Most executives are being asked to make consequential decisions about AI before they have personally experienced what the technology can actually do. That creates a fundamental leadership problem: how do you set strategy for something you understand primarily through presentations, demonstrations, and other people’s explanations?
In Episode 1 of Now to Next: The Signal, the new season of Jason Averbook’s Now to Next podcast, Jason sits down with Alison McCauley, two-time bestselling author and author of How to Think with AI, to examine the growing gap between what AI makes possible and what most enterprises are actually doing with it. Jason and Alison explore what that disconnect means for leadership, learning, trust, culture, work design, and the role of HR. They challenge conventional measures of AI adoption, examine what happens when employees understand the possibilities before leadership does, and ask how organizations should prepare for a workforce that increasingly includes both human and digital workers.
The conversation ultimately moves beyond AI itself. It asks whether executives, operating models, and institutions can learn and change quickly enough to make intelligent use of a technology that will not wait for them to catch up.
Episode Highlights
- Why leaders need direct experience with AI before they can shape a meaningful strategy.
- What changes when software learns from people instead of people learning the software.
- Why the gap between personal and enterprise AI is becoming impossible to ignore.
- How speed to learn can matter more than speed to launch.
- Why login rates reveal almost nothing about whether work is actually changing.
- What HR must do when the workforce includes both humans and digital workers.
About Jason Averbook
Jason Averbook has spent more than 30 years shaping HR technology and workforce transformation. His career includes leadership roles at PeopleSoft and Ceridian, co-founding and leading Knowledge Infusion from 2005 to 2012, serving as CEO of The Marcus Buckingham Company, and co-founding and leading Leapgen from 2018 to 2023. After serving as Mercer’s Global HR Transformation Leader, he co-founded Now to Next to help leaders prepare people and organizations for an AI-shaped world.
About Alison McCauley
Alison McCauley is a two-time bestselling author who has spent three decades operating as a conduit between Silicon Valley disruptors and enterprise leaders seeking to leverage new technology. As an adviser to both the enterprise C-suite and emerging technology founders, she has helped develop new market categories and partnered with early leaders in AI since 2010.
As a social scientist, Alison’s work is grounded in human behavior, organizational dynamics, and the challenge of translating innovation into performance. Her most recent bestseller, How to Think with AI, grew from a year of research studying hundreds of AI early adopters and turns those insights into a framework for helping people use AI as a cognitive advantage. Her work has appeared in Harvard Business Review and Forbes, and her executive education course has reached more than 100,000 learners.
Stay Connected
Alison McCauley
Website: https://www.alisonmccauley.io/
LinkedIn: https://www.linkedin.com/in/unblocked/
Jason Averbook
LinkedIn: https://www.linkedin.com/in/jasonaverbook/
X: https://x.com/jasonaverbook
Substack: https://jasonaverbook.substack.com/
Now to Next
Website: https://nowtonext.ai/
Podcast: https://podcast.nowtonext.ai/episodes
LinkedIn: https://www.linkedin.com/company/now-to-next-ai/
Instagram: https://www.instagram.com/nowtonext.ai/
YouTube: https://www.youtube.com/@nowtonextai
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Music licensed through Soundstripe.
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