Deeply Human Leading with Lee Ann Del Carpio & Gretchen Terry-Leonard

Deeply Human, Inc.
  • 5.0 (2)
  • Management

AI is transforming every industry. But the leaders deploying it are being asked to change faster than any model prepared them for. Deeply Human Leading is a weekly podcast for leaders navigating the gap between the intelligence they're deploying and the human capacity to lead alongside it. Hosted by Lee Ann Del Carpio and Gretchen Terry-Leonard — who've spent decades guiding leaders through disruption, complexity, and systems change — each episode explores what it takes to lead with clarity, courage, and discernment when the ground is shifting. New episodes every Tuesday. VISIT: https://www.deeplyhumanleading.com

Episodes

  1. Jun 3

    "It's a Practice Run": What AI's Speed Is Doing to Leaders | 010

    The technology is accelerating faster than our leadership institutions know how to steward it. That is the signal underneath a week of AI headlines, and it is the question Lee Ann and Gretchen sit with here. Three stories crossed the feed that looked unrelated: a Pope calling for guardrails, a wave of layoffs framed as inevitable, and the head of Google DeepMind describing today's AI agents as a "practice run" for what comes next. What connects them is speed, arriving without the consent, governance, or preparation that a moment like this asks for. Lee Ann Del Carpio and Gretchen Terry-Leonard explore what stewardship looks like when you don't control the global picture, why human-made work is about to become more valuable rather than less, the real cost of cutting a creative team for speed, and where agency begins. Their answer is smaller and more hopeful than the headlines suggest: it starts in your own home, your own team, the part of the system you influence. If this really is the practice run, the question worth holding is what kind of leaders we are practicing to become. Hosted by Lee Ann Del Carpio and Gretchen Terry-Leonard. New episodes weekly. Newsletter: https://deeply-human.kit.com/b1bfa01738 Web: https://www.deeplyhumanleading.com

    28 min

  2. May 19

    Learned Helplessness in the Age of AI: Why Leaders Are Disengaging (And How to Stop) | 009

    If technology is moving at a breathless pace and most organizations aren’t changing how they work, what does that mean for the humans inside them? In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard explore what it takes to see clearly when the ground is shifting beneath every leader, every team, and every family trying to make sense of AI’s acceleration. Drawing on Ethan Mollick’s updated “The Shape of the Thing” article (March 2026), they examine why our first instinct in uncertainty, reaching for the spreadsheet and the stopgap measure, may be the very thing keeping us stuck. TIMESTAMPS: 0:00 Introduction 1:13 Seeing Headlines Without Locking In 2:28 The Shape of the Thing — Revisited 4:53 From Using AI to Directing It 6:11 Why Organizations Aren't Keeping Pace 7:13 Layers of Human Resistance 8:46 Changing Your Relationship With Uncertainty 10:41 Learned Helplessness at Scale 13:09 What AI Is Actually Unlocking 15:05 What Leaders Need to Become 17:47 Hold Uncertainty AND Be Unambiguous 19:20 Nervous System Regulation as Leadership 22:03 Practical First Steps to Ground Yourself 24:14 The Window to Shape AI Is Closing 26:10 Practicing Discernment — Start Somewhere 27:28 Privacy, Learning Partners & the Flywheel 29:12 Closing Reflection ABOUT YOUR HOSTS: Lee Ann Del Carpio is the CEO and Founder of Deeply Human, Inc. and co-founder of the Center for Deeply Human Leadership. With 25+ years guiding senior leaders through transformation in healthcare, biotech, and mission-driven organizations, she helps leaders reawaken what only humans can bring: relational wisdom, discernment, and the ability to shape systems that serve life. Gretchen Terry-Leonard is the Chief Strategy & Impact Officer and co-founder of the Center for Deeply Human Leadership (CDHL). She has built 26 Health Equity Fellowships with top-tier academic medical centers, generated $35M+ in strategic value, and co-authored a policy brief on AI and health equity with The Economist Impact Group. Author of Your Second Prime: Does Aging Suck or Do We Suck at Aging? LINKS: 📬 Subscribe to The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738 🌐 Website: https://www.deeplyhumanleading.com 🎵 YouTube: https://www.youtube.com/@DeeplyHumanLeading 🎙 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv

