#87 Ken Woodward: The Anatomy of a Question

"The question was not broken. It was unfinished." - Ken Woodward

Buried in the introduction of the twentieth century's most famously unread book is the most precise dissection of a question ever written.

In this solo episode, we open Martin Heidegger's Being and Time and recover his anatomy of inquiry: every question has a subject, a source, and an intent, and most questions fail not from bad wording but from missing parts.

We test the anatomy against the streets of Washington, D.C., including a backyard in Marshall Heights where a five-hour-and-forty-five-minute conversation revealed what sixty-one years of an unasked question feels like.

Then the reckoning. The man who drew the map of questioning joined the Nazi Party, deleted his Jewish teacher's name from his own dedication page, and spent forty-three years refusing the one question that came addressed to him.

Knowing the anatomy is not the asking. This episode is about the difference, and the drive home.

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

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

#85 Larry Robertson: What Will You Soon Realize You Already Know?

" The more you play around with it, and the more you see the power in a question, the more you realize that it actually is the cure for the uncertainty that ails many of us." - Larry Robertson

Larry Robertson has spent three decades advising leaders on growth, innovation, and strategy. He is also a US Fulbright Scholar, a columnist, and the author of four award-winning books. His newest, Great Question: The Art of the Ask and Getting More of What You Really Want, draws on more than 140 interviews spanning neuroscience, psychology, business, and the arts.

Larry believes we are not a storytelling species. We are a questioning species. He arrived at that conviction book by book, pattern by pattern, over two decades of research.

In this conversation, we explore the power of questions as a form of agency. We examine intellectual humility and what happens when you stop performing certainty. We discuss leadership, polarization, and the Braver Angels framework. We also unpack Larry's five-element Art of the Ask.

Questions are not a technique. They are a behavior. They are something you already know how to do. This conversation is a reminder to start practicing again.

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

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

#83 Ken Woodward: What You Know Changes What You Can Ask

"A good answer can close a loop. A good question opens one." - Ken Woodward

What if the quality of your questions has less to do with how curious you are and more to do with how much you know?

A recent study from the Technion in Israel tracked 68 students over a semester of Introduction to Psychology. Researchers measured not just what students learned, but how their question-asking changed. The findings are worth sitting with. Domain-specific questions got sharper, more original, more complex. General questions did not improve. In some cases, they declined.

Knowledge doesn't flatten curiosity. It sharpens it.

This episode traces that finding through 32 years of Navy acquisition, through 1,300 conversations on a 2,085-mile walk through Washington DC, and through a conversation with Seth Godin about tension, rubber bands, and the question that only becomes possible after the preparation is done.

The argument is simple. You don't become a better questioner by wanting to ask better questions. You become one by learning more about what you're walking into.

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

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

#80 Ken Woodward: Still Asking: Ten Lessons From A Decade With Questions

"Claiming your agency to question is a renegade step into your full humanity." - Ken Woodward

April 12, 2016, marked the first public demonstration of Kenneth Woodward's obsession with questions. A decade, 80 episodes, and 140,000 downloads later, he returns to the shoreline to share what a decade of study, conversation, and lived experience has washed up at his feet.

From a daily inquiry blog that cost him sleep, to 1,300 conversations across 2,085 miles of Washington D.C. streets, to podcast conversations with some of the world's deepest thinkers, questions have been the through line.

In this milestone solo episode, Kenneth offers ten honest observations about questions, how they create space, signal desire for change, exercise agency, and reveal what we most need to face. Not conclusions from a master, but mile markers from a fellow pilgrim still very much on the road.

The practice continues. So does the asking.

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

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

#66 Ken Woodward: What Happens When A Question Is Asked?

"Questions are not neutral; they're interventions." - Ken Woodward

What actually happens inside us when a question is asked?

In this solo episode of Curated Questions, Ken Woodward explores the neurological, emotional, and psychological impact of being asked a question.

Moving beyond techniques or tactics, Ken examines how questions hijack attention, trigger chemical responses in the brain, open unresolved mental loops, and sometimes activate fear or defensiveness.

Drawing from neuroscience and a powerful encounter during his Washington, D.C. walking project, he reflects on a question that has remained open for years: What real difference are you making?

This episode reveals why some questions feel like relief before they’re answered, why others linger long after they’re asked, and how certain questions don’t just reveal who we are, but actively shape who we become.

Questions, Ken argues, are not neutral requests for information. They are interventions. And understanding their power changes how we ask, how we answer, and how we live with them.

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

Be sure to check out the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

#55 Ken Woodward: The Locked Door: How Avoided Questions Hold the Key to Transformation!

"Your avoided question isn't just personal development, it's an act of resistance." - Ken Woodward

In this episode of Curated Questions, host Ken Woodward explores the transformative power of confronting the questions we're avoiding. Delving into neuroscience, psychology, and personal reflection, he highlights why these avoided questions create discomfort and how they serve as a gateway to significant change.

