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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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🎙️ What if AI could help you lead with more clarity, empathy, and impact—not less?
In this forward-thinking episode of The Kind Leader Podcast, host Gino Degregori interviews Jonathan Mast, founder of White Beard Strategies and virtual Chief AI Officer, to explore how leaders can embrace AI as a servant leadership tool—not a threat to humanity. After discovering the power of AI in his mid-50s and speaking at over 150 events, Jonathan now helps leaders use AI to reduce stress, communicate with greater precision, and enhance team morale—all while staying deeply human.
From writing difficult emails to transforming team workflows, Jonathan shares actionable strategies for using tools like Copilot and ChatGPT to amplify leadership, not replace it. This episode is a practical, encouraging guide for leaders navigating the evolving future of work with empathy, kindness, and courage.
🔑 Key takeaways include:
The “Ask Me Questions” hack: A simple prompt tweak that leads to smarter, more context-aware AI responses
Use AI as an emotional buffer: Craft thoughtful, calm replies to tough messages—faster and more effectively
Adopt AI pragmatically: Start with what your team already has access to instead of waiting for the “perfect” tool
Eliminate team drudgery: Free your team from repetitive tasks so they can focus on meaningful, fulfilling work
Train AI in your culture: Teach AI how your organization communicates to protect brand voice and values
🎧 Listen now and discover how to lead in the age of AI—without losing what makes us human.
Important Links and Resources
🌐 Jonathan Mast's Website: JonathanMast.com
📚 Complete Resource Hub: JonathanMast.com/Linktree
🏢 White Beard Strategies: WhiteBeardStrategies.com
📖 Recommended Book: Start With Why by Simon Sinek – A powerful reminder to lead with purpose.
🌟 Kind Leadership Challenge
Think of one repetitive workflow or task that consistently slows your team down. This week, experiment with using Copilot, or any AI tool you prefer, to streamline or automate that process.
What changed? How did it impact your team’s focus, energy, or results?
Share your experience using #KindLeaderChallenge and tag @GinoDegregori and @JonathanMast to join the conversation and inspire other leaders to lead smarter and kinder with AI.
📌 Chapters00:00 Introduction: Why AI Matters for Today’s Leaders 03:04 How AI Can Strengthen Leadership and Communication 06:04 Balancing AI Integration with Human Connection 08:58 Exploring the Curve of AI Adoption 11:53 A Practical Approach to Using Available AI Tools 14:47 How Training and Context Shape AI Effectiveness 17:59 Using AI to Support Emotionally Intelligent Leadership 20:55 Everyday Examples of AI in Action 21:44 How AI Is Reshaping Learning and Development 24:00 Aligning AI with Organizational Culture 28:32 Ethical Considerations for Responsible AI Use 31:44 Real Stories: How Nonprofits Are Benefiting from AI 35:14 Applying AI to Improve Team Workflows 38:11 Quickfire Leadership Insights with Jonathan Mast
50 episodes
