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

The BIG Strategy Podcast

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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