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.

Job descriptions are supposed to clarify what a company needs. But what if they’re just educated guesses? In this episode, Josh looks at how AI is quietly breaking one of the most fundamental parts of hiring: defining the role itself. Drawing on stories from job seekers and hiring managers, he explores why candidates are getting rejected for jobs they already had interviews scheduled for, how roles are being rewritten mid-process, and why companies often don’t actually know what they’re looking for. AI may be speeding up job descriptions and postings, but it’s also removing the friction that once forced better thinking. The result is a system where confusion gets scaled, candidates absorb the cost, and hiring becomes a loop of trial and error—without anyone admitting that the job was never clearly defined in the first place.

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. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.

AI is supposed to help people get jobs. But what if it’s making it harder to tell who’s real? In this episode, Josh looks at how AI is creeping beyond résumés and into interviews—and even the work itself. Drawing on stories of impersonated candidates, AI-assisted cheating in technical interviews, and coordinated efforts to land remote jobs at scale, he explores how trust is breaking down across the hiring process. As companies respond with surveillance, in-person interviews, and increasingly strange screening tactics, the system starts to feel like an arms race with no clear winner. AI may be improving access and efficiency, but it’s also eroding the one thing hiring depends on most: knowing who you’re actually hiring.

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. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.