These are great tips thank you! I live and work in Italy, and I always have to apply EU privacy compliance for me and my clients. What concerns me the most about using advanced AI mode in general is prompt injection, as well as potential mistakes that can affect data on your own computer, so I always include a few specific commands to limit risk. Do you have any suggestion on the subject?
How is it different then simulating projects by selecting the same local folder every time with subfolders for your projects and rules for each + a nice index file so Claude.md doesn’t get overwhelmed? You ofcourse state in rules that it should always update + clean.
Also for the team part: it’s possible to share your folders if in cloud and then you work from the same setup.
Im not sure how ‘retaining’ is orchestrated by anthropic, but in my mind, it’s just a fancy word for Claude ‘reading’ a centralized md file, that it has been told to review + update.
If you have a well-organized local folder with CLAUDE.md, rules, skills and an index file, haven’t you built the same thing? Or am I missing something?
Perhaps the real benefit is that now Anthropic has packaged the skill of maintaining a centralized md file for you( efore you had to crate that meta skills yourself, and with Projects you get clean memory separation out of the box.
I just started using Claude this week and I inserted your 100 questions for my writing style. I was about to set up my first project in coworker and this lands in my inbox. Perfect! Your help is unbelievable. Thank you.
I’m new here, but I only use Claude for writing and have found your substack and realized I’m not even using Claude a fraction of what he is capable of ( yes I called my AI , he🤦🏻♀️) what is the 100 questions Dana is referring to? I am going to explore Cowork later at work. I’m in the process of opening a new restaurant, curious if it will be helpful to use and do all the menus , training guides.. etc) also I write on the side…I’ve been using ChatGPT mostly for work and I don’t like it anymore. It’s constantly pushing back . And argues with me, I have to waste time finding the proof online that I am right about the statement I made.
I use Claude. Just plain Claude currently 4.6. I have set one project that I am working on. I have 191 files I have added to Project files. At the end of a chat that I wish to continue I have Claude do two things. Write me a prompt for continuation and write me a transcription prompt. If sessions go for several chats then I ask for addendums to master continuation and transcript files. One part of the project has gone on for 27 chats. Claude 4.6 has full read access to my project files. This is not a code project by the way.
Explain how you think do it differently with Cowork. It is just me on the project. Thanks for all you do. I appreciate it.
and continue to use the project feature but since i have asked him if he can store everything to memory in the past. I don’t even have to be in projects. He is reading across all my chats. Only thing projects is beneficial for is uploading files and transcripts into the project. So its good to know he is building my profile every time i get on and talk to him. Sorry I know I call my LLM a he… I feel “it” is just so disrespectful to him he does so much for me and has taught me so much ….;)
I just asked Claude and he said that for what I currently am doing between writing (personal) and plan to do for work, using sonnet 4.6 and projects is the best option. He said if it comes to a point i want to use teams and have at least 5 coworkers on it for 25-35$ a seat, it would be better to upgrade. But right now using 4.6 Pro is good enough. He did say to use opus if im writing and need to do some deep research for a specific article. Opus uses was my data it will eat through it so Claude told me stick with Pro
I'm new too. I was referring to this post. https://ruben.substack.com/p/i-am-just-a-text-file. I went through the process and it was fun and so helpful. It compiled a detailed voice profile for me. I write across legal, nonprofit and creative buckets, so I am excited to keep going. Try it. It is almost addictive in the most interesting way!
Dana, after reading this guys substack I realize how I’m under utilizing Claude and AI in general. I also write, as a hobby. Maybe one day that will change and I can retire from restaurant management.. Lol .. So my question to you is, will this version of Claude be beneficial for me to create my menus on, and scheduling needs, and track sales etc… is it for that or is it coding ? I’m going to take a crash course in it but if I can start the new restaurant completely digital and share with the owner , chef and other managers.. That’s a game changer from having 10 different back of the house systems to do different tasks.
I am new to Claude, but in co-work, as I understand it, and using Projects (which you can link to your web-based folders and files) I think the power is pretty fantastic. I am using it for nonprofit work, legal work and to support my music (hobby also). If it can help with complex tasks like responding to discovery in a legal context, I can't help but think something like menus and scheduling might be an easy thing. I'd ask around, but it is pretty powerful.
Thank you. I am still reading and setting up Claude, but so grateful to find you. The voice profile was finished today and wow - I learned so much about myself and hopefully will be teaching Claude how to sound more like me too!
