#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!

#79 Andrew Caulk: Who Benefits From Me Believing This?

"It is easier simply to tell the truth, even if you've made a mistake, because what it does is build credibility over time." - Andrew Caulk

What happens when the questions leaders most need to ask are the ones they're most afraid to voice? Andrew Caulk spent two decades in the Air Force as an information strategist, and he's seen how institutions, military, political, and personal, manage their narratives by avoiding the hardest inquiries.

In this conversation, Andrew and Ken explore how misinformation and disinformation actually work, why truth is more strategically sustainable than deception, and how the attention economy is quietly rewiring our ability to think slowly.

Andrew shares what senior leaders refused to ask aloud in military war games, what the casualty projections for a Taiwan conflict actually look like, and why American will to fight may be the most underexamined variable in geopolitical strategy.

The conversation also turns to children, curiosity, and how the questions we allow, or suppress, in our homes shape the next generation's capacity to navigate a noisy world.

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!

#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.

Keep questioning!

#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!

#17 Amy Herman: Art And Inquiry As A Threshold To Our Humanity

Amy shares her experiences from law and art history, emphasizing how questioning can broaden knowledge and improve problem-solving skills. Additionally, her expertise underscores the significance of effective communication, human connections, and shared experiences across personal and professional contexts. The conversation touches on themes of situational awareness, self-reflection, and the growth that comes from embracing imperfections, drawing on real-life examples and anecdotes, like learning from a retired prison guard and understanding trauma through the art of kintsugi.