Stop Prompting, Start Onboarding: Claude Cowork for Agents

If you have opened Claude, typed a prompt, and thought "That's it?" — you have been using the wrong version. The browser chat is fine for quick questions. Claude Cowork is something else entirely, and most agents have no idea it exists.

Matthew Rathbun does. He is the Executive Vice President at Coldwell Banker Elite, oversees roughly 300 agents across DC, Maryland, and Virginia, and has quietly rebuilt how his firm creates listing kits, trains agents, writes addendums, and onboards buyers, largely on a downloadable desktop app. On Episode 7 of AI Agent Advantage, he walked JMan through the whole system.

Stop Treating AI Like a Search Box

The most common mistake agents make with any AI tool is the same one: they open it like Google. They type a short phrase, get a generic answer, decide the tool is not that useful, and close the tab. Matthew calls this treating it like a search instead of an assistant, and it is the difference between a tool that saves you minutes and one that saves you hours.

The fix starts with a single onboarding conversation. Matthew's starter prompt is to tell the AI you want it to interview you the way a new assistant would on their first day. You are not asking for output yet. You are asking the tool to ask you questions, learn your voice, understand your clients, and figure out where it can help. His first session ran an hour and fifteen minutes, mostly on a walk around his property.

"It's just like hiring a human assistant. There's a learning phase. It's just that AI does it in one hour, whereas my assistants have done it in six months."

— Matthew Rathbun

Voice mode speeds this up considerably. The average agent types at something close to five words a minute. You talk at two hundred. Matthew uses voice mode almost exclusively now, including on car rides. The quality of the session goes up when you stop hunting for keys and start having a conversation.

What Claude Cowork Actually Is

Claude Cowork is not a browser feature. It is a desktop application you download and install on your Mac or Windows machine. When you open it, you see three tabs across the top: Chat, Cowork, and Code. Most agents have only ever used something like Chat. Cowork is where the real estate work happens.

The difference between chat and Cowork is the difference between asking someone a question and handing them a task. With chat, you prompt and it replies. With Cowork, you give the app access to files on your computer, and it can work with those files, open your browser with permission, create documents, run searches, and build things on your behalf. Every meaningful step requires your approval before it acts, which is by design. And because Cowork runs locally, it only has access to what you give it — a controlled environment that makes it safe for a professional real estate practice.

The Folder: Your First Real Step

Once you have downloaded the app, the first practical step is creating a dedicated folder on your computer and granting Cowork access to it. Nothing outside that folder is visible to the tool. Matthew uses a Google Drive folder as his access point, so his files sync across devices while the access boundary stays clean.

What goes in the folder matters. Matthew loaded in roughly four hundred PowerPoint presentations from years of teaching, transcripts from one hundred CE classes, ten years of addendums, seventeen years of emails, and his notes vault of about five hundred files. The result: when he asks Cowork to build something, it is not guessing what he sounds like. It already knows. When he asks it to write a home inspection addendum, it knows his regional contract language, his voice, and the principles he teaches in his own negotiations class.

Projects and Skills: Where the Hours Come Back

A Project in Claude Cowork works like a custom assistant configuration. Matthew's buyer representation project includes his buyer counseling checklist, grant and loan program PDFs for first-time homebuyers in Virginia, his email templates, and a StoryBrand framework prompt. When a new buyer signs, he opens the project and says "I have a new buyer." He even configured it to run a 5 a.m. daily search across Redfin, Realtor, Zillow, and Homes.com for off-market and coming-soon listings that match his buyer's criteria.

Skills pull everything together. A Skill is a stored prompt — in Matthew's case a chain of seven prompts — that you activate with a forward slash and a keyword. His listing kit Skill pulls the property address, tax records, RPR seller report, comps, and unique selling features, then generates a twenty-page listing presentation in his brand colors, following fair housing guidelines, and skipping open houses because he does not do them. He told it all of that once. The Skill remembers it permanently.

"It takes four minutes instead of four hours. And it's specific to that property."

— Matthew Rathbun

Key Takeaways

• Download the Claude desktop app. Chat, Cowork, and Code are all built in.
• Start with an onboarding conversation in voice mode, not a typed prompt. Ask the tool to interview you.
• Create a dedicated folder, grant Cowork access only to that folder, and feed it everything that represents your voice: past presentations, emails, contracts, class notes.
• Build a Project for each repeatable client type — buyer, seller, investor — and attach your reference documents.
• Add the Skill Creator from the browse menu and build at least one Skill for your highest-volume task.

About Matthew Rathbun

Matthew Rathbun is Executive Vice President at Coldwell Banker Elite and a licensed broker across DC, Maryland, and Virginia. He oversees roughly 300 agents, has won national Instructor of the Year multiple times, and trains real estate professionals across the country on technology and practice.

• AI tutorials & resources: matthewrathbun.com/ai