

Curated Questions: Conversations Celebrating the Power of Questions!
Ken Woodward
Curated Questions: Conversations Celebrating the Power of Questions
Hosted by Ken Woodward, Curated Questions is a thought-provoking podcast that celebrates the art and science of asking profound questions. This podcast is for curious minds who understand that the right question can unlock new perspectives and drive personal growth.
What to Expect
Insightful Conversations: Experts from diverse fields share their journey in mastering the craft of inquiry, revealing how it has transformed their lives and careers.
Practical Techniques: Gain valuable skills to improve your questioning abilities, applicable in both personal and professional settings.
Thought-Provoking Topics: Explore how questions shape leadership, personal transformation, and societal discourse.
Why Listen?
In an age of abundant information, Curated Questions reminds us that true wisdom lies in asking better questions. This podcast will help you:
1. Enhance critical thinking
2. Improve communication
3. Gain new perspectives on complex issues
4. Develop a nuanced understanding of the world
Join Ken Woodward and his guests as they explore the transformative power of thoughtful inquiry. Curated Questions is more than just a podcast – it's an invitation to embrace curiosity, challenge assumptions, and unlock your full potential through the art of asking better questions.
Subscribe now and embark on a journey to master the craft of inquiry, one question at a time.
Website: CuratedQuestions.com
IG/Threads/YouTube: @CuratedQuestions
Hosted by Ken Woodward, Curated Questions is a thought-provoking podcast that celebrates the art and science of asking profound questions. This podcast is for curious minds who understand that the right question can unlock new perspectives and drive personal growth.
What to Expect
Insightful Conversations: Experts from diverse fields share their journey in mastering the craft of inquiry, revealing how it has transformed their lives and careers.
Practical Techniques: Gain valuable skills to improve your questioning abilities, applicable in both personal and professional settings.
Thought-Provoking Topics: Explore how questions shape leadership, personal transformation, and societal discourse.
Why Listen?
In an age of abundant information, Curated Questions reminds us that true wisdom lies in asking better questions. This podcast will help you:
1. Enhance critical thinking
2. Improve communication
3. Gain new perspectives on complex issues
4. Develop a nuanced understanding of the world
Join Ken Woodward and his guests as they explore the transformative power of thoughtful inquiry. Curated Questions is more than just a podcast – it's an invitation to embrace curiosity, challenge assumptions, and unlock your full potential through the art of asking better questions.
Subscribe now and embark on a journey to master the craft of inquiry, one question at a time.
Website: CuratedQuestions.com
IG/Threads/YouTube: @CuratedQuestions
Episodes
Mentioned books

Nov 27, 2025 • 0sec
The Insight Pause: When a Single Truth Rewrites Your Story! | Ken Woodward #59
"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?

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Nov 20, 2025 • 0sec
How Bridge-Building Questions Cross Divides! | Frank Sesno #58
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.

Nov 13, 2025 • 0sec
Building Enduring Trust Through the Questions We Ask! | Jaimie Reese #57
"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

Nov 6, 2025 • 0sec
Safety, Burnout, and the High-Achievement Mask! | Garrett Wood #56
"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

Oct 30, 2025 • 35min
The Locked Door: How Avoided Questions Hold the Key to Transformation! | Ken Woodward #55
