I’ve been spending a lot of time with Claude lately. Not because I want to but because AI agents are not a mindless effort if you want them to work correctly. Recently, I was at a networking event with other Fractional CFOs, and one of my friends there was explaining Claude to a newbie: “You just need to talk to it like an employee,” was the refrain. In another conversation I had over email with a CFO, he told me he automated a lot of his closing process using Claude Code by spending “4 to 5 hours a day for the last 30 days. Notwithstanding the fact that it sounds like his closing process was a mess to begin with, 4 to 5 hours a day for 30 days is quite a commitment and you would likely never do that with a human trainee.

The Management Paradox of AI Training

So what’s my point. On one end you have a CFO who said: talk to it like an employee. On the other end, a CFO who spent 150 hours to get a complex process to work. I’ve done work with Claude Chat, Claude Cowork, and Claude Code and can tell you the reality is somewhere in between. But what I want to focus on is this: if you lacked management patience for training and process improvement before all these AI innovations, you are in for a struggle. On the other hand, if you go through the struggle, it could make you a better manager.

TL;DR:

Training an AI agent exposes every gap in your own thinking that you’ve been papering over with informal communication and institutional memory. The operators who push through that frustration tend to come out the other side as clearer thinkers and better managers. The ones who walk away were probably avoiding that reckoning anyway.

Use Case Highlight: Three Tools, Three Different Commitments

Before I get into the management angle, it’s worth briefly grounding what each of these Claude tools actually is, because they are not the same thing.

Claude Chat

Claude Chat is the conversational interface most people start with. You ask questions, draft content, analyze documents, work through problems.