RC
rupertchesman.com
navigate   F facilitator notes
1 / 1
Facilitator notes

3-Hour Intensive · Updated June 2026

Build Your Own
AI Team

Hire, train and supervise a team of AI assistants for your small business — Claude-first, supervised, and built for the way Australian businesses actually work.

~3 hrs
Intensive
7
Modules
18
Lessons
1
Case study
Welcome

Built for small-business owners, not developers

If you've used a chatbot once, you're ready. You wear every hat and have no IT department — so we build a team of assistants that read your email, watch your cash flow and prepare your books, with you as the manager.

Owners & founders

Doing the work of five people and out of hours in the week.

Sole traders

No staff to delegate to — until now.

Ops & admin

Drowning in inboxes, invoices and receipts.

Anyone curious

No technical background needed.

"Claude is no longer a chatbot you ask things.
It's a workforce you can hire."

You hire each assistant for a bounded job, give it the right access, train it your way — and you stay the manager who signs off the consequential work.

The one rule

Automate the reads. Supervise the writes.

Your AI team prepares and checks; a human reviews and lodges. We build the team in stages of trust — read-only first, supervised acting last. This rule runs through every module.

Agenda

The seven modules

01

What an AI Team Is

The agent spectrum, MCP, name your first hire.

02

Meet Your Workforce

Cowork, Chrome & Office, connectors & Skills.

03

Your First Safe Hire

Read-only first: a brief, a connector, a Skill.

04

Delegating Real Work

Cowork jobs, supervised acting, choosing tools.

05

Trust & Compliance

Privacy, data sovereignty, your governance brief.

06

Your 30-Day Roadmap

A staged hiring plan you'll actually follow.

Bonus · Module 07 — Case study: a small-business AI team in action

01
Module One

What an AI Team Actually Is

The spectrum

A chatbot talks. An agent acts.

Prompting

You ask, it answers. One turn, no action in your systems.

Workflow

A fixed "if this, then that" sequence. Reliable, but rigid.

Agent

You give a goal; it decides the steps — observe, think, act, repeat.

Autonomous

Runs longer, coordinates sub-agents — still needs oversight.

An agent runs a loop — observe the situation, think the next step, act with a tool — until it's done or it needs you. Your job shifts from doing the work to supervising it.

The connective tissue

MCP — the standard plug for your apps

What it is

An open standard that lets Claude reach into your apps — Gmail, Drive, Calendar, QuickBooks, Canva and hundreds more. "USB-C for AI."

Why it matters

You don't integrate anything. You click "connect", approve it, and ask in plain English. No developer required.

The guardrail

Every connector tells you what it can do: read only, draft, or act with approval. That single question is the whole safety story.

Before you connect anything, know whether it can only read, can draft, or can act.

Your first hire

Pick the boring job you do every week

Pick the job

Recurring, bounded, low-stakes and annoying — inbox triage, the weekly cash-flow check, chasing invoices, sorting receipts.

Make it a role

The bookkeeper, the marketer, the ops assistant. Start your AI Team Org Chart, ranked by time it gives back.

Set the trust dial

Read-only, draft-for-me, or act-with-approval. This pre-loads the safe build that follows.

We're not automating you. We're hiring you a junior who does the first draft and the donkey work.

02
Module Two

Meet Your Workforce

The generalist

Cowork — your desktop coworker

What it does

Point it at a folder, give a goal in plain English, and it reads, edits and creates files and completes multi-step work — showing its reasoning as it goes.

How you stay in control

Steer it mid-task, grant permissions on purpose, and it asks before destructive actions like deleting files. Supervised, delegated knowledge work.

The clearest example of AI that does the work rather than telling you how. The researcher, the report-writer, the file-organiser. Runs from the desktop app.

In your browser & Office

Claude for Chrome & Microsoft 365

Chrome & Office add-ins

A browser agent that sees your tab and can navigate, click and fill forms; and Claude inside Excel, PowerPoint, Word and Outlook — reading, editing and drafting where you already work.

Handle with care

They act inside your logged-in session. Exposed to prompt injection — hidden instructions in a page. Never unsupervised on money, passwords or sensitive data.

Prompt injection is the new phishing. Treat any page or document an agent reads as potentially trying to give it secret instructions.

Hire & train

Connectors hire. Skills train.

Connectors = hiring a specialist

Plug Claude into a specific app — QuickBooks, Gmail, Canva, Stripe. Each has a scope: read, draft, or act with approval.

Skills = the induction manual

A .skill file teaches Claude to do a task your way, every time — your steps, your voice, your must-checks. MCP gives the tools; Skills give the method.

A connector hires a worker; a Skill writes its job description so it performs the same way every time. Only install Skills from sources you trust.

03
Module Three

Your First Safe Hire

Stage one — read only

Your first hire only reads and drafts

A scheduled brief

Connect one directory connector. A weekly read-only digest — cash flow, overdue invoices, the week ahead — that lands while you sleep.

Email triage with drafts

Claude searches and drafts replies; you hit send. The Gmail connector won't send for you — the tool enforces the discipline.

A "wow" with zero write-risk. Watch the drafts for a week. When you trust them, then we let it act.

The bookkeeper's first shift

Ask your books a question

What it reads

P&L, balance sheet, cash flow, aged receivables, sales. "Summarise my overdue receivables." "Flag unusual expenses this quarter."

What it can't do

It does not reconcile, categorise the bank feed, lodge a BAS or run payroll. Those come later — supervised.

The connector is a brilliant analyst and a terrible signatory. "The AI did it" is not a defence to the ATO.

