Questioning Our Questions

Alli Esker
4 min readOct 15, 2020

Below is an excerpt from my book, The Power of Pivot: A Female Perspective on Embracing Change, (Now available on Amazon: https://www.amazon.com/dp/B08DRXLVB4)

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Around 1480, Leonardo Da Vinci arrived at a cave in the Tuscan countryside. He describes his own emotionally charged reaction as he approached the cavern:

Unable to resist my eager desire and wanting to see the great . . . of the various and strange shapes made by formative nature, and having wandered some distance among gloomy rocks, I came to the entrance of a great cavern, in front of which I stood some time, astonished and unaware of such a thing. Bending my back into an arch I rested my left hand on my knee and held my right hand over my down-cast and contracted eye brows: often bending first one way and then the other, to see whether I could discover anything inside, and this being forbidden by the deep darkness within, and after having remained there some time, two contrary emotions arose in me, fear and desire — ­fear of the threatening dark cavern, desire to see whether there were any marvelous thing within it.

Da Vinci is known as one of the greatest inventors to have ever lived. His journals are littered with iterations of sketches and notes that depict everything from engineering contraptions to horses’ hooves and simple geometric shapes.

It’s easy to connect Da Vinci’s intellectual capacity directly to his ability to conceive ideas far ahead of his time like the parachute, armored tank, or helicopter. However, it’s important to understand that Da Vinci wasn’t focused on solution generating. His ability to ask, like the students taking part in the Right Question Institute activity, rather than pigeon-hole himself with the burden of finding the perfect answer, ultimately shaped his pervasive success.

‘Why is the sky blue?’ is a question that could be answered within seconds from a Google search today. In fact, it led me to over five billion results in less than one second. But, it was found in Da Vinci’s journal, along with a plethora of others like, “Why does a dog sniff another dog’s behind?” and “What makes a face beautiful?”

Today, with technology as our enabler, we have the ability to ask almost any question at any time and find an answer relatively seamlessly and without much friction. Yet, what’s troubling is that the rapid adoption and improvement of technologies like AI and machine learning provides us with systems that can predict not only what kind of question we might want to ask (What restaurants are near me?), but know what kind of answer we are seeking (Here are vegetarian, eco-friendly restaurants with patio seating near you). It’s helpful of course, but when we are asking bigger questions, (Who should I vote for?) the technologies already recognize what our biases are and the answers they display are in align with those biases, further confirming our own inherent predisposition and stifling us from discovery. In the case of attempting to utilize question asking to discover new insights and lead me down new paths, this truth is rather concerning and serves, even more so than being fearful of asking questions themselves, as the greatest inhibitor in practicing this principle effectively.

In a time when answers weren’t nearly as democratized and streamlined as they are currently, Da Vinci wasn’t afraid to ask questions that didn’t have a seamlessly discoverable answer by way of an optimized search engine. He asked question upon question, many of which wouldn’t be answered for centuries, and several of which would be labeled as “stupid” today.

There’s probably never been a more relevant time in history for questioning to lead us to a new place or new learning opportunity. As we’ve seen with Roshi and Polina, The Female Advantage is exemplified by the power of asking effective questions and being transfixed on discovery as a process. In the age of the information economy, we are oftentimes bombarded by too much information and are left with having to learn how to sift through the plethora of material available to us, rather than go on a treasure hunt to find the information.

As Eric Reis, a Silicon Valley entrepreneur and author of The Lean Startup, puts it: “In the old economy, it was all about having the answers. But in today’s dynamic, lean economy, it’s more about asking the right questions. A more beautiful question is about figuring out how to ask, and answer, the questions that can lead to new opportunities and growth.”

For all of us today, there’s plentiful opportunity to utilize our ability to ask questions as a powerful means to explore the unexplored, whether it be tangible concepts like a new job, a new city to move to, or even more abstract concepts like systemic racism or ancient art forms. By doing so, we will learn something new that could lead us down a new path.

When 20th century historian and philosopher Arnold Toynbee said, “Civilization is a movement and not a condition, a voyage and not a harbor,” he probably didn’t conceive the rate at which the world would be changing over the last few decades. Yet, his quote endures today as a reminder that we aren’t immovable or unchangeable. As simple as it seems, it’s in asking questions that has allowed women individually to learn and develop, and collectively, to reach new heights.

If civilization is both a movement and a voyage, perhaps it would do us some good to more critically question those points we are traveling both toward and from. Curiosity can help us get from point A to point B, but more importantly, it helps us question the As and the Bs themselves. In doing so, we become better equipped for asking the kinds of questions that might just lead us to new, undiscovered realizations.

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In this article series, I share excerpts, stories, and musings from my book, The Power of Pivot. I hope you enjoyed this post — if you enjoyed it and want to connect you can reach me via email [thepowerofpivot@gmail.com], or through my website: http://www.thepowerofpivot.co/#/

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