Episode Notes00:00 The Possibility Of Your Avoided Question01:21 Welcome to Curated Questions01:59 Tangled Wings' Impact04:31 The Question That Changes Questions07:43 When Your Brain Says "Nope" (A Friendly Science Tour)12:06 The Locked Door Model (Your Map to the Question)15:11 A Personal Interlude (When I Found My Door)16:10 From Boardroom to Living Room (How This Scales)19:45 When Giants Finally Ask (The Storm Before the Breakthrough)26:05 Integration Accelerators (Making It Stick)27:07 Why This Matters Now (The Gentle Urgency)28:22 Three Companion Questions (For Your Toolkit)29:32 Your Next 48 Hours32:01 Takeaways - Choose Your Own Adventure Resources MentionedSumner CrenshawJerry ColonnaDavid EaglemanLeonard MlodinowAntonio DamasioLeon FestingerSatya NadellaMary OliverProducer Ben FordBeauty Pill Questions AskedWhat question are you avoiding that would change everything?What topic made you slightly tense when I said “that decision you keep postponing”?Where does it hurt?What are you willing to give up that you love in order to change those conditions?How has it benefited you to maintain these conditions you say you don’t want?What am I avoiding right now, this week?What topic, if I brought it up right now, would make you want to skip ahead in this podcast?When will it be?How much is enough?What’s the cost of not asking?Is it above your integrity grade?What would our best competitor assume we’re too afraid to do?If my kid was watching me handle this, what would I want them to learn?Where are we optimizing for looking good instead of being good?What would be different if…?What does it look like to be a modern-day Freedom Rider?How does my embrace of the American myth change upon the discovery of the broken treaties and massacres enacted on Indigenous people?How do I hold dear to a faith when the church protected abusers and the powerful while endorsing slavery?Why is there no national memorial celebrating the resilience of those enslaved and holding to account those who perpetrated the evil in our American history?What if people don’t want to drive to a store?What if they didn’t have to?What if film is temporary?What if photos are social?What behavior does our incentive system actually reward?Are we helping our customers succeed, or just protecting Windows?What are we really afraid will happen if we plan for our own absence?What am I pretending not to know about what my partner needs?What question would my teenager ask if they felt truly safe?What story do I tell about why I can’t change this?What would I do if I knew I was already enough?What if the future isn’t about PCs?Are we a PC chip company, or are we a chip company that happens to make PC processors?What question am I avoiding?Are you? Or are you avoiding something more specific that might actually require change next Monday?What elephant do you see in my room that I keep walking around?Why do we keep this meeting?Why does the team need to be aligned?Why are we siloed?How would we design collaboration into our resource model?If we had zero history, zero sunk cost, and zero politics, what would we do?What would someone who loves our mission but sees our flaws say we’re avoiding?What question are we avoiding?What would change if we asked it?What is the smallest next step?Should I change jobs?Am I becoming who I want to be?Who do I want to be when I’m no longer afraid?Where have we stopped questioning?What are we pretending not to know?What would be different in 90 days if we faced this?What question am I avoiding this week that would change my next 90 days?What question am I avoiding today?What question do you think I’m avoiding?What question are we all thinking but no one’s saying?What assumption haven’t we tested since we wrote this?Where do our stated values and daily behaviors most diverge?What are we not discussing that our successors will wish we had?What would our most frustrated customer say we’re avoiding?What would we try if we knew we could iterate our way to success?

Oct 23, 2025 • 1h 18min
The Permission Paradox & Why Questions Matter More Than Approval! | Jill Reilly #54
"The most fundamental relationship in any change process is the one that you have with yourself. It's the questions that you ask yourself first and foremost that are the game changers." - Jill Reilly In this episode of Curated Questions, host Ken Woodward is in conversation with global citizen and author Jill Reilly to explore the power of questioning in navigating life’s complexities. Jill shares her journey from the Midwest to South Africa, Zimbabwe, and beyond, reflecting on her experiences as an aid worker and the lessons that shaped her understanding of change and personal agency. They discuss the importance of self-permission, processing grief, and the need to adapt amidst societal and technological upheaval. With insights from her new book The Ten Permissions: Redefining the Rules of Adulting in the 21st Century, Jill emphasizes the transformative potential of asking the right questions to unlock personal growth and resilience. