Another Day, Another Workshop !
How to Ask Questions That Build Trust ft. Chad Littlefield | #ADAW Ep. 12
18 Sep 2025
"Powerful questions don’t take power, they give it.”In this ADAW episode, Chad Littlefield, TEDx speaker, bestselling author, and co-founder of We and Me, shares how the right question, asked with the right intent, can completely transform the impact of your workshop.Quick heads-up: I’m launching The Workshop Deck : 52 cards to help you design better workshops in less time. Join the free live event on Oct 23 to see how it works. [Sign up here → https://luma.com/go6tr960 ]We dive into:✅ Why “icebreakers” should be renamed with connection before content✅ How to ask questions that create psychological safety and trust✅ What makes a question truly powerful — and how it can edit someone’s future✅ How intent and curiosity shape group dynamics✅ Why nailing your delivery is the best marketing✅ And the trap of becoming an “airport speaker” 🤐Whether you’re leading your first session or designing advanced offsites, Chad’s insights will help you ask better questions, build stronger connection, and run more meaningful experiences.⸻📌 𝗖𝗵𝗮𝗽𝘁𝗲𝗿𝘀00:00 - Meet Chad Littlefield: Connection Expert & Creator of We! Connect Cards06:40 - From Teenagers to Tech Teams: How the Cards Were Born10:05 - What Makes a Question “Powerful”?12:08 - The Problem with Icebreakers (and What to Say Instead)16:30 - The Phrase That Shifts Group Energy Instantly20:15 - Stop Asking “Why?” (And What to Ask Instead)26:10 - Presence Over Process: What Really Matters in Facilitation30:00 - The Marketing Power of a Truly Great Workshop35:30 - Thinking, Selling, Delivering — At the Same Time42:50 - Editing the Future with One Simple Question50:12 - The One Question Every Facilitator Should Ask54:00 - How to End Meetings That Actually Drive Action56:45 - Behind the Scenes: The Connector Summit + Priya Parker Keynote01:00:35 - Chad’s Thought Process: Purpose as a Shortcut to Depth01:05:10 - Boring Is the Enemy of Great Facilitation01:07:40 - Final Thoughts: Questions That Spark Real Change01:10:05 - Outro + Where to Find Chad⸻🛠️ 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀 & 𝗟𝗶𝗻𝗸𝘀• Register for the Connector Summit (Dec 10–12): https://weand.me/connectors-summit/• Chad’s Website: https://weand.me• Ask Powerful Questions (Book): [Insert Link]https://shop.weand.me/products/ask-powerful-questions• Register for the Connector Summit (Dec 10–12): https://weand.me/connectors-summit/• Follow Chad on LinkedIn:https://www.linkedin.com/in/chadlittlefield/• Chad’s YouTube Channel: https://www.youtube.com/@chad.littlefield
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