The Art of Asking Great Questions...(solo episode) | The Grateful Podcast Ep. 136 episode artwork

EPISODE · Jun 4, 2026 · 23 MIN

The Art of Asking Great Questions...(solo episode) | The Grateful Podcast Ep. 136

from The Grateful Podcast with Jack Wagoner · host Jack Wagoner

Send us Fan MailThe Grateful Podcast with Jack WagonerMost people think the person asking questions is the dumbest in the room. In this solo episode, Jack breaks down why the opposite is true, how he developed the skill of asking great questions through 130+ podcast episodes, and why curiosity might be the most underrated skill in business, relationships, and life.We go deep on why curiosity peaks at age 4 and declines from there, the moment Jack stopped reading questions off a script and started asking from instinct, what happened when he hired people based on their ability to ask rather than their ability to perform, and why human connection is dying in a world that has every answer at its fingertips. If you've ever sat in a room full of people and been afraid to raise your hand, this one's for you.Chapters:0:00 — "Fools and Fanatics Are Always So Certain of Themselves"1:41 — Someone Asked Me How I Ask Good Questions3:28 — The Kid Whose Hand Shot Up Every Time6:03 — Three Meetings in NYC Changed How I See This6:45 — How I Went From Reading Questions to Asking From Instinct9:59 — How You Can Get Better at This (Without a Podcast)12:22 — Why Every Great Founder Starts With a Question13:33 — Your Thoughts Are Questions (Tony Robbins, Bob Proctor)16:49 — Why This Matters More Than Ever Right Now17:11 — What I Looked For When I Hired Two People This Week18:37 — Human Connection, AI, and Why Nobody's Coming to Save Us21:15 — Go Ask Someone a Question TodaySupport the showInnerVue — a complete self-awareness tool→ yourinnervue.comUse code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report☕ Magic Mind — My daily performance shot:→ https://magicmind.com/wagoner20Use code WAGONER20 for 20% off a package or 48% off a subscription.🧠 More from Jack:► Website: https://jackwagoner.co► Instagram: https://www.instagram.com/jack_wagoner_/► 1:1 Coaching: [email protected]📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner⸻🎙️ About Jack:I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.Subscribe and turn on notifications so you never miss an episode.Stay grateful, stay hungry.

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The Art of Asking Great Questions...(solo episode) | The Grateful Podcast Ep. 136

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This episode was published on June 4, 2026.

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