Recent Episodes

78: AI is Expensive, Teaming is Free (ft. Clay Parker Jones)

Organization designer Clay Parker Jones, author of Hidden Patterns: A Playbook for More Human Workplaces, joins Peter and Jesse to argue that teams should index on trust rather than role clarity. The conversation covers why roles persist, the difference between…

76: Embrace the Chaos—Design Operations in the age of AI (ft. Z)

Peter and Jesse are joined by Chengying “Z” Zheng, who shares her experience migrating a design team to be AI-first — off Figma and into code. She discusses how design leadership and operations divide the work, what happens to roles…

75: The Steady State of Unsteadiness

Peter and Jesse compare notes from Config, Figma’s AI study, Lenny’s newsletter survey, and countless conversations to read the current state of design leadership. The signals: existential AI panic has cooled into exhaustion, organizational chaos and leadership churn are the…

LIMINAL—4: You As A Service (ft. Dave Gray)

Dave Gray, author of Liminal Thinking and founder of School of the Possible, joins Peter and Jesse to examine what’s actually getting in leaders’ way right now: not the disruption itself, but the expertise that blinds them to it. The…

73: Charting an Adaptive Path toward AI Transformation

Peter and Jesse compare notes from their respective listening tours and client work on how AI is reshaping design teams. The conversation moves through the operational chaos of proliferating tools, the urgent need to articulate a value proposition, why design…

72: The Worst Technology Rollout in History (Ft. Paul Ford)

Journalist, technologist, and Aboard co-founder Paul Ford joins Peter and Jesse with the perspective of someone running a services firm in the middle of being remade by AI. The conversation covers the collapsing cost of software, blurring roles, what machines…

71: Finding Our Way Live! (ft John Gleason)

Design consultant John Gleason returns to explore the leadership skills design needs to claim greater strategic influence. The conversation covers vulnerability and psychological safety, translating design value into business outcomes, the boldness required to assert a larger value proposition, and…

LIMINAL—3: The Waves within Waves

Jesse’s surfing metaphor opens a conversation about discernment and collective action in the liminal moment. Peter and Jesse explore why not every wave is yours to catch, how to find fellow travelers across functions and beyond your organization, and why…