    31 min

  3. May 12

    The Skills Under the Skills: What's Really Paying Top Dollar in the AI Economy Isn't Technical | 008

    The seven most in-demand skills in the AI economy aren't coding or machine learning. They're asking the right question. Sensing when something is about to go wrong. Knowing what to leave out.   Tech strategist Nate B. Jones recently studied what AI jobs are actually paying top dollar for, and the answer might surprise you. The skills he identified — like specification precision, evaluation and quality judgment, failure pattern recognition, and trust boundary design — sound technical. But underneath each one is a deeply human capacity that most leaders haven't been trained to develop.   In this episode of Deeply Human Leading, Lee Ann Del Carpio and Gretchen Terry-Leonard take Jones's framework and go beneath the surface. They explore how the Socratic method is becoming one of the most valuable professional skills of the AI age, why your body's felt sense is a legitimate source of data that AI cannot replicate, how systems thinking and holistic orchestration translate directly to working with AI collaborators, and why the ability to walk away from a failing path may be the most distinctly human capacity of all. They also share how they're applying these skills in their own AI workflows, including how Lee Ann navigates group process dynamics with AI the same way she does with senior leadership teams, and how Gretchen uses appreciative inquiry to check her own blind spots.   Whether you're a founder building with AI, a leader navigating your organization's AI rollout, or someone wondering where your career fits in this new landscape, this episode will help you see the skills you already have in a completely new light.   ───────────────────────── REFERENCES MENTIONED IN THIS EPISODE   Nate B. Jones, "Your AI Credentials Don't Matter. Your Artifacts Do." (Substack, March 2026): https://natesnewsletter.substack.com/p/your-ai-credentials-dont-matter-your   Nate B. Jones, AI News & Strategy Daily podcast: https://feeds.acast.com/public/shows/ai-news-strategy-daily-with-nate-b-jones   Julia McCoy, YouTube channel: https://www.youtube.com/@juliamccoy Julia McCoy, FLUID: The Adaptability Code Malcolm Gladwell, Outliers: The Story of Success   ───────────────────────── CONNECT WITH US   Website: https://www.deeplyhumanleading.com Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv YouTube: https://www.youtube.com/@DeeplyHumanLeading 0:00 Welcome to Deeply Human Leading 1:52 Skill 1: The Art of Asking Precise Questions 8:24 Skill 2: Discernment as Full-Body Wisdom 15:51 Skill 3: Systems Thinking & Holistic Orchestration 23:54 Skill 4: Failure Pattern Recognition 32:39 Skill 5: Trust Boundary Design

    40 min

  4. May 5

    What Holds You Steady When AI Changes Everything?

