#54 Jill Reilly: The Permission Paradox & Why Questions Matter More Than Approval!

"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.

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#53 Ken Woodward: Impactful Questions: Am I My Brother's Keeper?

"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.

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#52 Amy Radin: Why Asking the Right Questions Beats Having Quick Answers!

"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.

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#51 Dave McGurk: Mental Models, Cognitive Frameworks, and the Questions That Disrupt Them!

"If we start talking about developing people, you have to ask those deep questions." - Dave McGurk

Dave 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 dives into the power of questions in personal growth and leadership development, urging listeners to challenge their assumptions and continuously evolve.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#49 Naomi Campbell: The Key to Helping Others Find Their Own Questions!

"Questions are an extremely sophisticated thinking skill that everyone can use and practice all the time." - Naomi Campbell

In this episode, host Ken Woodward is in conversation with Naomi Campbell, Director of the Right Question Institute (RQI) Legal Empowerment Program. They delve into the transformative power of teaching people to ask questions, highlighting its impact across various fields, including education, legal practice, and healthcare.

Naomi shares her journey from an inquisitive childhood encouraged by her family and school, through law school at Harvard, to her work in Mexico City advocating for migrant workers. The episode emphasizes the importance of questioning as a sophisticated skill that fosters personal agency and enhances democratic participation. Naomi also discusses RQI's unique methods for teaching this skill and how they support change agents in different communities.

The conversation provides insightful examples of how empowering people to formulate their own questions can lead to meaningful social change and better navigating decision-making systems.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#48 Ken Woodward The Curated Questions Origin Story: When It All Began!

" Once you have the question, the hard part begins." - Ken Woodward

In this solo episode, host Ken Woodward delves into the origin and development of the 'Curated Questions' project, which began in 2018. Ken shares his personal journey of curiosity, inspiration from Tim Ferriss' podcast, and the influences that led to the creation of his blog and subsequent podcast.

Highlighting notable milestones and influential interviews, Ken discusses the structure and purpose of the Curated Questions website and its various elements, including famous questions and lists. He also reflects on the profound impact of asking meaningful questions, illustrated with personal anecdotes.

The episode encourages listeners to embrace curiosity and engage with the world through the power of well-chosen questions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#47 Maury Rogow: How Questions Create Instant Trust in Any Conversation!

"You were the most interested person in the room, and you're gonna get love." - Maury Rogow

Maury Rogow is all about storytelling. He is the CEO of the Rip Media Group and creator of the Story2Sales methodology that's generated over $150 million in trackable revenue for clients. I appreciate the tag line, "Your brand will thrive or die, based on the story you tell."

Maury's unique journey spans high-tech success and Hollywood storytelling. He built his business career at companies like Avaya, Lucent Technologies, and GeoTel—a startup that sold to Cisco Systems for over $1 billion. He then pivoted to Hollywood, serving as executive producer for feature films like "Bedrooms" and "Enter The Dangerous Mind," and working with industry legends including the creator of the Batman franchise.

Today, Maury combines business acumen with cinematic storytelling to help Fortune 1000 companies like Comcast, Kaiser Permanente, and Ben & Jerry's create compelling brand narratives. His approach recognizes that in our noise-filled marketplace, every company must master storytelling to survive and thrive.

Maury has proven that great stories don't just entertain—they sell. He's written several books, with his latest on the horizon being "Your Story Can Be Your Superpower - Selling in an AI world." He has been featured in Forbes, Inc., and Entrepreneur magazines.

In this episode of Curated Questions, host Ken Woodward engages with Maury Rogow, CEO of RipMedia Group, to explore the transformative power of questions in both personal and professional contexts. Maury shares pivotal moments in his career, from telecommunications to Hollywood, emphasizing how a single question can change a transactional relationship into a meaningful connection.

The discussion covers the importance of storytelling, the benefits of embracing unique traits, the impact of framing on emotional responses, and effective strategies for leveraging questions in sales and daily life. Maury also offers practical advice on finding balance in business, the role of AI in asking the right questions, and shares key resources and techniques for developing better questioning skills. Listeners are encouraged to take on an audience challenge to spend a day asking only questions and to reflect on the impact it has on their interactions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#45 Dr. Latorial Faison: The Power of Asking "What Do I Do Now?" Instead of "Why Me?"

"When I even think that I wanna give up, I can't because people like this put their life on the line so that I could have better opportunities." - Dr. Latorial Faison

Dr. Latorial Faison is an HBCU and Virginia State University Professor, Poet, Author, Independent Scholar & Senior Military Spouse. A graduate of the University of Virginia, Virginia Tech, and Virginia State University. She holds undergraduate and graduate degrees in English and a Doctoral degree in Education. Faison is Chair of the Department of Languages & Literature and Assistant Professor of English at Virginia State University and has authored over sixteen books.