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Keep questioning! Episode Notes00:00 Introduction: The Power of Self-Questioning00:49 Milestone Celebration: 100,000 Downloads03:13 Introduction to Jill Reilly05:23 Jill's Journey to South Africa07:37 Choosing a Different Path09:30 The Concept of Permission13:39 Exploring New Paths18:23 Jill's Work in Zimbabwe21:44 Engaging with Questions29:05 Political Uncertainty and Fear31:18 Grieving the Old Stories32:05 Reimagining Our Future35:36 Challenging Fixed Mental Models37:16 Questioning Traditions and Conventions38:54 Intentional Conversations Around Adaptation40:07 The End of Predictable Progress41:40 Exploring Personal Undoing43:18 The White Savior Complex45:49 The Importance of Self-Permission47:04 Engaging with Yourself for Change49:11 Navigating AI and Rapid Changes55:56 No Need To Blow Up Your Life59:09 The Value of Leisure Time01:02:31 Professional Adaptation and Evolution01:08:19 Right Now Question01:12:27 Final Reflections and Takeaways Resources MentionedShame: Confessions of an Aid Worker in Africa by Jill ReillyVain Aid TED Talk by Jill ReillyThe 10 Permissions: Redefining The Rules of Adulting in The 21st Century by Jill ReillyHughes Network SystemsRobert MugabeTen Permissions websiteJill Reilly on LinkedInJill Reilly email: jill@tenpermissions.comProducer Ben FordBeauty Pill Questions AskedWhen did you first understand the power of questions?How is it that you chose to pursue going to South Africa?Were we allowed to question it?Were we allowed to create alternatives to it?What else did you do?What are the things that you could do?Do we even feel allowed to have those conversations?Am I defaulting to just take the next safest step, or am I allowing him and myself to consider that?Isn't it a good opportunity to begin to explore a variety of options?Are we preparing them for this evolving reality, or are we continuing to default to what worked in our day or what we've always done?How did things go when you got to South Africa?Who am I? How am I introducing myself? What am I about?What do you think were some of the modality, spirit, and heart posture as you use questions to engage this new world for you?Can you contract aids from a public toilet seat?What are good questions to use when wrestling with political uncertainty, upheaval, and the like?Am I gonna be the one to try and fill the void that's being created right now with something new, something better, or is our only option to try and patch together what once was and keep hobbling along?Why haven't we done any more amendments? Why haven't we changed things?How far can we go? What are we allowed to do?Do we need to make changes?Why would we choose the old version?Isn't there a better way? Isn't there more? Isn't there different? Isn't there now?Do I feel allowed to do the thing that I think I should or they say I should? Or does fear, intervene in my own sense of permission? Are there external authorities whose power over me is so great that I'm not willing to take a risk? or am I the thing that's in the way of me actually taking a risk to do something different?What are the questions that you're asking?How are you poking into your own assumptions?How are you testing those? What questions are you intentionally using? And what is your practice for going after that?And are you gonna be ready for that or are you gonna be blindsided?Am I allowed? What's desirable? What's allowable?What do you wanna do with it? What does it look like for you? How is it a vehicle for you to live and experience in ways that maybe you haven't fully lent into yet?What is your Right Now Question?How can, and how will my book and these permissions support people to navigate this age of AI?What's possible in this time? What's allowable? We allow ourselves to imagine showing up to this moment differently, and what might that look like?What situation in your life right now feels unfamiliar or uncomfortable where you could experiment with leading with questions instead of assumptions?How might genuine curiosity change those interactions?Where in your life are you waiting for approval when what you actually need is to give yourself permission?What would change if you separated these two concepts this week?How might you make space to process loss and grief that continue to weigh you down?Can you identify three "shoulds" that are currently driving your decisions?What would happen if you spent 10 minutes each day this week asking yourself what YOU actually want, without editing or judging the answers?

