Madi PalermoAdvisory
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Live Workshop

Zero to Chief of Staff in 60 Minutes

Create your agentic Chief of Staff with zero coding knowledge.

Follow along live, or just watch. Either way you leave with the files to build her on your own work.

Download Starter Files

Before We Start

1

Claude Code

This is who you talk to. The AI assistant from Anthropic. Needs a paid Claude plan.

Install Claude Code
2

Cursor (or VS Code)

This is where you watch the work show up. Any editor works, we just need to see the files Claude creates.

Download Cursor
3

Starter Files

Unzip to a folder you can find easily. This is Reformed, the studio you're about to run.

Download starter files

The Scenario

For the next hour, you own a Pilates studio.

You opened Reformed in 2022. Two locations, six instructors, 220 members, and every one of them knows your name.

You want to grow. More members, a third location. Instead you spend your days on everything else: unanswered emails, an instructor out sick you have to cover at 7am, payroll, the schedule, the landlord.

You need a chief of staff. Hiring and training one is months and money you don't have.

We're going to build her in 60 minutes.

Four Reformed members sitting on the barre, making hearts with their hands
What's in the starter files

Every folder stands in for a real system you already use.

Today it's a file. Next week it's a connection. Same command.

  • CLAUDE.md: the house rules. Two rules today: speak plainly, and staff up for big jobs. By the end of the hour, this file is your employee.
  • context/: what a new hire needs. The studio, the team, this year's goals, and jess-notes.md, a messy brain dump off your phone.
  • reviews/: Google, Facebook, and ClassPass, raw. The renewal answer is buried in here.
  • feedback/: submissions from your website's contact form.
  • inbox/: your Gmail. Twenty-three emails, including one that hurts.
  • calendar/: your Google Calendar plus the booking system's fill report.
  • tasks/: wherever your to-dos live. Notion, Linear, your head.
  • meetings/: your meeting notes. The huddle, the landlord call, and a messy mentor call.
  • messages/: your team chat. Slack, Teams, a group text.
  • photos/: the shared Drive folder where instructors dump class shots. Here, an index with links.
  • market/: a friend's competitor scan and where your members actually live. Fuel for the long game.
  • templates/: how you like things formatted, and ten messages you actually sent.
  • drafts/: empty. Anything that needs your yes lands here.
  • sent/: empty. Where things go after you send them.
  • .claude/commands/: empty today. By the end of the hour it holds the two skills you built.
Cora can only see this folder. Not your real email, calendar, or bank. That's why you can try this tonight.
Act 1 · Monday

Hire Cora.

Give plain Claude some work, watch it earn the hire, then hire her live.

1.1

Read & Summarize the Business

A dozen messy files. Nobody compiled them. Nobody needs to.

Read everything in context/, reviews/, feedback/, and meetings/. Save what you learn to company-summary.md, then give me the short version: who we are and our goals.
What you learned
  • Claude works in your files, not a chat window
  • Big piles spawn parallel workers
  • The summary becomes a file. Every later step can read it
1.2

Audit Where My Time Goes

The goals say grow. The calendar says you can't.

From @calendar/this-week.md and @inbox/inbox.md: what share of my week goes to teaching, keeping the lights on, and growing the business? Then write what-to-delegate.md, what only I can do and what someone else could own.
What you learned
  • Percentages land harder than task lists
  • Big findings become files. The next step reads them
  • What stays yours is your call, not hers
1.3

Hire Her

The delegate list is the job. Now have the hiring conversation.

Step 1: Say what you need

You're my new chief of staff. The job starts with @what-to-delegate.md. Interview me for it with the AskUserQuestion tool, and ask what to call you. Don't write anything until I say go.

Step 2: Click what fits, say the rest

Her questions arrive as buttons. That's the AskUserQuestion tool: Claude asking you, not the other way around. Click what fits. When no option does, pick Other and talk, Wispr Flow turns speech into text, rambling included. Ours boiled down to: drafts only, you never send, except the internal team chat, that's undoable. Money means you never act, but track and remind me. Teaching and the lease are mine. I text my own no-shows. Spot repeatable work, propose it, I decide. Prep me every morning. And we called her Cora.

Step 3: Watch the file

Go. Write your job description into CLAUDE.md, keeping the house rules.

If she picked her own filename, fix it

Move that into CLAUDE.md. Only that file is read automatically at the start of every session.
What you learned
  • CLAUDE.md is read every session, automatically
  • Claude can interview you, with clickable questions
  • Spoken answers become standing rules in a file
1.4

Put Her to Work

Don't assign the work. Ask what the work is.

Step 1: Ask. Five words is enough now

Cora, what needs me today?

Step 2: You decide, she executes

Agreed. Rosa first. Show me the draft.

