Asking Great Questions

The quality of our lives is determined by the quality of our questions. Great questions lead to clarity, breakthroughs, and transformation. They shape our thinking, guide our decisions, and help us see beyond our limitations. Learning how to ask better questions is a skill that can change everything—from our relationships to our careers, to our sense of purpose.

Many of us go through life reacting to circumstances rather than questioning them. But the most successful people don’t settle for surface-level thinking. Instead, they constantly challenge themselves with better questions to gain deeper insights and solutions.

“I realized that the main difference between the people who seemed to be successful—in any area!—and those who weren’t was that successful people asked better questions, and as a result, they got better answers. They got answers that empowered them to know exactly what to do in any situation to produce the results they desired.” (Tony Robbins, Awaken the Giant Within)

One of the most powerful tools for personal development is self-inquiry. Taking time to reflect and ask deep, meaningful questions helps us understand our motivations, fears, and aspirations.

• What is one small thing I could do today that would make a meaningful impact on my future? (James Clear, Atomic Habits)

• Am I allowing fear or disappointment to rule my decisions?

• What pain do I cherish most?

Questions like these shift the focus from external obstacles to internal empowerment, helping us take control of our lives.

Brian Johnson, in a Philosopher's Note on How to Think Like Leonardo da Vinci, suggests an incredibly powerful exercise:

1. Find a quiet place where you won’t be disturbed for 45-60 minutes.

2. Bring a journal and a pen.

3. Write 100 questions—about anything that comes to mind.

4. Review the list and identify patterns—notice which themes emerge (health, relationships, purpose, etc.).

5. Select your top 10 most powerful questions.

6. Rank them in order of importance to your life.

This exercise can unlock hidden insights and life-changing clarity. It forces us to dig deep into what truly matters.

The best questions are those that move us forward. They challenge us to think differently and focus on growth rather than self-criticism.

• What would you do if you weren’t afraid? (Timothy Ferriss, Tribe of Mentors)

• What kind of person will I have to become in order to achieve all that I want? (Tony Robbins, Awaken the Giant Within)

• How do you see me limiting myself? (Jack Canfield, The Success Principles)

• How can I make this better? How can I do it more efficiently? How can I provide more value? (Jack Canfield, The Success Principles)

Asking these types of questions regularly ensures constant progress in both our personal and professional lives.

The best relationships—whether romantic, familial, or professional—are built on curiosity and understanding. Learning to ask better questions deepens our connections with others.

“Over time, we whittled it down to the most essential questions that got right to the most important beats of a couple’s relationship history: How did they meet? What had their courtship been like? How had their relationship unfolded over time? What had been the big ups and downs of their union so far?” (Julie Schwartz Gottman & John Gottman, Fight Right)

Instead of assuming we know what someone else needs, we can ask:

• What does it take for you to feel loved?

• What does it take for you to feel successful?

• What does it take for you to feel confident? (Tony Robbins, Awaken the Giant Within)

Great relationships are built on great conversations, and great conversations begin with great questions.

For centuries, spiritual traditions have encouraged deep questioning as a path to enlightenment.

“Buddha constantly warned his students against simply believing his teachings. Instead, he wanted all who came to ask questions and to test and confirm his words through their own experience. His wish for everyone was, and is today, the spiritual freedom empowering one to reach enlightenment.” (Lama Ole Nydahl, The Way Things Are)

Spiritual growth is not about finding all the answers—it’s about asking the right questions.

Every question we ask either expands or limits our potential. When we ask better questions, we get better answers.

• Be intentional with the questions you ask yourself.

• Challenge yourself with deep, meaningful questions.

• Use questions to gain clarity, strengthen relationships, and guide your future.

As Executive Coach Julie Gurner puts it:

“The questions you ask yourself will largely determine the answers you get. ‘Why am I not successful?’ You’ll get answers that berate you. ‘How can I succeed here?’ You’ll get answers that push you. Be deliberate in the questions you ask yourself.”

What is one great question you can start asking yourself today?

"Eight thinking prompts I have found particularly useful: