#223 – Greg Kaiser: Mastering Management, Letting Go, and Leading in the Age of AI
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#223 – Greg Kaiser: Mastering Management, Letting Go, and Leading in the Age of AI
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Greg Kaiser has over 30 years in the corporate world—including time at Hershey—and now running his own consultancy, Greg shares lessons in management, delegation, time optimization, and how to think about AI from a leadership perspective.
Jason and Greg dive into why most managers are spending time on the wrong things, how to stop micromanaging, and why meetings and communication are often a company’s real bottleneck—not the employees. Greg also shares how he's using AI as a research and decision-making tool, and why leaders shouldn't try to master it—but should know how to hire people who do.
We dive into:
🧠 The mindset shift from corporate exec to independent consultant
📊 How to delegate better and stop being the bottleneck
⏱️ Why time—not money—is your most valuable resource
👥 The problem with meetings and how to fix communication instead
🤖 How Greg is using AI in his consulting business today
Whether you're an executive, founder, or team lead, this episode is a crash course in managing smarter and leading more effectively.
⏱️ Timestamps:
[02:20] – Greg’s new venture: Management Mastery
[04:50] – Greg’s corporate journey from mailroom to managing global ops at Hershey
[09:20] – Why he left corporate after being told “you’ll never be COO”
[12:55] – First client story: how Greg launched into consulting
[15:15] – Why business owners need to stop doing everything themselves
[17:30] – The cost of micromanagement and poor delegation
[20:50] – How to help leaders identify time waste with “Know Thy Time”
[23:10] – 80/20 rule and Return on Invested Time
[25:15] – How to structure effective meetings in 2025
[28:50] – What remote work changed about team communication
[31:30] – The myth of multitasking & how to fix your focus
[34:10] – How Greg uses AI for research and decision support
[39:00] – Why AI works best when humans know how to prompt it
[41:20] – Where to find Greg online and learn more about his work
🔗 Connect & Support:
🌐 Website: https://jayhunt.social
📺 YouTube: https://www.youtube.com/@jayhuntofficial
Sponsor: https://chatello.ai