Articles

Articles on AI, coaching, product strategy, and building a business that matters.

293 posts tagged "product-work"

Everyone needs a Custom Assessment

product-workJun 4, 2026

Everyone needs a custom assessment, and when you think of your own experiences, you'll agree with me.

product-workai

Five Paradigm Shifts You Need to Embrace About AI

aiJun 1, 2026

Five paradigm shifts from three years building with AI: design time over runtime, judgment over prompts, real feedback loops, conversation, and knowledge that's built, not stored.

aiproduct-workinsights

How to Tell If Your Scoreboard Is Lying to You

aiMay 30, 2026

A pizza shop's flyer contest shows why your AI scoreboard can climb while the work gets worse - and why a measure that can't be gamed is the real job.

aiproduct-work

Ten Conversations to have with Claude before Vibe Coding

aiMay 26, 2026

One prompt gets you something. Ten conversations get you something better. Here are the ten you should have with Claude before any code gets written.

aiproduct-work

The Key Comes Before the Song

aiMay 22, 2026

When you build with AI doing the content generation, the obvious move is QA at the end. But if that's your whole strategy, you sat down at the piano without picking a key. Here's how I'm thinking about evals for a new product — and why guardrails belong upstream, not downstream.

aiproduct-work

Stop Selling a Privacy Policy

aiMay 18, 2026

When both sides have IP, current AI privacy answers force one of them to bleed. The fix isn't a better policy or a clever cryptographic trick. It's a design discipline: stop protecting what crosses the wire and start designing what's allowed to cross in the first place.

aiinsightsproduct-work

You don't have to be technical to own the architecture

aiMay 16, 2026

AI is changing everything and nothing at the same time. So where should you spend your scarce time? Three things will always matter: your domain, systems thinking, and architecture. And architecture isn't what most people think it is. It's the load-bearing decisions you care about, written down before the AI builds the wrong thing.

aiproduct-work

The 4 scans I run before I'm done with any AI-assisted project

aiMay 14, 2026

There are no magic prompts. But there are four scans I run after every first pass on AI-assisted code: race conditions, concurrency, idempotency, and dead code. Each one catches issues you'd otherwise debug months later.

aiproduct-work

Lovable, and the cardboard model problem

product-workMay 12, 2026

Most people who have ideas aren't developers, so their ideas live and die in one head. Lovable changes the cost of building a cardboard model to roughly zero. Here's what that means for the conversations you can finally have.

product-workai

The harness is the craft.

aiMay 10, 2026

Most engineers pick a model they trust, eyeball a couple of runs, and ship. I don't ship that way. Here's what eval-driven development actually looks like, and the seven principles I'd hand to anyone shipping LLM systems.

aiproduct-work

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