AI-Forward Insights for the Modern Chief of Staff

THIS WEEK’S BRIEF

Something shifted this week in the responsible AI conversation. Anthropic announced Project Glasswing, a coalition of major tech companies centered on an AI model capable of autonomously identifying software vulnerabilities that have survived decades of human review. The governance community is paying attention. Your executives will start asking questions you need to be ready for.

The timing felt right to share something I have been building for a while. Skip to the resource section to get your copy of the AI Use Policy (The AI Empowered CoS Version)

THE USE CASE

Most Chiefs of Staff I talk to are using AI every week for executive-facing work. Drafting communications. Synthesizing briefs. Prepping their principal for hard conversations. And almost none of them have a written answer to this question:

What are your rules for how AI is used in work that carries your name?

Not a policy. Not a framework. Just a sentence.

The absence of that sentence is not laziness. It is the natural result of adopting a tool faster than the governance conversation catches up. Only 28% of organizations have a formal AI policy in place (ISACA, 2025). The other 72% are operating on instinct, which works until it doesn't.

The moment it stops working often looks like this: a wrong number in a stakeholder update. An off-tone email that reaches your board. A hallucinated claim that no one caught because the output looked so clean and confident that the checkpoint got skipped.

I built a one-page checklist to close that gap. Three questions. Fifteen minutes. No jargon. It is free and available here. I’ve made this resource available for free and paid subscribers.

Here for Free Content?

If you are not yet a member, this is a good week to join. Please consider becoming a member at thecossignal.com to make sure you don’t miss anything!

The founding membership is open. $14.99/month or $99.99/year (locked in for life). limited spots to get in early and help shape what an AI Empowered CoS is, including early access to new resources, features, and products. 

Please visit me on LinkedIn at https://www.linkedin.com/company/ai-empowered-cos for continued free content.

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