Oct 16, 2025 • 45min
Impactful Questions: Am I My Brother's Keeper? Ken Woodward | Ken Woodward #53
"Am I my brother's keeper? Is answered in the daily work of showing up, being challenged, getting it wrong, being corrected, and showing up again." - Ken Woodward In this solo episode, Ken Woodward explores one of humanity's oldest and most challenging questions: "Am I my brother's keeper?" Born from Cain's evasion after murdering Abel, this question continues to shape how we answer fundamental issues about immigration, homelessness, healthcare, and who deserves our care.Drawing from his 101-week walk through every street and alley in Washington, DC, Ken reflects on how he spent 50 years answering "no" to this question while convincing himself he was answering "yes." He shares powerful conversations with Raymond Coates about the Sugar House in Charleston, encounters with a woman who demanded accountability, and the devastating costs of both saying yes and saying no.This episode challenges listeners to examine their own complicity, confront inherited assumptions, and honestly assess who they've decided doesn't count as "brother." Ken offers four concrete takeaways to help transform this ancient question from theological abstraction into daily practice.This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Keep questioning! Episode Notes00:00 The Work of a Brother's Keeper01:12 Welcome to Curated Questions01:50 Am I My Brother's Keeper02:36 The Origin: Cain's Evasion04:44 The Question I Avoided Asking09:09 The Question I Lived11:07 Who Counts As Brother?14:21 What This Question Reveals15:45 The Cost of Yes!19:51 The Cost of No23:50 the Present Moment27:22 The Military Exception28:42 Repentance & Reparation32:35 The Vulnerability of Yes34:00 The Question For You36:58 The Invitation38:41 Takeaway43:27 Final Closing Resources MentionedCain & AbelBook of GenesisJames BaldwinLies My Teacher Told Me: Everything Your American History Textbook Got Wrong by James W. LoewenCaste: The Origins of Our Discontents by Isabel WilkersonGeorge FloydBreonna TaylorAhmaud ArberyThe TorahThe parable of the Good SamaritanJesusJesus and the Disinherited by Howard ThurmanRaymond CoatesLorton PrisonSugar House, Charleston, South CarolinaTraining Day with Denzel WashingtonBuddy HarrisonMalcolm XJerry ColonnaAn Indigenous Peoples' History of the United States by Roxanne Dunbar-OrtizSouthern StrategyRedliningNegro BibleCivil Rights ActCivil Liberties Act of 1988Emmett TillJerry JonesMary OliverProducer Ben FordBeauty Pill Questions AskedAm I my brother's keeper?Where is your brother Abel?Who have I decided doesn't count?Whose suffering have I accepted as normal?Whose voice have I decided doesn't matter quite as much as others?How am I actually answering this question with my life, not with my words?Why didn't Black service members get access to the GI Bill after returning from World War II?How is the Republican adoption of the Southern Strategy to disenfranchise Black voters starting in the 1950s still functioning?How was a Black family supposed to build generational wealth when redlining was legal?What do I do with the half that's correct?Who is my neighbor?How are people with their backs against the wall supposed to relate to Christianity when Christians have their boot on their necks?Will my brother keep me?How have you been complicit in creating the conditions you say you don't want?You think that didn't affect him?You think he went home and was a good father? A good husband?You think that violence stayed contained in the Sugar House?You think you got something to say, don't you?Are you a racist?What do you think about slavery?What do you think about policing?What about reparations?What about income inequality?What is this project going to accomplish?How is this going to make a difference in my life?Are you really my brother's keeper, or are you just performing?What does repentance look like?What does turning away from these sins look like?What does making amends look like?Who have you decided doesn't count as your brother?How has your boundary line shifted over time?Who is included that wasn't before, and who has now shifted beyond that border?What would it cost you to say yes to someone you've been saying no to?What are the things your grandparents taught you—not explicitly, but through silence, through who was welcome in your home, through what neighborhood you lived in—that were actually answering "no" to this question?Which of those things are you still practicing?Am I ready to become my brother's keeper?What would it cost me to actually be this person's keeper?What have I taught you, through my actions and choices rather than my words, about who counts as your brother?Is that the inheritance you want from me?

