Curated Questions: Conversations Celebrating the Power of Questions!

Mitchell Osmond, founder of Dad Nation Co. and a motivational coach, shares his journey of transformation after a pivotal question at a funeral made him reassess his life. He discusses the importance of choosing which difficulties to embrace and how discomfort can lead to growth. They explore practical tools for fostering resilience in children and strengthening family bonds through honest communication. Mitchell emphasizes that confidence is built through keeping promises and encourages ongoing self-inquiry to define personal success and legacy.

"What are the questions you will be carrying into the year, such that it will be a celebration of your becoming?" - Ken WoodwardThis year-end Curated Questions episode is a reflective curation of the questions that shaped several conversations throughout 2025. Rather than offering a rapid recap of every episode, Ken highlights a handful of moments that reveal how intentional questioning can clarify purpose, interrupt unhelpful patterns, and guide meaningful becoming.Across stories from entrepreneurs, scientists, artists, and personal reflection, the episode explores questions that ask us to define the change we seek to make, consider who we are becoming, and choose where to place our attention. Along the way, listeners are reminded that good questions often emerge only after many imperfect ones, that perspective shapes dignity and connection, and that small mental reframes can act as powerful resets.As the year closes, the episode becomes an invitation: to name the questions that mattered most in 2025, to carry one forward with intention into 2026, and to trust that a better world is built by those willing to keep questioning.Sign up for the weekly Curated Questions Dispatch newsletter at https://curatedquestions.substack.com/This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Ensure to subscribe to the Curated Questions Dispatch weekly newsletter on Substack.Keep questioning!Episode Notes00:00 Highlight01:56 Introduction and Welcome02:51 Overview of 2025 Episodes04:09 Curated Questions Dispatch Newsletter05:10 Highlighting Seth Godin's Insights07:31 A Helpful Practice08:46 Lisa Wimberger on Neurosculpting09:25 Tim Molnar's Strategic Dating Guide10:14 Kevin Kelly on Questioning and AI11:30 Robert Sturman's Unique Perspective12:23 Conclusion and Call to ActionResources MentionedFlightcastSteven Bartlett, host of Diary of a CEOCurated Questions Dispatch on SubstackSeth GodinAsk the Dust by John FanteHannah FryLisa WimbergerNeurosculptingTim MolnarDate Smarter: A Strategic Guide for Navigating Modern Romance by Tim MolnarKevin KellyRobert SturmanSan QuentinProducer Ben FordBeauty Pill

"Direction often emerges not from knowing what you want, but from finally admitting what you don’t." - Ken WoodwardThe Inquisitive Almanack: 2026 Edition closes the year with something Curated Questions has never quite done before—an affectionate, slightly irreverent, and deeply thoughtful almanack for the inner life.Inspired by Benjamin Franklin’s Poor Richard’s Almanack, this episode blends dry wit, invented bureaucracy, and hard-won wisdom to offer forecasts not for the weather, but for the heart, mind, and questions we carry.You’ll hear interior weather reports, proverbs for the asking class, arbitrary rules of inquiry, lunar phases of curiosity, and predictions for the questions most likely to surface in 2026—across leadership, relationships, parenting, teams, and personal life.Released intentionally as the final episode of the year, this Almanack isn’t a recap or a resolution guide. It’s a pause. A breath. A lighter place to rest before the calendar turns and begins asking new things of us.Come curious. Leave rested. And carry one good question forward.Be sure to check out the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (LINK)This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Resources MentionedPoor Richard's AlmanackBenjamin FranklinProducer Ben FordBeauty Pill

