First Factory COO Talks AI and Human Judgment on System Override

Don Gregori, COO of First Factory, joins System Override by Leeg to talk about AI, human judgment, upskilling and leading through rapid change.

October 12, 2026
First Factory COO Don Gregori on System Override

Table of contents

Judgement Surge

Don Gregori, COO of First Factory, joined System Override by Leeg for a conversation about leading through fast technological change, and why human judgment matters more, not less, as AI takes on a bigger share of the work.

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The episode looks at how AI is changing workforce roles, decision-making and organizational culture, and what upskilling looks like when the tools change every few months. The conversation also covers new education models such as unaccredited academies, the systemic barriers that stall career progression, and why the human skills behind good leadership outlast any single technical skill. Those ideas run through Don's book, The Emergent Leader.

Judgment is also how First Factory puts AI to work. Our engineers build with Claude every day on real client codebases, and First Factory is a Select partner in Anthropic's Claude Partner Network.

Don Gregori is the Chief Operating Officer of First Factory, a multinational software solutions provider based in New York with nearshore operations in Costa Rica. A certified AI Business Leader, Don brings over 25 years of experience helping businesses from startups to Fortune 500 companies navigate product development, digital transformation, and AI adoption. He is a contributing author to The AI Journal and the author of The Emergent Leader, releasing June 16, 2026.