Explore every episode of the podcast TECHNICALLY JOYFUL - Building Change Capacity in the Age of AI
| Title | Pub. Date | Duration | |
|---|---|---|---|
| The Joy of Building: How to Design a Human + Agent Organization with Geoff Schaefer | 04 Sep 2026 | 00:48:56 | |
What happens when AI agents stop being tools we occasionally use and start becoming members of our teams? Geoff Schaefer is literally writing the book on it. Geoff joins Gabrielle to vision what the agentic organization will actually look like, and how we can build it deliberately rather than simply letting it happen to us. They explore Geoff‘s framework for Building an Agentic Organization, and Gabrielle’s change framework, spanning strategy, governance, and economics, and get into some of the wonderfully complicated questions hiding underneath “AI transformation.” How do humans and agents divide work? What happens when agents can produce in eight hours what used to take two months? How do you budget for a workforce that includes salaries and tokens? How should an agent earn our trust? And what work becomes more valuable when machines can do almost anything? Along the way, they talk about creativity, radically diverse teams, culture, customer experience, and why some of the most important human work may move both further upstream into imagination and strategy and further downstream toward relationships, judgment, taste, and value. And the theme running through all of it: agency in getting to build this.
• Why Geoff thinks agents should be treated as cultural actors, not just technology
Choose one recurring piece of work, ideally something mildly annoying. But don’t simply ask AI to do it. Give the AI a job description first. Ask it to interview you about what you’re actually trying to accomplish. Together, create a short role charter: its purpose, responsibilities, constraints, what good looks like, and when it should come back to you. Then do one small piece of the work together. The rep isn’t just about delegation. It’s practice in making your own intent clearer.
Geoff Schaefer is an AI strategy and governance leader and the author of the forthcoming Building an Agentic Organization: The Strategy, Governance, and Economics of Agentic AI. He previously served as Vice President of AI Strategy and Governance at Leidos and led responsible AI work at Booz Allen Hamilton. He is also one of Gabrielle’s favorite people to call with an unfinished idea because his instinct is rarely “that won’t work.” It’s “how could we build it?”
Building an Agentic Organization — Geoff Schaefer’s forthcoming book, expected Spring 2027 IDEO + Design Thinking The ELIZA Effect Kevin Allison + Minerva Technology Futures
If Technically Joyful is earning a place in your week, follow the show, leave a review, and subscribe on Apple Podcasts, Spotify, or YouTube. And send Gabrielle your own AI show-and-tells: the useful, surprising, joyful, or tragically funny experiments you’ve tried. Some may make their way onto the show. Email: gabrielle@gkstrategic.com Ways to Connect with Gabrielle Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com Newsletter: technicallyjoyful.com | |||
| No One Has the Whole Picture: Why Connection Is a Leadership Capability | 01 Sep 2026 | 00:16:25 | |
What if the reason you can’t figure something out isn’t that you haven’t thought hard enough? What if part of the answer lives with someone else? When change is moving quickly, no one person has the whole picture. The knowledge we need is distributed across the people closest to the work, technical experts, skeptics, customers, people navigating risk, and sometimes the person who quietly tried six months ago what everyone else is still debating. That changes what expertise looks like. In this episode of Technically Joyful, Gabrielle Kohlmeier explores why connection is not just a nice leadership trait. It is a capability for navigating complexity. Drawing on her experience leading generative AI transformation inside a Fortune 30 company, Gabrielle shares how what first looked like a technology challenge quickly revealed an interconnected system of people, processes, incentives, risks, dependencies, and knowledge that no one person or function could see alone. The job wasn’t to know every piece. It was to get better at finding the pieces, connecting them, and exercising judgment across what emerged. Connection also gives us something else: energy. Sometimes another person gives us the question we hadn’t thought to ask, shows us a possibility we’d stopped seeing, or simply makes a difficult problem interesting again. Hard things require energy. Change requires energy. Learning requires energy. Sometimes we borrow that energy from one another. That’s joy as fuel.
Think of one real thing you’re trying to figure out. Ask your AI tool: “I’m trying to figure out X. Give me five perspectives I may be missing, who might hold each one, and one question I should ask them.” Then pick one actual person who holds a perspective you need and ask: “I’m trying to figure out X. What are you seeing?” AI can widen your aperture. It can’t give you someone else’s lived knowledge. One person. One question. One rep.
