
AI-Forward Insights for the Modern Chief of Staff
A CASE OF THE MONDAYS
There are Mondays that test you before you even get to your desk.
Mine started with an accident on the highway, a computer that had spent the night updating itself, and a calendar full of back-to-back meetings I had zero time to prepare for. No brief. No coffee. Just me walking into a day I was completely behind on before it started.
I told myself I would catch up. I didn't.
Somewhere in the middle of the afternoon, my CEO found me. He wasn't angry. That almost made it worse. He just looked at me and said he hadn't realized, until that day, how much he had come to rely on the brief. That he could feel the difference.
I smiled. Inside, I was somewhere between panic and wanting to disappear entirely.
And then something shifted. Because what he said next wasn't a complaint. It was an admission. The brief had become infrastructure. Not a nice-to-have. Not a value-add. Infrastructure. Something so woven into how he operated that its absence had thrown off his entire day.
I had built that. It had mattered in a way I hadn't let myself fully believe until that moment.
That day ended in relief. And something that took me a while to name: validation.
THE USE CASE
The brief that caused all of this didn't start as anything sophisticated. It started as me trying to stop drowning on Monday mornings.
I was spending the first hour of every week just reconstructing context. What was open? What had moved? What my CEO needed to know before his first meeting. It wasn't strategic work. It was archaeology.
Fast forward to the present, the advent of AI everywhere, and going from one CEO to many. The fix wasn't just being better prepared. It was a well-engineered prompt. One prompt, run every Friday before I close my laptop. Admittedly, sometimes it's on Sundays. I'm sure you can all relate to those weeks.
I paste the week's open items, emails, and meeting notes into my AI of choice. One input. One output. A structured brief that tells me what needs a decision, what needs action, what can wait, and what has a deadline in the upcoming week. Monday morning, I re-read it before I do anything else.
On the days when chaos arrives before I do, it's already there waiting.
The brief didn't happen overnight, and it still isn't finished. I revise it regularly. It gets better every week because I treat it like a living document, not a setup I did once and forgot about. Every time it misses something, I figure out why and I add one line to the prompt.
That's the part nobody tells you. The prompt is not the destination. The prompt is the practice.
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THE PROMPT
This is the version I use now. It has two things most prompts skip: a quality standard for the output, and enough context about your role that the AI isn't guessing who it's writing for. There are other ways to prep your AI, but for now, we’ll keep it simple.
Start here. Change everything that doesn't fit how you work.
You are helping me prepare for the week ahead. I am a Chief of Staff [or insert your position/title]. I support [describe your principal/s here]. My job is to keep them informed, prepared, and unblocked. This brief is for my eyes only and feeds directly into how I run my week.
Below/Attached are my open items, emails, meeting notes, and anything else relevant from the past week and the week ahead.
Organize this into four sections:
1. Decisions only I can make, with a one-line summary of what needs to be decided and by when
2. Actions I need to take, ranked by urgency
3. Things I can delegate, with a suggested owner if I have named one
4. Things that can wait, and why
Flag anything with a deadline in the next 48 hours at the very top, before the four sections.
Write each item as a crisp, decision-ready statement. Assume I have 90 seconds per section. No filler, no repetition, no restating context I already know.
If anything seems incomplete, contradictory, or dependent on something I haven't mentioned, flag it at the end.
[Paste your notes here or attach them to the chat]
One thing definitely worth adding: flag items with dependencies, meaning things that can't move until something else does first. That one addition changed how I sequence my week.
After each use, note one thing the output got wrong or missed. That is your next edit. The prompt I use today looks nothing like the one I started with. Treat it like a living document.
Tip: The better your model knows you, the better the output. Check your memory settings!
THE SIGNAL
AI tools are getting meaningfully better at handling long, messy, unstructured inputs. That matters for this specific use case. You do not need clean notes for this to work. The whole point is that the prompt does the sorting, so you don't have to. Paste the mess. Read the brief.
THE RESOURCE
If writing down open items throughout the week feels like one more thing to keep up with, try voice memos instead. Speak them as they happen. Transcribe at the end of the week. Paste the transcript on Friday. The bar to capture something drops significantly when you don't have to type it. The majority of this newsletter was written in just that way.
ONE MORE THING
The CoS Signal is new. You got here early, and I don't take that lightly.
Future issues go deeper into each of the four areas where AI actually makes an impact for a CoS: decision support, noise reduction, system building, and voice training. Each one has a real story behind it, a prompt, and at least one failure moment worth learning from.
If this prompt saves you time on Monday, 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.
If you want to continue this kind of full access in future newsletters, founding membership is open. $14.99/month or $99.99/year (locked in for life). 26 spots to get in early and help shape what an AI Empowered CoS is.
FOUNDING MEMBERS
Welcome and thank you to the first two Founding Members, Janina H. & Rachael Goldfarb (from The Cold & Gold Briefing)!
UPCOMING TOPICS: MAIL CALL!
The CoS Signal has already received two great topic requests I will be covering soon. Make sure to reply or comment and send yours in as well!
“How to use AI use in high-confidentiality environments, how to train skeptical-but-smart teams, and what guardrails actually look like in practice rather than in theory.”
from Evelyn, EA turned CoS/Compliance Director | Finance & Family Office Operations
“How to use AI data analytics while protecting important company information.”
from Rebecca, VP of Strategic Initiatives
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
The CoS Signal by the AI Empowered CoS
The ideas, frameworks, and words in this piece are my own. I used Claude to assist with design and file production.