Step 3: The draft sounds corporate. Teach her your voice

Rewrite it using @templates/jess-messages.md as the style guide.

Step 4: Keep it forever

Add "How Jess writes" to CLAUDE.md so you never lose it.

Step 5: Save the morning ritual as a skill

I want that list every morning. Save it as a skill called /prep-me.

Have some fun with this...

Add a sign-off to it: end every brief with one hype line. Best-friend-before-a-big-day energy, funny, a little snarky, never the same line twice.
What you learned
  • Prompts shrink as CLAUDE.md grows
  • Voice is trained by example: ten real messages beat a paragraph about tone
  • One sentence saves repeatable work as a skill
1.5

Find the Opportunity

Skill saved, desk handled. Now back to the thing the summary flagged: renewals.

Pull up @company-summary.md and go deeper on the renewal problem: is this demand or supply, and can my current team cover it? Check @calendar/fill-report.md and @context/team.md. What would you do?
What you learned
  • Ask the analyst question, demand or supply, and she brings receipts
  • Good analysis ends in a verb. Hers is: hire
  • She proposes. You decide. Same as day one
1.6

Staff It and Show It

She said hire. You agreed. Now the paperwork and the marketing.

Step 1: The hire that staffs the new mornings

Write the job post for the new morning teacher with @templates/job-posting.md. Into drafts/.

Step 2: The posts that fill them. Open the file in your browser

Pick the three best shots in @photos/drive-export.md and mock up three Instagram posts as one HTML page in drafts/.
What you learned
  • A photo folder is just another readable file
  • Ask for HTML, get a prototype you can open
  • The voice rules now apply to everything she writes
1.7

Put Her on the Clock

She works when you're not there. That's the whole point of staff.

Step 1: Say what you want. She'll ask what goes in it

I want an end-of-day digest of what still needs me, and a morning digest to prep my day. Ask me what to include, then set both up as routines on this machine's scheduler.

Answer in your own words. Ours: what needs me, ranked, and what's waiting on my yes

Step 2: Prove it. Hands off the keyboard

Schedule one extra morning run for two minutes from now. Hands off, we watch the folder.

If the scheduler acts up, this is all a clock does anyway

claude -p "/prep-me"
What you learned
  • A routine is a request plus a clock. Nothing new to learn
  • The scheduled run is a brand-new session. She wakes up already knowing who she is, that's CLAUDE.md
  • The rules hold at 6am: drafts still wait for your yes
Act 2 · Next week

Hook up your own stuff.

Every folder in this kit was a stand-in. Swap the files for the real thing.

Nothing about Cora changes. Same prompts, same rules, same files, except the files become live connections to the tools you already use.

inbox/Gmail
calendar/Google Calendar
messages/Slack
tasks/Notion or Linear
photos/Google Drive
meetings/Granola, or any notes app

The plumbing is called MCP, a connector standard, think wall socket for tools. Plug one in once and Cora reads the real thing exactly the way she read these files. Most of the tools above already have one.

What I'm obsessed with right now
Grokbot. Everything we just built, made stupid simple. Agent candy. 🤖🍬

Look At What You Built

Open CLAUDE.md next to the folder. It didn't exist this morning. Now it's a page, every line yours, written by talking. That page is your employee, and it just ran.

Take it home

Your first week.

Ten minutes a day. The two commands never change.

Use what's yours. Your own calendar, to-do list, notes, messages. If you have a work laptop with a data policy, company email doesn't go in this folder. Your own notes and lists do.
  1. Day 1. Run /prep-me and /end-of-day on Reformed once more. Just watch.
  2. Day 2. Replace context/goals.md with your real goals and context/jess-notes.md with your own messy notes. Change "Jess" to your name in CLAUDE.md.
  3. Day 3. Replace templates/jess-messages.md with ten messages you actually sent.
  4. Day 4. Empty calendar/ and tasks/, paste in this week and your real list. Then build the big one: /cover-me, when I'm unavailable, read the whole desk and handle the next stretch under your rules. Run it: "I'm in back-to-backs until 2, handle the morning."
  5. Day 5. Empty meetings/, drop in your last two meetings' notes. Ask her to prep you for tomorrow's hardest meeting, and if you like it, save it as a third skill. You know how now.
  6. Day 6. Rewrite "What you may do" for your life. Be stricter than you think.
  7. Day 7. Connect one real thing, read-only: "Help me connect my Google Calendar so you can read it but not change it." First day that takes more than ten minutes. Let her read for a week before she touches anything.
Stuck, or want to show off?

Run it tonight and email me what Cora caught.

madi@madipalermo.com

I read every one.

Stuck at a step? The answer key has the expected output for every step, including the two skills, if you'd rather not type them.