Andrew Dunn's beginner's guide to Claude's Cowork feature for business automation
A solo presenter walkthrough of Claude Cowork — Claude's desktop AI agent — covering setup, live demonstrations, and limitations.
Summary
Andrew Dunn presents a beginner-friendly guide to Claude Cowork, Claude's desktop AI agent feature available exclusively through the paid desktop app. He argues that most people are using only a fraction of Claude's capabilities by treating it like a search engine, and that Cowork represents a fundamentally different mode of operation — an autonomous agent that can work directly on your computer and connected accounts. The video covers setup from scratch, three live demonstrations including file organization, bank statement analysis, and Gmail/calendar integration, plus a bonus web browsing demo. Andrew also addresses limitations that he says are rarely discussed, including the absence of cross-session memory, the requirement for the app to stay open, and heavy token consumption on lower-tier plans.
Key Takeaways
FULL TRANSCRIPT
Introduction and What Claude Cowork Is
Andrew Dunn: Most people using Claude are using about 5% of what it can actually do. They are treating it like a fancy search engine. But there is a feature inside of Claude that turns it into a totally different animal. It's something that sits on your computer and can do actual work for you. And it is called Cowork. And if you run any type of business, this is going to change absolutely everything for you.
In this beginner-friendly video, what we're going to be covering is what Cowork actually is, how I set it up in under five minutes, three real-life demos that you can copy today, and the limitations of Cowork that nobody talks about.
Setup: Getting the Desktop App and Paid Plan
The first thing that you need to know is that to have Claude Cowork, you actually need a paid subscription. If you come to claude.com/pricing, you are going to need to get either the Pro or the Max subscription. If this is your first time trying it out, $17 will get you started.
Once you are actually inside of Claude, this is the Claude interface. You can actually see a little button down here to download the desktop app, because that is the only place you can actually get Cowork. Here you'll find both the Mac OS version and the Windows version. You hit download, and then it's going to download a file just like this. That is how you will install it on your desktop.
Inside of the actual Claude application, you can see it looks identical to what we just saw in the browser with two key differences. At the top here we have Chat, we have Cowork, and we have Code. Now, Cowork is basically the non-technical, user-friendly version of Code. And that is why this is so powerful, because Claude Code has just changed absolutely everything about being able to build businesses, build apps, and do work. Claude Cowork has basically brought that to the absolute masses.
Navigating the Cowork Interface and Adding Connectors
Inside of Claude Cowork, you will see that it looks very similar to the normal Claude interface. You have a chat functionality, you have folders, and you have some of the tasks you can do. On the left-hand side, you've got Search, Scheduled, and Customize.
We're going to start with the Customize section because inside of Claude Cowork — and this is one of the most powerful parts — we can actually give it certain skills and plugins to basically make it a genius at certain specific tasks. Imagine giving it a plugin on how to be an amazing accountant, or a skill on how to do PowerPoint presentations. You do that all through here.
The thing we do need to do for this video is actually download some connectors. You click the plus button and click Browse Connectors, and here are the pre-built ones that companies have already provided — everything from Intercom, there's Stripe, there's Fireflies for note-taking, and Clay.com. There are so many that are already here.
I want to use the Gmail and the calendar integration for one of the demos we're going to be showing you later. You can just literally click the Connect button and it is going to prompt you to add that connector. Then you can see all the connectors that are now connected to your Cowork account.
Demo 1: Organizing and Renaming Screenshot Files
Let's actually put Cowork to the test. I want to start with something very simple. If you are anything like me, I take a ton of screenshots and I've got a ton of files on my desktop that I need to organize and rename. So I'm going to type in here. I have a lot of YouTube screenshots on my desktop. I'd like you to go in, find them, organize them, and make a new folder called YouTube Thumb Inspo.
Then, what you do is select the folder where you want it to work. You can choose a specific folder, but because I want it to organize my desktop, I actually select the whole desktop, and then it's going to have access to everything. The deeper you go and the more restricted the folder, the less it will find — it's only going to work within those files. I hit Open on that and it asks if I want to give it the ability to change the files. I'm going to say Always Allow, and then I'm going to hit go.
What it's now going to do is go on my desktop and actually start organizing these files, making the folder, and it's going to let me know when that is done.
Let's have a look at what it found. It's found a total of 18 screenshots and it has also made the folder YouTube Thumb Inspo. We come back here and we can actually see it on my desktop. And as you can see, there are all these screenshots.
Now, if you're like me, I actually want some more clarification on what these screenshots are. So I'm going to come back and tell it to go back in and do an update — add descriptions to the filenames. And candidly, I could have done this straight off the rip.
