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

"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 [https://deeply-human.kit.com/b1bfa01738] Web: https://www.deeplyhumanleading.com [https://www.deeplyhumanleading.com]

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 [https://deeply-human.kit.com/b1bfa01738] 🌐 Website: https://www.deeplyhumanleading.com [https://www.deeplyhumanleading.com] 🎵 YouTube: https://www.youtube.com/@DeeplyHumanLeading [https://www.youtube.com/@DeeplyHumanLeading] 🎙 Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv [https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv]

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 [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 [https://feeds.acast.com/public/shows/ai-news-strategy-daily-with-nate-b-jones]   Julia McCoy, YouTube channel: https://www.youtube.com/@juliamccoy [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 [https://www.deeplyhumanleading.com] Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 [https://deeply-human.kit.com/b1bfa01738] Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv [https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv] YouTube: https://www.youtube.com/@DeeplyHumanLeading [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

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 title * Lee Ann's "divine genius" framework for uncovering the value only you can bring * Gretchen's "inconvenient dream" concept from Your Second Prime * Peter Diamandis's three waves of disruption (2025–2036) and what they mean for your career * Why nervous system regulation is a prerequisite for navigating accelerating change * The 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/ [https://www.cnbc.com/kevin-oleary/] * Peter Diamandis / Abundance 360 Summit: https://www.abundance360.com/ [https://www.abundance360.com/] * Gretchen's book, Your Second Prime: https://www.amazon.com/Your-Second-Prime-Aging-Suck/dp/B0DHN2RJWB [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 [https://www.limitlesslearningnow.com/recalibrate-for-impact] 📬 Subscribe to The Deep Signal newsletter: https://deeply-human.kit.com/b1bfa01738 [https://deeply-human.kit.com/b1bfa01738] 🌐 Website: https://www.deeplyhumanleading.com [https://www.deeplyhumanleading.com]

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 [https://www.deeplyhumanleading.com] Newsletter (The Deep Signal): https://deeply-human.kit.com/b1bfa01738 [https://deeply-human.kit.com/b1bfa01738] Spotify: https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv [https://open.spotify.com/show/4r7WnDnCOKqsgE8ShClMcv] YouTube: https://www.youtube.com/@DeeplyHumanLeading [https://www.youtube.com/@DeeplyHumanLeading] Lee Ann on LinkedIn: https://www.linkedin.com/in/leeanndelcarpio/ [https://www.linkedin.com/in/leeanndelcarpio/] Gretchen on LinkedIn: https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/ [https://www.linkedin.com/in/gretchen-terry-leonard-8a92ab36/]