AI Manager Skill #1: Coach Your People Better With AI (Substack Preview)

Most leaders are using AI to go faster. This skill is about going deeper.

Coach Your People With Better AI is the first entry in The Sh*t List, the paid Substack companion to The Job Market Sh*t Show. It starts with a simple question: what if, before your next difficult one-on-one, you spent 15 minutes with an AI tool working through everything you actually know about that person?

This one's built around a conversation with Kathrin Fleer, who spent 12 years leading luxury retail teams for Saint Laurent and Tiffany & Co across Europe. What she said about the ceiling every manager eventually hits — and where AI fits in — stuck with Josh.

The full piece includes four specific prompts and a framework you can use before your next one-on-one. If you're not on The Sh*t List yet, this is a good week to start.

About The Job Market Sh*t Show

The Job Market Sh*t Show: How AI Broke Hiring and What Might Be Next is an investigation into how hiring actually works now, how AI and automation have upended the process, and why the old rules no longer apply. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.