Leadership in Change with AI - Podcast
TL;DR - Michael Bungay Stanier has spent a decade teaching leaders to be more coach-like, and the core of it, “ask more, tell less,” matters more now than when he wrote The Coaching Habit ten years ago. In this Substack Live, he gave me four principles for leading in the age of AI: clarity over certainty, context over content, connection over cocooning, and courage over collusion. We got into why AI’s confidence is a trap, why the real work of a leader is helping people find the right question instead of handing them the answer, and the three coaching questions that still hold up in 2026. Watch the full conversation above. 🎥 Catch all future interviews, subscribe on YouTube [https://www.youtube.com/channel/UCaws3oD3t4KiWU1qSaXDQpA] 🎧 Prefer audio? Listen on Apple Podcasts [https://podcasts.apple.com/ca/podcast/leadership-in-change-with-ai-podcast/id1884921599] 🤝 Want to chat one-on-one? Book a free intro call. [https://jsalinas.org/call/] Outline (0:43) – Leadership WTF: what it even means to lead now (1:34) – Does coaching still matter when everyone has ChatGPT (3:12) – Ask more, tell less, and why it’s harder than it sounds (5:44) – Daniel Goleman’s six styles and the one leaders skip (8:35) – The four Cs, laid out (9:05) – Clarity over certainty (11:08) – Courage over collusion (12:45) – The sycophancy trap: six months chasing a fake theorem (14:31) – Connection, and why humans rubbing up together still matters (19:01) – Why big change plans fail: capacity and agency (23:11) – The productivity fear: save 25%, produce 25% more? (26:09) – Coaching a team in 2026: the three questions (30:27) – Three books Michael recommends My Takeaways The four Cs. This was the spine of the whole conversation, and it’s the thing I’m still going over. Michael has been sitting with a simple question, what do we actually need to do as leaders in a time of AI, and he came back with four moves. “Clarity over certainty, context over content, connection over cocooning, and then courage over collusion.” I made a chart of it because I want to keep it in front of me, and honestly, once you hear all four together, you can’t unsee the tension in each one. Every C is a choice between the easy thing AI is great at and the harder thing that’s still ours to do. Clarity over certainty. So here’s where it got real for me. Michael’s point is that AI is fantastic at sounding sure, and that confidence is exactly the trap. “AI is brilliant at being certain,” he said, and then he told a story from a conversation with Dan Ariely (the behavioral economist behind Predictably Irrational) about a researcher who wasted six months chasing a new math theorem that ChatGPT told him he’d found, and that turned out to be complete nonsense. Certainty is cheap now. The leader’s job is clarity, which is the slower work of asking what the real problem even is before you go solve the confident-sounding one. Connection over cocooning. This is the one I keep chewing on. Michael admitted something I think a lot of us feel and don’t say out loud, that one of the strangest things about AI is he almost doesn’t need to talk to other human beings anymore, because it’s just him and his agent going back and forth. “It feels like it’s human, but it’s not human.” And I sat with that, because I could open Claude right now and ask it how Michael would answer a question and get a close approximation, which is exactly the thing that should scare us a little. His answer is that leaders create more than the sum of their parts when there’s real connection, and there’s something about humans rubbing up together that no agent replaces. Capacity before change. The most practical thing he said is that big change plans almost always fail, because leaders keep pouring water into a full glass. If your people are already at capacity, a shiny new AI rollout has nowhere to land. And this landed against a real moment for me, when someone on my team heard “AI will save you 25% of your time” and asked me straight up whether that meant I’d now require 25% more output. That fear is the whole game. Michael’s take is that the promise of AI isn’t just doing more stuff, it’s creating the capacity and the agency for people to run small experiments and actually manage the change instead of drowning in it. The three questions that still work So if you take one thing you can use Monday morning, take these. Near the end I asked Michael what coaching a team actually looks like in 2026, and he gave me three questions from The Coaching Habit that still hold up when AI can answer almost anything. The strategic question, “what are we going to say yes to, and if we say yes to this, what must we say no to?” The real-challenge question, “what’s the real challenge here?” And the learning question he closes every conversation with, “what was most useful or valuable here?” I’ve started using that last one, because it makes sure everyone walks away a little smarter, including me. I made a second card of these so you can keep them in front of you. If AI can generate every answer in your organization, what’s the one thing your people still need a human leader for? Sit with that, then watch the full conversation above, and if you want the real depth on any of this, go grab The Coaching Habit [https://thecoachinghabit.com/] and subscribe to Michael’s Change Signal podcast [https://thechangesignal.com/]. About Michael Bungay Stanier Michael Bungay Stanier is the author of The Coaching Habit, one of the best-selling coaching books of all time, now celebrating its ten-year anniversary. He also wrote How to Work with Almost Anyone and hosts the Change Signal podcast, [https://thechangesignal.com/] where he cuts through the blather to find what actually works in change. His whole mission is helping leaders be more coach-like: stay curious a little longer, rush to advice a little more slowly. Find his books and free resources at thecoachinghabit.com [https://thecoachinghabit.com/]. About me Joel Salinas is an AI Strategy Coach [https://jsalinas.org/#services] for leaders at small and mid-sized businesses and nonprofits. AI is everywhere; judgment is scarce. Joel helps leaders adopt AI without outsourcing their judgment to it, through a monthly live workshop and 90-day engagements. Creator of the AI Leadership Triad. He writes Leadership in Change. Written by a human, for humans. This is a public episode. 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