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

Deeply Human, Inc.
  • 5.0 (3)
  • 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

  1. Aug 11

    Blinded by the Light: Why Google, Intel and Kodak All Saw It Coming | 019

    Google published the Transformer architecture in 2017, the design underneath every modern chatbot, and then chose not to put a chatbot of its own in front of the public for years. Intel discussed taking a stake in OpenAI in the same period and walked away. In both cases, the information was there. So what actually obstructs the view? In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard take on a question a seasoned executive put to them this week: Has human discernment ever really been defined, or do leaders simply get it wrong? Their answer moves the question. The failures we point to as failures of clarity are rarely that. We get blinded by the light of what we already know, by what already rewards us in the short term, and by the way we are recognized for being right. CHAPTERS: 00:00 Blinded by the light 02:16  Google and Intel both saw it 04:26  Freeze, flight and fight in a team 05:36  The non-decision was a decision 07:04  Companies are organisms 09:24  Let's form a committee 11:43  Naming a quarter for experimenting 13:47  Fujifilm and the courage to be unsure 16:17  Utilization is not transformation 16:51  Green trucks 19:36  A thousand CEOs, ten honest hands 21:34  Change the question you ask in reviews 23:11  What a leader can do this quarter 25:34  Close ABOUT THE HOSTS: Lee Ann Del Carpio is the founder of Deeply Human, Inc. 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. Website: https://www.deeplyhumanleading.com  The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738

  2. Aug 4

    AI Leadership in 2026: Why the Pro vs. Anti Debate Is Costing Your Team | 018

    In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard explore what changes when you stop treating AI as a position to hold and start treating it as a condition to lead inside of. Gravity does not care whether you are for it or against it. The energy spent arguing either side is energy not spent building capability. From there the conversation moves into Geoffrey Hinton's argument that advanced AI will need maternal instincts, Mo Gawdat's case for raising AI the way you would raise a child with values, and what it means to lead when the tools in your organization are learning from your team every day. In this episode, you'll explore: Why the energy leaders spend at the pro-AI and anti-AI poles is the most expensive thing in the roomGeoffrey Hinton on maternal instincts, and Mo Gawdat on raising AI like Superman, and why both land on relationshipWhat shifts when intelligence stops being the advantageFour leader's moves you can make this week, including grapple before you grabHow to ask an AI collaborator what it has learned about you, and why the answer is worth having CHAPTERS: 00:00 Nobody has started a foundation to abolish gravity 02:10 Gravity is a bummer, and other honest reactions 03:58 The rate of information and what it does to the body 05:24 Geoffrey Hinton and the case for AI that cares 06:42 Mo Gawdat, Scary Smart, and raising AI like Superman 08:22 Who is the parent and who is the child 11:00 The power differential and human agency 11:50 We didn't get it right with social media 13:20 The courage to steward the middle 14:33 Leader's move: notice where you're leaking energy 15:47 Leader's move: name what must stay human 16:43 Leader's move: grapple before you grab 18:06 Leader's move: lead like something is learning from you 20:14 The first generation modeling for AI 22:27 We must be what good looks like 23:59 Messy is not the same as sloppy 25:30 A day in the pet emergency room 28:15 What have you learned about me? 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: Gretchen's book, Your Second Prime: https://www.amazon.com/Your-Second-Prime-Aging-Suck/dp/B0DHN2RJWB Lee 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

  3. Jul 28

    Why More AI Can Lead to Worse Decisions | 017

    In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard explore why organizations can run AI everywhere and still make worse decisions. The real challenge is no longer information, which has become abundant. It is perception, discernment, and judgment, the human moves that turn a flood of data into a clear call. They lay out a simple progression leaders can practice and two concrete moves to keep judgment sharp in the age of AI. In this episode, you'll explore: - Why information has become noise, and what that does to decision-making - The four-step progression: information, perception, discernment, judgment - The confidence paradox: why less information can make us more sure - Desirable difficulty and the risk of offloading every decision to AI - Two leader's moves: reclaiming the skill of summary and the meaning-making journal CHAPTERS 00:00 Everyone had the data, and missed what mattered 00:56 When information becomes noise 02:24 Executive judgment and the speed of AI 05:09 Information, perception, discernment, judgment 09:27 More AI, and still worse decisions 10:03 The confidence paradox 12:02 Perception, the nervous system, and healthy stress 14:48 Desirable difficulty and cognitive offloading 15:48 The ancient and the modern: relearning discernment 17:15 Leader's move: reclaim the skill of summary 22:50 Leader's move: notes by hand and the meaning-making journal 25:56 The signal beneath the noise About the Hosts: Lee Ann Del Carpio is the founder of Deeply Human, Inc. 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 David Bohm, On Dialogue (Routledge) 📩 Subscribe to The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738 🌐 Website: https://www.deeplyhumanleading.com