"Not being a hundred percent sure all the time is a weird strength." - Haru YamadaIn this episode of Curated Questions, Ken Woodward is in conversation with Dr. Haru Yamada, a sociolinguist, intercultural communication scholar, and author of Kiku: The Japanese Art of Good Listening, to explore what it really means to listen. Haru traces her early understanding of questions back to age four, when she moved from Tokyo to New York and had to use questions as a tool for language, belonging, and survival.Together, they unpack how culture shapes communication: English often rewards “flashlight” questioning, the precise, content-driven clarity, while Japanese culture tends to favor a “lantern” approach that illuminates context, relationship, and what isn’t said. Haru also shares the harrowing accident that reshaped her understanding of listening as a health practice, linking felt-heard experiences to relational, mental, and even physical well-being.In a noisy, multitasking world, this conversation reframes listening as an active, life-giving skill, and a compass for navigating each other with empathy.Be sure to check out the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 Introduction: Embracing Uncertainty01:57 Introducing Dr. Haru Yamada02:23 The Art of Listening: Kiku03:12 A Life-Altering Accident03:37 Welcoming Dr. Yamada04:02 Early Experiences with Questions04:57 Navigating Cultural Differences07:28 The Journey of a Third Culture Kid08:19 Academic Pursuits in Linguistics10:32 The Strength in Uncertainty16:04 Questioning Anti-Fragility As A Goal23:02 Flashlight vs. Lantern: Different Approaches to Questions26:57 Cultural Context in Business Meetings28:16 Interpersonal Communication Challenges32:12 The Importance of Listening39:51 Personal Anecdotes and Reflections44:11 The Healing Power of Being Heard47:42 Reflecting on Past Medical Experiences48:16 The Evolution of Listening Post-COVID49:41 Remote Work and Multitasking52:24 The Impact of Isolation on Communication54:02 Curated Interactions in the Digital Age55:34 The Shift in Media Consumption57:48 The Importance of Visual and Auditory Listening59:04 Personal Experiences with Hearing Loss01:00:58 Advancements in Hearing Aid Technology01:03:20 The Value of Ambiguous Questions01:04:23 The Fear of Uncertainty in Listening01:05:05 The Role of Multitasking in Communication01:07:24 Learning from Students' Unique Needs01:11:29 The Changing Nature of Academic Inquiry01:19:23 Better Understanding The Lantern View01:22:35 Cultural Differences in Language Learning01:24:52 The Complexity of Bilingualism01:26:48 The Challenges of Cross-Cultural Communication01:31:07 Final Reflections and TakeawaysResources MentionedKIKU: The Japanese Art of Good Listening by Dr. Haru YamadaLynn Borton at Choose To Be CuriousJeff WetzlerAustin K GraffAntifragile: Things That Gain from Disorder by Nassim Nicholas TalebThe Power of Introverts TED Talk by Susan CainStanford Interpersonal Dynamics ClassDr. Haru Yamada on LinkedInProducer Ben FordBeauty Pill

Rob Walker, a writer and cultural observer known for The Art of Noticing, discusses the transformative power of asking questions. He shares how his passion for journalism at 18 gave him permission to ask, fueling his curiosity. Rob highlights the unique storytelling culture of New Orleans and how small noticing assignments can enrich everyday life. He illustrates the significance of narratives in valuing objects through his Significant Objects project and emphasizes that questions hold the key to creativity, agency, and societal progress.

"We vote with our labor for the world we want to create. If you don't reflect on what you're doing, how do you know you're casting the right vote?" - Radhika DuttIn this episode of Curated Questions, host Ken Woodward engages entrepreneur and author Radhika Dutt in a profound exploration of how questions can transform organizations from goal-driven to puzzle-solving entities. Radhika is the author of "Radical Product Thinking" and shares her journey from MIT to becoming a serial entrepreneur to developing the puzzle-based leadership OHLA framework (Objectives, Hypotheses, Learnings, Adaptations).The conversation reveals how traditional goal-setting, rooted in 1940s assembly-line thinking, fails in today's complex environment, where creative problem-solving matters more than repetitive execution.Radhika demonstrates through a live experiment how "puzzles" energize while "goals" burden, explaining that puzzles tap into internal motivation rather than external pressure. She emphasizes the critical importance of reflection, a practice she credits with enabling better decision-making both personally and professionally.Drawing from her nine languages and global experience, including living in post-apartheid South Africa, Radhika offers insights on creating psychological safety for questions across cultures. The episode culminates with practical guidance on implementing puzzle-based thinking in organizations, showing how asking better questions leads to ownership, engagement, and transformative results.Be sure to check out the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Resources MentionedRadical Product Thinking: The New Mindset for Innovating Smarter by Radhika DuttLobby SevenMITAvid TechnologyMonetary Authority of SingaporeChatGPTSam AltmanGates FoundationWhat has the Gates Foundation done for Global Health?Muhammad YunusMicroloansEsther DufloAbhijit BanerjeeFrank BlakeAdobeAppleOnly The Paranoid SurviveDavid Eagleman Management by Objectives detailed in The Practice of Management by Peter DruckerGeneral MotorsLean StartupAdidasBryn Mawr CollegeMonument LabAlbert EinsteinDrama of the Gifted Child by Alice MillerOHLA Framework Toolkit (Objectives, Hypotheses, Learnings, Adaptations)Radhika Dutt on LinkedInRadicalProduct.comProducer Ben FordBeauty Pill

