AI-Forward Insights for the Modern Chief of Staff

The 90-Day CoS Framework, Now with AI

Maggie Olson's 9-step framework for your first 90 days as Chief of Staff is one of the best starting points for anyone new to the role.

But I kept thinking: what would this look like if you had AI in your corner the whole way?

So I built it.

What I Made

I took each of Maggie's 9 steps and wrote a ready-to-copy AI prompt for each one. Very beginner-friendly. No AI experience required. No paid tools. No jargon.

If you're more advanced, the prompts are easy to build on. But you don't need to be.

What It Covers

How to prep for 1:1s like you've known someone for years. How to decode your principal's decision-making style from meeting notes. How to document the current state without spending a week on it. How to pressure-test your ideas before you say them out loud. And five more.

How to Use It

Just open whatever AI tool you already use, paste the prompt, fill in your details, and go. That's it.

The RESOURCE: Get It Here

This was previously offered for free through AI Empowered CoS, a resource library I built specifically for Chiefs of Staff who want to use AI with confidence.

Thanks to Maggie Olson for the framework that started me on the path to creating this PDF!

ai_empowered_cos_prompt_guide.pdf

ai_empowered_cos_prompt_guide.pdf

124.06 KBPDF File

Know a CoS who'd find this useful? Forward it to them. Founding member spots are open at a locked rate before standard pricing kicks in.

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Until next week,
Stephanie

P.S. The thinking and words here are mine. I used AI to pressure-test the ideas before I hit post.

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