Oct 9, 2025 • 1h 35min
Why Asking the Right Questions Beats Having Quick Answers! | Amy Radin #52
"Asking the right questions the right way at the right time can often be more of a determinant of your success than being the person to raise their hand and come up with the answer." - Amy Radin Amy Radin is a pioneer in corporate innovation and strategic questioning. Amy shares her journey from the influence of her father's corner drugstore to becoming one of the world's first Chief Innovation Officers at Citi, and her roles at American Express, E-Trade, and more. The conversation delves into the importance of curiosity and questioning for personal growth, achieving corporate goals, the emotional and practical aspects of leading change, and the role of strategic questioning in innovation. Amy also discusses her experiences as an early-stage investor and advisor, highlighting the significance of asking the right questions to assess founders' pitches and provide guidance as they build their companies. Sign up for Amy's newsletter, Uncommonly Pragmatic, at her website amyradin.com. Amy is available for live or virtual keynotes and workshops. She can be easily reached through LinkedIn direct messages to collaborate on how to bring her expertise to positively impact your organization. This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com. Keep questioning! Episode Notes00:00 Introduction: The Power of Questions01:28 Welcome to Curated Questions02:06 Meet Amy Radin: A Pioneer in Innovation04:01 Amy's Early Influences and Corporate Journey05:13 Transition to Early Stage Investing07:29 Understanding Founders Through Questions10:51 The Importance of Diverse Expertise17:16 Building a Personal Advisory Board18:22 Handling Resistance with Questions21:43 Effective Interview Questions30:42 The Power of Asking Questions in Teams36:10 Emotional Aspects of Change40:49 Modern Change Management43:46 Multi-Generational Workforce Challenges46:14 Coalition Building for Change48:07 Balancing Historical Knowledge and Innovation50:37 Understanding Resistance and Fear51:28 The Role of Experimentation52:21 Digital Channels in Customer Acquisition53:20 Designing Experiments with Skeptics54:36 Financial Discipline and Digital Innovation55:47 Customer Service and Digital Channels56:12 Prioritizing Questions and Experiments59:05 Becoming a Chief Innovation Officer01:00:59 Challenging Assumptions with Questions01:08:39 Qualitative Insight Gathering01:12:28 The Emotional Side of Finances01:16:33 Career Reflections and Resilience01:21:23 Teaching and Strategic Advocacy01:22:30 Celebrating Success and Staying Curious01:23:46 Morning Walks and Creative Thinking01:25:38 Final Thoughts and Places to Connect With Amy Radin01:27:36 Closing Remarks and Takeaways Resources MentionedThe Change Maker's Playbook by Amy RadinSoundboard Venture FundA More Beautiful Question by Warren BergerKotter's Eight Steps For Leading ChangeLarry Keeley on LinkedInThe Diary Of A CEOJohn Dewey High SchoolSpike LeeJohn DeweyAmy Radin Website for the Uncommonly Pragmatic NewsletterAmy Radin on LinkedInProducer Ben FordBeauty Pill Questions AskedWhen did you first understand the power of questions?What am I gonna do with myself now?My first question was, well, what's that?What were some of those right questions to be able to get a little bit deeper?What questions am I gonna ask?Can you tell me more about that? How did you figure that out? Or I'd love to understand that better. Can you dig in a little more?Do we wanna go to the next step?Have there been some particularly insightful questions that founders have asked of your team that have resonated with you?What else do they bring to the table?I would ask tell me a little bit about some of your recent experiences working with some of your other portfolio companies and how you've helped them out. Tell me about a situation when another portfolio founder when the market changed and they almost had the rug pulled out from under them, what was your reaction and were you able to step in and help them?Tell me a story, not what would you do?Has there been anything this new venture has taught you about questions that all of your other previous experience hadn't taught you?What do you think might be a personal bootcamp that somebody could do that could help build that experience?Ask, wow, I'd love to understand more where you're coming from. Could we walk through it? Because I wanna appreciate what you're trying to do and why you're uncomfortable with this. So, can you help me understand your perspective better?How did I do? Did I do this three times?What do you think makes for a good question?What are the key requirements? What do I really need from this person? What would you do about X, Y, Z?Help me understand what you did. What you felt and what you thought, and how did you actually handle that situation?What metrics should we consider that would be appropriate to helping us understand the potential for this idea that would make us feel good about this tiny little investment you wanna make for prototype?How can they bring the entire questioning game in the conversation up another level,What do I really wanna understand better about this opportunity?What do I really wanna understand better about working with these investors?Do