"The Insight Pause is sitting in the rubble of your shattered worldview before clearing a single stone." - Ken WoodwardIn this solo episode, Ken Woodward introduces The Insight Pause—a five-step framework for navigating the moments that crack open our worldview. Through his own story of confronting the hidden history behind the Indigenous names and artifacts that shaped his childhood landscape, Ken explores how insights arrive fully formed, unsettle our identities, and demand more than quick fixes or defensive reactions.He walks listeners through the foundational skills that prepare us for these moments, the instant of recognition, the sacred pause that follows, and the slow work of integrating unsettling truths into a new, liberated worldview.Whether you're rethinking long-held beliefs, noticing contradictions you can’t ignore, or sensing that something in your life no longer fits, this episode offers a practical and compassionate guide for holding discomfort without collapsing into denial or overreaction.Discover how the Insight Pause can transform the questions you carry—and the person you’re becoming.Be sure to check out the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 Introduction and Welcome01:55 Personal Story: Early Realizations02:36 The Cracks in the Story02:51 Framework Introduction03:37 Manifest Destiny and Indigenous Names04:29 A Shattered Worldview05:37 The Moment of Insight05:56 Step One: Foundation07:38 Step Two: Insight08:47 Step Three: Insight Pause10:23 Step Four: Integration12:04 Step Five: Liberation13:28 Insight Pause Deep Dive16:14 Practical Applications17:11 Creating Your Own Pause Practice19:36 Final Thoughts and Call to ActionResources MentionedYavapai County (https://www.yavapaiaz.gov/Home)Hopi (https://www.hopi-nsn.gov/)An Indigenous Peoples' History of the United States by Roxanne Dunbar-Ortiz (https://a.co/d/8xO1EDb)Manifest Destiny (https://en.wikipedia.org/wiki/Manifest_destiny)Prescott, Arizona (https://en.wikipedia.org/wiki/Prescott,_Arizona)Quinnipiac River (https://en.wikipedia.org/wiki/Quinnipiac_River)Niantic (https://en.wikipedia.org/wiki/Niantic_people)Montauk Point (https://en.wikipedia.org/wiki/Montauk_Point_Light)Mashantucket Pequot (https://www.mptn-nsn.gov/)Mohegan (https://www.mohegan.nsn.us/)Bison herds (https://en.wikipedia.org/wiki/American_bison)American exceptionalism (https://en.wikipedia.org/wiki/American_exceptionalism)Founding Fathers of the United States (https://en.wikipedia.org/wiki/Founding_Fathers_of_the_United_States)Piscataway (https://en.wikipedia.org/wiki/Piscataway_people)Narragansett (https://en.wikipedia.org/wiki/Narragansett_people)Producer Ben Ford (https://www.producerbenford.com/)Beauty Pill (https://www.beautypill.com/)Questions AskedWhat question are you avoiding that would change everything?What questions float at the edge of your consciousness?What contradictions do you live with daily?Even if 50% of the book was false, what do I do with the 50% that's true?What do I do with the 50% that's true?What truths are hiding in plain sight in your life?Why do our best people keep leaving?Why do I keep having the same fight?Why does this success feel empty?Why does this certainty require so much defending?What am I working hard not to see?Where do you feel the truth in your body?What truths are hiding in plain sight in your life?What feedback have you been deflecting?What patterns have you been rationalizing?What questions are you unwilling to ask?What costs are you refusing to calculate? (What names are you driving past?What pottery shards are you collecting without asking whose hands shaped them?What “half-truth” would change everything if you faced the true half?What seedling of truth needs protection in your sacred uncertainty?

Frank Sesno, an Emmy Award-winning journalist and former CNN bureau chief, delves into the art of strategic questioning. He shares how curiosity shaped his career, starting from a childhood question about astronauts. Frank introduces the 'echo question' technique for deeper conversations and discusses how to balance respect with directness in interviews. He emphasizes the importance of bridge-building questions in today’s polarized world and explores how AI can enhance human curiosity. Frank inspires listeners to make an 'appointment with curiosity' for richer dialogues.

