From global campaigns and TEDx Singapore to rebuilding life in Southeast Asia at 50+, Christopher Smith has spent three decades mastering the skill machines can’t replace: asking better questions.

In Episode 52 of The Generalists, Christopher joins Michael and Raz to unpack the real advantage humans have in the age of AI — lived experience, cultural intelligence, curiosity, and the willingness to interrogate assumptions. He shares the story of arriving in Singapore “with a chip on his shoulder” and how being publicly called out in a StarHub meeting reshaped his leadership forever.

Christopher reveals why AI isn’t a threat, but a multiplier — if you know how to use it. From launching Rock Paper Scissors, a fully AI-augmented creative studio, to publishing his book Question Is to Answer, he shows how reinvention becomes possible at any age once you realize better questions = better outcomes.

This is a conversation about humility, creativity, and how to future-proof yourself — no matter what technology does next.

📖 What You’ll Learn in This Episode

• The #1 human skill AI can’t replicate: questioning & critical thinking
• How getting humbled in Singapore unlocked cross-cultural leadership
• Why “Asia isn’t one market” and how to actually work here successfully
• How generative AI expands creative depth and pattern recognition
• The danger of binary questions — and how to ask expansive ones instead
  • Why experience becomes a competitive advantage in the AI era
  • The mindset behind lifelong reinvention — especially after 50

👥 Hosts

• Michael Smith Jr.: https://www.linkedin.com/in/smittysgp
• Raz Kotler: https://www.linkedin.com/in/razko282/

👤 Guest

• Christopher Smith: https://www.linkedin.com/in/christophersmithsg/

🔗 Resources & Links Mentioned🚀 Companies & Projects

• Rock Paper Scissors: https://rockpaperscissors.sg

• 50 Over 50 Campaign (Singapore): https://www.a50over50.com

📚 Books & Ideas

• To Question Is to Answer by Christopher Smith: https://www.amazon.sg/Question-Answer-Think-Critically-Thrive/dp/B0DZ2YM6K1/
• Idea Flow by Jeremy Utley & Perry Klebahn: https://www.amazon.com/Idea-Flow-Creative-Businesses-Win/dp/0593239613
• The Algebra of Happiness by Scott Galloway: https://www.amazon.com/Algebra-Happiness-Equations-Meaning-Life/dp/0593084195

🧠 Concepts & Frameworks

• Cross-Cultural Intelligence & Listening Before Designing – Harvard Business Review: https://hbr.org/2015/09/what-is-cultural-intelligence
• The Humility Framework for Global Leaders – INSEAD Knowledge: https://knowledge.insead.edu/leadership-organisations/why-humility-works-for-leaders
• Creative Empathy in the AI Age – MIT Sloan Management Review: https://sloanreview.mit.edu/article/human-creativity-in-the-age-of-ai/