I wanna use the opportunity of this call/pitch session/diligence to ask them their advice about something? And can I be candid about?Why can't you...? How might you...?How do you think about that feeling or that component of us and bringing that into the workplace?How is this change going to affect my career and what happens to me and my ability to pay my mortgage and send my child to college?How do you feel?Why does Sally seem so upset at the meetings?As you are engaging with a company and helping them think through change, how do questions play a role in that process?Who's gonna be there? What's their mindset about learning? Is it a curious organization? How would you describe the culture?What role do questions play in change?How do I really accomplish this change?How does fostering curiosity and questions play a role in coalition building?How do you get that tipping point?What role can digital channels be effective to attract new customers?What aspects do we think that innovating around the digital experience could favorably impact those aspects, those financial drivers of the business?What role could digital channels play in customer service that could improve the customer relationship, lower costs, improve customer satisfaction, reduce attrition, and increase people's usage of the card?What role does digital technology play in our business to benefit customers and shareholders?How did you become a chief innovation officer?What's that?What do you think about specifically on questions in challenging assumptions?Why are we doing it like this?Where did that assumption come from?When people go online, what happens to call volume?What do we measure?How do you see questions playing a role in sparking insights?How are people managing their financial lives in the context of dealing with all the fallout from the financial crisis?Are things filed, or is it a big mess in a paper stack? Why is it set up like that?What are all the things that I could do?You had mentioned early on about not being the cookie-cutter person, and wanting to be out there on the edges a little bit and mixing things up. How has that served you?What can we do about this?Would you be interested in teaching this Strategic Advocacy course? What the hell is that?What do you need to do next?What are your right now questions or question that you're working with?I'm wondering why some of my best questions seem to come to me when I'm talking to my dog?Are there any areas of questions that we didn't touch on that you were hoping to or excited to be able to touch on?Where is this the best place for folks to track you down and see the things that you're working on and the things that you're excited about?How would your career trajectory change if you spent the next year becoming known for asking brilliant questions rather than providing quick answers?Can you identify three times over the coming week when you could practice asking "Help me understand your perspective" instead of explaining why someone is wrong?Who are the people in your network who know what you don't know, and how could you formally invite skeptical perspectives into your most important decisions?What would happen if you designated a regular meeting as question-only, where solutions are forbidden and curiosity is the only currency?

Oct 2, 2025 • 1h 27min
Mental Models, Cognitive Frameworks, and the Questions That Disrupt Them! | Dave McGurk #51
"If we start talking about developing people, you have to ask those deep questions." - Dave McGurkDave is a transformational leader who bridges military precision with cutting-edge organizational development. As Founder and CEO of Veridian Perspective and Vice President at Apogee Global RMS, Dave brings over 20 years of executive leadership experience. His impressive 30-year military career includes Training Operations Director at the U.S. Army Command and General Staff College, Army Enterprise liaison and senior executive advisor to U.S. Army European, African and Special Operations Command teams.He has managed multi-billion-dollar budgets, led teams of hundreds, and influenced policy at the highest levels of government—including presidential-level decisions. His approach blends 30 years of military leadership, adult education, & neuroscience to create AI-powered diagnostics, hyper-personalized development, and dynamic simulations for resilient leaders in a volatile world.Ken Woodward engages in a profound discussion with Dave McGurk, a transformational leader with a rich background in military leadership and organizational development. Dave shares his experiences, including a pivotal moment during his deployment in Iraq where he learned the cultural importance of time through the simple act of removing his watch. This revelation led him to question the embedded cognitive frameworks that shape our understanding of the world.Through deeply reflective questions, Dave emphasizes the importance of framing problems accurately, understanding inherited mental models, and fostering genuine connections with others. He introduces his innovative seat swap counseling method, which promotes genuine feedback and psychological safety. This episode explores the transformative power of questions in personal growth and leadership development, encouraging