#60 Radhika Dutt: From Goals to Puzzles: How Questions Outperform OKRs in Real Teams!

"We vote with our labor for the world we want to create. If you don't reflect on what you're doing, how do you know you're casting the right vote?" - Radhika Dutt

In this episode of Curated Questions, host Ken Woodward engages entrepreneur and author Radhika Dutt in a profound exploration of how questions can transform organizations from goal-driven to puzzle-solving entities. Radhika is the author of "Radical Product Thinking" and shares her journey from MIT to becoming a serial entrepreneur to developing the puzzle-based leadership OHLA framework (Objectives, Hypotheses, Learnings, Adaptations).

The conversation reveals how traditional goal-setting, rooted in 1940s assembly-line thinking, fails in today's complex environment, where creative problem-solving matters more than repetitive execution.

Radhika demonstrates through a live experiment how "puzzles" energize while "goals" burden, explaining that puzzles tap into internal motivation rather than external pressure. She emphasizes the critical importance of reflection, a practice she credits with enabling better decision-making both personally and professionally.

Drawing from her nine languages and global experience, including living in post-apartheid South Africa, Radhika offers insights on creating psychological safety for questions across cultures. The episode culminates with practical guidance on implementing puzzle-based thinking in organizations, showing how asking better questions leads to ownership, engagement, and transformative results.

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

Keep questioning!

#57 Jaimie Reese: Building Enduring Trust Through the Questions We Ask!

"When you have a trusting environment, it is exactly to hold each other accountable." - Jaimie Reese

What 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!

#56 Garrett Wood: Safety, Burnout, and the High-Achievement Mask!

"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 Wood

In 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!

#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.

Keep questioning!

#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.

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!

#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.

#32 Patrick Dubois: Why Curiosity Converts Better Than Commission

Patrick Dubois, a seasoned sales professional discusses the power of questions in sales and personal growth. Patrick emphasizes the importance of understanding the real reasons behind lost sales and how genuine curiosity can enhance relationships and build trust. He shares his journey from aspiring veterinarian to corporate sales and the transformative impact of knowing one's strengths and values. The conversation also explores the intersections of Patrick's passions for animals, wine, and coaching, providing deep insights into aligning one's career with personal strengths and authentic self-expression.