Ken introduces tools and methodologies to help listeners identify and tackle these questions, both in their personal lives and within organizations. With practical advice and real-world examples, this episode encourages listeners to pause, reflect, and take actionable steps towards growth.

Ken also underscores the importance of curiosity and its role in overcoming avoidance, ultimately leading to meaningful transformation.

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

Keep questioning!

#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.

Keep questioning!

#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.

Keep questioning!

#31 Kevin Kelly: The Future Belongs to the Question-Makers

Host Ken Woodward talks with Kevin Kelly, who shares his insights on the power of questioning for personal and societal growth, discussing the role of questions in driving innovation and fostering understanding. He emphasizes the importance of inefficiency and exploration in formulating impactful questions, contrasting this with AI's tendency to provide average answers. Kelly also discusses his long-term projects, such as the 10,000-year clock with the Long Now Foundation, emphasizing the importance of long-term thinking and striking a balance between stability and adaptability. The discussion highlights the value of embracing disequilibrium for intellectual and technological advancement and challenges the notion of productivity by suggesting that waste and failure are integral to the discovery process.

#30 Tim Molnar: Intentionally Cracking Love's Enigma Through Analytics

Host Ken Woodward talks with Tim Molnar, who shares how he developed his strategic dating framework by applying research principles to dating, emphasizing the importance of asking better questions about ourselves and potential partners. He explores how traditional metrics like "feeling a spark" can be misleading compared to questions about safety, visibility, and energy levels after being with someone. The conversation highlights how self-awareness, intentional action, and thoughtful questioning can increase the probability of building fulfilling relationships while also creating space for continued growth and evolution within partnerships.

#29 Dave Reynolds: Cultivating Transformational Growth Through Questions

Host Ken Woodward talks with Dave Reynolds, CEO of the Rumin8 Group, about the impact of purposeful questioning in leadership and coaching. Reynolds shares his journey of learning the value of questions through his mentor Pablo, emphasizing transformation over transactional leadership. They discuss the importance of preparing for coaching conversations, asking in-depth questions, and fostering a culture of coaching and accountability in organizations. Reynolds also introduces concepts from his new book "Radicle Growth," which focuses on using questions to drive personal and organizational growth. The episode highlights the need for leaders to go beyond surface-level interactions, commit to ongoing development, and engage more deeply with their teams through strategic questioning.

#28 Lisa Wimberger: From Lightning's Wrath to Neuro Resilience

Host Ken Woodward converses with Lisa Wimberger about the transformative power of curiosity and the practice of Neurosculpting. Lisa shares her harrowing experiences of being hit by lightning and suffering from non-epileptic seizures, which led her to develop a unique healing modality by combining brain science and mindfulness. Through this dialogue, Lisa explains how asking the right questions can lead to profound personal growth and healing, providing practical insights into emotional regulation and neuroplasticity. Listeners also gain a deeper understanding of how Lisa has utilized her experiences to help corporate leaders, law enforcement, and first responders improve their mental resilience.

#27 Ken Woodward: A Fork, A Precipice, A Decision

Host Ken Woodward shares a personal and professional dilemma faced upon receiving an unexpected resignation offer from his government employer. Reflecting on extensive conversations and internal contemplation, Ken explores the strengths and vulnerabilities of his situation.

Highlighting the obstacles and emotional turmoil faced while deciding to stay the course or resign, Ken raises numerous thought-provoking questions and discusses the considerations influencing his final decision. Through analyzing the risks and rewards, Ken aims to inspire others to leverage questioning for personal growth and decision-making even in uncertain times.

#26 Chad Littlefield: The Catalyst for Collaborative Conversations

Chad Littlefield is the co-founder and Chief Experience Officer of We and Me (www.weand.me). The organization aims to help leaders, educators, and events make connection easy. His successful 2015 Kickstarter for We! Connect Cards: Create Conversations that Matter, which is comprised of cards with questions on the front and a stretch on the back intended to make conversations fun and meaningful. Forbes calls Chad a “global expert on asking questions that build trust and connection in teams.” He is a TEDx speaker, bestselling author, and creator of Connection Toolkit™, which is now being used to create conversations that matter on campuses and companies in over 80 countries worldwide.

Chad and his late partner Will Wise launched their books How to Make Virtual Engagement Easy and Ask Powerful Questions: Create Conversations that Matter, both #1 Amazon Bestsellers. Chad's YouTube channel has over a million views, and he hosts the annual Connectors Summit in December to bring people together to hone their skills and meet like-minded people leading the vital work of connecting. He lives and delivers the enthusiasm you expect for someone trying to change the world through intentional connection.

