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AI-Forward Insights for the Modern Chief of Staff

WE ALL HAVE TOO MANY…

…meetings. There, I said it. We also have all the questions and follow-up items that come from those meetings.

What we don’t have is too much context. There are moments when your exec needs more context than a meeting provided, or when an item from a town hall was missed or not answered. Most of them never get answered. Not because leadership doesn't care, but because no one has a system

I’ve seen this scene play out like the protagonist's storyline of every horror movie out there. The ending eventually works out, but none of us wants to continue with the level of struggle required to simply survive.

The last time it happened to me, I watched an executive flounder when an employee raised a question that had first been asked long ago.

I swore to never let it happen again.

I built and iterated on the prompt in today’s issue while juggling multiple clients, all of whom needed the context to field questions and find solutions.

I’m sad it took me so long to put the solution together. It has helped me make a profound impact on CEOs and executives, who simply don’t have the bandwidth to track all of this themselves.

Honestly, do any of us?

The relief I can see and feel when the system works is palpable. And I want you to learn from my trials and tribulations.

THE USE CASE

A reader asked this week how to use AI to detect patterns in town hall questions and surface them to leadership. The short answer: you already have the data. If your company records town halls, the transcript exists. The system most CoS and operators are missing is not due to the lack of data.

It is a repeatable prompt and a dedicated project with a standing context, so the output is actually useful to your client.

The key instruction to add to your project: "I will be sharing this analysis with my client, so the output needs to be clear enough to act on without me walking them through it." That one line changes how the AI formats everything it returns.

One heads up: when you bring pattern analysis to an executive, your read on the room goes with it. Make sure the output is clean, the framing is neutral, and the recommendations are specific.

AI handles the pattern detection. The judgment call is still yours.

Here for Free Content?

This week’s issue includes a paywall. Please consider becoming a Founding Member or visit me on LinkedIn at https://www.linkedin.com/company/ai-empowered-cos for continued free content.

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