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Why Do Enterprise AI Rollouts Keep Failing? with Rob Lion

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Everyone was told to adopt AI, tried it, got burned — so why do enterprise AI rollouts keep failing? Jonathan Green talks with organizational strategist Rob Lion about the real reasons big AI initiatives miss: unrealistic expectations set by the hype, skipping change management, and the employee mindset of "make my job easier, but not so easy that I'm replaceable." Key Takeaways: • Most enterprise AI failures are change-management failures, not tech failures • The "promise of the commercials" sets expectations the rollout can't meet • If you skip how you roll it out, you bypass the most common path to success • Employees quietly resist: "make my job easier — but not so easy I'm replaceable" • Teach people the why and the workflow, not just "what's an LLM" Notable Quotes: "Make my job easier — but not so easy that I'm replaceable." — Rob Lion "When someone doesn't know what direction they're heading, the rollout's already in trouble." — Rob Lion Connect with Rob Lion: LinkedIn: https://www.linkedin.com/in/robertlion Website: https://blackriverpm.com Enjoyed this? Follow The Artificial Intelligence Podcast and share it with a leader rolling out AI.

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