Finding Our Way

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.