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Better Questions Lead to Better Quests

Written by Mark Glicini | Aug 6, 2026, 11:00:00 PM

Here is one of the best pieces of leadership advice I ever received: it is not about having all the answers; it is about asking better questions.

Rather than, “What’s wrong with you?” … ask, “How do you think you could improve next time?” Instead of doubtfully questioning ourselves: “Why do I always do this?” … we could compassionately inquire, “What should I do to be better at this in the future?” We cannot change anything that occurred five minutes, days, nor years ago. As opposed to asking, “Why does that always happen to me?” … we ought to ask, “Who can help me with this situation going forward?” Every problem can be solved alongside the right relationships, in due time, through better questions.

Positivity does not always work.

Negativity works negatively 100% of the time.

Optimism, via honest reflection, opens doors of opportunity for greater adventures, achievements, and accolades.

The unexamined life is not worth living.

Socrates, renowned philosopher known for his ideas around self-reflection, intentional living, and the pursuit of wisdom

Alongside a mentor, I have come to find the following five questions are fundamental for fortune in any field:

  1. Where are you? Before we select a destination, we must first understand our current location. Different locations and stages of life require different mentalities, states of mind. Knowing where we are, internally and externally, is a prerequisite to choosing where we go next. Every journey has a starting point. Where are we?

  2. What do you really want? The more specific, the more terrific. The key word inside this inquiry is really. When we really desire something, our aperture of attention narrows in. We become less distracted, less persuaded by peer pressure, and less focused on the irrelevant. We experience positive emotion by having an aim and seeing ourselves progress towards that aim. Happiness and progress are the same thing. We are happy when we are progressing. In order to proceed and progress, we must first decide: What do we really want?

  3. How can you get from where you are now to where you want to be? Life is a strategy game, not a talent game. Everyone is talented in different ways. Not everyone taps into their talent by operating through optimal strategies. Like a GPS showing a few routes to a specific destination, a system of strategies helps us navigate life’s terrain effectively. We must enter through the narrow gate (Matthew 7:13-14). Success leaves clues — we must seek, understand, and utilize those clues. How do we go from here to there?

  4. Who can help you? Nobody is born a doctor, lawyer, nor teacher. Abilities are found and honed through guiding guardians, mentors, and role models. Friends and peers may assist, too. Loved ones might help the most! By developing and maintaining the right relationships, we will certainly end up alright. Next time an issue arises, perhaps we could inquire to ourselves: Who can help us?

  5. Why sacrifice short-term satisfactions for long-term legacies? High performance comes from higher purpose. The greater our reasons are for taking on any endeavor, the greater our gumption will be to achieve its end. We need reasons to survive. We need reasons to strive. We need reasons to thrive. Once we decide what we really want, how we will get there, and who can help us, we must ask: Why should we sacrifice hedonism for heroism?

Questions are religious by nature. The deeper a question is, the more religious it is, too. When we pray (as we all do in one way or another), we are making a request. The word prayer means “to ask earnestly.” As it is written in the Gospel of Matthew, 7:7, ask and we shall receive.

Analogous to climbing any mountain, wrong questions lead to wrong quests down dangerous paths. Right questions light up powerful paths toward bright quests. We ought to begin with the end in mind (7 Habits of Highly Effective People), inquiring and praying along the way.

Jeff Bezos, in building the tech giant of Amazon, used a Regret Minimization Framework. He asked himself what we would regret most in the future. Implementing his idea of an online bookstore was at the top of his list.

Bill Gurley, venture capitalist who recently authored the best-selling book titled Runnin’ Down a Dream, emphasizes chasing one’s curiosity. All cures come from curiosity. Gurley argues we have a personal responsibility and moral obligation to ask ourselves better questions, honing our crafts from there on out.

As a final example: Ella Langley, an exceptional country music singer, once asked herself, “Are we sure that’s really what we want to do?” [when contemplating a career in music]. Although she was merely a kid at the time when did this reflection, a response still came up from within. “There was this thing inside of me that said, “If you don’t do it, you are going to hate your life for your whole entire life.” That’s a powerful internal response to a seemingly simple question.

“I just know it’s what I must do when I made my mind up.” Langley, as a young girl, had the prudence to ask herself a motivating question. She had the temperance to listen to an answer within her. She had the courage, willingness, and resolve to follow through. Langley brought herself to fame by asking herself the best possible question she could about her life’s purpose and aim.

Bad lives derive from zero introspection.

Honest self-reflection catalyzes self-affection.

From there, better questions lead to better quests!

 

- MG

 

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