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In this episode of Generate Now!, host James Caton sits down with Jason Baumgarten, a senior partner at the leadership advisory firm Spencer Stewart. As a consultant who works directly with C-suite executives, CEOs, and board members, Jason provides a unique perspective on how the world's top leaders are—and aren't—adapting to the AI revolution.
The conversation explores his three-phase roadmap for leaders to move from AI novices to visionary evangelists. Jason explains why the biggest hurdles to AI adoption aren't technical, but cultural, and why every leader must personally get on the keyboard to understand the future of their business.
The AI Adoption Gap: Why many executives are still using AI as a basic search engine rather than a transformative productivity tool.
The "Steno Pad" Parallel: Comparing today's AI hesitancy to the 1980s transition when some executives resisted using PCs.
Red Teaming Your Leadership: Using AI agents to create "digital twins" of a board of directors to predict questions and refine strategy.
Data Swamps vs. Strategic Data: How to identify the "fumes" of your business—the unique data assets that actually create a competitive moat.
Culture Over Code: Why AI initiatives fail when rigid corporate cultures penalize the "trial and error" required for learning.
Start with low-stakes, high-impact tasks to become familiar with the technology:
Evaluate Communications: Use AI to audit the tone and receptivity of your emails from various stakeholder perspectives.
Audit Time Allocation: Analyze your calendar data to see if your schedule actually aligns with your strategic priorities.
Automate a Workflow: Move beyond simple prompting to automating a daily task, such as competitive landscape monitoring.
Move beyond the surface to understand the "how" and "why" of the technology:
Find an AI Mentor: Partner with someone—even a junior employee or "AI native"—who uses these tools to transform their daily work.
Master the Core Areas: Gain literacy in machine learning, model architecture, data engineering, and responsible AI governance.
Transition from personal use to organizational leadership:
Set the Ambition: Determine if your goal is 5% efficiency in customer service or a 50% shift in work product generated by agents.
Manage the Change: Foster a "typing class" mentality where employees are given the time and safety to learn without penalty.
"If you put the lawyers in the room first to talk about governance, you're probably not going to get to a good end state view of what this can do because you'll spend all the time talking about what it shouldn't do." — Jason Baumgarten
"This is not about delegating it to a team. This is about your personal journey of learning where the future is headed... get on the keyboard." — Jason Baumgarten
Jason Baumgarten is a leader at Spencer Stewart, specializing in CEO and board advisory services for companies ranging from high-growth startups to the Fortune 10. He is a leading voice on how AI is redefining the "what" and "how" of modern leadership.
Unlock the C-suite AI roadmap with Spencer Stewart’s Jason Baumgarten. Learn how CEOs use "digital twins" and personal sandboxes to lead the AI revolution.
