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He Used Claude Cowork to Build a Massive Skill in 10 Minutes
Published January 22, 2026 · 147 views on YouTube
Key takeaways
- Claude Cowork can be pointed at an entire desktop or cloud directory instead of requiring individual file uploads.
- It compared an existing skill against the full file hierarchy, flagged missing worksheets and templates, and offered to create or enhance files to close the gaps.
- The rebuild produced 3,712 lines of reference material in roughly 10 minutes, after the user hit usage limits trying to do it manually in Claude Desktop.
What did this Claude Cowork user actually build?
A community member named Jason used Claude Cowork to review and rebuild a skill he’d created for his team, an “ask, quiz, survey” method skill with a large supporting file set. Cowork scanned his desktop and cloud directories, found gaps in the existing skill, and generated 3,712 lines of new and enhanced reference material in about 10 minutes.
Why did he turn to Cowork instead of just using Claude Desktop?
He had originally built the skill in Claude Desktop, but the file set was so large that he kept hitting usage limits and could only upload a certain number of files at a time, forcing him to keep restarting and re-explaining context. Cowork solved this because it already had connector access to his desktop and cloud files, so it could review everything at once without manual uploads.
What steps did Claude Cowork take to rebuild the skill?
- He opened Cowork and asked it to make sure his existing skill covered everything found in his files.
- Using the plus sign in chat, he pointed it at the directory instead of uploading files.
- Cowork found it had access not just to his desktop but also to his cloud server.
- It analyzed the existing skill against the full subdirectory hierarchy and reported specific gaps, including missing worksheets and templates.
- It recommended enhancing existing files and adding advanced segmentation, then offered three options: create new reference files for the gaps, enhance existing files with missing content, or pull specific details.
- Jason told it to do all three, starting with option one.
- Cowork created the new files, enhanced existing ones, and finished with 3,712 lines of comprehensive reference material available to download.
How does pointing Cowork at a directory differ from using the file-upload icon in regular Claude Desktop?
During the discussion, another participant noted that Claude Desktop’s plus icon does let you select multiple files, and Jason confirmed that Desktop can also be told to search through a whole folder. The real difference he described was scale and friction: with a large, comprehensive file set that kept hitting usage limits during upload, letting Cowork search the directory itself was far faster and more reliable than manually feeding files in one at a time.
How did he validate the AI-generated content, and where is Cowork available?
Jason said he reviewed all the generated files himself and then used them in practice, noting he’s very familiar with the underlying method so he could judge whether the output was accurate; he was working with Opus. On availability, another participant mentioned Cowork had recently become available on the $20 plan, though still Mac-only, with hope that PC support would follow.
Full video transcript
Sharing how you’ve set up Cowork to work with your Mac files and enhancing an existing skill. I would love it if you’re open to sharing your win with Claude Cowork.
Yeah, for sure. So I had no idea if Cowork would do this. This is Claude Desktop and I’ve been creating for my team an ask, quiz, survey method skill. But the issue was its masterclass is so big that I was running into usage limits, and you can’t upload only a certain amount of files, yada yada, I had to keep on restarting, asking it to remember everything. So I was like, huh, Cowork actually has access to my… I’ve set up access via connector to my desktop. So I just went to Cowork and said, I want to make sure my ask Claude skill covers everything found here, can you help? And through the plus sign in the chat I went to the directory, and first it said upload files, and I said, I gave you access, genius. And it’s like, okay, not only was it on my desktop, it was on my cloud server, which was cool.
So it can access your cloud server as well. And so it basically went through and it analyzed my skills, says okay, I have all this, and then it basically went through the entire subdirectory system hierarchy and said, I found gaps, you’re missing these elements. And I recognized immediately, like, holy crap, I really needed this, this really needs to be included. So it found all missing worksheets and templates and gave me recommendations and says, hey, we can enhance existing files and you should consider adding advanced segmentation. Would you like me to help? One, create new reference files for the gaps, enhance existing files with missing content, pull specific details. I said, do them all, starting with number one. Said perfect. So it goes through, created the new files, enhanced the new files, and I just kept on talking with it, and then all of a sudden it’s boom, done. 3,712 lines of comprehensive reference material. It gave me the file to download and it’s all done. Probably like 10 minutes.
