The Sign You Didn’t See
Josh Woosley Josh Woosley

The Sign You Didn’t See

A product manager, a CFO, and a skeptic hear the word "agile." None of them are talking about the same thing. None of them know it.

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Words are Vague
Josh Woosley Josh Woosley

Words are Vague

Want proof that context is everything? Watch someone say "let him cook" about a person dominating a debate. Now watch someone else say "he's cooked" about the same person losing the next one.

Elon Musk is gaming with his brother. He gets wrecked. "I'm cooked!" he yells.

Meanwhile, somewhere on X, a fan watches Elon dismantle a competitor's argument and posts: "Let him cook."

Same root word. Opposite meanings. Cooking means dominating, winning, being on fire. Cooked means toast, burnt, washed up, destroyed. It's only a tiny 4-letter word, but everything rides on context.

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Schrodinger's I-Pad
Josh Woosley Josh Woosley

Schrodinger's I-Pad

The gap between probabilistic output and deterministic expectation is where business risk lives. So the engineering problem isn't "add more constraints." It's "where does this tool fit?" When you ask an LLM to validate data, approve a workflow, or check a compliance flag, you're asking a dice roll to behave like a Newton's cradle. It's a bold move, one that will inevitably fail.

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From Knowing to Doing
Josh Woosley Josh Woosley

From Knowing to Doing

You can't successfully automate the unknown. And you definitely can't hand it to an AI agent that doesn't understand the process it's supposed to execute.

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Tacit knowledge capture
Josh Woosley Josh Woosley

Tacit knowledge capture

How do you capture your employees knowledge before it walks out the door? Writing is a secondary form of information transmission. Speaking is the one everyone is born with.

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The Tacit Knowledge Problem
Josh Woosley Josh Woosley

The Tacit Knowledge Problem

Every organization has that one performer that everyone relies on, their knowledge, skill, and intuition. But how do you capture that knowledge when they decide to leave?

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