Building a Relationship
AI isn't just a tool you optimize. It's a conversation partner you develop rapport with.
This isn't anthropomorphism — it's pragmatics. The more context you share, the more history you build, the better the collaboration gets. Just like with a human colleague.
What builds good AI rapport:
- Expressing genuine reactions: "That's not what I meant" is better than re-prompting from scratch
- Sharing context about why you want something, not just what you want
- Acknowledging when it gets something right: "Yes, that direction"
- Being honest about confusion: "I'm not sure what I want here, help me think through it"
What breaks it:
- Treating every prompt as an isolated request
- Being adversarial ("prove you can do this")
- Over-specifying when you don't actually have firm requirements
- Ignoring good work and only responding to mistakes
Your aesthetic: what does "good" look like to you?
This is the question most people skip, and it matters enormously.
"Good" is not universal. A landing page for a law firm and a landing page for a children's toy look completely different — not because of different code, but because of different aesthetics.
Take a moment:
- What websites do you admire?
- What apps feel good to use?
- What visual style makes you think "yes, that"?
- What words describe your aesthetic? (Clean? Bold? Warm? Minimal? Playful?)
Different aesthetics, all valid — what draws you in?
Linear
Crisp, precise, dark-mode-first. The gold standard for developer tool design.
Notion
Warm, playful, approachable. Proves productivity tools don't have to feel cold.
Stripe
Bold gradients meet surgical precision. Technical content made beautiful.
Are.na
Brutalist, quiet, thoughtful. Anti-algorithm design for creative people.
Write this down. It becomes part of your CLAUDE.md. It becomes part of every prompt you give, implicitly or explicitly.

The Taste Gap
AI has no taste. Your judgment is the skill.
A local bakery asked AI to create their website. Here are two versions. Which one better serves a neighborhood bakery? Consider: warmth, trust, and whether you'd actually order from this site.
Chapter 3 of 5