# Why Do Enterprise AI Rollouts Keep Failing? with Rob Lion

Page: https://stenobird.com/podcast/artificial-intelligence-podcast-chatgpt-claude-midjourney-and-all-other-ai-tools-52214/why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion
Text version: https://stenobird.com/podcast/artificial-intelligence-podcast-chatgpt-claude-midjourney-and-all-other-ai-tools-52214/why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion.md
Podcast: [Artificial Intelligence Podcast: ChatGPT, Claude, Midjourney and all other AI Tools](https://stenobird.com/podcast/artificial-intelligence-podcast-chatgpt-claude-midjourney-and-all-other-ai-tools-52214)
Published: 2026-08-31T13:00:00+00:00
Episode link: https://www.buzzsprout.com/606496/episodes/19524043-why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion.mp3
Audio file: https://www.buzzsprout.com/606496/episodes/19524043-why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion.mp3
Processing state: not_requested
JSON: https://stenobird.com/v1/public/podcasts/artificial-intelligence-podcast-chatgpt-claude-midjourney-and-all-other-ai-tools-52214/episodes/why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion
Duration seconds: 1814

## Resource

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...

## Actions

- request_transcript: `POST https://stenobird.com/v1/public/podcasts/artificial-intelligence-podcast-chatgpt-claude-midjourney-and-all-other-ai-tools-52214/episodes/why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion/transcription-requests` — Idempotently request low-priority transcript generation for this episode.
- read_markdown: `GET https://stenobird.com/podcast/artificial-intelligence-podcast-chatgpt-claude-midjourney-and-all-other-ai-tools-52214/why-do-enterprise-ai-rollouts-keep-failing-with-rob-lion.md` — Read the agent-friendly Markdown representation of this episode resource.

A page view does not enqueue transcription. Agents should invoke `request_transcript` explicitly when they need this episode processed.

## Transcript

Full transcripts are not published on public pages unless there is a clear rights basis.