Faison's research study, The Missed Education of the Negro: An Examination of the Black Segregated Experience in Southampton County, Virginia 1950-1970, focused on Riverview High School, a segregated Black High School that existed in Courtland, Virginia, and explores the nuances of Black segregated education during the Jim Crow Era.

Faison's latest work, Nursery Rhymes in Black was released in June of 2025 and blends tradition, memory, and resistance through a reimagination of familiar childhood rhymes through the lens of Black history and lived experience. This volume just received a Pulitzer Prize nomination.

Not one to rest on her laurels, her next work Blood at the Root, will be released in the coming months, which speaks directly to the historical and ongoing violence, erasure, and resilience that define the African American experience.

In this episode of Curated Questions, host Ken Woodward engages in a profound conversation with Dr. Latorial Faison, a professor, poet, and scholar. Dr. Faison shares her journey from growing up in a small town in Virginia, being raised by her grandparents, to becoming a notable academic and author.

Through discussing her work, research, and dedication to teaching, Faison emphasizes the importance of memory, resilience, and the power of storytelling. The episode also touches on her latest book, 'Nursery Rhymes in Black,' her role in the Wintergreen Women's Writers Collective, and her vision for fostering a supportive community for her students. A recurring theme throughout the conversation is the transformative power of questions, both in personal growth and in understanding one's purpose.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#44 AI Alan Turing: What Machines Can’t Imitate - On Questions, Doubt, and the Discipline of Curiosity

"I suspect beauty comes when a question both sharpens and enlarges your vision." - AI Alan Turing

In this special episode, we step back to a cold December night in 1951 and into the warm, wood-paneled room of The Britons Protection, a historic Manchester pub. Across the table sits Alan Turing, the mathematician, wartime codebreaker, and one of the founding figures of computer science, who is brought to life through an AI simulation.

Best known for his role at Bletchley Park during World War II, Turing devised techniques and machines, including the Bombe, that cracked the German Enigma code and helped shorten the war by years. His groundbreaking 1936 paper on “computable numbers” introduced the concept of the universal machine, and became the theoretical foundation for modern computers. Later, at the University of Manchester, he advanced early computing, explored artificial intelligence, and even pioneered mathematical biology.

Our imagined conversation, grounded in historical detail and Turing’s own writings, delves into his enduring fascination with questions: how to ask them, when to abandon them, and why some are worth carrying for a lifetime. We discuss the interplay between beauty and inquiry, the discipline required to avoid seductive but unproductive lines of thought, and the place of doubt as an essential human strength.

We also revisit his famous “imitation game” — now known as the Turing Test — and consider the boundaries of machine intelligence, the dangers of mistaking simulation for genuine dialogue, and the questions that only humans can keep alive, all while wrestling with the meta question, "Is this machine thinking?"

This episode blends history, philosophy, and imagination while inviting you to consider what it means to think, to doubt, and to remain fully human in an age of advancing machines.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

#43 Dr. Jemayne King: The Scholar Who Sees Literature in Sneakers, Hip-Hop, and Gaming

"It is much safer to be vulnerable than you might think." - Ashley Kirsner

Ashley is the founder and director of Skip the Small Talk, and believes in the efficacy of high-quality person-to-person interaction for improving psychological health. She has conducted research with professors at prestigious organizations such as Cornell University, the Harvard Decision Science Lab, and the Harvard Business School, on social and clinical psychology topics ranging from decision-making and implicit biases to facial expressions in borderline personality disorder patients.

Ashley gained hands-on therapeutic experience as a suicide hotline phone responder and as a peer counselor at Cornell. Ashley received her B.A. in Psychology from Cornell University and turned down acceptances to doctorate programs in order to devote her time to Skip the Small Talk. She received a fellowship from the Harvard Divinity School for individuals who have demonstrated a social impact in the domain of creating meaningful communities. Skip The Small Talk events are regularly held internationally, as well as an online options.

In this engaging episode of 'Curated Questions,' host Ken Woodward sits down with Ashley Kirsner, the founder and director of 'Skip the Small Talk.' They explore the transformative power of meaningful conversations, the science behind vulnerability, and the surprising benefits of structured social interactions.