Train your specialist

Finish one Skill — your job, your way, every time

Two strong starters

A weekly cash-flow brief (reads QuickBooks + drafts the summary), or an on-brand newsletter draft (research → draft → your voice).

Bake in the checkpoints

The induction manual should say where the junior must stop and ask a human. Save it once; it runs the same every time.

A Skill is the difference between training someone once and re-explaining the job every Monday.

Hands-on · 10 minutes

Ship your first read-only assistant

On a sandbox or personal account, stand up a scheduled brief or email-triage-with-drafts, and review the first output live. Nothing gets sent. You stay the one who decides.

04
Module Four

Delegating Real Work

Stage two — delegate bigger

Hand over a whole multi-step job

Steer

Guide mid-task

Correct course as it works — like managing a person.

Permit

Grant access on purpose

Give it the folder and tools it needs — and nothing more.

Review

Sign off the result

Accept or reject the finished deliverable before it's used.

This is the moment people feel it: you described a whole job and a finished thing came back.

Only now — supervised acting

The bookkeeper on a sandbox

The agent can

Drive a sandbox QuickBooks via Chrome — reconcile, categorise, prepare a draft pay run, produce an exceptions list, pull super and PAYG totals.

A human must

Lodge with the ATO, approve or release payroll, move money, make final compliance calls. Keep a registered BAS/tax agent in the loop.

Australian context: Super Guarantee 12% (from 1 Jul 2025); Payday Super from 1 Jul 2026. Conceptual only — confirm with the ATO. The point is where the human acts.

Build the right stack

Claude vs Zapier / Make / n8n

Reach for Claude

Conversational, judgment-heavy, document work, or one-off-but-complex — research, drafting, analysis, "do this whole task for me."

Reach for a platform

Triggered, repetitive, high-volume, deterministic, runs unattended — "every time a form is submitted, do X, Y, Z."

They combine — and integrations aren't set-and-forget. Use the simplest stack that runs reliably under supervision, and give every automation an owner.

05
Module Five

Trust, Compliance & the Australian Context

Before you connect anything

Four questions to ask every time

1 · What?

What data is being sent?

2 · Where?

Where is it processed or stored?

3 · Who?

Who else receives it?

4 · Approvals?

What contracts and disclosures are required?

Under APP 8 you stay accountable for your customers' data even after it leaves your laptop. Processing personal info through an overseas-hosted tool can be a "disclosure." Prefer in-region deployment for sensitive data; disclose overseas handling.

Safe & defensible

Guardrails & your governance brief

The failure modes

Prompt injection and compound failure across long tasks. The fix: bounded tasks, clear checkpoints, simple recovery paths.

The guardrails

Least-privilege access, a human in the loop for anything consequential, never unattended on financial pages.

The one-pager

A connector & permissions map and a governance brief — scope, checkpoints, who's accountable.

A one-page brief turns "I used AI" into "here's how we govern AI" — what your accountant and clients want to see.

06
Module Six

Your 30-Day AI Team Roadmap

Make Monday concrete

Hire one assistant a week

Week 1

Read-only

A brief or triage-with-drafts, reviewed daily.

Week 2

Connector + Skill

QuickBooks read-only insight; finish one Skill.

Week 3

Cowork job

A real multi-step job on a sandbox folder.

Week 4

Supervised acting

Only if ready — one acting task, human lodges.

Plan thresholds: start on Pro; move to Max only when you hit limits; Team/Enterprise for 5+ people or governance.

Commit · out loud

Name your Week 1 hire — and the date

Write the read-only assistant you'll stand up first, and when. The people who get value aren't the most impressed — they're the ones who hire one assistant next week.

07
Bonus · Self-paced

Case Study: An AI Team in Action

The bookkeeper

Reconciliation & pay-run prep

The agent prepares

The connector pulls P&L, aged receivables and cash flow; Chrome drives the sandbox UI to reconcile and categorise; a draft pay run and exceptions list come back.

The human lodges

You review and lodge the STP event; a registered BAS/tax agent stays in the loop. The agent prepares the books — it doesn't sign them.

The marketer

Research → on-brand newsletter

1

Research

Cowork synthesises across sources into a structured draft.

2

Draft in your voice

A brand-voice Skill enforces house style; connectors produce on-brand visuals.

3

You publish

Drafts on-brand at speed — a human still hits publish.

The ops assistant

Briefs, triage & scheduling

Scheduled briefs

Weekly cash-flow + overdue invoices + the week ahead — read-only, while you sleep.

Email triage

Searches and drafts replies; you send.

Scheduling

Blocks time and books meetings — with approval.

The quiet backbone of the team — and the third box on your org chart.

The real lesson

The best hires know when to hand back.

A great AI team does the 90% that's tedious, surfaces the 10% that needs a human, and leaves a clean trail for both. It prepares and checks; you review and lodge.

Automate the reads, supervise the writes — and never cross from "prepare/check" to "lodge/pay" without a human.

You didn't just learn about AI agents

You walked in doing everything yourself. You're leaving with a team — and a plan.

Hire read-only in week one, one new role a week, supervised — and in a month you have a small team, not a pile of half-finished experiments.

Next steps

Keep going

Open the dashboard

18 interactive lessons to revisit, at your own pace, any time.

Go deeper on the books

The Banking & Taxes / QuickBooks course for the bookkeeper in detail.

Bring it to your team

A private session on one of your real workflows — corporate training.

rupertchesman.com

Rupert Chesman — AI educator, filmmaker, author of The AI-Native Playbook · ru@rupertchesman.com

Educational only — not legal, tax or financial advice. Verify product features and Australian compliance specifics against official sources before relying on them.