Curated Questions: Conversations Celebrating the Power of Questions!

Episode Summary"If all you do is pay attention to what everyone else is paying attention to, then  by definition you're not likely to innovate anything or create anything very original or different or surprising." - Rob WalkerWriter and cultural observer Rob Walker joins Ken to explore how questions and noticing reshape the way we move through the world. Rob traces his origin story back to discovering journalism at 18, a framework that gave a shy, introverted kid permission to ask questions on behalf of others.They dig into his book and newsletter The Art of Noticing, talking about everyday noticing assignments, why “what am I missing?” is a powerful self-question, and how small acts of attention can mark time and make life more memorable.Rob shares the story behind the Significant Objects project and why story, and not a price tag, creates real value in the objects we keep. From New Orleans as a “conversational city” to his teaching on point of view and manifestos, Rob reflects on questions as both agency and responsibility, in democracies, organizations, and personal life. Be sure to subscribe to Rob's Substack The Art of Noticing newsletter at https://robwalker.substack.com/This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 Introduction to Overlooked Ideas01:56 Introducing Rob Walker03:19 Rob Walker's Early Life and Career04:28 Discovering Journalism and the Power of Questions05:54 Embracing Curiosity and Askew Perspectives08:57 The Influence of Laurie Anderson13:30 Living in New Orleans14:56 The Unique Culture of New Orleans21:21 The Art of Noticing22:32 Personal Experiences with Noticing27:50 The Impact of Noticing on Daily Life33:21 Noticing and Questions40:56 The Power of Asking Questions42:39 Questions and Agency44:26 The Importance of Questions in Organizations45:14 Inspirations and Heroes in Questioning46:11 The Art of Asking Questions46:37 Early Lessons in Journalism47:42 Challenges of Interviewing Law Firms48:12 Curiosity-Driven Interviews48:35 The Sharpie Story50:15 Preparing for Interviews50:51 The Flow of Conversation52:58 Finding Unique Angles in Business Stories55:09 The Power of Longevity and Community56:39 Mindfulness and Creativity59:21 Significant Objects Project01:01:04 The Value of Story in Objects01:06:23 The Gift of a Questioning Mindset01:11:59 Teaching and Point of View01:12:51 The Role of Questions in Design01:14:20 Student Challenges with Questions01:18:57 Personal Reflections on Questions01:19:25 End of Year Reflections01:22:48 Final Takeaways and ReflectionsResources MentionedConsumed column in the New York Times MagazineThe Art of Noticing by Rob Walker (book)Buying It by Rob Walker (book)Significant Objects ProjectLynn Borton of Choose to Be CuriousLaurie Anderson United States Live (album) (https://en.wikipedia.org/wiki/United_States_Live)Pacifica radio station (Houston)Brooklyn Academy of Music / BAMJourney (band)Foreigner (band)University of TexasHand Grenade (cocktail)Anne RiceDave Isay Sound PortraitsNew Orleans Center for Creative Arts (NOCA)The Art of Noticing (newsletter)The American Lawyer (publication)Am Law 100Martindale-Hubbell (legal directory)Karen DillonSharpieFast CompanyStarbucksCracker Barrel Logo ControversyAustin KleonWaking Up Meditation AppJoshua GlennMeg CabotWilliam GibsonProject ObjectLost ObjectsLost Objects Book by Rob WalkerIgnorance by Stuart Firestein (book)Inconspicuous Consumption newsletter by Paul LucasJerry ColonnaDavid WhyteSchool of Visual Arts in New YorkPoint of View Class at SVAProducts of DesignRob Walker Substackrobwalker.netHypothetical Development OrganizationProducer Ben FordBeauty Pill

"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.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.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?

"I'm gonna make an appointment with my curiosity." - Frank SesnoEmmy award-winning journalist Frank Sesno shares how curiosity and strategic questioning shaped his four-decade career covering presidents and world leaders as CNN's Washington Bureau Chief and White House correspondent. From a fourth-grade question about astronauts to interviewing five U.S. presidents, Frank reveals the power of deliberate curiosity and active listening.Frank breaks down his approach to preparing for high-stakes interviews, explaining how he blocks conversations into thematic acts while remaining flexible. He introduces the "echo question" technique, which is simply repeating a person's emotionally charged word back to them, that transforms surface answers into more profound truths. Frank emphasizes that the best questioners are the best listeners, focusing on what people say and what they don't say.In "Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change," Frank discusses why bridge-building questions are critical in our polarized moment. He explores how AI makes human curiosity more valuable and shares his practice of "making an appointment with curiosity" to create time to deliberately formulate meaningful questions.This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 Introduction and Welcome02:04 Meet Frank Sesno: A Legendary Journalist03:05 Early Encounters with the Power of Questions05:01 Curiosity Encouraged: School Days05:54 The Art of Interviewing: Following Curiosity08:37 Touchstone Moments in Journalism09:35 Holding Power to Account10:42 The Journey to Asking Tough Questions12:48 Understanding Human Stories18:25 Complexity of Human Experience22:38 Listening: The Key to Great Questions24:37 Echo Questions: A Powerful Technique27:29 Preparing for Interviews: A Structured Approach29:40 Structuring Interview Questions30:27 The Importance of Flexibility in Interviews31:16 The Power of Walking and Reflecting32:01 Lessons from the Galapagos34:13 Traveling with Curiosity36:38 Fostering Curiosity in Students40:46 Question Categories That Are Needed Today47:04 The Role of AI in Questioning50:39 The Human Touch in Questioning52:21 Building Rapport with Interviewees53:26 The Right Now Question53:54 Finding Hope in Challenging Times57:26 Connecting with Frank Sesno58:51 Summary and TakeawaysResources MentionedAsk More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change by Frank SesnoThe Sesno SeriesGeorge Washington UniversitySenator Mark WarnerGeorge Washington University School of Media and Public AffairsWashington PostShohei OtaniYoshinobu YamamotoLos Angeles DodgersNancy KanwisherCal FussmanPlant ForwardStoryfest CompetitionGalapagos IslandsLindblad Expeditions1882 Morgan Silver DollarNancy PelosiFrank Sesno on LinkedInFrank Sesno websiteProducer Ben FordBeauty Pill

"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