Michelle Hamilton has spent almost 40 years as a glass sculptor. She's also the Director of AI Adoption at Answer Rocket, running enterprise AI rollouts for Fortune 50 clients. On this 80th episode of the Bald Ambition Podcast, Mookie sits down with her to find out how those two careers connect and reinforce each other.

Both jobs, Michelle argues, come down to the same skill: visualizing a client's vague need, walking them through it verbally and mentally, and translating "what's keeping you up at night" into something concrete. She's currently engineering an 8-foot exterior glass sculpture — over a thousand melted glass pieces, lit from within, built to survive Midwest snow and rain — and she did it by uploading her hand sketches to an AI and working through the full engineering scope with it as a thinking partner. That's the same kind of conversation she has with enterprise clients trying to figure out where their AI investment went.

And that's the real subject of this episode: AI capability, sure, but also AI adoption: the much harder problem of getting human teams to actually use the tools their company already paid for. Michelle's central finding, after two and a half years doing this full-time, is that the technology is rarely the bottleneck. Fear is. Employees quietly assume they're being trained to replace themselves. Executives nod along to acronyms like LLM without admitting they don't know what it means. And meanwhile, "shadow AI" runs rampant, with employees bypassing whatever model IT approved to use their own personal one instead, because humans are, in her words, "incredibly curious creatures" who will always go around a tool that frustrates them.

Mookie and Michelle dig into the mechanics underneath that fear: the bot-talking-to-bot feedback loop that makes analysts redundant if they're not careful, the sycophancy problem where AI models cave and flatter instead of pushing back, and why real prompt engineering has quietly evolved into something closer to full context-setting. The temptation for treating the first message in a chat less like a search query and more like the "who, what, where, when, why, how" of a school essay is strong. Michelle also walks through a genuinely moving example: teaching her 80-something mother to do physical therapy workouts with an AI coaching her in real time through video, correcting her posture mid-squat.

While most grapple with AI nirvana or AI doom, Michelle shares her working methodology for the messy middle. That's the actual, unglamorous work of getting a legacy-infrastructure company and a scared, curious workforce to meet a powerful new transformative tool halfway.

The Guest

Michelle Hamilton leads AI adoption and change management at AnswerRocket, an enterprise AI firm that's guided Fortune Global 2000 companies through AI transformation since 2013. After more than 30 years in complex business transformation, she now focuses on the gap most companies miss: heavy investment in AI tools, almost none in the people expected to use them. She also founded Spark AI Strategy and AI Class Lab, chairs the board of both, and speaks internationally on her keynote "Imagine IF: Humanizing AI to Drive Strategy, Adoption, and Competitive Advantage." Outside of consulting, she's spent almost 40 years as a glass sculptor, with work installed in museums, hospitals, and corporate spaces worldwide.

About AnswerRocket

https://answerrocket.com/

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