    Kevin O'Leary, Shark Tank investor, says if you're a CEO just pushing the button on AI, you're generating garbage. He's naming what a lot of leaders feel but haven't said out loud yet: the technical models or corollary tech skills are not enough. The human underneath the technology is what determines whether AI creates value or erodes trust. In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard explore what actually holds leaders steady when waves of AI disruption keep coming. They unpack Kevin O'Leary's call for storytelling and critical thinking, Peter Diamandis's three-wave framework for what's ahead (automation, deflation, post-scarcity), and the deeper question beneath all of it: Do you know who you are when the title, the credentials, and the familiar lane all shift? Rather than the gold rush era craze of keeping up with AI that is populating your social media feed, this conversation is about you - and what you want amplified when AI amplifies everything. In this episode, you'll explore: Why Kevin O'Leary says CEOs generating AI output without human judgment are creating "AI slop"The difference between a leadership brand and knowing who you are underneath your titleLee Ann's "divine genius" framework for uncovering the value only you can bringGretchen's "inconvenient dream" concept from Your Second PrimePeter Diamandis's three waves of disruption (2025–2036) and what they mean for your careerWhy nervous system regulation is a prerequisite for navigating accelerating changeThe principle: "Never waste a good disruption"The most important question to ask yourself right now: What do you want amplified? About the Hosts: Lee Ann Del Carpio is the founder of Deeply Human, Inc. and the Center for Deeply Human Leadership. With 25+ years guiding senior leaders through transformation in healthcare, biotech, and complex systems, she helps leaders reawaken relational wisdom, discernment, and the ability to shape systems that serve life. Gretchen Terry-Leonard is the Chief Strategy & Impact Officer of the Center for Deeply Human Leadership and author of Your Second Prime: Does Aging Suck or Do We Suck at Aging? She brings 26 Health Equity Fellowships, a published policy brief with The Economist Impact Group, and a career of systems thinking to the defining question of this decade. References & Links: Kevin O'Leary on AI and CEO leadership: https://www.cnbc.com/kevin-oleary/Peter Diamandis / Abundance 360 Summit: https://www.abundance360.com/Gretchen's book, Your Second Prime: https://www.amazon.com/Your-Second-Prime-Aging-Suck/dp/B0DHN2RJWBLee Ann's coaching program, Recalibrate for Impact: https://www.limitlesslearningnow.com/recalibrate-for-impact📬 Subscribe to The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738 🌐 Website: https://www.deeplyhumanleading.com

    23 min

  5. Apr 28

    AI Made Every Dashboard Green. Then Customer Trust Collapsed. | 006

    What happens when an AI gold rush mentality drives boards and senior leaders to drive for cost savings and efficiency at a breathless pace? Klarna replaced 700 customer service employees with AI. Month one: 2.3 million conversations handled. Resolution time cut to two minutes. $60 million in projected savings. Every metric on the dashboard was green. Then customer satisfaction collapsed, complaints surged, and the CEO went on Bloomberg and said four words: "We went too far." In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard explore the seductive pull of cost savings, speed and efficiency in AI deployment at the expense of other measures of organizational vitality, and why the things that look measurably successful can quietly destroy the things that matter most: trust, institutional knowledge, and the human relationships that built your brand in the first place. What you'll explore in this episode: • Why Klarna's "green dashboard" masked a collapse in customer trust • How Air Canada's chatbot hallucinated a bereavement fare and triggered a legal ruling • What happened when CNET used AI to write 77 financial articles with inaccurate math • The paradox leaders face: speed AND quality, not speed OR quality • How AI amplifies your existing leadership clarity (or your existing confusion) • The difference between measurable gains and immeasurable losses • Why the most critical leadership skill in the AI age may be knowing when to slow down CHAPTERS: 0:00 – Introduction 1:14 – The Klarna case: 700 employees replaced, every metric green 7:27 – Air Canada's chatbot hallucination and legal fallout 9:14 – When AI damages your leadership brand (the 360-feedback story) 11:29 – Institutional knowledge, context, and what AI replaces without asking 12:56 – The intent gap: AI amplifies your leadership clarity or your confusion 14:14 – CNET's 77 inaccurate AI-written financial articles 16:30 – The AI arms race and adrenaline-driven decision making 17:30 – The paradox: speed AND quality as mutually complementary forces 21:17 – Reputational damage, trust, and the real cost of going too fast 22:35 – What we gain in efficiency vs. what we lose in the immeasurable 23:45 – The question to take with you: Where can you balance speed and quality? ABOUT THE HOSTS: Lee Ann Del Carpio is the founder and CEO of Deeply Human, Inc., with 25+ years guiding senior leaders through transformation in healthcare, biotech, and mission-driven organizations. Gretchen Terry-Leonard is the Chief Strategy & Impact Officer at the Center for Deeply Human Leadership, building the research institution investigating what sustained AI-assisted decision-making does to human judgment and moral agency. CONNECT WITH US: Website: https://www.deeplyhumanleading.com Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv YouTube: https://www.youtube.com/@DeeplyHumanLeading Lee Ann on LinkedIn: https://www.linkedin.com/in/leeanndelcarpio/ Gretchen on LinkedIn: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/

