How to use Claude Cowork: your first working session
Claude Cowork rewards good setup more than clever prompt wording. This is a practical walk-through of your first working session — how to start one, how to keep it safe, and how to give it the context it needs to hand back something useful.
Start a Cowork session
Open Claude on the desktop app, and in the message box choose "Cowork" instead of chat — the two share one home. Then describe the outcome you want, not the steps. "Read every PDF invoice in this folder, pull the vendor, date and amount into a spreadsheet, and file each PDF into a sub-folder by month" is a good Cowork instruction; "help me with invoices" is not.
Choose the right permission mode
Cowork has three permission modes and picking the right one is the single most important safety decision. Start in Manual while you're learning and for anything sensitive.
- Manual — Claude pauses and asks before each action. Use this first.
- Auto — Claude self-reviews each step and blocks unsafe actions (uses more of your allocation).
- Skip — no pauses and no automatic checks; only for low-risk, well-understood tasks.
Give it context with Global Instructions
Cowork doesn't carry memory between sessions by default, so standing context lives in Global Instructions (Settings → Cowork → Edit Global Instructions). Put your team's conventions there — house style, file-naming rules, which folders are off-limits — and every session starts with them applied. For one-off context, point Claude at a reference file at the start of the task.
The rule of thumb from experienced users is simple: if a colleague with minimal context would be confused by your instruction, so will Claude. Rich context beats clever wording every time.
A worked first task
A reliable first task is bulk file work. Ask Cowork to convert a folder of Word documents to PDF, or a set of HEIC images to JPG, and to rename them to a consistent pattern. It plans the steps, does the conversion in its sandbox, and returns the organised output. From there, graduate to a transcript-to-proposal or notes-to-deck task, then turn the workflows that work into reusable Skills.
Frequently asked questions
Do I need technical skills to use Claude Cowork?
No. Cowork was built for non-technical knowledge workers, with a plain-language interface and no terminal. The main skill is writing a clear instruction and giving good context — if a colleague with minimal context would be confused by your prompt, so will Claude.
Does Cowork remember previous sessions?
Not by default — chat memory doesn't carry into Cowork and each session starts fresh (Projects are an exception). Use Global Instructions for persistent context, and point Claude at reference files at the start of a task.
Can Claude Cowork run tasks on a schedule?
Yes — type /schedule in a Cowork session, or use the Scheduled sidebar, to set recurring or on-demand tasks. Scheduled tasks run remotely on Anthropic's servers, so your computer doesn't need to be awake.
Want a hand putting this into practice?
Our hands-on Claude Cowork training takes your team from the basics to a repeatable practice, using your own data.