What happens when we stop asking AI to do everything faster and start asking how it might help us understand people better?

In this episode, Jeff sits down with Andy Sitison, CTO of Share More Stories, for a conversation about empathetic AI, story collection, and why trust may be the real differentiator in the next phase of technology. Andy shares how his work uses AI not just as a productivity tool, but as a way to surface patterns in human experience by gathering and analyzing stories from real people.

Together, they explore what gets lost when efficiency becomes the main goal, why intent matters so much in AI use, and what educators can learn from the way thoughtful organizations listen to communities. Andy explains how story-based analysis can reveal not only answers, but better questions, helping leaders move beyond surveys and toward a deeper understanding of what people are actually feeling and needing.

The conversation also turns to schools. Jeff and Andy discuss why educators are often well positioned to use AI well, especially when the goal is support rather than replacement. From drafting difficult parent emails to making sense of complex data sets, Andy argues that AI works best when it helps humans communicate more clearly, think more creatively, and act with more care.

There is also a clear caution running through the episode: not every use of AI is a good one. Jeff and Andy push on the difference between meaningful application and empty automation, questioning whether some so-called AI advances are really just profit-driven systems wrapped in new language. It is a useful discussion for school leaders trying to separate signal from noise.

This episode is a thoughtful listen for anyone trying to hold onto human connection while navigating rapid technological change.

In this episode, we discuss:

What Andy means by "empathetic AI"
How Share More Stories collects and analyzes human stories at scale
Why stories can reveal questions leaders did not know to ask
What gets lost when efficiency matters more than empathy
Why trust and intent matter in AI adoption
Skills educators may need to help students live well with emerging technology
Practical, human-centered uses of AI in schools
Why better questions may matter more than faster answers
The difference between useful AI and AI added for its own sake

Memorable ideas from the episode:

"Trust is the next big X factor."
AI can help humans connect better when it is applied with care.
Story collection can be therapeutic for the storyteller and revealing for the organization.
The real power of AI may be in helping us handle complexity, then validate what matters most.
Schools need more than tools. They need thoughtfulness, context, and purpose.