#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)

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#65 Mitchell Osmond: Everything Is Hard - Choose Your Hard

"Literally everything in life is hard. The question is, what cost are you willing to pay? And you pay that willingly and happily because you value it." - Mitchell Osmond

In this episode of Curated Questions, Ken Woodward sits down with Mitchell Osmond, founder of Dad Nation Co., and host of the Dad Nation Podcast (Top 5% globally), to explore a hard but liberating truth: everything in life is difficult; the question is which difficulty we choose.

Mitchell shares the moment a single question at a funeral, “Are you living a life worthy of imitation?” forced him to confront his health, marriage, finances, and legacy. From that reckoning emerged a framework for growth rooted in discomfort, integrity, and honest self-inquiry.

Together, Ken and Mitchell examine why confidence is built through keeping promises, how avoiding hard questions quietly shapes our futures, and why legacy is forged at home as much as at work.

The conversation challenges the myth of ease, reframes struggle as a signal of alignment, and invites listeners to define success on their own terms. Ultimately, this episode is a call to stop outsourcing meaning, and to choose the hard that leads to a life worth living.

Mitchell is launching a new group coaching program, the High Performance Husband Accelerator! All the details can be found at https://www.dadnationco.com/accelerator

Mitchell is offering The Connection Code as a gift. 50 questions to spark the fun and get the fire back is available at https://www.dadnationco.com/code

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

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#63 Ken Woodward: The Inquisitive Almanack: 2026

"Direction often emerges not from knowing what you want, but from finally admitting what you don’t." - Ken Woodward

The Inquisitive Almanack: 2026 Edition closes the year with something Curated Questions has never quite done before—an affectionate, slightly irreverent, and deeply thoughtful almanack for the inner life.

Inspired by Benjamin Franklin’s Poor Richard’s Almanack, this episode blends dry wit, invented bureaucracy, and hard-won wisdom to offer forecasts not for the weather, but for the heart, mind, and questions we carry.

You’ll hear interior weather reports, proverbs for the asking class, arbitrary rules of inquiry, lunar phases of curiosity, and predictions for the questions most likely to surface in 2026—across leadership, relationships, parenting, teams, and personal life.

Released intentionally as the final episode of the year, this Almanack isn’t a recap or a resolution guide. It’s a pause. A breath. A lighter place to rest before the calendar turns and begins asking new things of us.

Come curious. Leave rested. And carry one good question forward.

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

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#62 Haru Yamada: Flashlights, Lanterns, and the Way We Listen

"Not being a hundred percent sure all the time is a weird strength." - Haru Yamada

In this episode of Curated Questions, Ken Woodward is in conversation with Dr. Haru Yamada, a sociolinguist, intercultural communication scholar, and author of Kiku: The Japanese Art of Good Listening, to explore what it really means to listen. Haru traces her early understanding of questions back to age four, when she moved from Tokyo to New York and had to use questions as a tool for language, belonging, and survival.

Together, they unpack how culture shapes communication: English often rewards “flashlight” questioning, the precise, content-driven clarity, while Japanese culture tends to favor a “lantern” approach that illuminates context, relationship, and what isn’t said. Haru also shares the harrowing accident that reshaped her understanding of listening as a health practice, linking felt-heard experiences to relational, mental, and even physical well-being.

In a noisy, multitasking world, this conversation reframes listening as an active, life-giving skill, and a compass for navigating each other with empathy.

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

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#61 Rob Walker: The Art of Noticing: How Asking Better Questions Changes What We See!

"If all you do is pay attention to what everyone else is paying attention to, then by definition you're not likely to innovate anything or create anything very original or different or surprising." - Rob Walker

Writer and cultural observer Rob Walker joins Ken to explore how questions and noticing reshape the way we move through the world. Rob traces his origin story back to discovering journalism at 18—a framework that gave a shy, introverted kid permission to ask questions on behalf of others.

They dig into his book and newsletter The Art of Noticing, talking about everyday noticing assignments, why “what am I missing?” is a powerful self-question, and how small acts of attention can mark time and make life more memorable.

Rob shares the story behind the Significant Objects project and why story—not price tag—creates real value in the objects we keep. From New Orleans as a “conversational city” to his teaching on point of view and manifestos, Rob reflects on questions as both agency and responsibility, in democracies, organizations, and personal life. Be sure to subscribe to Rob's Substack The Art of Noticing newsletter at https://robwalker.substack.com/

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

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#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.

