Worklife with Molly Graham Worklife with Molly Graham

Can AI make you a better manager? with Hilary Gridley

Aug 11, 2026 · 46m

Summary

Molly Graham interviews Hilary Gridley about using AI to enhance, not replace, human-centric management. They discuss how AI can automate menial tasks, allowing leaders to focus on judgment, taste, and relational work. Gridley shares practical examples, like creating custom GPTs for communication coaching, while warning against "slop" from lazy prompting. The episode emphasizes that AI amplifies existing skills, requiring managers to clarify standards and teach teams to use tools thoughtfully.

Topics discussed

Sponsors: LinkedIn, Kohler, and Range Rover Introduction: AI as an amplifier for human judgment Guest Intro: Hilary Gridley's background in wilderness instruction The Manager's Role: Context, truth, and team alignment AI in Management: From skepticism to building useful tools Sponsors: Upwork, AT&T, and Whatnot Case Study: Building a custom GPT for executive communication AI Pitfalls: Why synthesis and formatting shouldn't be automated Defining Quality: Using AI to articulate taste and judgment Sponsors: Apple Card, Panoxal, and Rula Adoption Strategies: Combating lazy AI use and holding standards Conclusion: The value of explicit context and final sponsors
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