In this episode of The AI Chicks, Lana Hout and Aisha Corpas Wynn sit down with Will Cady, founder of Heal Movement and former Reddit executive known as the “Shaman of Reddit,” to explore the future of leadership, culture, and human connection in an AI-powered world.

Will shares why the most effective leaders of the future won't simply know how to use AI—they'll understand how to create meaning, foster trust, and build alignment during times of rapid change. Together, they discuss the evolving relationship between humans and machines, the growing importance of storytelling and the humanities, and why emotional intelligence may become one of the most valuable leadership skills in the AI era.

The conversation also tackles the difficult questions organizations are facing around bias, ethics, moral responsibility, company culture, and decision-making as AI becomes increasingly integrated into everyday work. From leading through uncertainty to treating AI as a collaborator rather than just a tool, Will offers a thoughtful roadmap for leaders navigating one of the most significant technological shifts in history.

Whether you're an executive, entrepreneur, manager, or emerging leader, this episode provides valuable insight into how to lead with clarity, purpose, and humanity in the age of artificial intelligence.

00:00 Importance of the humanities

04:18 Moving to LA and joining Reddit

06:56 Aligning with Online Communities

10:42 Understanding cultural language in leadership

15:50 AI-driven business growth

17:25 Balancing creativity and routine tasks

22:37 The importance of emotional intelligence

24:28 Challenges with AI in the workplace

27:18 AI fluency for business leaders

32:58 Understanding Department Communication

36:15 Building and Sharing Context

39:10 Discussing the value of humanities

40:53 Technology reflecting human complexity

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