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. 3d ago

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. Jun 17

    What Does Your Body Know That AI Doesn't? | Deeply Human Leading Ep. 011 with Shannon Gomez

    We ask AI before we ask ourselves, and somewhere in all that speed, we stop hearing what our own bodies are trying to tell us. In this episode of Deeply Human Leading, Lee Ann Del Carpio talks with Shannon Gomez, a licensed acupuncturist and Traditional Chinese Medicine practitioner with more than two decades of experience, about what it means to stay human and embodied in an age where answers are always available. This is not a debate about whether AI is good or bad. It is about the one thing a machine cannot do for us: integrate what we are actually living. They explore the rise of "Dr. AI" and self-diagnosis, the difference between information and integration, the illusion of understanding that sets in when a fluent answer poses as wisdom, intuition as a built-in human capacity, and simple practices for returning to the body's own knowing. Guest: Shannon Gomez is a licensed acupuncturist, herbalist, and creator of the Rebel Deck, based in Phoenix, Arizona. Find her at goshannongo.com and rebeldeck.com. Chapters: 00:00 Welcome and introducing Shannon Gomez 03:30 Personal sovereignty and what acupuncture restores 05:24 Taking your power back 08:22 "Dr. ChatGPT": arriving with the diagnosis already done 10:40 Listening to the body's wisdom 13:19 Embracing both: Western, Eastern, and AI 13:54 Information vs. integration 16:25 What the body does best: integration 18:53 What's shifting in our collective nervous system 20:24 Drowning in competent answers, short on discernment 22:08 Epistemia: the illusion of understanding 24:15 Knowing how to ask, and correcting AI 25:49 Intuition as our superpower 28:13 Anchoring in your own knowing 29:54 Self-trust and tuning into the body 30:56 Where to find Shannon, and a Rebel Deck card pull 33:27 Closing: stay curious, stay human More at deeplyhumanleading.com. Subscribe to The Deep Signal Newsletter Mentioned in this episode • Epistemia, the illusion of understanding — Emory University's Goizueta Business School (December 2025) • "AI can deliver information and insight, but it cannot deliver integration" — Erin Cutrone, Academy of Therapy Wisdom

  7. 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

  8. 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

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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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