Ways to Connect with Gabrielle Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com Newsletter: technicallyjoyful.com | |||
| The Joy of Exploring: Leading AI Change Before the Map Exists | Anna Gressel, Partner and Co-Chair of AI Practice at Freshfields | 01 Sep 2026 | 00:46:18 | |
How do you lead through AI-driven change when the map hasn’t been drawn yet? Anna Gressel, partner and global co-head of AI at Freshfields, has built a career exploring questions without established answers, from neuroscience to some of the hardest legal, safety, governance, and strategy questions in AI. In this conversation, Anna and Gabrielle explore what it takes to move into unfamiliar territory with curiosity, creativity, and sound judgment. For Anna, the fact that something is new isn’t a reason to avoid it. It can be the reason to explore. That mindset shapes how she approaches novel problems: turning the prism, connecting ideas across disciplines, asking what might still be missing, and “scaffolding forward” toward challenges that haven’t fully arrived yet. But exploration isn’t the opposite of rigor. Anna works on high-stakes AI matters where safety, compliance, liability, and judgment matter enormously. The joy comes from helping clients solve hard problems, create responsibly, and find a wise path forward. The conversation also moves from individual AI fluency to organizational strategy. AI often doesn’t create entirely new organizational problems; it throws existing questions into sharper relief. What should we preserve? What needs to change? What is our competitive edge? Are we adopting AI because it serves a strategic goal, or simply for adoption’s sake? The goal isn’t predicting exactly where AI will be in five years. It’s building capabilities now that create more options later. In This Episode
Think of one thing you hate doing or one familiar process you rarely question. Ask AI to interview you about how it works today, where the pain points are, and what might be removed, simplified, or done differently. Then ask: What could I stop doing? What could AI help me automate? What would I redesign if I were starting from scratch? You don’t have to automate everything. The rep is to challenge the comfort of the pattern and explore what might be possible. Chapter Markers 02:32 Everyday AI joy: spreadsheets as a thought partner Sources & Resources
Ways to Connect with Gabrielle Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com Newsletter: technicallyjoyful.com | |||
| You Don’t Need to Catch Up on AI: Curiosity Is Your Change Strategy | 01 Sep 2026 | 00:22:43 | |
Feel like everyone else has figured out AI while you’re still trying to catch up? Here’s the problem: “caught up” may be the wrong goal. AI is changing too quickly for any of us to finish learning it. The leaders who will navigate this era best won’t be the people who know everything. They’ll be the people who build the capacity to keep learning, ask better questions, exercise judgment, experiment, and adapt as the ground moves. In the first episode of Technically Joyful, Gabrielle Kohlmeier explores why curiosity may be one of our most important change strategies in the AI era, especially for accomplished people who are used to being the ones with the answers. Drawing on her own journey from perfectionism to leading AI transformation, Gabrielle explores growth mindset, digital fluency, intellectual humility, psychological safety, and the power of becoming comfortable being experienced and a beginner at the same time. And this is where joy matters. Joy is not the opposite of rigor or discipline. It is fuel for exploration. Fear narrows our field of view. Curiosity, interest, and positive emotion can help broaden it, giving us more capacity to see possibilities, take smart risks, and keep learning when the work gets uncomfortable. Because you don’t need to catch up before you begin. Beginning is how you catch up.
Pick one thing you keep thinking you should already understand. Ask your AI tool to explain it at progressively deeper levels: ELI7: Explain it like I’m seven. Keep going until you move from “I don’t understand this” to “I have a foothold.” Then verify what matters. AI can hallucinate, oversimplify, and miss nuance. The goal is not to hand over your judgment. It is to use AI to accelerate curiosity while retaining it.
Ways to Connect with Gabrielle Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com Newsletter: technicallyjoyful.com | |||
| Welcome to Technically Joyful! | 24 Aug 2026 | 00:01:10 | |
What if joy could make us better at navigating change, not by making hard things easier, but by helping us stay curious, engaged, and willing to keep going? As AI reshapes how we work, lead, and make decisions, the challenge isn’t simply keeping up with technology. It’s building our capacity to navigate constant change and having the agency to help shape what comes next. This show explores the people, ideas, systems, and wonderfully human messiness behind meaningful change. Expect hard questions, fascinating conversations, unexpected connections, and practical ideas about AI, leadership, innovation, and what actually helps people and organizations move. Because change is a muscle. Joy helps us build it. Welcome to Technically Joyful. Ways to Connect with Gabrielle Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com Newsletter: technicallyjoyful.com | |||