AI Chief of Staff · Setup Guide
Your AI Chief of Staff
A single Claude Project that knows your priorities, your operating frame, and your recent decisions — so it can synthesize meeting prep, pressure-test decisions, draft your board memos in your voice, and turn six months of reading into searchable memory. Also called a Strategic Advisor, Operating Brain, or Strategic Second Brain — same Project, different names.
This page is how to set one up. Step-by-step, free generator included, no consulting required. If you'd rather have help — Nicole walks you through it live in the Executive 1:1.
What it does
Five jobs your Chief of Staff does for you
Not a generic assistant. A specific role with a specific frame — so it can push back on the question instead of just answering it.
Synthesizes meeting prep in 5 minutes
Pulls your priorities, recent decisions, and the relevant context for the meeting you're about to walk into. Returns a 1-page brief and the three questions you should be asking.
Pressure-tests your thinking before you commit
Devil's-advocate built in. When you ask 'should I do X,' it surfaces what you're not seeing — not what you want to hear.
Drafts board memos, all-hands letters, exec emails
Knows your voice. Drafts in plain English, short sentences, no corporate-speak. You edit instead of writing from blank.
Tracks the decisions you've already made
Six months from now, you can ask 'why did we say no to that acquisition' and get a real answer. Your strategic memory compounds instead of evaporating.
Holds your reading and turns it into searchable memory
Books, essays, podcast notes, pitch decks all flow into one Project. The framework that changed your thinking last fall is reachable when you need it during board prep this fall.
How to set it up
Five steps. About an hour.
If you stall on any step, the most common reason is missing context — go back to step 2 and let the generator write a fresh version with the right priorities.
Open Claude.ai and create a new Project
Settings → Projects → New Project. Name it something simple — 'Chief of Staff' or 'Strategic Advisor.' Keep it private (private Projects let you connect Google Drive files; team-visible ones don't).
Generate the Project instructions
Use the free Strategic Advisor Generator — it asks for your priorities, role, and operating frame, then writes BRIEF-format instructions tuned to how you actually work. Paste the output into your Project's Custom Instructions field.
Open the Strategic Advisor Generator →Upload your context as knowledge files
Five files cover most CEOs: (1) current quarter operating priorities, (2) recent decision log, (3) reading & research notes, (4) calendar lookahead, (5) board/investor history. Either upload as documents or link from Google Drive so they stay live.
Set your global instructions
Your Claude account also has account-level instructions that apply to every Project. Use those for tone (direct, plain English, no corporate-speak) and meta-rules (push back, don't validate, cite sources). The Project instructions handle the specific role. See the guide on the difference →
Global vs project instructions guide →Open it daily for two weeks
Habit beats configuration. Open Chief of Staff first thing in the morning, ask one real question, and edit the instructions when the answer is wrong. By week two, it knows you.
Free · No email required
Strategic Advisor Generator
Paste your priorities, role, and operating frame. The generator writes BRIEF-format Project instructions tuned to how you work. Regenerate whenever your focus shifts.
Common questions
Things people ask before they start
Is this the same as a Strategic Advisor or Operating Brain?
Yes — different names, same Project. 'Strategic Advisor' is the technical role description; 'Chief of Staff' is how most operators describe it day-to-day; some call it an 'Operating Brain' or 'Strategic Second Brain.' Same architecture, same setup. Use whichever phrasing fits how you talk about your work.
Do I need Claude Teams or Enterprise for this?
No. A personal Claude Pro account is fine for a personal Chief of Staff Project. If you want company-confidential context in there, the right answer is a Claude Teams seat under your organization's plan with zero-retention turned on — not your personal account.
Why a Project instead of just chatting?
A Project is a dedicated space with persistent instructions AND uploaded knowledge files. It remembers your operating frame between sessions. A regular chat starts cold every time. The whole point of the Chief of Staff pattern is the context compounds.
How is this different from a regular Claude assistant?
A regular assistant helps with the task in front of you. A Chief of Staff Project knows your priorities, recent decisions, and operating frame — so it can push back on the question itself, not just answer it. You're hiring strategic judgment, not just a writer.
What scales on top of it
The Chief of Staff is Build 01. Two more extend it.
Build 02 - Scheduled tasks in Claude Cowork. Once the Chief of Staff knows your operating frame, hand the recurring stuff to Cowork. A 6 a.m. brief that runs against your calendar. A Monday pipeline digest. An end-of-quarter review that drops in your inbox the last Friday of the month.
Build 03 - A dashboard or live site, powered by MCPs. Connect MCPs to your Drive, Linear, Stripe, or Supabase and put Claude behind a small internal interface. The Chief of Staff Project becomes the brain; the dashboard becomes the surface your team sees.
Want help setting all three up?
The Executive 1:1 is a premium 1:1 with Nicole across three working sessions - an alignment intake to confirm what to build, a live build session, and a follow-up a week later to extend. Most clients build the Chief of Staff in depth during the live session, then layer in Build 02 or 03 during the follow-up. From $5,000, recording and reference guide included.