"When you have a trusting environment, it is exactly to hold each other accountable." - Jaimie ReeseWhat does it take to build trust in one of the world’s largest bureaucracies? Former U.S. Navy Senior Executive (SES) Jaimie Reese joins Ken Woodward to explore how genuine curiosity and courageous questioning can reshape systems, teams, and lives. From the aftermath of 9/11 to boardrooms and the Pentagon, Reese shares hard-won lessons on leadership, timing, and the art of listening when stakes are high.Through stories that move from crisis to calm, she unpacks why trust isn’t granted by authority but earned through everyday inquiry—how slowing down, asking better questions, and truly hearing the answers can transform any organization. Jaimie traces the invisible threads between humility, communication, and change, revealing what happens when leaders replace certainty with curiosity.This episode challenges every listener to reimagine leadership as an ongoing dialogue. Because, as Jaimie reminds us, “Leadership is a conversation you have with the future—one question at a time.”This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 Building Trust and Accountability01:07 Introduction to Curated Questions01:51 Meet Jamie Reese03:05 Jamie's Early Career and Learning the Power of Questions05:36 The Importance of Prioritizing Questions06:37 Building Relationships Through Questions10:17 Navigating Requirements and Funding in the DOD14:31 Engaging Stakeholders22:16 The Role of Diverse Voices in Decision Making28:29 Creating a Safe Space for Questions36:44 The Importance of Time in Asking Questions37:36 Reflections on Time Management39:21 The Importance of Time Management40:03 AI and the Art of Asking Questions40:52 Balancing Speed and Quality43:07 The Cost, Schedule, Performance Triangle43:26 Applying Business Principles to Human Capital45:38 Managing a Large Workforce46:08 Strategic Workforce Development52:38 Data-Driven Decision Making55:10 The Role of Questions in Leadership59:11 Navigating Organizational Change01:02:42 Finding The Skeletons in The Closets01:11:14 Building Trust and Accountability01:12:50 The Value of Trust in the Workplace01:14:09 Balancing Organizational Trust and Personal Sacrifice01:15:04 The Decision to Leave the Federal Workforce01:15:56 The Importance of Trust in Relationships01:17:11 Facing Unhappiness and Making Changes01:17:59 Reflecting on Career and Organizational Loyalty01:19:49 The 9/11 Experience: A Day of Chaos and Leadership01:21:13 Evacuation and Immediate Aftermath01:23:07 Returning to Work Post-9/1101:24:15 Leadership Lessons from Crisis01:30:44 Navigating Healthcare for a Loved One01:35:20 The Importance of Being Present in Healthcare01:38:31 Final Thoughts and Ways to ConnectResources MentionedThe PentagonDASNOSDNAVSEA (Naval Sea Systems Command)Kevin Kelly – Wired magazine founder, author of The InevitableFerris Bueller’s Day OffReeseReimagined.comJaimie Reese on LinkedInProducer Ben FordBeauty Pill

"The closer you become with these people while you're wearing that mask, the more distant you actually feel from the people around you." - Garrett WoodIn this episode of Curated Questions, host Ken Woodward engages in a deep conversation with Garrett Wood, a national board-certified health and wellness coach and certified clinical hypnotherapist. Garrett shares his insights on the hidden tolls of high achievement, addressing issues such as perfectionism, imposter syndrome, and burnout. He explores the power of questions and how they can transform our understanding of identity, worth, and achievement.The discussion dives into the paradox of wearing masks to gain social acceptance, the first signs of burnout manifesting as cynicism, and the importance of creating authentic connections. Garrett also discusses practical strategies, such as non-sleep deep rest, to enhance performance and creativity, as well as the role of self-compassion in maintaining mental health.This episode offers valuable perspectives on how to navigate and make sense of the world through the power of questioning.This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 The Mask of Perfectionism01:11 Welcome to Curated Questions01:55 Meet Garrett Wood02:57 Garrett's Early Experiences with Questions05:14 The Power and Danger of Questions06:02 Socratic Method and Questioning Authority08:50 Curiosity and Childhood12:32 The Role of Questions in Executive Coaching15:13 Creating a Safe Space for Growth20:22 Helping Clients Trust The Process32:02 The Therapeutic Relationship34:22 Understanding Pain and Healing38:17 Non-Sleep Deep Rest46:55 The Mundane Tasks and Mind Wandering47:39 Non-Sleep Deep Rest Explained48:29 The Power of Journaling51:25 Practical Applications of Non-Sleep Deep Rest54:20 Recognizing and Addressing Burnout56:08 The Importance of Biofeedback56:58 Understanding and Identifying Cynicism01:01:43 The Concept of Masking01:06:36 Living Authentically01:11:30 The Journey of Self-Discovery01:13:56 The Role of Questions in Personal Growth01:20:48 Exploring Identity and Attachment01:29:31 Final Thoughts and TakeawaysResources MentionedGnosis TherapySocratesDouglas AdamsImmanuel KantAmy RadinExplain Pain Theory by David Butler and Lorimer MoseleyNociceptionThomas EdisonAlbert EinsteinCarl JungFive Levels of Attachment by Don Miguel Ruiz Jr.Garrett Wood on LinkedIn at Gnosis TherapyGnosis Therapy on InstagramProducer Ben FordBeauty PillProducer Ben FordBeauty Pill