E068: Wicked Problems – Design Thinking, Expertise and the Human Element in Modern Strategy

Jess Roberts, affiliate faculty at the University of Minnesota School of Public Health and the Minnesota Design Center, is a master at navigating complexity. With a background spanning design thinking, public health and systems change, Jess dives into the world of “wicked problems” – the messy, stubborn challenges that resist quick fixes. In this episode, he explores why traditional approaches fall short, and reveals how design-based thinking can unlock fresh solutions in business, health and even AI.

In this episode, we explore:

(00:58) Differences between wicked and traditional problems

(04:47) Unlocking creativity through childlike curiosity

(08:20) Framing problem-solving approaches

(14:33) Navigating expertise and experience

(16:41) Targeting Gen Z with agile strategies

(20:49) How AI disrupts career progression

(23:04) Reframing AI for better outcomes

(27:45) Human-centered design in systems

(30:12) Balancing professional and personal health

(34:19) Design thinking: desirability vs viability

(36:29) Map vs territory in design

(40:40) Designing communication for togetherness

(45:09) Rethinking problem-solving strategies

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