listeners to challenge their assumptions and continually evolve.This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.Keep questioning!Episode Notes00:00 Reflecting on Leadership and Influence01:16 Welcome to Curated Questions02:02 Introducing Dave McGurk04:03 Dave's Military Background and Leadership Experience04:40 Cultural Challenges in Iraq06:36 Learning from Iraqi Commanders11:11 Building Trust and Relationships13:44 The Importance of Asking the Right Questions19:14 Teaching Critical Thinking in the Military20:25 Challenging Assumptions and Mental Models22:51 The Role of Vulnerability in Leadership31:07 Navigating Authority Bias34:21 Transition to Defense Contracting and Consulting35:06 Understanding Mental Models and Cognitive Frameworks35:54 The Power of Disruptive Questions36:36 Teaching Creative Thinking and Problem Solving39:56 Developing a Questioning Practice44:49 Reflecting on Mental Models and Growth45:39 Sports Analogies and Human Development46:24 Personal Journey and Military Experience48:22 The Impact of Suicide in the Military49:22 Leadership and Connection with Soldiers49:43 A Pivotal Moment: Jeremy LeClair's Story50:03 Psychological Autopsy and Leadership Reflection51:30 Commitment to Authentic Leadership52:21 The Importance of Deep Questions52:38 Understanding Mental Models59:17 Challenges of Egocentric Thought01:00:46 Feedback Mechanisms and Counseling01:02:27 Connecting with People in Leadership01:03:25 Deployment and Leadership Challenges01:06:52 Empowering Teams and Challenging Authority Bias01:08:09 Excitement for Future Leadership Development01:14:35 Curated Questions and Continuous Improvement01:21:01 Final Thoughts and TakeawaysResources MentionedGeneral DempseyArmy's Command General Staff CollegeCONOPMk PalmoreApogee Global RMSThinking Fast and Slow by Kahnemanexperiential learning modelJeremy LeClairthe Leadership Student 2.0 podcastProducer Ben FordBeauty Pill Questions AskedWhen did you first understand the power of questions?What else am I missing?As an American who is over here supporting this country and this culture, what else do you not think I understand?What do you think sets you apart in your approach versus those who came behind?What are they really getting after?What is it that you're really looking for?What's the problem?What am I missing? How do I see the problem? What are the facts that are relevant to the problem? And what's gonna allow me to open my aperture to see a different dimension of the problem?How did that question rubric land with those that you were teaching or bringing up behind?What is the question that you need to ask somebody to turn that into a fact?What do you think?What are the things that you're struggling with? What are the questions that you're trying to figure out? What haven't you had answered?Am I trying to disrupt it in the right way?Why did you jump on the one that was wrong?What are the things that you think about that really drive the way you think?How does your brain work?How do we challenge that?How do we challenge our own ability to understand how we're thinking and how we're gonna make a difference for us?How can we develop a questioning practice or a way of living that ensures that we look beyond just the top drawer?What are those echoes that kind of govern how we think?What assumptions had to be made here that would turn into facts that are still applicable here?How do we match that against what we think our inherited mental model is that is driving that for us?Am I aware of those shortcuts that my brain is making?Am I a reflection of the rewiring and the response?How do I change the framework?What is this doing to me?Do you have any idea where that came from?What is it that's going on?What are those reflexive interpretations that are coming?What are those echoes that are coming back and feeding us?What was it about me that made you think that I was a good leader?What invasive cognitive model has colonized your mind without your permission?What is that question really trying to get at the heart of?How does ego fit into all of this story?Is this the right perspective? How do I shape that perspective?How are you doing? How's your wife? You get a birthday next week, how does it feel to be getting old?How did you take that staff and turn it into such a machine in such a short period of time?How are our customers doing?How would you feel if you would have one of your VPs sit down and give you counseling about what you're doing? Are you crazy? Why would I do that?What elements are you most excited about in this next season that you're going into, with all that you've been creating?Did we miss anything about questions?What are the questions that you're working with right now for you personally?How are you gonna experience catastrophic success?What inherited beliefs about the right way to operate might you be clinging to without questioning their validity in different contexts?How might your current problem be completely reframed if you ask, what am I missing instead of how do I solve this?Which of your firmly held beliefs did you actually choose versus inherit from your environment? And are they still serving you?What would change in your relationships if you literally or figuratively swap seats with those you lead or work alongside?

