Communication Style with AI

Dave Jimison shares the idea of asking your LLM how you communicate with the prompt:

Review the way I’ve communicated with you across our past conversations and give me an honest, direct assessment of my communication style with AI. Tell me how I express dissatisfaction, how I tend to work through conflict or disappointment, how I give positive feedback, and what strengths, blind spots, or recurring patterns you notice in how I collaborate with AI.

I got a lengthy analysis from Claude Code. Here are some highlights:

How you express dissatisfaction

Blunt, factual, and almost never emotional. Across 1,345 messages there is no profanity, no sarcasm, and the strongest emotion on record is “ugh.” Your dissatisfaction has a consistent anatomy: name the mismatch, then supply the missing fact or the intended mental model.

I’m pretty sure I’ve written fewer than a handful of profane words to AI before. It certainly wasn’t when using Claude Code. It’s usually in response to something that was surprising. It doesn’t make sense to me to use profanity or sarcasm with an LLM. Doing so feels like anthropomorphising the agent.

The overall shape: you run AI like a staff engineer runs a team — high-trust delegation inside an explicitly constrained envelope, mandatory personal review at the reputational boundary, adversarial review as a habit, and a deliberate teach-the-agent loop that turns every correction into a durable rule. The through-line of both your strengths and your blind spots is the same trait: you optimize for keystroke economy and trust the machine to hold state. When the state-holding works, you’re an unusually effective collaborator; when it doesn’t, that’s where every cycle you lose comes from.

Interesting learnings, and nothing surprising for me here. I think I’m pretty deliberate in thinking like an engineer when using AI agents. I understand the harness is keeping memory, and I use it to make sure I’m not repeating myself (too often). But I can see that I can sometimes lean too much on the agent’s memory and state, so it’s important for me to know (or more likely intuit and feel) the limits of the agent.