Your AI Chief of Staff

What Is an AI Chief of Staff?

A chief of staff is the person behind the scenes who keeps everything running — knows your schedule, anticipates what you need, handles the stuff that eats your time. Traditionally, that's a human. An expensive one.

This guide is about building that for yourself using AI. And what makes it different from every "how to use ChatGPT" tutorial: it's not a template. You build it with your AI, based on how YOU actually work, what drains you, and what you're trying to achieve. The result gets better the longer you use it.

(I know that sounds like a lot. It's not.)

Setup

A couple of things before you dive in:

1. You'll need a paid Claude subscription. Grab one here: claude.ai/subscribe
2. Install Claude Code using the official setup guide: Claude Code Setup Guide. Follow the instructions for your operating system and come back when you're done.
3. Open your terminal. (Mac: Cmd + Space, type "Terminal," hit enter. Windows: search "Terminal" in your Start menu.)
4. Type this exactly, hitting enter after each line:
   mkdir my-chief-of-staff
   cd my-chief-of-staff
   claude
5. You should see a Claude Code prompt waiting for you. That's it. You're in.

What your terminal should look like once Claude Code is open and ready.

Tell It Everything — Before You Start

Before you open the terminal, do this first. Copy the prompt below, open Notes (or any text app), paste it in, and fill out your answers. Be honest — there are no right answers. The more specific you are, the better this works.

(The "dream a little" question usually surfaces the thing you actually need. Pay attention to what comes out of you there.)

(The guidelines section is the part that makes it YOURS. Don't skip adding your own.)

Fill it out somewhere you can type freely — then paste the whole thing into Claude Code at once.

Claude gets the full picture at once and comes back with a real, personalized plan.

Decide Where Your Day Lives

Before you get too far, there's a practical question worth thinking about: when your chief of staff builds your daily plan, where do you actually want to see it?

There are three options, and the right one depends on how you work.

• In the chat The simplest version. Claude lays out your schedule as a time-blocked plan right there in the conversation — you read it, you know your day. Nothing to set up, nothing to maintain. Works great if you're just getting started or if you mainly want the thinking partner piece and don't need it to live anywhere persistent.
• Google Calendar events If you live in your calendar, this might be the most seamless fit. Claude creates actual calendar events — they show up on your phone, sync everywhere, and slot into your existing workflow. Takes a bit of setup (you'll need to connect Claude to your Google Calendar), but once it's running, your AI-built plan and your real calendar are the same thing.
• A custom web app This is what I built for mine, and honestly it changed how I use the whole system. Instead of scrolling through a chat to find my plan, I have a dashboard — a simple webpage that shows my day, my tasks, whatever I've told it to track — always there, always current. Claude writes and updates the code itself; you just open it in a browser.
  
  It's a bit more to build upfront. But it means your chief of staff isn't trapped inside a terminal window. It feels like a real product, because it is one.

My dashboard — built by Claude, updated every morning. Opens in a browser like any other webpage.

Start Small, Let It Evolve

You just gave your AI a lot to work with. Here's what NOT to do: try to build the entire system in one sitting.

Pick one thing from the list it suggested. One. Work with it for a few days. See what breaks, what feels off, what you wish it did differently — then tell it. That feedback is how the system gets better.

This isn't a product you set up once and forget. It's a working relationship. The version you have in a month will look nothing like what you built today, and that's exactly how it's supposed to go.

• To talk to your chief of staff, always go back to the terminal. Open it, type cd my-chief-of-staff, then type claude. That's how you start a session. If you close the terminal, it's not running — you have to start it back up.
• This is where you share everything. New tasks, feedback, updates on your day, things that aren't working — all of it happens right there in that terminal window. Talk to it like you'd text a person.
• You can tell it anything mid-conversation. "That response was too long." "Stop asking me that." "From now on, always do X." It learns as you go.
• It has memory. Claude Code automatically saves context about you and how you work behind the scenes. Just always come back to the same folder and it picks up where you left off.

The goal isn't a perfect system. The goal is a useful one.

(You've got this.)