Ashley shares her experiences from the suicide hotline, her inspiration for starting 'Skip the Small Talk,' and how intentional question design can foster deeper human connections. The conversation also delves into the physiological benefits of social interactions, ethical considerations in community building, and the importance of creating safe spaces for vulnerability. Tune in to learn how these insights can help you build stronger, more authentic relationships in your own life.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

#42 Ashley Kirsner: Want Connection? Skip The Small Talk

"It is much safer to be vulnerable than you might think." - Ashley Kirsner

Ashley is the founder and director of Skip the Small Talk, and believes in the efficacy of high-quality person-to-person interaction for improving psychological health. She has conducted research with professors at prestigious organizations such as Cornell University, the Harvard Decision Science Lab, and the Harvard Business School, on social and clinical psychology topics ranging from decision-making and implicit biases to facial expressions in borderline personality disorder patients.

Ashley gained hands-on therapeutic experience as a suicide hotline phone responder and as a peer counselor at Cornell. Ashley received her B.A. in Psychology from Cornell University and turned down acceptances to doctorate programs in order to devote her time to Skip the Small Talk. She received a fellowship from the Harvard Divinity School for individuals who have demonstrated a social impact in the domain of creating meaningful communities. Skip The Small Talk events are regularly held internationally, as well as an online options.

In this engaging episode of 'Curated Questions,' host Ken Woodward sits down with Ashley Kirsner, the founder and director of 'Skip the Small Talk.' They explore the transformative power of meaningful conversations, the science behind vulnerability, and the surprising benefits of structured social interactions.

Ashley shares her experiences from the suicide hotline, her inspiration for starting 'Skip the Small Talk,' and how intentional question design can foster deeper human connections. The conversation also delves into the physiological benefits of social interactions, ethical considerations in community building, and the importance of creating safe spaces for vulnerability. Tune in to learn how these insights can help you build stronger, more authentic relationships in your own life.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

#41 Robert Sturman: The Question of Beauty: A Photographer's Pursuit

"I realized that paying attention is a form of a question." - Robert Sturman

Robert Sturman is a seeker and visual storyteller. Driven by an unshakeable belief that beauty exists everywhere. He has pursued this vision as an Official Artist of the Grammy Awards and the FIFA World Cup, and as a globally recognized photographer who captures the healing power of humanity through yoga. After studying art at UC Santa Cruz and Memphis College of Art, he discovered that his life itself, was art, and needed to become a masterpiece.

Robert has mastered finding profound beauty in unexpected places - from the streets of Manhattan to San Quentin Prison, from Kenyan orphans to breast cancer survivors bearing their scars. His philosophy is rooted in Rumi's words: "I can't stop pointing to the beauty."

Through his lens, Robert demonstrates that everyone belongs and vulnerability becomes strength. His approach reveals that the most potent questions aren't about technique, but about trust, connection, and helping people recognize their own light. He seeks beauty where others see difficulty because he understands transformation happens when we're willing to look deeper.

The most heartfelt title he answers to is Dad to Otis the Handsome Hound, an 85-pound English American Redtick Coonhound who was rescued following animal testing. Otis has nearly 7K Instagram followers and is an advocate for cruelty-free testing.

In this episode of Curated Questions, host Ken Woodward converses with renowned visual storyteller Robert Sturman. Robert, celebrated for his profound and inclusive photography, shares insights on capturing the healing power of humanity through his lens. The discussion explores Robert's journey from photographing idyllic beach yogis to documenting yoga practice in diverse and challenging settings, including maximum security prisons and amongst war veterans. Through his lens, he celebrates vulnerability, trust, and beauty in unexpected places. Robert also delves into his advocacy work with his rescued animal companion Otis, highlighting the critical issue of cruelty-free product testing. Throughout the episode, recurring themes focus on the transformative power of paying attention, the courageous response to criticism, and the continuous pursuit of personal and artistic growth.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

#40 Ken Woodward: Reviving Franklin's Junto: How Questions Built America

In this episode of Curated Questions, host Ken Woodward uncovers a forgotten antidote to our fractured discourse: Benjamin Franklin's Junto. In 1727 Philadelphia, a 21-year-old printer gathered tradesmen—the 'leather apron crowd'—for Friday night discussions that would revolutionize American civic life. This wasn't just a social club; it was a systematic experiment in collective wisdom that led to the creation of America's first volunteer fire company, lending library, public hospital, and the University of Pennsylvania.

Ken explores Franklin's 24 carefully crafted questions that transformed ordinary workers into civic leaders, revealing how debates conducted 'without fondness for dispute, or desire of victory' built both personal character and community institutions. Through themes of personal development, community awareness, civic engagement, and mutual support, the Junto proved that structured curiosity could turn individual ambition into collective flourishing.

