Like many people these days, I’m obsessed with Claude Cowork.
Anthropic made this announcement earlier this year, just days before I received a call from Inman reporter Nick Pipitone asking for a story about how real estate professionals are using ChatGPT, Gemini, Claude, and Perplexity.
One of the main takeaways from this story was that most real estate professionals only use AI, like an advanced version of Google. But for many agents and operators, AI is a tool for listing descriptions, social captions, and email drafts. What started as a writing tool has now become a full-fledged assistant, or in my case, chief of staff.
AI is moving from content generator to team member. The real value goes beyond just seeing words on the page faster. You can see your work getting done in your email, calendar, and task manager.
Claude suggested I start with a chief of staff who could scan the area where my job is, pick up the signals, and give me a morning briefing that would tell me three things:
What do I need to pay attention to today? What are my deadlines and deliverables? What should I prioritize before starting my day?
The first thing I had to do was upgrade to Claude Pro. I chose the annual plan.
Claude then suggested connecting my Gmail, Google Calendar, Slack, ClickUp, and Google Chrome browser extensions via Claude Connections. We created my first agent, a chief of staff who gave me a brief day-to-day briefing every morning.
This has been a great addition to my workflow and routine, and I hope you find it useful as well.
Three days later, I learned that my company, Rechat, had been nominated for a Webby, not through my inbox, but through my new boss. It was an exciting moment. Before I even opened the email, my chief of staff had already revealed important news.
my boss’s job
Every morning, my chief of staff reviews the systems I’ve connected to and writes a briefing summarizing them.
Your top priorities for the day Key emails that need your attention Action items and deliverables Calendar context Deadlines that can be missed if ignored
This is the kind of signal that can take hours if you’re moving too fast. Instead of forcing me to go hunting across four or five different star systems, my chief of staff brings it to me.
How to build Claude Cowork Chief of Staff
Here is a step-by-step version of the setup:
Step 1: Upgrade to Claude Pro
My first step was to upgrade my Claude subscription to gain access to Claude Cowork. Currently works only on Mac computers. I opted for an annual subscription and upgraded to Max to help with my daily life, rather than as a one-time experiment.
Step 2: Connect your tools to your workstation
Settings within Claude allow you to connect to the platforms you use every day. For me it was:
Gmail Google Calendar Slack ClickUp Google Chrome Browser Extension
This is the crux. My inbox lets Claude know what’s going on with me. My calendar gives it context. Slack reveals your team’s communications and active threads. ClickUp displays deliverables, projects, and deadlines. The Google Chrome extension gives Claude access to everything he needs to get his work done.
Step 3: Tell Claude what kind of chief of staff you want
This is where it gets interesting and you can customize it to suit your own work.
Don’t just connect a tool and expect the model to figure it out. Tell them exactly what you want them to look for. Prompts don’t have to be overly complex. All you need to do is be specific.
Below is a simple version that you can adapt.
“Revisit your Gmail, Calendar, Slack, and ClickUp. Create a concise morning briefing that communicates your top three priorities for the day, important emails to respond to, meetings to prepare for, deadlines and deliverables at risk, and action items that are blocked or waiting. Be clear, practical, and concise.”
That way you can reach 80%.
Step 4: Request fixed output format
Briefings are only useful if they are easy to skim.
I trained Claude to organize my stuff into sections like this:
Today’s Top 3 Priorities Email Priorities Calendar Overview Deliverables and Deadlines Recommended Focus
Its structure turns information into action. The top three priorities provide a clear ranking. Email priority separates the signal from the noise. Deliverables provide visibility into revenue-generating work. The recommended focus will tell you where to start. The last one is very valuable. The answer usually surprises me.
Step 5: Adjust after a few mornings
Your first version doesn’t have to be perfect. Use it for a few days and then tighten it.
You’re probably seeing a lot of emails. Maybe there’s a lack of urgency to follow up. Perhaps you need to focus more on communicating with your clients. Perhaps you need to prioritize roster appointments, contract deadlines, pending trades, or team follow-up.
That’s normal. Think of this like onboarding for a new chief of staff. We don’t expect perfection from day one. You are expanding your team.
Step 6: Make it part of your morning routine
This is where value gets complicated. Build it, admire it, and don’t forget it.
Use it every morning. Please read the instructions before opening your inbox. before starting the reaction. Before Slack takes over your morning. Before your day becomes someone else’s priority.
That’s the habit that makes this useful. Not only will you watch the briefing with Claude, but I’ll also CC you on Slack for a copy in case you want to join in first.
What real estate professionals should build next
Once you have the basic version working, you can proceed further.
Agents can build versions to look for new leads, display requests, discount opportunities, follow up with clients, prepare listing presentations, contract deadlines, open house tasks, and more.
Team leaders can build teams around agent performance, pipeline movement, recruiting conversations, marketing deliverables, or emergent team communications.
Brokerage executives can build this for strategic priorities, partner communications, executive meetings, departmental roadblocks, or important projects that are delayed.
The exact tools you’re connecting may be different, but the principle is the same. Connect your systems, define what’s important, and train your chief of staff to account.
The briefing begins from there. But the same connections that power it can evolve even further. Heads of staff can draft replies to flagged emails and save them in Gmail for review before hitting send. You can accept meeting invitations on behalf of users. You go from being informed to being ahead of the curve. Our AI agent Lucy performs many of these tasks for agents and their managers every day.
In recent years, the AI conversation in real estate has been centered around content. Please write this. Please summarize it. Create a draft of your caption. Clean up your email. It’s convenient. This is just the tip of the iceberg.
An even bigger opportunity is coming.
When AI can read across your tools, understand what’s important, and provide clear instructions before the day starts, you’ll stop using AI like Google and start using it like an additional team member.
The morning briefing was my entry point. My chief of staff doesn’t just inform me. It works.
Looking for more great resources? Check out Anthropic Academy and AI Daily Brief.
May is Inman’s seventh annual Agent Appreciation Month. Find profiles of top producers, their thoughts on the state of the industry, and concrete takeaways you can implement in your career today. Additionally, the prestigious Real Estate Future Leader Award is back.
Audie Chamberlain is Vice President of Strategic Growth and Communications at Rechat and Founder of Lion & Orb. Connect with us on LinkedIn.