  4. Jul 21

    Why AI Shoppers Convert 40% Better, and What Leaders Risk Losing | 016

    In this episode, Lee Ann Del Carpio and Gretchen Terry-Leonard explore what happens to the customer experience as AI gets this good at the transactional. A laptop purchase goes to Claude, and on Prime Day, shoppers referred by AI assistants convert 40% better than any other channel for the first time (Adobe data, reported by Forbes, June 27, 2026). They open Episode 016 inside that number, then ask the question underneath it: as the transactional gets this easy, what happens to the parts of an experience people stay for? In this episode, you'll explore: The Prime Day data, and why contextual understanding is becoming the new conversionThe seduction of ease: why cognitive offloading feels so good, and the decision fatigue underneath itThe CPG "bliss point" that dropped when the orange coloring was removedThe Wizard of Oz test that separates a spectacle from an experienceThe courage it takes to defend the human touch under efficiency pressure CHAPTERS: 00:00 The customer experience, from both sides 00:40 Offloading a laptop purchase to Claude 02:17 Prime Day 2026: AI referrals convert 40% better 03:26 The seduction of ease and decision fatigue 04:16 "I just want a human" 04:41 Transactional help vs. immersive experience 05:59 The Cheetos bliss point 07:00 When every scorecard looks green 09:34 What else belongs on the dashboard 10:59 Love marks and shared experiences 13:38 The trend under the trend 15:01 The Wizard of Oz test 15:37 Designing the human plus AI customer journey 17:12 The bank betting on humans, and the courage it takes 19:22 Leadership readiness and a closing reflection 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: The HBR article mentioned in the episode: https://hbr.org/2026/07/why-the-best-immersive-experiences-succeedGretchen's book, Your Second Prime: https://www.amazon.com/Your-Second-Prime-Aging-Suck/dp/B0DHN2RJWBSubscribe to The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738Website: https://www.deeplyhumanleading.com

  5. Jul 15

    When AI Has All the Answers, Who Makes the Meaning? with Stacy McCarthy | 015

    In this episode, Lee Ann Del Carpio sits down with Stacy McCarthy, founder of Learning Design Network and a designer of dialogue for thirty years, to explore what real conversation gives us that no tool can, and how leaders keep making meaning together as AI speeds everything up. They start with a distinction the old languages knew: to discuss is to break a thing into pieces, while to dialogue is to make shared meaning. One we can now do at machine speed. The other still asks us to slow down. In this episode, you'll explore: Why dialogue and discussion are not the same thing, and why the difference matters more as AI accelerates- Coherence as the antidote to fragmentation, and how leaders build shared meaning across real differences- The quiet resurgence of craft and gathering, and what it reveals about what humans need in the AI age- Why the problem was never the tool, and what it means to design our interaction with AI on purpose- How to keep the uniquely human capacities, judgment, connection, and meaning-making, strong while the machines get fasterCHAPTERS: 00:00 Two friends, thirty years, one question 02:33 Why dialogue: language, Japan, and how culture shapes thought 06:28 What coherence really means 10:21 When fear fills the vacuum 12:05 Handwriting, improvisation, and being real 14:02 You cannot shift perspective until you shift the story 15:06 Designing dialogue: grappling, not debating 18:01 Discussion versus dialogue 20:57 The return to craft: pottery, gathering, presence 25:15 The trend underneath the trend 27:38 The problem was never the tool 29:55 From tool to thought partner to teammate 32:28 What patient-centric really asks of a system 34:52 Let the machine do the grunt work 43:07 Co-authors, not passengers 46:44 Wayfinding and what speed made us forget 50:36 The AI poem at the birthday table 53:40 Where to find Stacy 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. About the Guest: Stacy McCarthy is the founder and president of Learning Design Network. Over more than thirty years she has designed experiential, game-based learning that helps organizations turn a leadership vision into daily behavior people own, reaching close to a million people across organizations including Kaiser Permanente, Johnson & Johnson, Humana, and Gap. Her work is rooted in cross-cultural communication, dialogue, and discovery learning, shaped by years living and working in Japan and Europe. Find her at learningdesignnetwork.com and on LinkedIn. References & Links: Stacy McCarthy, Learning Design Network: https://www.learningdesignnetwork.com Subscribe to The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738 Website: https://www.deeplyhumanleading.com

