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AI-Forward Insights for the Modern Chief of Staff
THIS WEEK’S BRIEF
Think about the last time you used AI for something sensitive.
Performance feedback. Board dynamics. A hiring decision you hadn't announced yet.
Did you check whether the tool was storing that conversation before you started typing?
Most people don't. And most AI tools have conversation history turned on by default. That means the names, context, and details that could identify your client's situation may be stored in a training dataset somewhere.
That is a problem that is easier to prevent than to explain later.
This week's issue is the protocol I use before anything sensitive goes into a prompt.
THE USE CASE
I was helping a CEO work through a difficult board dynamic that had been building for months. Relationships under strain. A past decision that hadn't landed well. A trust issue nobody had named out loud yet.
I wanted to use AI to help me think through the framing before the conversation.
I stripped the context first. The CEO became [Principal]. The board member became [Board Chair]. A specific incident became "a resource allocation decision from last quarter." A dollar figure became "a seven-figure commitment."
I gave the AI enough context to be useful. Every detail that would identify the people involved stayed out.
The output was useful. I went into that conversation better prepared. And I didn't spend three days afterward wondering what I'd handed over.
This week's issue covers one of the highest-stakes things you can do without a protocol. To keep reading, consider becoming a founding member. This is the kind of content that's inside every week. Founding spots are $14.99/month, locked for life. You can join below.
Please visit me on LinkedIn at https://www.linkedin.com/company/ai-empowered-cos for continued free content.
FREE RESOURCE
Free for all subscribers: The AI Content Checklist (The AI Empowered CoS Version). Three questions to answer before AI touches executive work. Grounded in Google's responsible AI framework, translated for operators.
Inside the membership: The AI Use Policy Template. One page, five sections, grounded in the NIST AI Risk Management Framework. Something you can show your executive if they ask. If this week's issue made you think twice about your own practices, that is a good reason to join.
Also worth your time this week: The prompt in this issue is about giving AI the right context for a sensitive situation. Caitlin Ferguson teaches something that takes that idea much further. The Keystone is a permanent context layer that tells AI how you think, what you value, and how you make decisions. Not a one-time prompt. A reusable foundation that travels with every task.
That's the difference between a tool that executes and one that thinks with you.
Her cohort, AI for Operations, starts April 29. Four live sessions, small group, hands-on builds. You'll build your Keystone, map your highest-value automation opportunities from a catalog of 340+ business-ready use cases, and work through governance, legal, and ROI measurement. Built for operators who need to deploy AI inside a real organization. $750. A few seats left.
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