives — and, crucially, the ability to ask a different kind of question.

One of the most valuable investments in my own learning journey was exploring philosophy. For my PhD, reading Comte, Hume, Hobbes, the Vienna Circle, Popper, Ayer, Hart and Hans Kelsen (just to name a few) helped me understand not only what knowledge is, but how we question it. Even if philosophy is not your main interest, immersing yourself in the history of thought can dramatically elevate the quality of your thinking, your questioning, and your ability to problem-solve.

Even now, I am on a new learning path — developing skills in game development. From 3D modelling and control rigging to animation, artificial intelligence, level design, and coding, the learning curve felt overwhelming at first. But by breaking each element into manageable sections, I have gradually built a solid foundation and now find myself exploring more advanced stages of development. Game development is a vast pipeline, requiring not just one way of thinking but many — it combines attention to detail with creative vision, technical understanding with design flow.

Let Your Mind Breathe

You should not always brute force your learning. There will be productive days and unproductive ones. The key to long-term progress is knowing how to listen — to your mind and your body. During my PhD, I would sometimes read dozens of academic articles in a single day, only to find myself rereading the same paragraph over and over without absorbing anything. That was always a clear signal to stop.

Taking rest and breaks when you become aware of your diminishing returns in terms of work is key to maintaining balance, not burning out and being even more effective. You will be surprised how much you can achieve through a few focused hours following a break rather than forcing yourself to push through. Just as athletes rest different muscle groups between workouts, we must learn to rotate our mental focus — to rest one part of the mind while exercising another.

Keep Asking

Consider how far we have come as a species — from discovering fire to exploring artificial intelligence. The technologies we use today were once things our ancestors did not even know they did not know. Every breakthrough began with a question.

So, keep asking. Keep exploring. Build your knowledge brick by brick. At some point, you will uncover the key that unlocks the idea, the insight, or the solution you have been searching for. You may not find all the answers — but in the pursuit of knowledge, each question brings you one step closer to something new (that, is what I find most exciting!).

Dr Davide D'Aleo is the founder and lead tutor at Scientiarum Vis, where we offer personalised support in law, business, CV and interview preparation, proofreading, and moot coaching. If you are interested in learning more or would like to discuss how we can support your goals, please feel free to get in touch and send us an email at info@scientiarumvis.com. For more information on our services, see here.