Asking Great Questions to Gain Insight and Wisdom

Guest Post by Jeremy Chandler

Originally Posted @

Millennials are thirsty for knowledge. Most of us are extremely interested in learning through the experiences of others.

As a result, almost every Millennial I know has the desire to be mentored — to sit down with someone older than us and pick their brain.

But there’s an important principle most Millennials miss when trying to get ideas or advice from those with a little more perspective. When it comes to gaining wisdom or insight during a conversation — asking great questions is essential.

Asking great questions is an art. Rather than simply trying to understand the principles that made them successful so we can implement them too, it requires a genuine interest in the other person’s story. Rather than focusing on we’re going to say next, it requires us to slow down and truly listen.

Why Great Questions Are Important for Gaining Insight & Wisdom

Here are a few benefits I’ve found from learning how to ask great questions:

Great Questions Reveal the Important Things

Most questions help us identify what’s evident on the surface. Why do you think you were successful? What would you do if you were in my shoes? These are questions a third-party could probably answer on behalf of the person.

Great uncover truths we might not know otherwise. They “pull back the curtain on the wizard” and give us a more accurate view of reality. They help us discover what is really important to that person, what really happened, what factors were really the most important for the outcome.

Great Questions Get to the Heart of the Matter

Most questions help us identify what’s evident on the surface. A great question is a surgeon’s scalpel that cuts deep below the surface to tap into the issue behind the issues. They help us double-click into an important concept or lesson rather than copying and pasting it.

Great Questions Unlock Principles, Not Tactics

If we want mentoring to make a difference in our life, we shouldn’t try to copy what people do… we should learn how they think. This is an idea I’ve talked about before. Great questions help us learn how people think. Rather than trying to replicate the tactics they used to be successful, great questions help us unlock the principles they used to make important decisions.

Great Questions Transform

Good questions inform, but great questions transform. They produce an answer that inspires the person, encourages him or her, and makes them want to be a better person. Asking great questions that inspire and transform is a small, simple way we can provide value to the person we’re trying to gain insight and wisdom from.

Four Questions that Get to the Heart of the Matter:

There are literally hundreds of great questions you can ask.

Here are a few of my favorites:

1. What is a factor that helped you succeed that most people on the outside wouldn’t realize?

Successful people are asked all the time what makes them successful. They’ve probably given the same answer dozens of times. This question helps unlock a different perspective to consider factors that not be recognizable from the outside looking in.

2.  What times in your life truly “tested your mettle,” and what did you learn from dealing (or not dealing) with them?

The challenges or failures we experience in life often shape us the most. However, most people don’t ask about the difficult moments. Asking this question helps us tap into the lessons or insights a person learned in a season or circumstance in which they were truly being stretched.

3.  What do you think the world needs more of right now?

This question changes our perspective. We lift our eyes from the day-to-day tasks and responsibility to really think about the values we cherish most. Uncovering what someone values is an incredible way to understand how they see the world.

4.  … Why?

“What” questions are a great conversation starter. “Why” helps you double click and discover the important insights and ideas below the surface. Taking the time to listen and ask “why” the person believes or feels a certain way can help lead you to insights you wouldn’t have discovered without asking the second question of “why”.

Asking great questions isn’t easy. But the more I practice, the more I’m convinced that Learning the Art of Asking Great Questions is critical for truly gaining the insight and wisdom we’re looking for.

Jeremy Chandler


Jeremy Chandler is a Millennial who writes for Thin Difference on the topics of leadership, career development, and personal growth. He currently lives in Nashville, TN and jumps at any opportunity to connect over coffee.


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