Most AI training keeps its syllabus vague, which is usually a sign there is not much of one. We take the opposite approach and publish ours. Here is the actual curriculum we use to train teams on Claude Cowork, session by session, along with what each team walks away owning. We run our own consultancy on Cowork, so this is not a theoretical course outline. It is documentation of how we actually teach the thing we use every day.
Why Cowork needs its own training
Chat training and Cowork training are not the same course with a different logo. Chat teaches conversation: how to ask Claude for something and refine the answer. Cowork teaches delegation: granting folder access, briefing a multi-step task, reviewing completed work, and supervising automation that runs on a schedule. That is a different skill with different failure modes, and it deserves its own training rather than a bolt-on slide at the end of a chat session.
The curriculum, session by session
The program runs across four sessions, each building on the last and each ending with the team doing real work rather than watching a demo.
Session 1, foundations. What Cowork can and cannot touch, how folder permissions work, the task loop, and how to review Claude's work like a manager rather than a spectator.
Session 2, working with files. Documents, spreadsheets, and decks built from the team's real templates, plus their first three delegated tasks, chosen deliberately for quick wins.
Session 3, connections and plugins. Email, calendar, and CRM connectors with scoped access, and the plugins and skills relevant to the team's particular function.
Session 4, automation and governance. Scheduled tasks with sensible failure behaviour, the draft-never-send rule for client-facing output, and clear escalation paths when something is ambiguous.
The order is deliberate. People need to trust the access model before they will delegate anything real, and they need a few quick wins under their belt before they will hand over scheduled automation. Teach automation first and you get nervous staff who never switch it on.
A note on who attends. The best results come from training the people who actually do the repetitive work, not just a manager who will relay it second-hand. Cowork rewards hands-on practice during the session, so we keep groups small enough that everyone delegates a real task while we are in the room to catch mistakes. A room of twenty passive observers learns far less than a room of six people doing the work live.
The artefacts the team keeps
Training that leaves nothing behind fades in a fortnight. Each team finishes the program owning three things.
A written operating rulebook: what runs autonomously, and what needs human approval before it goes out.
A workflow register with a named owner against each entry, so nothing is orphaned.
Session recordings, so onboarding the next new hire does not mean booking us again.
What it costs and what it returns
The two-week enablement program is a fixed-fee engagement, so there is no open meter. In document and admin-heavy roles, teams commonly reclaim 5 to 15 hours per person per week once the workflows are bedded in. Put that against salary: at a $100,000 Australian salary, ten hours a week reclaimed is worth roughly $25,000 a year per person. Across a team, the program pays for itself well inside the first quarter, and the artefacts keep returning value long after we have left.
We also keep one session in reserve for a follow-up about a month later. By then the team has hit the real friction points, the ones that never come up in a clean training environment, and an hour spent on their actual stumbling blocks is worth more than another scripted module. That follow-up is where good intentions turn into habits, and it is the part most one-and-done training programs leave out.
Honest prerequisites
This works far better when a few things are true going in, and we would rather say so than oversell. You need a reasonably tidy folder structure, because Cowork cannot impose order on chaos. You need a named internal owner who will carry the workflows after the training ends. And you need genuine willingness to review AI output properly for the first month, before trust is earned. Teams missing all three should fix that first, and we will tell you as much rather than take the booking.
This curriculum sits inside our full Cowork implementation, and it is part of how we run Claude training across Sydney. If you want your team trained on the version of Cowork we actually run, book a discovery call and we will scope it to your workflows.
