The Boring AI Show

In this episode... Tim and Tally take on a packed week in AI, where questions about safety, governance, regulation, and rapidly advancing models are getting harder to separate from the hype. The conversation starts with a lesson carried forward from the Medicaid Enterprise Systems Conference: organizations rarely get unlimited time to prepare for new technology expectations. Whether the pressure comes from legislation, leadership, customers, or the market, the groundwork for responsible AI ad...

In this special edition... Tim is joined by Tally, Sandra Warner, and Sam Hopkins for a recap of the Medicaid Enterprise Systems Conference. After a week on the conference floor in Portland, the team brings Tim up to speed on what they heard from Medicaid leaders, federal partners, vendors, and public servants working through the next wave of Medicaid technology modernization. The conversation gives listeners a practical look at the themes shaping the Medicaid enterprise space, from data read...

In this midweek update... The Boring AI Show checks in live from MESC 2026 for a quick real-time recap from the conference floor. Tally is joined by Ken Lawrence and Sandra Warner from Mind Over Machines to share a few early themes emerging across the Medicaid technology space, from modernization and data strategy to change management, procurement, and the human side of transformation. Rather than a full conference wrap-up, this episode offers a quick pulse check on what the team is hearing, ...

In this episode... Tim and Tally explore a deceptively simple question: What work is best suited for people, and what work should be handled by AI? Rather than treating the decision as a competition between humans and machines, they consider how the two can work together—and why the right balance may look different across organizations, teams, and individual tasks. The conversation examines how culture, risk, responsibility, and the intended experience all influence where AI belongs in a proc...

In this episode... Tim and Tally sit down to tackle one of the most requested topics on The Boring AI Show: AI governance. While governance may sound like a dry policy conversation, the episode quickly turns into a practical discussion about trust, risk, responsibility, and what it really takes to bring AI into an organization without creating avoidable surprises. The episode starts with AI news stories that set up the broader theme. From AI literacy efforts in education to a brand mishap inv...