Sep 25, 2025 • 1h 26min
Why "Who Do I Say I Am?" Changes Everything! | Mike Hilson #50
"Who am I? Was never gonna turn out well. Who do I say I am? Had a chance." - Mike HilsonHost Ken Woodward welcomes Pastor Mike Hilson, senior pastor of New Life Church. They delve deep into how questions shape identity, leadership, and personal growth. Mike shares his journey, from wrestling with self-identity as a child to leading a thriving network of churches. Key discussions include the necessity of creative boredom, the evolution of the question 'Who do I say I am?', the importance of strategic delegation, and balancing doctrinal adherence with familial love. Episode Notes00:00 The Origin of a Pivotal Question01:51 Introducing Mike Hilson03:18 Mike's Early Life and the Power of Questions04:16 Struggles in School and the Importance of 'Why'05:18 College Years and Career Decisions05:49 Journey into Ministry06:14 Challenges and Realizations in Ministry08:21 Creative Boredom and Leadership11:00 Self-Awareness and Personal Growth11:24 Marriage and Life Decisions15:38 Parenting and Fatherhood17:24 Wrestling with Identity and Faith18:17 Leadership and Church Growth22:40 The Impact of Lifelong Questions30:36 What is a Good Dad?36:16 Delegation and Empowerment38:57 Handling Authority and Humility40:38 Church Planting and Community Building41:58 Maintaining Humility and Perspective42:46 Mentorship and Church Growth43:33 Rabbinical Mentoring Approach44:04 Coffee with the Pastor Series44:37 Rick Warren's Baseball Diamond Structure45:39 Impact and Ministry Goals48:52 End Game Thinking50:36 Succession Planning53:27 Communism and Totalitarianism54:14 End Game Thinking in Personal Life58:37 Questions and Anger in Society01:00:48 Philosophical Base Choices01:03:57 Biblical Truths and Cultural Application01:06:04 Personal Identity and Roles01:07:26 Future Plans and Family01:13:13 Living a Full Life01:15:51 Common Question: Proving God's Existence01:16:10 Philosophical Game: What If I'm Wrong?01:19:43 Final Thoughts and Gratitude01:19:48 Summary Takeaways Resources MentionedNew Life Church in La Plata, MarylandProducer Ben FordSouthern Wesleyan UniversityAppalachian State UniversityJohn MaxwellRick WarrenNapkin Theology by Mike HilsonSpeak Life by Mike HilsonA Significant Impact for Christ by Mike HilsonCoffee with the Pastor by Mike HilsonTheo BoldenOutlive by Dr. Peter AttiaBrett FavreMike Hilson on LinkedInBeauty Pill Questions AskedWhen did you first understand the power of questions?Why am I here, why am I here without anybody? Why don't people like me?Why is that bird doing that? Why does that rabbit hide there? why does that snake stand in that tree?Why am I doing this [college class]? Why am I here? Why am I doing this?What's this gonna be like?Why am I a Wesleyan? Why do I believe this about the Bible versus that?Could I be a Baptist? Could I be a Pentecostal?Where is your creative boredom?How have you used questions in that journey of self-awareness?If I keep dating this girl, I'm going to marry her. And I had to stop and say to myself, am I okay with that?Who do you say I am?Who do I say she is?Am I, Mike the guy who's gonna be a businessman who's gonna do this? Or am I, Mike the guy who's gonna be a pastor? Am I pastor Mike?How do I figure it out?How do I help other people deal with this?Who do I say I am? Who does God say I am?How could you leave?What do I think a father ought to be?What does a good father do right now?How do you properly unpack things?Which matters more?What did Jesus die for?If I fail to show grace here, how is it that I'm being like Jesus?How does a dad show Grace?What is a good dad, and how do I live that out?Who do I say that I am?What can I not, not do?How quickly did you embrace load shedding and being okay with that as a leader?How do I make sure we're taking care of them properly?What is the logical outcome of what I am currently doing?What is end game thinking?What do I leave behind?How do you think through what that building's gonna be worth in 30 years?What's the natural outcome if I continue to treat my wife the way I'm treating her right now?What happens if you silence half or a third of your nation and tell them they can't talk anymore?How generous am I being to other people?What does that mean for my life? What does that mean for how I live?What measure did I just use?What measure do I want God to use back to me?What does it mean to love my child, even if my child's gonna reject my faith?How do I balance these?How do you now do your job? What can I not not do to fit inside of that?Why would I believe in a God that you can't prove exists?What have I missed in my life by following a biblical worldview and the biblical tenets of how I should live?What if I'm wrong?What if I'm right? What have you missed?