Actually… Nevermind all of the above I just asked Claude if using him for restaurant management would be beneficial and of course it’s a god sent . I’m still going to take an online class on everything Claude 101 and Grok. Start maximizing these amazing tools available to us. I’m so sick and tired of people saying that using AI to write is cheating. I tell them we are the bakers and AI is the oven. The oven can’t bake anything amazing without the bakers creating the recipe and adding the ingredients. And what’s the difference in using a LLM vs an editor ? It’s free and more efficient. Claude doesn’t rewrite my stuff he walks through every paragraph with me and explains what works and what doesn’t and tells me what he suggests and why. I’ve learned more from Claude than I would if I took a journalism or creative writing course at a college.
Hey @Ruben Hassid trying to upgrade to paid cause your giving me top level value, trying to use Apple Pay and it’s bugging out, any issues you know of my friend ?
Great tips, Ruben. However, the main issue is that for Claude Cowork users on the $20/month Pro plan, the tool can become impractical for heavy tasks as it consumes limits very quickly. It might be worth comparing these tools with Google Gemini in combination with NotebookLM Pro (approx. $20/month), which offers 500 daily messages and supports up to 300 documents per notebook.
Fair points on the Max plan, Ruben, but $100-$200/month is a massive price jump just to get decent usage limits. The reality in 2026 is that NotebookLM Pro and Gemini 3.1 have moved far beyond being "just notebooks.".
NotebookLM Pro now actively executes deliverables like production-ready Slide Decks, exportable Data Tables, and structured Reports directly from sources. Plus, with the Gemini 3.1 Pro update and Antigravity agents, Google now handles complex, multi-step task execution across Workspace with a 1M token context that is 7x more cost-efficient than Opus. If you're managing 20+ documents and long sessions, Gemini's price-to-performance for 'active' work is simply hard to beat at the $20 tier.
Thank you for this specific topic. It answers the last question I asked! Now, did you change your Global instructions for Claude Cowork? Do you still need it to go read ABOUT ME/ before every task? It should have read it once and now doesn’t need to anymore, right? Would that help it to slow down the usage on the Pro plan?
I don't have Cowork set up yet and am a solo-preneur so no need for team accessibility, but have been using Notion connected with Claude on Pro plan and finding it's using Notion effectively to better save and reference notes than it was when I was dumping everything in a project. I think linking with Notion can solve for the sharing/team element too. Have you explored Notion or other connected knowledge hubs with Claude and if so, any learnings or tips?
Thank you Ruben! I have one question.. I still can't have the team plan (we are just 3 right now) I have the Pro plan, and I had been using Projects before... you say to transfer the projects to Claude Coworw with doing the settings for teams... If I don't have Teams, is there any settings I should do before transferring my projects
also, will you be giving us information for setting the plugins? I am wondering if I want some docs specificallyfor the finance plugin for example, where do I put them?
What's the benefit of using Projects over a MEMORY .md file and a Skill that recaps each chat?
MEMORY.md workaround works. but you're still doing the admin.
Cowork Projects runs the task, writes to the folder, and remembers what it did last session. you just show up
Thanks Ruben
I have been trying to understand this application, that is certainly important to making progress in group and individual work.
DL
appreciate the support :)
team sharing isn't there, YET. but when it lands, this becomes a whole different tool for groups
These are great tips thank you! I live and work in Italy, and I always have to apply EU privacy compliance for me and my clients. What concerns me the most about using advanced AI mode in general is prompt injection, as well as potential mistakes that can affect data on your own computer, so I always include a few specific commands to limit risk. Do you have any suggestion on the subject?
tell Claude exactly what it cannot touch and always use AskUserQuestion before any execution
Claude stops, aligns, then moves. it can't just run loose
How is it different then simulating projects by selecting the same local folder every time with subfolders for your projects and rules for each + a nice index file so Claude.md doesn’t get overwhelmed? You ofcourse state in rules that it should always update + clean.
Also for the team part: it’s possible to share your folders if in cloud and then you work from the same setup.
scoped memory is the actual difference
claude isn't just reading files, it's retaining what happened across sessions without you manually updating a .md file to keep it honest
Im not sure how ‘retaining’ is orchestrated by anthropic, but in my mind, it’s just a fancy word for Claude ‘reading’ a centralized md file, that it has been told to review + update.