The conversation delves into the transformative power of asking meaningful questions and building connections. Chad shares his journey of discovering the impact of questions, We Connect Cards' origin, and intention's role in effective questioning. The discussions also explore practical strategies for fostering deep connections and the societal impact of genuine curiosity. Full of insights and practical advice, this episode is a must-listen for anyone interested in enhancing their communicative skills and fostering stronger relationships.

#25 Seth Godin: Embracing Tension & Unleashing Questions Strategic Potential

Seth Godin is a bestselling author of 22 books in 39 languages, entrepreneur, and speaker. In April of 2025, he will upload his 10,000th daily blog post to one of the most popular blogs in the world; yeah, that's over 27 years of daily writing. Seth founded Squidoo and Yoyodyne (acquired by Yahoo!) and is credited as the inventor of email marketing (the good kind).

Seth has given five TED talks, including two that rank as the most popular of all time. By teaching about everything from effective marketing and leadership to the spread of ideas and our responsibilities as leaders, Seth has motivated and inspired people worldwide.

The conversation delves into Seth's background, achievements, and philosophy behind the power of asking questions. They discuss how questions can create tension, drive more profound understanding, and foster meaningful connections. Seth shares anecdotes from his experiences, offering practical examples of strategically using questions in various contexts, from personal interactions to professional settings.

The episode underscores the necessity of intentionality in asking questions to effect change, highlighting the strategic importance of inquiry in personal growth and leadership. It concludes with reflections on empathy, systemic challenges, and the enduring significance of caring and trying to make a difference, no matter the state of the world.

#24 Ken Woodward: Impactful Questions: Are You Better Off...

This episode dives into the significant political question posed by Ronald Reagan during the closing moments of his 1980 presidential debate with Jimmy Carter: 'Are you better off than you were four years ago?'

Ken Woodward explores the context of the 1980 political climate, marked by economic difficulties, high inflation, unemployment, and international issues such as the Iran hostage crisis and concerns about U.S. global standing and nuclear threats. Reagan's question, which became iconic in U.S. political discourse, was noted for its simplicity, personal relevance, emotional resonance, and strategic timing. The question invited voters to reflect on their circumstances rather than abstract policies, ultimately contributing to Reagan's landslide victory.

The episode details six crucial lessons for crafting influential questions, emphasizing audience perspective, engagement, simplicity, timing, self-reflection, and a call to action. Listeners are encouraged to consider how such questions have shaped their decisions and to apply these insights in personal and professional contexts.

#23 Ken Woodward: Right Now Questions Explored

This episode explores 'Right Now Questions,' a concept introduced in an earlier 2024 podcast episode. The episode compiles various interviews where individuals share their current pressing questions.

Featured guests include author Chazz Scott, who discusses life post-book release and physical recovery, and sisters Shreyaa and Esha Venkat from the nonprofit NEST4US, who are considering their future plans and educational transitions. Other contributors include educator Kwame Sarfo-Mensah reflecting on his roles, business leader Bill Reed sharing deep questions on emotional triggers and passions, and multi-hyphenate EbonyJanice Moore contemplating her priesthood journey. Art Historian and problem solver Amy Herman ties in personal and professional life experiences, and Executive Coach Jerry Colonna speaks on his transitional stage. The audience is invited to share their own Right Now Questions, fostering a continuous journey of learning and inspiration.

#15 Kwame Sarfo-Mensah: The Vocabulary of Identity & Creating Culturally Affirming Classrooms

Kwame explores the concept of identity, including personal and social identities, and how these can affect one's experience in the world. The conversation delves into the challenges of addressing identity in educational settings and the importance of diversity, equity, inclusion, and accessibility. Kwame shares his experiences and insights on the power of questions in navigating contract negotiations, understanding student backgrounds, and self-growth. The dialogue also touches on unlearning ingrained biases and recognizing privileges. The discussion concludes by reflecting on the role of questions in fostering a more inclusive and understanding society.

#14 Bill Reed: Questions At The Heart Of Leadership, Mentorship and Relationships

The discussion delves into how questions have shaped Bill’s parenting, leadership, and mentoring approach, emphasizing the importance of curiosity and intentional relationship-building. We also explore the impact of effective questioning in meetings and mentoring relationships, focusing on Bill's current endeavors and insights into fostering a culture of transparency and authentic inquiry.

#12 Jimmy D. Smith: Navigating Leadership, Friction, Mentorship, and Legacy

Smith shares his inspiring career journey from an aspiring pilot to a guardian of the nation's nuclear arsenal, highlighting the importance of persistent inquiry, mentorship, and community engagement. He discusses his unique work habits and strategies for career advancement and introduces the 'Talk Backwards' methodology for relationship building. Smith also emphasizes selflessness, integrity, and his initiatives in STEM programs, particularly with HBCUs, providing scholarships, internships, and job opportunities. Personal anecdotes and life lessons from his mentor, Vice Admiral Paul Sullivan, are woven throughout, encouraging listeners to question, grow, and help others succeed.