Question Everything

Techniques for Turning Answers into Strategies

"Why the sky is blue?"

A reasonable question for a young human to ask. But I didn't just ask that. I followed up by asking why everyone believes the sky to be blue. And, when given an answer, I unveiled what I imagined in my young mind to be a well-architected argument that that the sky was in fact NOT blue.

It was for sport, mostly. The spar was everything. Might still be sometimes. Of course, my inquisitive nature did not entertain my parents, teachers, coworkers and a few friends as much as it did me. In fact, I assuredly displayed early symptoms of being a pain in the ass. Yeah, I was that kid.

The demand for evidence and spirit of debate to press an answer or concession combined to be both entertaining and enlightening. It allowed me to extract information and gather opinions simultaneously that I could combine to take some sort of action. Or at least to make sense of the world and exert some sort of influence on it.

As a seemingly mature adult, I now see clearly that questions produce insights, insights inform strategies, and strategies make things happen. The point of using questions to develop strategy lies in the power of inquiry to stimulate critical thinking, encourage collaboration, and facilitate a deeper understanding of the various factors that influence an outcome.

I recently began thinking about how, by asking the right questions, a skilled and/or experienced inquisitor, can gain clarity, explore parallel possibilities and outcomes, foster involvement, uncover risks, and discover new ideas and concepts. But, not all questions are built the same way.

There are different questioning strategies with unique benefits depending on the context, goals, and desired outcomes. For example, open-ended questions encourage deeper, more detailed responses from the subject and can invite extra information shared accidentally, while closed-ended questions typically result in brief, specific answers that are fact-based and designed to offer data rather than opinion. Both types have their place in developing strategies, but open-ended questions explore ideas while closed-ended questions confirm understanding.

Probing questions should sometimes be used to delve deeper into a topic or explore underlying assumptions. Use these to uncover hidden information, assess the accuracy of what you think you understand, and encourage and inform your critical thinking.Probing questions are often used in cross-examination to pull apart or pokes holes in prior testimony.

Have you ever heard of "leading the witness"? Leading questions guide the respondent towards a specific answer or perspective that you intend them to make. While they can be helpful in some cases, it's important to use them sparingly to avoid biasing responses. Or, if you want to guide someone to offering a specific answer, they can be useful. I've found this to be particularly helpful in communications when trying to capture a specific quote from someone.

Funneling or sequential questions involves starting with open-ended questions and gradually narrowing the focus by asking more specific, closed-ended questions until arriving at the core truth or information sought. This approach is also useful for guiding a conversation or exploring complex issues in a structured manner.

These final two types of questions are among my favorite tools. Empowering questions are designed to challenge assumptions, stimulate creativity, and empower individuals to take responsibility and make decisions. They often start with phrases like "What if...?" or "How might we...?" These are particularly good to get a group thinking about a project or challenging the status quo and norms. The trick is to ask the question and then be silent and see what happens.

Finally, the granddaddy of all questioning techniques: Socratic questioning. Inspired by the teaching method of ancient Greek philosopher Socrates, this strategy involves a series of probing questions aimed at fostering critical thinking, uncovering underlying beliefs, and challenging assumptions. Such questions probe assumptions, logic, evidence and reason. This type of questioning is the foundation of the Socratic method of teaching and inquiry and it could be said has driven intellectualism in the Western world for two millennia.

Finally, there is one additional technique baked into any questioning strategy. The reaction that people have when asked questions sometimes offers as much data as the answer itself. It's never just what the answer is that is given, but how it is given. Complete? Incomplete? Animated? Defensive? Collaborative? Obtuse? All of these are clues as to the perspective of the source of the answer and are often as useful as the answer itself.

The ability and capacity to ask a question, any question, and to question everything and everyone, without risk of reprisal beyond surreptitious responses, is the ultimate expression of freedom. Question the world around you. Question authority. Question hierarchy. Question me. Even question yourself.

Question absolutely everything.

Any questions?