    24 min

  6. Apr 21

    Women Founders and AI: Why the Biggest Opportunity Is Right Now | 005

    Jensen Huang just told podcaster Lex Friedman that AGI is here. But while the media debates what that means, a different conversation is happening among founders: What will I build with it? In this episode of Deeply Human Leading, Lee Ann Del Carpio and Gretchen Terry-Leonard explore what the coming of artificial general intelligence means for people with ideas, purpose, and the courage to create — especially women and founders over 50 who bring decades of wisdom to a moment that desperately needs it. In this episode, they discuss: • What AGI actually means and why Jensen Huang’s definition has relevance for everyday founders • The 25% gap in women’s AI adoption and why that’s both a challenge and an opportunity • The $1.6 trillion economic gap that won’t close with technology designed by teams that don’t understand it • Why people over 50 represent 25% of all new entrepreneurs (AARP data) • How AI has demolished the technical barrier that used to stand between a good idea and a real business • The shift from participation to creation and why whoever builds the technology determines what it becomes This is not AI hype. This is a grounded, honest conversation about what it takes within yourself to step into this moment to create real impact in a rapidly changing world. CHAPTERS 0:00 — Jensen Huang says AGI is here: what does that mean? 1:57 — AGI vs. narrow AI: the real difference 3:44 — Why this moment is uniquely powerful for founders in their 50s 5:02 — The 25% gender gap in AI adoption 10:21 — Shaping what AI learns about humanity 15:46 — From participation to creation: the real invitation ABOUT THE HOSTS: Lee Ann Del Carpio is the founder and CEO of Deeply Human™ and the Center for Deeply Human Leadership. With 25+ years guiding senior leaders through transformation in healthcare, biotech, and complex systems, she helps leaders reawaken what only humans can bring: relational wisdom, discernment, and the ability to shape systems that serve life. Gretchen Terry-Leonard is Chief Strategy & Impact Officer at CDHL. She built 26 Health Equity Fellowships with top-tier academic medical centers and generated $35M+ in strategic value through partnerships that compound. She is the author of Your Second Prime: Does Aging Suck or Do We Suck at Aging? CONNECT WITH US: Website: https://www.deeplyhumanleading.com Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv YouTube: https://www.youtube.com/@DeeplyHumanLeading Lee Ann on LinkedIn: https://www.linkedin.com/in/leeanndelcarpio/ Gretchen on LinkedIn: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/