If you have a well-organized local folder with CLAUDE.md, rules, skills and an index file, haven’t you built the same thing? Or am I missing something?
Perhaps the real benefit is that now Anthropic has packaged the skill of maintaining a centralized md file for you( efore you had to crate that meta skills yourself, and with Projects you get clean memory separation out of the box.
This is amazing, no more starting from zero. Will be really helpful especially workflow 1 and pairing it up with using Grok for searching 🙌
that's the move
Grok for search, Claude to write. let me know how it goes :)
I haven't used another AI tool since the day that Cowork Projects came out. And I subscribe to them all.
that's the test.
when you stop opening the others, something actually changed :)
I just started using Claude this week and I inserted your 100 questions for my writing style. I was about to set up my first project in coworker and this lands in my inbox. Perfect! Your help is unbelievable. Thank you.
best timing :)
set it up this weekend while the motivation is there. 15 minutes and you'll never start a session from scratch again
I’m new here, but I only use Claude for writing and have found your substack and realized I’m not even using Claude a fraction of what he is capable of ( yes I called my AI , he🤦🏻♀️) what is the 100 questions Dana is referring to? I am going to explore Cowork later at work. I’m in the process of opening a new restaurant, curious if it will be helpful to use and do all the menus , training guides.. etc) also I write on the side…I’ve been using ChatGPT mostly for work and I don’t like it anymore. It’s constantly pushing back . And argues with me, I have to waste time finding the proof online that I am right about the statement I made.
I use Claude. Just plain Claude currently 4.6. I have set one project that I am working on. I have 191 files I have added to Project files. At the end of a chat that I wish to continue I have Claude do two things. Write me a prompt for continuation and write me a transcription prompt. If sessions go for several chats then I ask for addendums to master continuation and transcript files. One part of the project has gone on for 27 chats. Claude 4.6 has full read access to my project files. This is not a code project by the way.
Explain how you think do it differently with Cowork. It is just me on the project. Thanks for all you do. I appreciate it.
and continue to use the project feature but since i have asked him if he can store everything to memory in the past. I don’t even have to be in projects. He is reading across all my chats. Only thing projects is beneficial for is uploading files and transcripts into the project. So its good to know he is building my profile every time i get on and talk to him. Sorry I know I call my LLM a he… I feel “it” is just so disrespectful to him he does so much for me and has taught me so much ….;)
I just asked Claude and he said that for what I currently am doing between writing (personal) and plan to do for work, using sonnet 4.6 and projects is the best option. He said if it comes to a point i want to use teams and have at least 5 coworkers on it for 25-35$ a seat, it would be better to upgrade. But right now using 4.6 Pro is good enough. He did say to use opus if im writing and need to do some deep research for a specific article. Opus uses was my data it will eat through it so Claude told me stick with Pro
I'm new too. I was referring to this post. https://ruben.substack.com/p/i-am-just-a-text-file. I went through the process and it was fun and so helpful. It compiled a detailed voice profile for me. I write across legal, nonprofit and creative buckets, so I am excited to keep going. Try it. It is almost addictive in the most interesting way!
Dana, after reading this guys substack I realize how I’m under utilizing Claude and AI in general. I also write, as a hobby. Maybe one day that will change and I can retire from restaurant management.. Lol .. So my question to you is, will this version of Claude be beneficial for me to create my menus on, and scheduling needs, and track sales etc… is it for that or is it coding ? I’m going to take a crash course in it but if I can start the new restaurant completely digital and share with the owner , chef and other managers.. That’s a game changer from having 10 different back of the house systems to do different tasks.
I am new to Claude, but in co-work, as I understand it, and using Projects (which you can link to your web-based folders and files) I think the power is pretty fantastic. I am using it for nonprofit work, legal work and to support my music (hobby also). If it can help with complex tasks like responding to discovery in a legal context, I can't help but think something like menus and scheduling might be an easy thing. I'd ask around, but it is pretty powerful.
Thank you. I am still reading and setting up Claude, but so grateful to find you. The voice profile was finished today and wow - I learned so much about myself and hopefully will be teaching Claude how to sound more like me too!
