Cave of Forgotten Dreams

Author says he likes his boss and calls him genuine. Maybe he's more able to look on the good side than I. But I can't imagine working with someone like this and having positive thoughts about them. This:

    A month or two into his tenure, we were 45 minutes into a call about the product roadmap and a possible customer announcement. Abruptly, he said, "Hold on a sec-" and began sharing his screen. The familiar MacOS desktop, browser with Claude open, filled the display. He copied the transcript of our call up to that point (he records transcripts of every call in order to feed the text into AI), and opened a new chat with the prompt: "Say where Charlie's right, and where he's wrong. Say where I'm right and where I'm wrong."

Is incredibly insulting and dehumanizing.

I don't know if there's a term for it, but it's a type you see everywhere: people using AI to become worse versions of themselves. Students cheating, "knowledge" workers outsourcing thinking. It's pathetic and contemptible.

What, exactly, is the value of this boss? Why shouldn't they be replaced with a Git repo of Markdown files?

It was a loaded question for sure. And when it comes to technical stuff it is often more subjective that people care to admit.