    19 min

  7. Apr 16

    How to Lead When No One Can Predict What AI Will Do Next | 004

    A powerful new AI documentary is leaving audiences shaken. Lee Ann saw it opening week and Gretchen has been studying the debate from the outside. Together they unpack what it means for leaders who are trying to hold both the promise and the peril of AI without collapsing into either hyper optimism or panic. This is not another episode about AI tools or productivity hacks. This is about the deeper question: How do you lead when nobody can predict what happens next? When the old model of predict-and-control no longer works? When every interaction you have with AI is quietly shaping what AI learns about humanity? In this conversation, Lee Ann and Gretchen explore: • What the "Apocaloptimist" stance is and how it seeks to balance both the existential risk and extraordinary promise of AI • What happens to your nervous system when you first grasp the full scope of AI’s impact (and how to move through it) • Why the predict-and-control operating model from the Industrial Era is failing leaders in the Age of AI • Five practices for co-creating with AI that preserve your agency, values, and discernment • How every single interaction you have with AI teaches it something about humanity and why that matters more than most people realize • The difference between intelligence and wisdom, and why that distinction is the leadership question of our time CHAPTERS: 00:00 — The AI documentary that frames both AI promise and peril 05:36 — When AI awareness hits your nervous system 07:39 — Personal agency and the role of corporations 09:57 — Why predict-and-control is the wrong operating model 12:22 — Changing your relationship with uncertainty 22:21 — What co-creation actually looks like in practice ABOUT THE HOSTS: Lee Ann Del Carpio is the founder and CEO of Deeply Human™ and the Center for Deeply Human Leadership. With 25+ years guiding senior leaders through transformation in healthcare, biotech, and complex systems, she helps leaders reawaken what only humans can bring: relational wisdom, discernment, and the ability to shape systems that serve life. Gretchen Terry-Leonard is Chief Strategy & Impact Officer at CDHL. She built 26 Health Equity Fellowships with top-tier academic medical centers and generated $35M+ in strategic value through partnerships that compound. She is the author of Your Second Prime: Does Aging Suck or Do We Suck at Aging? CONNECT WITH US: Website: https://www.deeplyhumanleading.com Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv YouTube: https://www.youtube.com/@DeeplyHumanLeading Lee Ann on LinkedIn: https://www.linkedin.com/in/leeanndelcarpio/ Gretchen on LinkedIn: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/

    34 min

  8. Apr 7

    Raising Kids Who Can Lead in an AI World - Without the Panic | 003

    Something is changing faster than your brain can clock. You already feel it… at the dinner table, in school conversations, in the quiet worry about what your children will actually be equipped for. This episode doesn't add to the noise. It helps you find your footing.   Lee Ann Del Carpio and Gretchen Terry-Leonard, both parents and leaders, sit down to have the conversation most people are having in their heads but not yet out loud: what does it actually mean to raise humans who can thrive in an age of intelligent machines?   In this episode, you’ll explore: Why our brains are notoriously bad at processing exponential change and how that affects our ability to guide the next generationThe concept of 'desire difficulty': why choosing the hard thing is not old-fashioned, it's neurological infrastructureThe calculator precedent and what history teaches us about every new tool that threatens educationGrapple before you grab for AI… one phrase that changes What Gretchen's 11-year-old building a Roblox game with zero coding experience teaches us about human-AI co-creationMetacognition as the defining leadership skill: learning to observe your own mind as a practice, not a conceptHow to use AI as a thought partner rather than an order-taker and why the difference matters enormously Timestamps: 0:00 — Introduction: Raising humans in the age of intelligent machines 1:26 — Matt Schumer’s viral post: “Something Big Is Happening” 3:34 — The before and after: processing the pace of change 6:32 — Absorbing disruption: fear, grief, and the 10% test 14:30 — What schools are (and aren’t) teaching about AI 21:43 — Why Silicon Valley sends their kids to Montessori and Waldorf schools 31:32 — Cognitive offloading, desire difficulty, and metacognition 43:06 — Designing your relationship with AI About the hosts: Lee Ann Del Carpio is the CEO & Founder of Deeply Human, Inc., with 25+ years guiding senior leaders through transformation in healthcare, biotech, and mission-driven organizations. Gretchen Terry-Leonard is the Chief Strategy & Impact Officer at the Center for Deeply Human Leadership (CDHL), bringing a track record that includes 26 Health Equity Fellowships with top-tier academic medical centers and $35M+ in strategic value through purpose-aligned partnerships. Together, they co-founded CDHL to investigate what sustained AI-assisted decision-making does to human judgment, discernment, and moral agency. Connect with us: Website: https://www.deeplyhumanleading.com Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv YouTube: https://www.youtube.com/@DeeplyHumanLeading Lee Ann on LinkedIn: https://www.linkedin.com/in/leeanndelcarpio/ Gretchen on LinkedIn: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/

