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

Design leader Emily Campbell joins Peter and Jesse to share the pragmatic details of her experience as a VP of Design for an organization embracing AI as a medium, material, and means of development.

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 psychological and structural safety, organizational rule of law, and why demonstrating better teams beats trying to convince skeptics.

Dr. Stefanie Hutka, design researcher, Berkeley educator, and author of What Your Machines Should Do, joins us to look to the history of industrial automation for lessons on AI transformation. From Toyota's jidoka and the andon cord to Taylorism's lingering grip, we explore why AI amplifies whatever conditions it finds, and why strategy and values must come before the tools.

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 and titles when everyone becomes a builder, and how to make good design easier than bad design. Z on LinkedIn: https://www.linkedin.com/in/changyingz/ Z's Substack: https://changying.substack.com/ Jesse James Garrett: https://jessejamesgarrett.com/ Peter Merholz: https://petermerholz.com/

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 new normal, and design still stumbles on business acumen. Their case for thriving—lead, don't just design, and reclaim design's unfinished mandate.

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 conversation moves from beginner's mind to the compression of corporate work, landing on a provocative question — what does your value look like when you define it yourself?

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 operations got cut right before they were needed most, and the window of expertise power that won't stay open.

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 do well and badly, what design's value proposition becomes, and Paul's practical advice for staying upright through indefinite change.

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 how to avoid burnout while navigating organizational complexity.

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 sustainable pace — not anxious intensity — is what keeps leaders navigating when uncertainty has no end date.