Chief of Staff Workflow Using Claude Code

Part 1: Tutorial

The problem: Claude doesn’t remember anything between sessions. Every conversation starts fresh. But I need a thinking partner who knows my projects, clients, deadlines, and what I’m avoiding.

The solution: A slash command + session files that Claude reads every time.

Setup:

  1. Create the slash command at ~/.claude/commands/chief-of-staff.md:
# Chief of Staff

You are my Chief of Staff.
[Define the persona, values, responsibilities...]

## First thing: Read the session files
Always start by reading: /path/to/chief-of-staff-sessions/

$ARGUMENTS
  1. Create a session folder with a brain dump file:
/chief-of-staff-sessions/
├── brain-dump.md          # Main state: all clients, tasks, open loops
├── topics-for-connor.md   # Running list for specific people
└── [add more as needed]
  1. Structure the brain dump by client/project:
## CLIENT: Stacks & Joules
- **Status:** Social scheduled for month ✓
- **This week:** End-of-year report deck
- **Owed:** Fran & Amoret thank-you post

## CLIENT: FMLY
- **Deadline:** Dec 22
- **Status:** Website prototype in progress
...

How I use it:

  1. Run /chief-of-staff
  2. Claude reads all session files — instant context
  3. I update Claude on what changed (“sent the invoices”, “here’s a meeting transcript”)
  4. Claude updates the files in real-time
  5. Next session, it picks up right where we left off

Bonus: Drop meeting transcripts into /Clients/[name]/call-notes/ — Claude summarizes them and updates the brain dump.

Part 2: Blog Post

The thing about AI assistants is they have amnesia.

Every conversation starts from zero. You explain your projects, your clients, what you’re working on — and then next time, you do it all again. It’s like having a brilliant coworker with a Men in Black memory wipe between every meeting.

Here’s what’s both true: Claude is incredibly capable AND it forgets everything the moment you close the window.

So I built a workaround. A slash command called /chief-of-staff that reads a folder of markdown files before we start talking. My brain dump. My running task list. Notes on what I owe each client and who’s waiting on me.

Now when I start a session, Claude already knows. It asks “how’d the Hannah meeting go?” instead of “who’s Hannah?” It remembers I’ve been avoiding the BATCAVE scheduling. It knows the FMLY website is due the 22nd.

The unsexy truth: it’s just text files. Markdown documents that Claude reads and updates as we talk. No fancy database, no special app. Just files in a folder.

But that’s the thing about good systems — they’re usually boring. A folder of notes and a command that reads them. That’s it. That’s the whole trick.

The magic isn’t the technology. It’s having a thinking partner who remembers what you’re avoiding.