Actually… Nevermind all of the above I just asked Claude if using him for restaurant management would be beneficial and of course it’s a god sent . I’m still going to take an online class on everything Claude 101 and Grok. Start maximizing these amazing tools available to us. I’m so sick and tired of people saying that using AI to write is cheating. I tell them we are the bakers and AI is the oven. The oven can’t bake anything amazing without the bakers creating the recipe and adding the ingredients. And what’s the difference in using a LLM vs an editor ? It’s free and more efficient. Claude doesn’t rewrite my stuff he walks through every paragraph with me and explains what works and what doesn’t and tells me what he suggests and why. I’ve learned more from Claude than I would if I took a journalism or creative writing course at a college.
Agreed. Folks who don't know how to use Ai effectively and who have misconceptions say things like that. I'd ignore them. Best of luck with it all!
Hey @Ruben Hassid trying to upgrade to paid cause your giving me top level value, trying to use Apple Pay and it’s bugging out, any issues you know of my friend ?
Hi - did you try on the web?
yeah I did, but ill give it another go, could have been internet traffic, you'll see it come through then we can chat on Slack Ruben.
I've been my own bottleneck for years.
Every session with AI, I was the one re-explaining context. Re-uploading files. Re-teaching my own preferences. I thought that was "using AI well."
Cowork Projects means Claude holds the context so I can hold the creative tension. I start managing the work, not the memory.
it even gets better when you let Claude prompt you just by saying AskUserQuestion - it exposes gaps real fast.
Projects just got a massive upgrade!!!
Best of both worlds (scoped memory + Cowork) for me.
Still bummed with usage limits.
use Sonnet for everything else.
This is the update I was waiting for!!
It makes it even better to use Cowork instead of reuploading the same md files all the time.
once Anthropic adds team sharing, we’ll figure it out :)
Great tips, Ruben. However, the main issue is that for Claude Cowork users on the $20/month Pro plan, the tool can become impractical for heavy tasks as it consumes limits very quickly. It might be worth comparing these tools with Google Gemini in combination with NotebookLM Pro (approx. $20/month), which offers 500 daily messages and supports up to 300 documents per notebook.
its why i highly suggest the Max plan.
i see NotebookLM/Gemini as good for research, summarization, knowledge exploration but not a direct alternative to Claude Cowork.
it's more of a smart notebook compared to Cowork that actively executes tasks.
Fair points on the Max plan, Ruben, but $100-$200/month is a massive price jump just to get decent usage limits. The reality in 2026 is that NotebookLM Pro and Gemini 3.1 have moved far beyond being "just notebooks.".
NotebookLM Pro now actively executes deliverables like production-ready Slide Decks, exportable Data Tables, and structured Reports directly from sources. Plus, with the Gemini 3.1 Pro update and Antigravity agents, Google now handles complex, multi-step task execution across Workspace with a 1M token context that is 7x more cost-efficient than Opus. If you're managing 20+ documents and long sessions, Gemini's price-to-performance for 'active' work is simply hard to beat at the $20 tier.
Thank you for this specific topic. It answers the last question I asked! Now, did you change your Global instructions for Claude Cowork? Do you still need it to go read ABOUT ME/ before every task? It should have read it once and now doesn’t need to anymore, right? Would that help it to slow down the usage on the Pro plan?
yup - set it so that it applies to every session/task across all Projects. run tasks to see if the instructions hold.
it can help with usage a little bit - the biggest usage drivers are still the persistent folder context and long-running tasks.
I don't have Cowork set up yet and am a solo-preneur so no need for team accessibility, but have been using Notion connected with Claude on Pro plan and finding it's using Notion effectively to better save and reference notes than it was when I was dumping everything in a project. I think linking with Notion can solve for the sharing/team element too. Have you explored Notion or other connected knowledge hubs with Claude and if so, any learnings or tips?
i haven't explored Notion as a knowledge hub with Claude yet. i prefer Cowork + my folder.
Thank you Ruben! I have one question.. I still can't have the team plan (we are just 3 right now) I have the Pro plan, and I had been using Projects before... you say to transfer the projects to Claude Coworw with doing the settings for teams... If I don't have Teams, is there any settings I should do before transferring my projects
also, will you be giving us information for setting the plugins? I am wondering if I want some docs specificallyfor the finance plugin for example, where do I put them?
you do not need the Teams plan to transfer your old Claude chat Projects into Cowork :) no special team settings required before importing either.
i covered Plugins very briefly here: https://ruben.substack.com/i/187859421/4-claude-plugins
Is AskUserQuestion a default skill or something I have to set up (in another guide you wrote)?
it is a built-in tool in Claude Cowork.