The AI-Driven Leader

Geoff Woods
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6 snips
Oct 28, 2025 • 4min

14. Season One Finale — From Curiosity to Courage

This finale highlights the transformation of six leaders from curiosity to action in the AI landscape. Discover how AI became their thought partner, revealing solutions at lightning speed. The discussion emphasizes that anyone can lead in this new era by asking better questions and thinking differently. Additionally, there's a focus on personal and organizational growth, as well as the practical tools available for leaders to drive enterprise value. The journey to becoming an AI-driven leader is just beginning, and the future is now!
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10 snips
Oct 23, 2025 • 36min

13. CRIT™: Harnessing Abraham Lincoln to Write Your AI Manifesto

Geoff Gilmore, President and CEO of Worthington Steel, discusses a transformative journey into AI adoption. He reveals how AI served as a strategic advisor, shaping clear listening systems and innovative structures like a startup studio. A surprising influence comes from Abraham Lincoln, who inspires Geoff to craft a human constitution for AI, emphasizing that technology should elevate human potential, not replace it. This enlightening interaction produced actionable insights in minutes, showcasing the remarkable efficiency of AI in driving change.
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6 snips
Oct 21, 2025 • 45min

12. Shifting the Mindset of an Enterprise Workforce with Geoff Gilmore

Geoff Gilmore, President and CEO of Worthington Steel, shares his transformative journey from AI skeptic to advocate. After being introduced to pivotal texts, he led a sweeping AI adoption across 6,000 employees, mandating its use in daily operations. He emphasizes hands-on training and open vulnerability as key to fostering acceptance among staff. Highlights include rapid pilots for predictive inventory and machine reliability, all while maintaining a focus on work-life balance. Geoff encourages leaders to embrace AI early and learn alongside their teams.
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Oct 16, 2025 • 38min

11. CRIT™: How to Reinvent Your Business Model with AI

In this enlightening session, Amy Ansira, a senior talent strategist, and Velvet Schmidt, a human-centered facilitation expert, explore the transformative power of AI in strategic talent planning. They unpack how AI can revolutionize the conventional business model by enabling real-time planning and continuous updates. The duo emphasizes that while AI can automate mundane tasks, the essential human elements of trust and emotional support must remain intact. Their vision for the future? An AI-augmented copilot that enhances strategy while preserving the human touch in facilitation.
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23 snips
Oct 14, 2025 • 46min

10. Building an AI-Driven Culture at HireBetter with Velveth Schmitz & Amy Ancira

In this engaging discussion, Velveth Schmitz, CEO of HireBetter, and Amy Ancira, Chief Experience Officer, delve into their transformative journey of embedding AI into their organizational culture. They share how AI tools have revolutionized workflow, collapsing hours of work into minutes, and promoting human connection. Hear how they overcame skepticism, designed personalized training, and created an AI policy collaboratively. Their insights on redefining roles and harnessing AI to enhance creativity reveal a future where technology empowers rather than replaces.
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28 snips
Oct 9, 2025 • 27min

9. CRIT™: Building Your Leadership Playbook for Growth

In this insightful discussion, Brian Lang, CEO of UpsideCFO, shares his expertise in financial strategy for SMBs. He explores the challenges of scaling leadership and reveals how AI can be leveraged to create a robust leadership playbook. Brian discusses the Working Wealthy Operating System, emphasizing its role in aligning goals and providing clarity through metrics. Key tactics include integrating visual dashboards and strategic questions in forecasting. The conversation highlights how AI amplifies leadership capacity and transforms instinct into effective systems.
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32 snips
Oct 7, 2025 • 45min

8. Scaling Your Leadership Team Using AI with Brian Lang

Brian Lang, CEO of UpsideCFO and an expert in fractional CFO services, explores the transformative power of AI in business leadership. He shares his innovative approach of creating AI personas, like a virtual CRO that revives lost deals and a tailored business coach that delivers strategic advice. Lang reveals how he compressed an 80-hour workflow into a 4-hour playbook with an AI-driven system called the 'Clarity File.' His insights show that AI can be a significant multiplier for leadership and operational efficiency, both in business and personal life.
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51 snips
Oct 2, 2025 • 43min

7. CRIT™: Recruit Your Legendary Board with "Steve Jobs"

Rusty Cagle, founder of 100YearImpact.org, aims to transform philanthropy by helping nonprofits build endowments. His innovative approach involves using AI to recruit a legendary advisory board for long-lasting impact. Cagle's journey reveals the importance of crafting a compelling invitation and the influence of an audacious vision. In a unique twist, AI role-plays as Steve Jobs, advising Rusty to frame his initiative as a revolutionary movement rather than a mere charity. The result is a powerful legacy blueprint where board members become co-founders of change.
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67 snips
Sep 30, 2025 • 45min

6. Burn the Ships, Build an AI-Driven Company with Rusty Cagle

Rusty Cagle, CEO & Founder of ASE Private Wealth™, shares his journey of transforming his firm into an AI-driven powerhouse. He reveals how a painful past loss spurred him to declare a swift 90-day transition to AI. Cagle discusses slashing process times from hours to mere minutes with AI's help and highlights the critical mindset shift he fostered in his team. He also dives into regulatory hurdles, overcoming resistance, and using AI to secure a $10M line of credit, emphasizing that failing to adapt could erode enterprise value.
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23 snips
Sep 25, 2025 • 33min

5. CRIT™: How to Build a CEO Succession Plan

Josh Wand, founder and CEO in the CPG space, explores the emotional yet strategic challenge of CEO succession. He discusses the role of AI as a daily coach during this transition, enhancing leadership without replacing it. The conversation highlights creating structured communication and prioritization frameworks using CRIT, 30-minute weekly check-ins, and a powerful AI dashboard. Josh shares newfound possibilities revealed by AI, showcasing how it can elevate a founder’s role from merely playing instruments to conducting an entire orchestra.

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