Demo 2: Running Multiple Agents in Parallel — Vibe Consulting Screenshots
What I'm going to do now is start running another task in parallel. This is one of the hugely powerful things about Cowork — you don't just have one agent running for you, you can have loads of agents.
I'm going to select a certain folder off my desktop and I am going to find the VC screenshots. These are all screenshots — about a hundred of them — of people in the Vibe Consulting community who've closed deals and made a lot of money. The problem is I've screen-grabbed them so I can use them in content and newsletters, but I have no idea what is actually going on in each screenshot. So I want it to do the same thing it's currently doing for the YouTube folder — go in, read them, and rename them descriptively.
And there we go. We've just started a second agent in parallel. You can see there are now two agents working in tandem.
Coming back to the YouTube thumbnails — it has renamed all 18 files. We'll come to the YouTube Thumb Inspo folder, and as you can see it has renamed all of them. "Automation, the ugly truth, dark grunge text style." Totally accurate. What a great descriptor. This is massively helpful to me, especially as someone who is ultimately quite messy.
The VC screenshots task is continuing to run. It's adding more screenshots and doing its thing, so we'll check on that one later.
Demo 3: Bank Statement Analysis
Now we're going to fire up a third agent. We're going to hit New Task up here. This time we're going to cover something that I absolutely loathe.
A fun little fact: I've been in business about a decade, and I have had one member of staff for that entire decade. She has never left my side. Her name is Vicki and she is my accountant. And I promise you, if she were here, she would attest to the fact that the thing I hate most is gathering all my data and building the accounting documents that are required, because it's messy and stuff's all over. I use personal and business expenses across different cards — I'm a terrible business owner on that front.
So, I want to get Claude Cowork to help clean up all the bank statements, figure out how much money I've made, what I've spent money on, personal expenses versus business expenses, and so on.
I'm going to come and find that folder under my Downloads, click on Bank Statements, and say Always Allow.
I'm also going to use the dictation feature on Mac here — another great tip. A lot of people use Whisper Flow, which is great but paid. On Mac, you can actually set up a double-tap of Control and speak directly. So that's another little fun fact.
I dictate: I have a load of bank statements here that I need you to run through and organize. I need you to figure out where my biggest expenses were and put together an in-depth report. Also a chart so I can visually see it. And I want to be able to send this off to my accountant, but it's really just for me to understand where all my money has been going.
That one is now up and running.
As Cowork works through the bank statements, it's learned what I want and is asking for certain approvals along the way. It's come back saying it's going to build a comprehensive Excel spreadsheet with all the categories. It found six months of data and is now going ahead and building the spreadsheet.
It's taken probably about five minutes to do this, and it's found 89 transactions. It says all the formulas are clean and there are zero errors. It's made the report with five tabs: Dashboard, Transactions, Charts, Monthly Detail, and Key Insights.
Let's open this up. Here we can see the opening balance in October was just over a quarter of a million, total deposits were 170,000, total withdrawals visible, transactions broken down by category — investments, transport, dining. I spent 12 grand on eating out. That's too much McDonald's. Then we've got the largest individual expenses, then we can go to All Transactions and literally see everything coming in and out, then there's Monthly Detail, and then Key Insights.
Total income was three-quarters of a million. Total spending was just over 400,000. So I netted 300,000. Average monthly spending is 70,000. It's a bad habit.
You can see the full breakdown of the finances. That is incredible. I am actively using this for all my banks across all my businesses. I have six different bank providers, different investment accounts, everything. I am now able to give that information to an AI agent and start doing deep analysis.
Demo 4: Gmail and Calendar Integration with Scheduled Tasks
Now I want to cover the third demonstration — something you can genuinely use daily. We're going to click New Task, and this is where we're actually going to need one of our connectors. If you haven't already, you need to come to Connectors and make sure the connection is active. We're going to be using Gmail and Google Calendar.
I type: "Can you check how many meetings I have this week?"
It is going to totally autonomously go — I've given it access to my calendar — find all of the meetings I have this week, and give me a rundown.
Bear in mind, if you have multiple Gmail accounts, it's going to only work for the one you've actually connected. If you're like me and have many, you have to use your main one for this to be useful. I actually have all mine funneled into a central account these days.
That's taken about a couple of minutes and it's come back and told me all of the events I have on my calendar. Now, you might be thinking, "I can check my calendar way quicker than a couple of minutes." I get that. But there's something I'm going to show you in a second that makes this make way more sense and way more valuable.