  6. Jul 7

    Is It You or Is It AI? Leading Without Losing Yourself | 014

    DESCRIPTION: A strategy memo goes to Claude, the summary goes to ChatGPT, Perplexity checks the facts, and a final pass makes it all sound human. Lee Ann and Gretchen open Episode 014 inside that meeting, then ask the question underneath it: with all this saved time, where are the hours going? Along the way: a ninety-minute punch list that could have taken three, a grocery-store shopper consulting a chatbot instead of the label, an executive’s inbox filling with writing that has no one inside it, and the practice both hosts land on, cognitive hygiene, deciding intentionally what stays yours. CHAPTERS: 00:00 Cold open: a strategy meeting run through four AIs  02:23 What did all of that save us?  03:28 The simplicity trap and the prettiest list  05:04 In the grocery aisle: just read the label  05:59 Trying it on: transition or new habit?  06:42 Dueling chatbots and outsourced conversation  07:50 On a coaching call: the email with no one inside it  10:01 Sunday driving: where the tools serve and where they extract  11:33 Abundant analysis, scarce attention  12:55 Cognitive hygiene and cognitive boundaries  13:36 Who are we at core? The leadership brand question  15:00 The invitation: slowly, slowly, suddenly  16:01 Take it for a Sunday drive 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. 📬 Subscribe to The Deep Signal Newsletter: https://deeply-human.kit.com/b1bfa01738  🌐 Website: https://www.deeplyhumanleading.com

  7. Jun 30

    You Can't Run a Business on One Banana: AI Monoculture and Model Collapse | 013

    When AI starts learning mostly from itself, where does anything genuinely new come from? Anthropic reported that more than 80 percent of Claude's code is now written by Claude, and a premier model vanished from the team's plans overnight. Lee Ann and Gretchen use the humble banana to explain AI monoculture and model collapse: almost every banana we eat is a Cavendish, a near genetic clone that one disease could wipe out. They get into the reflex to overtrust machines and undertrust humans, how quality quietly erodes from good to "it'll do", and what the AI itself said when asked how it avoids becoming a clone of a clone. The throughline: diversity is insurance you have to design in, across models, money, and the counsel you trust. CHAPTERS: 00:00 Two things that knocked us offside 02:29 Why Gretchen's mind went to bananas 02:43 The Cavendish problem: one banana, one disease 05:31 You can't run a business on one banana 06:44 Blind spots and the autocorrect bias 08:21 Overtrust the machine, undertrust the human 09:22 Running out of naive data: getting high on your own supply 10:12 Where the AI constitution fits in 11:56 Asking the AI to confront itself 14:00 Variance has to come from outside the loop 15:47 Diversity is insurance, never a guarantee ABOUT THE HOSTS: Lee Ann Del Carpio is CEO and Founder of Deeply Human and Founder of the Center for Deeply Human Leadership. Gretchen Terry-Leonard is Co-Founder and Chief Strategy and Impact Officer of CDHL and author of Your Second Prime. WEBSITE: deeplyhumanleading.com NEWSLETTER (The Deep Signal): https://deeply-human.kit.com/b1bfa01738

  8. Jun 23

    What Too Much AI Is Quietly Doing to Leaders | 012

    Everyone is racing to use AI faster. Almost no one is asking what the speed is doing to the people doing the thinking. Lee Ann Del Carpio and Gretchen Terry-Leonard name the cognitive exhaustion that builds when leaders absorb too much, decide too often, and leave no margin for the thinking the moment requires. Not burnout.. Brain fry. Inside: the neuroscience of depletion, the move from generic to strategic to conscious use of AI, and why the future of leadership is more human, not less. CHAPTERS: 00:00 What too much AI is doing to us 02:15 Brain fry vs. burnout: the distinction 05:30 How AI-era decisions accelerate it 09:00 The neuroscience: PFC and amygdala 13:45 The recovery paradox 18:00 What it looks like in the room 21:30 Recovery as strategy, not self-care 24:00 The one move that actually helps RELATED READING: Gretchen's article "The Seduction of Ease" (Life Science Daily)NEWSLETTER: The Deep SignalWEBSITE: Deeply Human Leading #DeeplyHumanLeading #AILeadership #Leadership #FutureOfWork

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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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