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.

Information architect and consultant Jorge Arango returns five years later with a pointed question at the center of his practice: when AI can handle the surface work, what is design actually for? The conversation explores first principles, the conditions for skillful AI adoption, and why going faster without clarity just accelerates you in the wrong direction.

When the ground is shifting and the destination isn't clear, how do you lead? Peter and Jesse explore the mindset and skills required to navigate the liminal moment—when old ways have dissolved but new ones haven't taken shape. From core mindsets of maintaining situational awareness and striving for balance, to core skills around communication, persuasion and connection to build lifelines, this is a conversation about what it actually takes to lead through uncertainty.

When the old ways no longer hold and the new hasn't taken shape, you're in a liminal moment. Peter and Jesse explore what it means to lead through that in-between space—navigating uncertainty without retreating to the past, letting go of what defined you, and finding opportunity in the chaos rather than being consumed by it.

Stanford professor Christina Wodtke joins Peter and Jesse in exploring the real contradictions of AI in design and product work: revolutionary prototyping speed versus the need for critical thinking, efficiency gains versus cognitive loss, and loving the technology while hating the exploitative companies building it. She shares exactly what designers and PMs must vigilantly protect.