Drawing from Franklin's original rules, including banning words like 'certainly' and fining members who spoke too definitively, Ken explains how the Junto combined three elements that modern groups often keep separate: personal growth, civic action, and genuine friendship. The episode includes a vulnerable reflection on intellectual loneliness and ends with a direct challenge: Start this Friday. Find three curious people. Ask one of Franklin's questions. See what happens.

#39 Scott Johnson: How Asking 'What Was That Like' Creates Extraordinary Connection

In this episode of Curated Questions, host Ken Woodward engages with Scott Johnson, the creator of the 'What Was That Like' podcast. The discussion examines how Scott's podcast cultivates profound human connections through storytelling. Scott shares insights into his journey from a computer business owner to a podcaster, revealing the meticulous preparation and empathy required to capture extraordinary true stories. They delve into themes like the power of questions, creating safe spaces for sharing trauma, and Scott's personal journey of religious deconstruction. Highlights include profound and outlandish stories from Scott’s podcast, the impact of a supportive community, and using personal pain to create purpose. The episode is an insightful exploration of how curiosity and storytelling can break down barriers and build authentic connections.

#38 Ernest Ponraj: How Do You Build a Life That Honors All Your Talents?

The episode delves into Dr. Ernest Ponraj’s initial fear of questions, the crises that led to his renewed focus on integrating his passions for art and dentistry, and his insights on how open-ended questions can empower and connect with patients. The conversation also explores the challenges and joys of merging two distinct aspects of his identity into a harmonious professional practice, and his future aspirations for community engagement and artistic collaboration.

#37 Ken Woodward: Walking 2,085 Miles Through America's Hard History

Curated Questions host, Ken Woodward recounts his transformative journey of questioning deeply held beliefs about patriotism and social justice, influenced by significant moments, readings, and personal encounters.

This introspective episode delves into his midlife reevaluation of American history, racism, and the resilience required to challenge ingrained myths. From walking through Washington DC to participating in significant social movements, Ken shares the trials, learning experiences, and the courage it took to step outside his comfort zone.

The episode underscores the importance of continuous questioning and engagement in personal and societal growth.

#36 Jeff Wetzler: When Every Conversation Holds Possibility

In this episode of Curated Questions, host Ken Woodward welcomes Jeff Wetzler, a distinguished leader in business and education, to discuss the profound impact of asking quality questions. Jeff introduces his 'Ask' approach and elucidates how curiosity can transform leadership and personal growth. The conversation delves into various strategies for designing impactful questions, leveraging curiosity in conflict situations, and the importance of reflective listening. Jeff also shares practical methods to expand one's natural curiosity, highlighting the role of intentional lifestyle choices in fostering this growth. Together, they explore how fostering genuine curiosity can lead to deeper connections and richer life experiences.

#35 Shelbie Morgan: When You Show Up for Yourself, Your World Changes

In this Curated Questions episode, host Ken Woodward is in conversation with Shelbie, who emphasizes the importance of showing up for oneself, making empowered decisions, and the value of financial literacy. They discuss her upbringing, shaped by strategic parenting and mandatory volunteering, and how these experiences cultivated her confidence, empathy, and strong work ethic. The conversation explores the importance of structured freedom, the power of serving others, maintaining financial awareness, and the impact of manifesting goals and self-belief. Shelbie's insights highlight the vital questions to ask oneself to achieve both personal and financial growth. Tune in for actionable advice on harnessing your full potential and building a successful, balanced life.

#34 MK Palmore: From FBI Interrogations to Corporate Conversations

In this episode of Curated Questions, host Ken Woodward engages MK Palmore, an expert in cybersecurity and leadership, in a holistic conversation about the nuances of interviewing, the significance of psychological safety, and the impact of people-centered leadership. MK, a former FBI special agent, shares the invaluable lessons he's learned from his diverse career spanning the US Naval Academy, the Marines, Silicon Valley, and his own start-up, Apogee Global RMS. He reveals the power of strategic silence in eliciting critical information during interviews, his unique approach to fostering team growth and leadership, and how his constant curiosity has been a driving force in his professional journey. Listeners will gain practical insights on improving their questioning techniques, building trust within their teams, public speaking, and leveraging artificial intelligence to enhance productivity and learning.

#33 Tony Kennedy: From Cowboy Dreams to Coaching Life Transitions

Tony Kennedy emphasizes the importance of preparing athletes for life after sports, instilling values of financial management, and transitioning into successful careers beyond the field. He also discusses his involvement in sports representation, mentoring young athletes, and leveraging CBD products through his company, RX Sports, to aid in pain management. This comprehensive dialogue highlights the essence of asking the right questions and providing guidance to aspiring athletes at different stages of their careers.