The next thing I'm going to do is ask: what emails have I had today? Now it's going to go into my Gmail account and give me a summary of my emails.
You want to take this up a notch, right? Because you're thinking, I can just jump into my calendar — it's easier to check it, easier to check your emails — which I totally get. But as you get bigger, or if you do have a lot of emails coming in — I get a couple of hundred emails a day now across all my different businesses — it's important to get in-depth summaries of what's actually going on and understand where needles are being moved, what's a priority, and what's not.
We can see here I've got an accountant asking me for stuff, as per usual. I've got calendar events that have come through, Fathom call recordings, and a cigar promotion. That was just what came through today on this email account.
Scheduling Automated Daily and Weekly Briefings
If you don't want to be running this every day because it's just much faster to run through manually, what you can actually do is schedule this. And this is what I love to do.
I have a daily scheduled event. What it does is summarize all the emails that have come in through the night and give me that at 9 a.m. So when I wake up, I have a full rundown and summary of priorities, what's coming in, and what I need to focus on. And then also at the beginning of every single week, I have it run to tell me the meetings that are due — what's coming up, what are sales calls, what are team meetings, new offers. There's a whole plethora of things we work on and I get it to categorize those.
If I want to create a new one, I'll just put in a name, then the prompt — say, "I want you to go into my email every day and give me a summary of all the important stuff I need to do" — and then select where you want the information put and what frequency. If I wanted it weekly, weekdays, or hourly, I'd select the time and what day I get it. Then hit Save.
The more in-depth the prompt, the more specific the outcome. And the nice thing about Claude is that it does learn. As you evolve the skills and tasks you're running, it is learning what you want to see and will keep updating itself.
Bonus Demo: Web Browsing via Chrome Extension
Now I want to come to a bonus task — Claude actually has a web browsing feature. To use this, you need to go to the Chrome Web Store on Google and download the Claude extension. It'll prompt you to log in, and then this is Claude, but now it's in your browser. The Claude desktop app can actually use this integration to do things on the internet for you.
Let me give you an example. I type: "Can you see if the domain DoneandCompany.com is available on GoDaddy?"
What this is now going to do — because it's logged in on the Claude Chrome extension — is take control of Chrome in the background, actually go to GoDaddy, search for that domain name, and then bring me back whether it's available.
Something I do want to mention about the browsing feature specifically: can it buy stuff for you? The short answer is yes. But the real question is, do you want it to have access to your credit card or debit card? And the answer is no. Because if there is a hack or anything like that, you wouldn't want someone to have totally unfiltered access to all the money in your bank.
There is one way around this. There's a company called Privacy.com where you can buy — almost disposable cards — where you can put money on them, there's a limit, and it has to authorize every transaction. So if you really did want the AI to be able to purchase things for you — or go on Amazon and buy lower-amount items — you could do it, but I would highly recommend using a separate card from your normal bank account that you've preloaded money onto.
It's now back from GoDaddy and has said it found the result. DoneandCompany.com is not available, but DoneCompany.co is. You can see the results listed out. That's what it's done — totally autonomously.
Limitations of Claude Cowork
So let me talk about some of the limitations that people don't talk about with Claude and Claude Cowork specifically.
Firstly, it currently doesn't have memory across sessions. If you open one task and then open another task, it doesn't currently know that the other task ran. It can't communicate between tasks. Normal Claude does have memory between chats, the same way ChatGPT does. Claude Cowork currently doesn't.
The other big thing with Cowork is the app has to be open to run. If you want it to run those scheduled sessions, the app always has to be open. Your desktop has to be on. It can't currently run autonomously without the computer having power and the app running.
The other thing is token usage is very heavy, especially with big tasks. If you want it to go and do all this analysis, research, and put together documents and files, it will use a lot of tokens and you will run out very quickly on the $17 plan. I now pay $100 for the Max plan and I'm still regularly hitting the limit — and I'm also doing some stuff in Claude Code.
One thing I do want to mention, which you've probably picked up on in this video, is that it can be quite slow. Taking a minute to check my emails and calendar is something you could do in two seconds. Throughout this video, you've seen it take a few minutes to do relatively simple tasks. But the idea is you are telling it to do these tasks while you are off working on much more important things. Once you are comfortable with how it functions, you are letting it go and concentrating on other work. So I don't think it's as big an issue as maybe people think, but it's something to be aware of — you're not sat here watching Cowork the whole time.
And the final thing: remember, this is the worst it's going to get. This is a very new feature by Claude, and they actually built Cowork using Claude Code in a matter of days. That's how powerful Claude Code and Claude Cowork is, and it's only going to get better.