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AI-Forward Insights for the Modern Chief of Staff

THIS WEEK’S BRIEF

The first time AI governance landed on my desk, I went looking for a guide written for the Chief of Staff.

I found compliance frameworks. Enterprise risk documents. NIST standards. Legal checklists.

Everything I found was written for a CISO, a general counsel, or a dedicated AI ethics officer with a full team behind them.

Nothing was written for the person who gets handed this responsibility because they're the one who coordinates across functions when no function owns the answer.

So I built one.

This week's issue is different. In place of the usual prompt, I want to walk you through the framework, give you something you can use today regardless of where you are in this process, and share the full resource for founding members.

THE USE CASE

A few months ago, a CoS I know got a question from her executive that she wasn't expecting.

"What AI tools are people actually using?"

She didn't have an answer. Not because she wasn't paying attention, she was. But nobody had built the infrastructure to track it, nobody had asked employees directly, and the assumption had been that IT had a handle on it.

IT didn't.

She spent the next two weeks piecing together information from expense reports, procurement data, and hallway conversations. What she found: eleven tools in active use across the org. Two of them were feeding sensitive business context into models with no data retention policy in place. One of them, the CEO, was using daily.

None of it was malicious. All of it was invisible.

That is a governance gap. And closing it is exactly the kind of work Chiefs of Staff are built for.

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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THE FRAMEWORK

In place of the usual prompt this week, here's the framework that makes the prompt make sense. The prompt is at the end of this section and is free for everyone.

AI governance responsibility in most organizations lives across three tiers. The problem is that nobody maps those tiers to the CoS role. Here's what they actually mean for you.

Tier 1: Board and executive leadership

Sets organizational stance on AI. Approves major policies. Owns accountability for organizational risk. Your role: make sure they have the information they need to make decisions, and that those decisions get made.

Tier 2: AI Governance Board or cross-functional committee

Translates executive intent into policy. Coordinates across departments. Reviews vendor decisions. Your role: own the calendar, keep the committee moving, and make sure nothing stalls between functions.

Tier 3: Center of Excellence or operational layer

Implements policies, trains employees, tracks tools in use, and flags issues up the chain. Your role: make sure someone owns this layer, even if that someone is you, to start.

The CoS sits at the intersection of all three. Your job is to make sure the right conversations happen, the right people own the right decisions, and nothing falls through the gaps between functions. Technical expertise is not required. Coordination is.

This week's free prompt: the AI inventory survey

You can't govern what you can't see. This prompt generates an anonymous survey to start building visibility into what AI tools are actually in use across your org.

You are helping a Chief of Staff design a short anonymous employee survey. The purpose is to build an initial AI use inventory: a baseline picture of which AI tools are in use across the organization, what they are being used for, and whether employees have received any guidance on data handling.

The CoS needs this information to identify governance gaps before a formal policy is in place. This is not an audit. Employees should feel safe being honest.

Design three survey questions that are:

  • Short enough to answer in under two minutes total

  • Specific enough to surface actual tool names and use cases, not just yes or no responses

  • Framed to signal curiosity rather than investigation

Then suggest one optional open-ended follow-up for employees who want to share more context.

Return each question as a numbered item with a one-sentence note explaining what it is designed to surface.

You don't need a governance program to ask this question. You need a form and the willingness to read the results.

For all subscribers: The prompt above is yours. Run the inventory survey this week. The results alone will tell you more than most governance audits.

The full CoS AI Governance Playbook is inside the membership and included for paid subscribers. If you’d like to access it without subscribing, you may do so for $19.99 at https://cossignal.com/products/the-cos-ai-governance-playbook

THE SIGNAL

Legal and HR teams are, for the first time, asking how AI tools are being used with employee and executive data. Several CoS professionals I've spoken with this year have been asked by their executives to document the company’s AI use practices without notice, in preparation for a question from the board.

The operators who have a clear structure before it becomes a requirement are the ones their executives trust with more. And the ones who get asked to own the next thing.

ONE MORE THING

The CoS Signal is new. You got here early, and I don't take that lightly.

Each issue and resource is created with your support.

If this prompt or these documents save you time, hit reply, or comment on the web, and tell me what you changed to make it your own. The best iterations will make it into future issues.

If you know a CoS still doing this by hand, forward this to them.

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