Wow, thank you for sharing.
So you use it to create the skills, or you created it to use to create, to put the repository inside Claude projects?
So I use regular Claude Desktop to create this.
Okay. But I was running into issues because there were so many files with usage limits and you could only upload a certain amount of files at a time, and restarting. So I used the connection to my desktop to view all the files in my Claude directory, and it basically reviewed my skill that I already had existing and reviewed the directories of the files and said, oh, your skill is missing X, Y and Z, let me fix your skill, or enhance your skill.
Okay, so basically you used it to update your skills and then you took those and put them into Claude, or still keeping them in Claude Cowork?
No, it’s in Claude now. So in the future I would use Cowork, Darby, to actually possibly start the skill creation from scratch, because it would have to make sure it had access to everything.
Question from Bob here about how are you reviewing and validating all the content it created? Were you just reviewing it as it was producing it? Did you go back through and check to double check and verify anything, Jason?
Yeah, I reviewed all the files and then I started using it, and I’m very familiar with the method so it’s legit. I was using Opus too.
Awesome, thank you for sharing, Jason. Cool to see how you’re tapping into Cowork. And again, like, Cowork just came out a week ago, so we’re still understanding where it fits into this process, and much of what is happening as Cowork is doing what Jason was demonstrating is a lot of how Claude Code operates in terms of agentically being able to go and research and check out files, do all that sort of stuff. I don’t know, Jason, if you have tried setting it up inside of a GitHub repository or something like that, that may be something that you still want to jump into the Claude Code side of things for, but were you able to have it?
Yeah, that’s something I need to do.
Okay, cool. See Bo, Peter, when in the last week, used to identify SEO gaps in HFS to see what kind of linkable assets I could, I should build, and then we built out an ROI calculator into a deployable format. Ideally will be a great web asset for link building. Awesome win, thanks for sharing. If you’re open to sharing any more about that, let me know.
See another question here. And yeah guys, feel free to drop your questions about that, because Cowork is still relatively new and I think each of us are going to find our own uses with how it fits inside of our own workflows. But John asks, I’m confused about what part Cowork played in Claude Desktop parsing ask method files. Maybe some clarity on how and where it was finding those files and updating or reviewing that information. Jason?
Yeah, basically if you go into settings, and can you share your screen by chance? Yep. It’s a desktop app extension and then you can give it access to your file system, and you can control your Mac desktop commander. You can give it access to Excel, PowerPoint, Word, all that. So basically you just say go to this directory, you can give it the direction and say, hey look, I need to find everything on my desktop about surveys, and it’ll look through your desktop and find it. It’s really that simple, which is very cool.
Jason and Darby, can I just ask a clarifying question? So the difference, and John maybe trying to paraphrase, but feel free to chime in if I didn’t understand your question, is there a question about the difference between just asking Claude to review something and asking Claude Cowork to do something, is the fact that it could go and just search an entire drive instead of uploading an individual file? Is it the scope at which it can do the analysis, is that the difference?
Yeah, I think the big difference is, let’s just say you had eight files, you could just upload that into chat and it wouldn’t be a big deal. But I had this huge comprehensive force that was causing issues, and it was a thousand times easier and faster and more efficient to let Cowork find it all and make sure I had every single file and framework and strategy and all that.
Okay, so is it fair to say that when you go to click that plus icon in a regular Claude chat, desktop or web, you’ve got to give it a file, or maybe select multiple files, but you can’t just point it to a folder?
Yes, you can.
Oh, you can?
Yeah, in desktop. Yeah, you could just say look through all of…
That’s why I was confused, that nothing, I didn’t see anything there that wasn’t desktop, that you couldn’t do in desktop, that’s all. So I don’t have access to Cowork, but that’s why I was trying to see where is Cowork coming into, what’s it adding, of course it’s difficult when you can’t use it.
I see Marcel just dropped a tip that Cowork is at least in the last couple days also available on the $20 account, still for Mac only though.
I think hopefully sooner than later they’ll open this up to PC as well.
Okay, that’s interesting, because I just inherited an old Mac, so maybe I’ll try it myself.
And thanks for trying to clarify, Bob.
Yeah, yeah, of course.