    47 min

  9. Mar 31

    For Every $1,000 Spent on AI, Only $1 Goes to Understanding Its Human Impact | 002

    “I'm only human." We say it like an apology… for forgetting, for falling short, for being imperfect. But what if being human isn't the limitation? What if it's the thing we haven't invested in deeply enough? In Episode 002 of the Deeply Human Leading podcast, Gretchen and Lee Ann unpack the difference between being "only human" — what Lee Ann calls our "default human" mode, the fight-flight-freeze response we fall back on under stress — and being deeply human: intentional, grounded, discerning, and awake to the inner capacities that no technology can replicate. In this episode, you’ll explore: — Why your nervous system is your most underrated leadership tool — The “default human” trap — and how to recognize when you’re in it — Why McKinsey is now hiring liberal arts majors over technical specialists — The staggering $1,000-to-$1 AI spending gap — and why it matters to every leader — How AI can serve as a mirror for human self-discovery — The “inner technologies” that match the pace of outer technologies — Why knowing what you stand for is now a survival skill, not just an exercise Headlines referenced in this episode: https://fortune.com/2026/01/14/how-to-get-hired-at-mckinsey-ai-tools-liberal-arts-creativity/ https://longnow.org/ideas/inspired-by-intelligence-rediscovering-human-purpose-in-the-age-of-ai/ https://brenebrown.com/book/daring-greatly/ https://a.co/d/0fLAVzvm https://a.co/d/0bByTecZ About the hosts: Lee Ann Del Carpio is the CEO & Founder of Deeply Human, Inc., with 25+ years guiding senior leaders through transformation in healthcare, biotech, and mission-driven organizations. Gretchen Terry-Leonard is the Chief Strategy & Impact Officer at the Center for Deeply Human Leadership (CDHL), bringing a track record that includes 26 Health Equity Fellowships with top-tier academic medical centers and $35M+ in strategic value through purpose-aligned partnerships. Together, they co-founded CDHL to investigate what sustained AI-assisted collaboration does to the human brain, to human discernment, decision-making, and to personal agency. Connect with us: Website: https://www.deeplyhumanleading.com Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv YouTube: https://www.youtube.com/@DeeplyHumanLeading Lee Ann on LinkedIn: https://www.linkedin.com/in/leeanndelcarpio/ Gretchen on LinkedIn: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/

    27 min

  10. Mar 25

    What Happens to Human Leadership When AI Gets Smarter Than You? | 001

    What happens to your identity, your expertise, and your leadership when AI can do parts of what you've spent your career building?  In the first episode of the Deeply Human Leading Podcast, hosts Lee Ann Del Carpio and Gretchen Terry-Leonard explore the question no one is asking loudly enough: as AI becomes embedded in how we work, decide, and lead, what happens to the humans inside the system?  This isn't a podcast about AI tools or tactics. Deeply Human Leading sits in a third space — between AI anxiety and AI hype — exploring what it actually means to lead in an era of accelerating intelligence.  New episodes weekly.  The Future of Leadership is Deeply Human.  SUBSCRIBE: youtube.com/@DeeplyHumanLeading  NEWSLETTER: https://deeply-human.kit.com/b1bfa01738  VISIT: https://www.deeplyhumanleading.com   LINKEDIN: Deeply Human Leading  Lee Ann: https://www.linkedin.com/in/leeanndelcarpio/   Gretchen: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/

    22 min
  • 10 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

AI is transforming every industry. But the leaders deploying it are being asked to change faster than any model prepared them for. Deeply Human Leading is a weekly podcast for leaders navigating the gap between the intelligence they're deploying and the human capacity to lead alongside it. Hosted by Lee Ann Del Carpio and Gretchen Terry-Leonard — who've spent decades guiding leaders through disruption, complexity, and systems change — each episode explores what it takes to lead with clarity, courage, and discernment when the ground is shifting. New episodes every Tuesday. VISIT: https://www.deeplyhumanleading.com

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