The Chief Strategy Officer Podcast
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The Chief Strategy Officer Podcast
#23—Why AI Adoption Is a People Problem, Not a Technology Problem: Joanne Sheppard
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Outthinker
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Most AI strategy conversations start with the wrong question. They ask which tools to use — when the real question is why people aren't using them.
Joanne Shepherd, strategic advisor to Holtzbrinck Group (Macmillan Publishers, Springer Nature, Die Zeit) and board member across multiple companies, has lived this problem firsthand. In this conversation, she shares what actually drives AI adoption inside large, complex organizations — and it has almost nothing to do with the technology.
We get into the IKEA case (8,500 people upskilled, over $1B in new revenue), Holtzbrinck's own rollout mistakes, the "AI Tuesdays" initiative that unlocked grassroots innovation, and the three strategic options every board should be pressure-testing right now.
If you're a strategy leader navigating AI adoption, this one will shift how you think about it.
In this episode:
Why top-down mandates backfire — and what to do instead
The psychological safety factors that determine whether adoption is real or performative
What to do with the productivity AI frees up (this deserves a quarterly board conversation)
The architects, bridgers, and catalysts framework — and why your catalyst probably isn't who you'd expect
The "windshield wiper" problem: why eliminating all routine work isn't the goal
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Additional Resources:
- LinkedIn: https://www.linkedin.com/in/joannesheppard/
- Holtzbrinck Group: https://www.holtzbrinck.com
- Outthinker Strategy Network: https://outthinker.com
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Thank you to our guest Joanne Shepherd for such a generous and genuinely practical conversation. Thank you to our executive producer, Zach Ness, our editor, James Pearce, and the rest of the team. If you liked what you heard, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff. Thank you for listening.
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