Amazing Work!

Productivity to What End? Dan Riley on Building AI That Puts Humans First

What if the entire conversation about AI productivity is asking the wrong question? Dan Riley has been building technology at the intersection of people and work for over a decade — first as a pioneer in continuous employee listening, and now as co-founder of RADICL Work, an AI platform designed to help teams understand each other deeply and do extraordinary things together. He is also a musician, a filmmaker, and someone who thinks about creativity the way most people think about strategy. In this conversation — the one that inspired Amazing Work! to exist — Dan and I go deep on the questions that don't get enough airtime. What does it actually mean to be productive? What happens when we let AI move faster than our ability to understand what we just did? And what does it cost us, as individuals and as organizations, when we optimize for speed at the expense of connection? This isn't an anti-AI conversation. Dan is building AI. I'm implementing it. We both believe in it. But we also believe the current narrative — replace headcount, maximize output, move fast — is leaving something essential behind. If you've ever felt the quiet anxiety of not knowing where you stand in all of this, this episode is for you. In this episode: — Why productivity is an outcome, not a goal, and what you actually need to get there — The hidden cost of eliminating junior roles without reskilling pathways — How RADICL is building AI that knows you as a person, not just a skill set — What Dan calls "human in the loop" and why he thinks it's non-negotiable — The moment I realized I was getting addicted to instant answers, and what it made me question — Why work will find a way — and what it needs from us to get there Amazing Work! Because there's a human way through this. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit amazingwork.substack.com [https://amazingwork.substack.com?utm_medium=podcast&utm_campaign=CTA_1]