Expand Your Philosophy: Master the Art of Restating Questions – Better Clarity, Connection, and Communication

Learned Wisdom
Written By Chris Read

Short principles for long-term clarity—and occasional epiphanies.

How can restating and rephrasing questions enhance understanding?

“The right question, asked with curiosity and clarity, doesn’t just seek answers - it reshapes how we think, illuminates insight, and turns confusion into revelation and discovery.”

Humans use questions every day, but what are they? They are communication and reflective tools that help you uncover something that you don’t currently know. By asking a question, you are seeking information to assist you in creating a more complete map of your world. Who you target with the question, like the orientation of a map, changes how it is perceived and therefore how our target feels about being questioned.

The complication with much of human communication comes down to the fact that when we ask a question of another person we do so from our own unique perspective. Your context as the asker shapes what makes sense to you. This does not necessarily translate to the context that another person holds, leading to miscommunication. As an example, someone can ask a question you think is “stupid” because it appears obvious to you, however, from their context and perspective it appears to be a pertinent question. For example, imagine someone who has never seen the sky asking, ‘What colour is the sky?’. From your perspective, not understanding their life experience, you might think they are daft despite the fact they have never seen this thing called “sky” before. Such judgments can harm our relationships.

On the flip side, when we receive unclear questions it can take us to a different place, anger and confusion. This is likely for a couple reasons, the most salient of which are that you do not like explaining yourself or that there are not enough intellectual handholds for you to use to answer the question you have been asked.

The first case is an issue of energy and effort. It’s even more frustrating when someone repeatedly asks the same question - e.g., ‘How do I tighten this bolt?’ - when the answer (‘with the socket wrench’) hasn’t changed. This is especially true if the same questions have been asked multiple times. The burden of explanation falls on you due to their lack of understanding.

The latter case is an ambiguity problem. When you receive a question that is too vague, it becomes difficult to answer as, without a clarifying question, there are too many possible answers – most of which are unlikely to be what the asker wanted. An example of this would be a question like “is the hat blue?” – to which I might answer “which hat? mine, my friend’s, the one in the advertisement, or the prime minister’s?”. Another example might be “how many ducks live in France?” where the question’s relation to the conversation you are having may seem totally inconsistent and inconsequential to your current discussion about, for example,  “living expenses”.

So, how do we remedy this issue in communication?

First, ask more specific questions. Stripping away ambiguity in what you ask other people can ensure that you are aligned with each other. This ensures that the answer that is provided will be relevant and avoid miscommunication. For example, instead of “is the hat blue?” you could ask “is the hat you have upstairs, blue?” – it is a simple manipulation and appears more effortful, but, by avoiding miscommunications you avoid more costly arguments.

Secondly, and this is my favourite, you rephrase the question you receive. Most questions act as a single datapoint, so when you receive them, you must try to parse details through the lens of the question you were asked which may not always be helpfully phrased. So, as the receiver, add a new datapoint that helps you self-clarify the question.

To self-clarify, try rephrasing the question using a different preposition (Who, What, When, Where, Why, How). For example, “What do you want for dinner?” could be rephrased as internally to “Which cuisine do I feel like for dinner?”. The more of these questions you ask, the clearer the original question becomes. This is because it helps to elucidate either: the clarifying question you need to ask to get more context, the answer that better meets the needs of the asker, or both.

The goal isn’t to magically know the answer but to gain another perspective. It reduces the friction and confusion of misunderstanding and puts you in a more curious mindset. The exciting thing is that we do not just have to use this for when other people ask us questions. We can do it when we ask ourselves questions too.

Throughout your life, you don’t just question others, but you also question yourself. The power we give ourselves is through another perspective as if someone else has asked us a clarifying question, another datapoint. Examples of this might be “Why did you do that [Insert own name]?”, “How could they do that to me?”, and “Why do things like this always happen to me?”. When you start to use different prepositions, the frame of how you look at the “problem” loosens a little, giving you more freedom:

  • “Why did you do that [Insert own name]?”

    • “[Name], what were you trying to accomplish there?”

  • “How could they do this to me?”

    • “What is going on with that person causing them to do this to me?”

  • “Why do these things always happen to me?”

    • “How do these things keep happening?”

    • “Where do these things keep happening to me?”

    • “Who is present when these things happen to me?”

You probably can feel that with each subsequent question you ask yourself, you gain momentum towards resolution. You’re not limited to just one self-clarification question - you can ask as many as you need. Why stop at one question? What function could asking more questions have? How could more questions provide more clarity? Why are multiple questions good or bad? (yes Chris, ha-ha, very funny).

The answer to these communication issues with others and ourselves can be remedied by rephrasing the exact same question in different ways. It is like shining separate spotlights onto the thing you are seeking information about. At first, it’s a giant, amorphous blob. But with each spotlight (‘self-clarification’), its true form becomes clearer, reducing confusion. So, if you feel powerless in the face of your own or other people’s stale and ambiguous questioning – rephrase the question and empower yourself with more clarity. Take control of it.

Questions shape our understanding, but how you wield them determines whether they limit or liberate you. When faced with uncertainty - whether from others or within ourselves - don’t accept confusion as the final answer. Reframe. Rephrase. Illuminate. Every question holds the potential for greater clarity, deeper insight, and more meaningful connections. You are not at the mercy of ambiguity - you have the power to shape the conversation, to see beyond the obvious, and to chart a clearer path forward. So, take the question, turn it over, and ask again—this time, with purpose.

Reflection Questions:

  • Imagine you were a robot that could only rephrase your question without adding any new meaning - what would it say?

  • If I stripped away all assumptions and made my question fully explicit, how would it sound?

  • If I asked this question to a child with no context, how could I rephrase or reframe it so they understand?

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Chris Read
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