Are You Asking the Right Questions?

About Brilliance Brief

Hi friends! If you’re new here, welcome to your go-to source for practical, no-nonsense advice. Each week, I share real-world tips from my years in the C-Suite and now as an entrepreneur—helping you lead with confidence, grow your career, and live with purpose.

Today at a Glance

• The power of questions: Why they matter more than answers.

• A 4-step framework for asking better questions.

• A bonus question to unlock hidden opportunities.

Looking for my library of 80+ cheat sheets? Subscribe to Brilliance Brief and you’ll receive a link in your welcome email.

A Big Thanks to Our Sponsor: Coaches Who Close

Want to scale a group coaching program without a packed schedule of back-to-back 1:1 meetings? My friend Ryan has earned more than $800K in coaching sales and he’s hosting a free workshop on February 10 and 11 to teach you how to craft 1 group coaching offer and turn it into a $20K launch event.

There are only 30 spots available, so apply now: Coaching for Cash Workshop

I’ve learned so much from Ryan and recommend him to all my friends in the coaching world. If you’re a coach, you don’t want to miss this!

[5-min read]

Why Questions Matter More Than Answers

What’s the secret to unlocking creativity, trust, and innovation? It’s not about knowing everything.

Great leaders know that questions—not answers—drive progress.

Take Jensen Huang, CEO of Nvidia, who’s been hailed as the world’s best CEO by Harvard, Fortune, and Time Magazine. He spends entire days simply asking his team questions.

Why? Because great questions empower people to discover insights they didn’t know they had.

This isn’t just a leadership tool. It’s a life skill.

Whether in conversations, relationships, or personal growth, the right question can open doors you didn’t realize existed.

A Personal Note on Curiosity

This lesson hits close to home for me right now. My daughter is turning five next week, and her endless curiosity inspires me every day.

“Why is the sky blue?” “What makes the stars twinkle?” “How does this work?”

Her questions are simple yet profound because they remind me to keep asking, exploring, and wondering. Curiosity isn’t just for kids. It’s a skill we need to nurture as adults.

Watching her explore the world has taught me that great questions don’t just uncover answers. They change how we see things.

Let’s explore how you can channel that same curiosity in your own life.

The Benefits of Asking Better Questions

• Build Connection: Genuine curiosity makes people feel valued.

• Boost Innovation: A well-placed “What if…?” can spark breakthrough thinking.

• Navigate Complexity: Questions help uncover blind spots and challenge assumptions.

How to Ask Better Questions

Here’s a simple framework to elevate your question-asking game:

1. Start with Purpose

   • Clarify your goal before asking anything. Are you solving a problem, building connection, or sparking ideas?

2. Ask Open-Ended Questions

   • Replace “Did the project succeed?” with “What challenges did you face during the project?” Open-ended questions invite deeper responses.

3. Use Follow-Ups

   • “Can you tell me more about that?” signals active listening and draws out richer insights.

4. Create Safety

   • Frame questions thoughtfully. Instead of “Why did this fail?” try “What did we learn from this?” It shifts the tone toward collaboration.

5. Challenge Assumptions

   • Use prompts like “What if…?” or “How might we…?” to explore beyond the obvious.

✨ Bonus Insight: The One Question to Start Asking Today

Here’s a challenge: The next time you’re in a conversation, ask, “What’s something we haven’t considered yet?”

This simple question can open doors to fresh thinking and uncover opportunities hiding in plain sight.

Practice Makes Progress

Want to sharpen your question-asking skills? Try this:

1. Think of a recent conversation where you felt stuck or uninspired.

2. Write down 5 questions you could’ve asked to make it more curious, open-ended, or specific.

3. Use these in your next conversation and see what unfolds.

Diving Deeper: Mastering the Art of Questions

Here are 3 of my favorite resources to keep your curiosity sharp:

1. Book: The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier

2. YouTube Video: The Art of Asking the Right Questions by Tim Ferriss, Warren Berger, Hope Jahren & more

3. Online Course: Curiosity: A Necessary Ingredient for Successful Innovation by ASU

Final Thoughts

Leadership isn’t about having all the answers. It’s about modeling curiosity, building trust, and unlocking creativity.

My daughter’s relentless curiosity reminds me daily that we all have the power to see the world differently. As long as we keep asking.

So, are you asking the right questions?

I’d love to hear from you: What’s a question you use to prompt deep conversations? Or what’s the best question someone has ever asked you? Hit reply and share your story—I’m all ears.

Here’s to leading with curiosity,
Justin

P.S. I recently started posting on Instagram. If we’re not connected there yet, come say hi 👋.