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Out of the box, Claude is a brilliant colleague locked in an empty room. It has read most of the internet, but it has never seen your inbox, your ticket queue, your contracts folder, or your calendar. Every fact about your actual Tuesday has to be carried into the room by hand: pasted, uploaded, re-explained. This section is about opening the room. Two upgrades do it, and they compound:
Upgrade oneConnectors

Live, permissioned lines into the systems you already use. Claude searches your Drive, reads your tickets, and files your issues itself, with your credentials and under your rules.

Gives Claude reach
Upgrade twoCowork

The same agentic engine that powers Claude Code, pointed at ordinary work. You describe an outcome, Claude plans it, works it across files and connectors, and returns finished deliverables.

Gives Claude initiative
Neither upgrade is about intelligence. The model is identical before and after. What changes is what the same intelligence can touch, and how much of a task it is allowed to carry at once.

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Feel the difference on one real task

Here is one job: “Find every contract renewing this month and draft a reminder email for each owner.” Push the lever through its three positions and watch who does the walking.
Read the meter, not just the checklists. At every position the thinking is Claude’s. What moves is the fetching, the cross-checking, and the assembly. Those are exactly the parts of your week that feel like work but are not judgment.

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The one rule underneath everything

Connectors and Cowork share a single design principle, and it is the through-line of this whole section:

Reach is granted, never assumed. Claude can only see what you have connected, only do what the tool permissions allow, and only act as far as your own account could act.

A connector inherits your permissions in the source system. If you cannot open a file in Drive, Claude cannot open it through the Drive connector. Every write-capable tool can be set to ask first, or blocked outright. Cowork adds approval modes on top, and asks before anything is permanently deleted, in every mode. You will meet each of these controls in detail, and you will also meet what happens when they are set carelessly.

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What is in this section

Connectors

What a connector actually is, the directory, and the anatomy of a real tool call, down to the JSON.

Cowork

Where a session really runs, how it uses your folders and connectors, and the three approval modes.

Failure modes

Plumbing, permissions, judgment, and injection. Four ways connected work goes wrong, and the tells for each.

Lab: Wire it, work it, break it

Connect a real service, run a real task through chat and Cowork, then deliberately trip three failures.

Quiz: Skills, connectors & Cowork

Shared check covering Skills plus this section. Ten instructor-led questions.