AI Can Make Work More Visible Without Making Leaders Better

I keep thinking about the phrase “measuring and mentoring.”

Cloudflare’s CEO recently explained cutting middle managers by saying AI allows managers to have more direct reports while still measuring and mentoring teams effectively.

I understand the measuring part. AI can give leaders more visibility than they’ve ever had. That part makes sense.

The mentoring part is where I get curious. Because measuring and mentoring are two wildly different functions. Measuring tells you what happened. Mentoring helps someone understand what happened, what it means, and how to potentially think or act differently next time.

Maybe Cloudflare has a strong internal plan for this. I don't know their system and I’m not pretending to. But their approach raises a critical question for any organization looking to replace management layers with AI:

Are you actually making your leadership team more impactful? Or are you just making the work easier to monitor? Those are very different outcomes.