In this episode, I sit down with David C. Banks, former Chancellor of New York City Public Schools, to unpack what it really takes to lead a large, complex organization. Drawing on his experience leading New York City Public Schools, we explore decision-making under pressure, managing competing priorities, and building culture at scale. This is a candid conversation about leadership when the stakes are high, the spotlight is constant, and every move matters.

In this episode, I sit down with Andy Rotherham, co-founder and senior partner at Bellwether and the longtime voice behind Eduwonk, for a conversation about the uncertainty surrounding artificial intelligence and its potential impact on education. Drawing on a recent essay, Andy compares the current moment with AI to the early days of the COVID-19 pandemic when signals of major disruption were emerging, but institutions had not yet fully grasped what was coming. We discuss what leaders in education should be watching for, how to separate meaningful developments from hype, and what lessons from the pandemic might help schools and universities navigate the rapidly evolving AI landscape.

In this episode, I sit down with cybersecurity expert Suresh Sankaran Srinivasan to unpack what today’s organizational leaders need to understand about digital risk. We explore the different levels of the internet (what exists on the surface web, the deep web, and the dark web) and how those layers shape real-world threats. We discuss who should be concerned about cybersecurity breaches, why no organization is too small to be targeted, and the practical steps leaders must take to strengthen oversight, culture, and resilience in an increasingly connected world.