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#59 Ken Woodward: The Insight Pause: When a Single Truth Rewrites Your Story!

"The Insight Pause is sitting in the rubble of your shattered worldview before clearing a single stone." - Ken Woodward

In 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.

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#58 Frank Sesno: How Bridge-Building Questions Cross Divides!

"I'm gonna make an appointment with my curiosity." - Frank Sesno

Emmy award-winning journalist Frank Sesno shares how curiosity and strategic questioning shaped his four-decade career covering presidents and world leaders as CNN's Washington Bureau Chief and White House correspondent. From a fourth-grade question about astronauts to interviewing five U.S. presidents, Frank reveals the power of deliberate curiosity and active listening.

Frank breaks down his approach to preparing for high-stakes interviews, explaining how he blocks conversations into thematic acts while remaining flexible. He introduces the "echo question" technique, which is simply repeating a person's emotionally charged word back to them, that transforms surface answers into more profound truths. Frank emphasizes that the best questioners are the best listeners, focusing on what people say and what they don't say.

In "Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change," Frank discusses why bridge-building questions are critical in our polarized moment. He explores how AI makes human curiosity more valuable and shares his practice of "making an appointment with curiosity" to create time to deliberately formulate meaningful questions.

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

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#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.

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#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.

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#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.

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#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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#50 Mike Hilson: Why "Who Do I Say I Am?" Changes Everything!

"Who am I? Was never gonna turn out well. Who do I say I am? Had a chance." - Mike Hilson

Mike Hilson is the Senior Pastor of New Life Church based in La Plata, Maryland. Since 1999, the church has grown under his leadership from a congregation of less than 100 into several churches and video venues. The New Life Network of churches now averages more than 5,000 in regular attendance across Maryland, Northern Virginia, and online.

Mike currently serves on the Board of Trustees at Southern Wesleyan University. He is also a member of the Chesapeake District Board of Administration for the Wesleyan Church. He lives in the D.C. Metro Area with his wife, Tina and their three adult sons.

Mike has written several books, including Napkin Theology, Speak Life, A Significant Impact for Christ, Heart of a Leader: Moses, and a series of books called Coffee with the Pastor.

These successes led to numerous invitations to teach and coach leaders from multiple regions, states, denominations, and nations.

In this episode, host 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.

The episode addresses how asking the right questions can uncover more profound truths, facilitate effective leadership, and nurture valuable relationships.

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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#46 Dr. Matt Lampe: Why the Right Question Feels Like an Invitation

"The meaning of your communication is the result you are getting." - Dr. Matt Lampe

With a Doctorate from Alliant International University's California School of Professional Psychology, Matt has dedicated his career to transforming how organizations approach change, leadership development, and workplace agility.

He is currently leading enterprise-wide organizational change efforts as part of Business Oregon's flagship modernization initiative, which focuses on aligning internal systems, strengthening operational infrastructure, and enhancing statewide service delivery to help businesses throughout Oregon.

Sponsored by the non-profit Science For Work, Matt hosts the "Science for Work Podcast," where he explores the science behind creating healthier, more effective work environments through conversations that translate heady scientific research findings into practical action steps.

His consulting practice helps organizations navigate complex transformations through change management, leadership development, strategic planning, and project management—combining data-driven insights with compelling storytelling.

Matt's philosophy centers on creating cultures where people can thrive. He's learned that data alone isn't enough to drive change; it's the combination of solid research with relatable storytelling that truly motivates action and engagement. And if that wasn't enough, he is also a contributing writer to PositivePsychology.com.

In this podcast episode, host Ken Woodward delves into the significance of questions in both professional and personal spheres with Dr. Matthew R. Lampe, an expert in organizational change and leadership development. Highlighting the vital role questions play in verifying communication, navigating change, and building trust, Matt shares insights from his experience in managing organizational transformations and personal growth. The conversation also touches on the deep tradition of yearly trips to Yosemite, offering a unique perspective on how consistent reflection against an unchanging backdrop can facilitate personal growth and evolution. Additional elements include updates about the curated questions community, announcements of new features, and an introduction to the Science for Work Podcast.

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

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